All Related Questions of Organic Chemistry

Q: For each of the following compounds, determine whether the two protons

For each of the following compounds, determine whether the two protons shown in red are homotopic, enantiotopic, or diastereotopic:

Q: For each of the following compounds, identify the expected chemical shift

For each of the following compounds, identify the expected chemical shift for each type of proton:

Q: The following table provides relative rates of oxymercuration for a variety of

The following table provides relative rates of oxymercuration for a variety of alkenes with mercuric acetate. Provide structural explanations for the trend observed in the relative rates of reactivity...

Q: 9-Borabicyclo[3.3.1]nonane (

9-Borabicyclo[3.3.1]nonane (9-BBN) is a reagent commonly used in the hydroboration of alkynes (Section 10.7), but it can also be employed in reactions with alkenes. The following table provides the re...

Q: Propose a plausible mechanism for the following transformation, which was used

Propose a plausible mechanism for the following transformation, which was used as the key step in the formation of the natural product heliol.

Q: Reserpine can be isolated from the extracts of the Indian snakeroot Rauwolfia

Reserpine can be isolated from the extracts of the Indian snakeroot Rauwolfia serpentina and has been used in the effective treatment of mental disorders. R. B. Woodward employed the following reactio...

Q: Draw the expected major product for each of the following reactions:

Draw the expected major product for each of the following reactions:

Q: Identify the reagents that you would use to achieve each of the

Identify the reagents that you would use to achieve each of the following transformations:

Q: Draw a mechanism for each of the following transformations: /

Draw a mechanism for each of the following transformations:

Q: The bicyclo[3.1.0]hexane ring system

The bicyclo[3.1.0]hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One m...

Q: Predict the products for each of the following reactions. Note:

Predict the products for each of the following reactions. Note: in some cases, the reaction produces a new chiral center, while in other cases, no new chiral center is formed.

Q: Draw a mechanism for each of the following transformations: /

Draw a mechanism for each of the following transformations:

Q: A compound with the molecular formula C5H10O2 has the following 1 H

A compound with the molecular formula C5H10O2 has the following 1 H NMR spectrum. Determine the number of protons giving rise to each signal.

Q: Carbocation rearrangements during hydrohalogenation reactions can involve shifts of carbon atoms other

Carbocation rearrangements during hydrohalogenation reactions can involve shifts of carbon atoms other than a methyl group. For example, the addition of HBr to compound 1 leads to carbocation 2, which...

Q: In each of the following cases, identify the alkene that is

In each of the following cases, identify the alkene that is expected to be more reactive toward acid-catalyzed hydration.

Q: Identify whether you would use dilute sulfuric acid or concentrated sulfuric acid

Identify whether you would use dilute sulfuric acid or concentrated sulfuric acid to achieve each of the following transformations. In each case, explain your choice.

Q: Draw a mechanism for each of the following transformations: /

Draw a mechanism for each of the following transformations:

Q: If an alkene is protonated and the solvent is an alcohol rather

If an alkene is protonated and the solvent is an alcohol rather than water, a reaction takes place that is very similar to acid-catalyzed hydration, but in the second step of the mechanism the alcohol...

Q: Predict the product for each reaction, and predict the products if

Predict the product for each reaction, and predict the products if an acid-catalyzed hydration had been performed rather than an oxymercuration-demercuration:

Q: In the first step of oxymercuration-demercuration, nucleophiles other than

In the first step of oxymercuration-demercuration, nucleophiles other than water may be used. Predict the product for each of the following cases, in which a nucleophile other than water is used.

Q: Below are several examples of hydroboration-oxidation. In each case

Below are several examples of hydroboration-oxidation. In each case, consider the expected regioselectivity and then draw the product:

Q: Compound A has the molecular formula C5H10. Hydroborationoxidation of compound A

Compound A has the molecular formula C5H10. Hydroborationoxidation of compound A produces 2-methylbutan-1-ol. Draw the structure of compound A:

Q: Predict the product(s) for each of the following transformations

Predict the product(s) for each of the following transformations:

Q: A compound with the molecular formula C10H10O has the following 1 H

A compound with the molecular formula C10H10O has the following 1 H NMR spectrum. Determine the number of protons giving rise to each signal.

Q: α-Pinene can be isolated from pine resin and is a

α-Pinene can be isolated from pine resin and is a primary constituent of turpentine (paint thinner). Both enantiomers of α-pinene are naturally occurring. To determine the...

Q: Predict the product(s) for each of the following reactions

Predict the product(s) for each of the following reactions:

Q: Compound 1 has been shown to be a useful precursor in the

Compound 1 has been shown to be a useful precursor in the synthesis of natural products. In principle, four stereoisomers are possible when this compound is subjected to catalytic hydrogenation. Draw...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Predict the major product(s) that are expected when each

Predict the major product(s) that are expected when each of the following alkenes is treated with Br2/H2O:

Q: Bromonium ions can be captured by nucleophiles other than water. Predict

Bromonium ions can be captured by nucleophiles other than water. Predict the products of each of the following reactions:

Q: When trans-1-phenylpropene is treated with bromine, some

When trans-1-phenylpropene is treated with bromine, some syn addition is observed. Explain why the presence of a phenyl group causes a loss of stereospecificity.

Q: Predict the products that are expected when each of the following alkenes

Predict the products that are expected when each of the following alkenes is treated with a peroxy acid (RCO3H) followed by aqueous acid:

Q: Under acid-catalyzed conditions, epoxides can be opened by a

Under acid-catalyzed conditions, epoxides can be opened by a variety of nucleophiles other than water, such as alcohols. In such a case, the nucleophile will generally attack at the more substituted p...

Q: Compound A and compound B both have the molecular formula C6H12.

Compound A and compound B both have the molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). a. The epoxide resulting from compound A was treated with aqu...

Q: A compound with the molecular formula C4H6O2 has the following 1H NMR

A compound with the molecular formula C4H6O2 has the following 1H NMR spectrum. Determine the number of protons giving rise to each signal.

Q: Predict the product(s) for each of the following reactions

Predict the product(s) for each of the following reactions. In each case, make sure to consider the number of chiral centers being formed.

Q: Predict the products that are expected when each of the following alkenes

Predict the products that are expected when each of the following alkenes is treated with ozone followed by DMS:

Q: Identify the structure of the starting alkene in each of the following

Identify the structure of the starting alkene in each of the following cases:

Q: Synthetic chemists utilize a large variety of strategies for the synthesis of

Synthetic chemists utilize a large variety of strategies for the synthesis of natural products. Indeed, new strategies are constantly being developed, many of which are inspired by (and mimic) the syn...

Q: Predict the products of each of the following reactions: /

Predict the products of each of the following reactions:

Q: Syn dihydroxylation of the compound below yields two products. Draw both

Syn dihydroxylation of the compound below yields two products. Draw both products and describe their stereoisomeric relationship (i.e., are they enantiomers or diastereomers?):

Q: Determine whether syn dihydroxylation of trans-2-butene will yield

Determine whether syn dihydroxylation of trans-2-butene will yield the same products as anti dihydroxylation of cis-2-butene. Draw the products in each case and compare them.

Q: Compound A has the molecular formula C5H10. Hydroboration-oxidation of

Compound A has the molecular formula C5H10. Hydroboration-oxidation of compound A produces a pair of enantiomers, compounds B and C. When treated with HBr, compound A is converted into compound D, whi...

Q: Identify the reagents that you would use to accomplish each of the

Identify the reagents that you would use to accomplish each of the following transformations:

Q: AZT was the first HIV treatment to be approved by the Food

AZT was the first HIV treatment to be approved by the Food and Drug Administration. HIV may become AZT-resistant over time, so new drugs are always being sought. As part of this effort, compound 2 was...

Q: In the human body, the amino acid phenylalanine is normally processed

In the human body, the amino acid phenylalanine is normally processed by an enzyme that converts it to cinnamic acid. Infants with phenylketonuria (PKU) have a defective enzyme, resulting in a buildup...

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations:

Q: Bioethanol, ethanol produced by fermentation of sugars, is a desirable

Bioethanol, ethanol produced by fermentation of sugars, is a desirable starting material for chemical synthesis since it comes from renewable resources. Identify the reagents you would use to accompli...

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations:

Q: Compound 3 below, called mycoepoxydiene, has been isolated from a

Compound 3 below, called mycoepoxydiene, has been isolated from a marine fungus and has been shown to possess anti-cancer and anti-inflammatory properties. It contains an unusual oxygen-bridged cycloo...

Q: At high temperatures, alkanes can undergo dehydrogenation to produce alkenes.

At high temperatures, alkanes can undergo dehydrogenation to produce alkenes. For example: This reaction is used industrially to prepare ethylene while simultaneously serving as a source of hydrogen...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Propose a mechanism for each of the following reactions: /

Propose a mechanism for each of the following reactions:

Q: Compound A reacts with one equivalent of H2 in the presence of

Compound A reacts with one equivalent of H2 in the presence of a catalyst to give methylcyclohexane. Compound A can be formed upon treatment of 1-bromo-1-methylcyclohexane with sodium methoxide. What...

Q: Suggest an efficient synthesis for each of the following transformations:

Suggest an efficient synthesis for each of the following transformations:

Q: For each of the following compounds, determine the multiplicity of each

For each of the following compounds, determine the multiplicity of each signal in the expected 1H NMR spectrum:

Q: Suggest an efficient synthesis for the following transformation: /

Suggest an efficient synthesis for the following transformation:

Q: How many different alkenes will produce 2,4-dimethylpentane upon

How many different alkenes will produce 2,4-dimethylpentane upon hydrogenation? Draw them.

Q: Compound A is an alkene that was treated with ozone (followed

Compound A is an alkene that was treated with ozone (followed by DMS) to yield only (CH3CH2CH2)2C=O. Identify the major product that is expected when compound A is treated with a peroxy acid (RCO3H) f...

Q: Suggest an efficient synthesis for each of the following transformations:

Suggest an efficient synthesis for each of the following transformations:

Q: Compound A has the molecular formula C7H15Br. Treatment of compound A

Compound A has the molecular formula C7H15Br. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated wit...

Q: Suggest suitable reagents to perform each of the following transformations:

Suggest suitable reagents to perform each of the following transformations:

Q: (R)-Limonene is found in many citrus fruits, including

(R)-Limonene is found in many citrus fruits, including oranges and lemons: Draw the structures and identify the relationship of the two products obtained when (R)-limonene is treated with excess hydr...

Q: Suggest suitable reagents to perform the following transformation: /

Suggest suitable reagents to perform the following transformation:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: The volatile organic compounds (VOCs) produced by decomposing tissue and

The volatile organic compounds (VOCs) produced by decomposing tissue and organs were studied in an effort to identify possible human-specific markers. Of 452 VOCs isolated, six were found to be unique...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Explain why each of the following alcohols cannot be prepared via hydroboration

Explain why each of the following alcohols cannot be prepared via hydroboration-oxidation:

Q: Compound X is treated with Br2 to yield meso-2,

Compound X is treated with Br2 to yield meso-2,3-dibromobutane. What is the structure of compound X?

Q: Identify the alkene that would yield the following products via ozonolysis:

Identify the alkene that would yield the following products via ozonolysis:

Q: The following reaction is observed to be regioselective. Draw a mechanism

The following reaction is observed to be regioselective. Draw a mechanism for the reaction and explain the source of regioselectivity in this case:

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations:

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations:

Q: Identify which of the following two reactions you would expect to occur

Identify which of the following two reactions you would expect to occur more rapidly: 1. addition of HBr to 2-methyl-2-pentene or 2. addition of HBr to 4-methyl-1-pentene. Explain your choice.

Q: Predict the major product(s) of the following reaction:

Predict the major product(s) of the following reaction:

Q: Compound A has the molecular formula C5H10. Hydroborationoxidation of compound A

Compound A has the molecular formula C5H10. Hydroborationoxidation of compound A produces an alcohol with no chiral centers. Draw two possible structures for compound A.

Q: Below are NMR spectra of several compounds. Identify whether these compounds

Below are NMR spectra of several compounds. Identify whether these compounds are likely to contain ethyl, isopropyl, and/or tert-butyl groups:

Q: In much the same way that they react with H2, alkenes

In much the same way that they react with H2, alkenes also react with D2 (deuterium is an isotope of hydrogen). Use this information to predict the product(s) of the following reaction:

Q: Identify what reagents you would use to achieve each transformation:

Identify what reagents you would use to achieve each transformation: a. Conversion of 2-methyl-2-butene into a secondary alkyl halide b. Conversion of 2-methyl-2-butene into a tertiary alkyl halide...

Q: Identify the reagents you would use to achieve each of the following

Identify the reagents you would use to achieve each of the following transformations: a. Convert tert-butyl bromide into a primary alkyl halide b. Convert 2-bromopropane into 1-bromopropane

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations: a. Convert 2-methyl-2-butene into a monosubstituted alkene b. Convert 2,3-dimethyl-1-hexene into a tetrasubst...

Q: When 1-methoxy-2-methylpropene is treated with HCl

When 1-methoxy-2-methylpropene is treated with HCl, the major product is 1-chloro-1-methoxy-2-methylpropane. Although this reaction proceeds via an ionic mechanism, the Cl is ultimately positioned at...

Q: The accepted mechanism for the following transformation involves a carbocation rearrangement.

The accepted mechanism for the following transformation involves a carbocation rearrangement. Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby c...

Q: When (R)-2-chloro-3-methylbutane is

When (R)-2-chloro-3-methylbutane is treated with potassium tert-butoxide, a monosubstituted alkene is obtained. When this alkene is treated with HBr, a mixture of products is obtained. Draw all of the...

Q: Compound Y has the molecular formula C7H12. Hydrogenation of compound Y

Compound Y has the molecular formula C7H12. Hydrogenation of compound Y produces methylcyclohexane. Treatment of compound Y with HBr in the presence of peroxides produces the following compound: Pred...

Q: Muscalure is the sex pheromone of the common housefly and has the

Muscalure is the sex pheromone of the common housefly and has the molecular formula C23H46. When treated with O3 followed by DMS, the following two compounds are produced. Draw two possible structures...

Q: Propose a plausible mechanism for each of the following reactions:

Propose a plausible mechanism for each of the following reactions:

Q: Each of the three vinylic protons of styrene is split by the

Each of the three vinylic protons of styrene is split by the other two, and the J values are found to be Jab=11 Hz, Jac=17 Hz, and Jbc=1 Hz. Using this information, draw the expected splitting pattern...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: a. 4,4-Dimethyl-2-pentyne b. 5-Ethyl-2,5-dimethyl-3-heptyne

Q: When naming cycloalkynes that lack any other functional groups, the triple

When naming cycloalkynes that lack any other functional groups, the triple bond does not require a locant, because it is assumed to be between C1 and C2. Draw the structure of (R)-3-methylcyclononyne....

Q: (+)-Citronellal is the main compound responsible for the lemon scent of

(+)-Citronellal is the main compound responsible for the lemon scent of citronella oil. In addition to its well-known insect repellant properties, it also has some antifungal properties. (+)-Citronell...

Q: In each of the following cases, determine if the base is

In each of the following cases, determine if the base is sufficiently strong to deprotonate the terminal alkyne:

Q: Treatment of acetylene with a suitable base affords lithium acetylide, which

Treatment of acetylene with a suitable base affords lithium acetylide, which was used as a reagent in a partial synthesis of the antitumor natural product (+)-acutiphycin. a. Draw the structure of li...

Q: For each of the following transformations, predict the major product and

For each of the following transformations, predict the major product and draw a mechanism for its formation:

Q: When 3,3-dichloropentane is treated with excess sodium amide

When 3,3-dichloropentane is treated with excess sodium amide in liquid ammonia, the initial product is 2-pentyne:

Q: Draw the major product expected from each of the following reactions:

Draw the major product expected from each of the following reactions:

Q: Draw the major product expected when each of the following alkynes is

Draw the major product expected when each of the following alkynes is treated with sodium in liquid ammonia:

Q: Draw the expected 1H NMR spectrum for each of the following compounds

Draw the expected 1H NMR spectrum for each of the following compounds:

Q: Identify reagents that you could use to achieve each of the following

Identify reagents that you could use to achieve each of the following transformations:

Q: An alkyne with the molecular formula C5H8 was treated with sodium in

An alkyne with the molecular formula C5H8 was treated with sodium in liquid ammonia to give a disubstituted alkene. Draw the structure of the alkene.

Q: Predict the major product(s) expected for each of the

Predict the major product(s) expected for each of the following reactions:

Q: Suggest reagents that would achieve the following transformation: /

Suggest reagents that would achieve the following transformation:

Q: An alkyne with the molecular formula C5H8 is treated with excess HBr

An alkyne with the molecular formula C5H8 is treated with excess HBr, and two different products are obtained, each of which has the molecular formula C5H10Br2. a. Identify the starting alkyne. b. I...

Q: The following enols cannot be isolated. They rapidly tautomerize to produce

The following enols cannot be isolated. They rapidly tautomerize to produce ketones. In each case, draw the expected ketone and show a mechanism for its formation under acid-catalyzed conditions (H3O+...

Q: Warfarin is a blood-thinning drug (anticoagulant) that is

Warfarin is a blood-thinning drug (anticoagulant) that is used to prevent heart attacks and strokes. Including stereoisomers, there are at least 40 distinct tautomer forms of warfarin. Shown below are...

Q: Draw the major product(s) expected when each of the

Draw the major product(s) expected when each of the following alkynes is treated with aqueous acid in the presence of mercuric sulfate (HgSO4):

Q: Identify the alkyne you would use to prepare each of the following

Identify the alkyne you would use to prepare each of the following ketones via acid-catalyzed hydration:

Q: Draw the major product for each of the following reactions:

Draw the major product for each of the following reactions:

Q: Butane (C4H10) exhibits only two different kinds of protons,

Butane (C4H10) exhibits only two different kinds of protons, shown here in red and blue. a. Explain why all four protons shown in red are chemically equivalent. b. Explain why all six protons shown...

Q: Gamma-hydroxybutyric acid (GHB) is used in the treatment

Gamma-hydroxybutyric acid (GHB) is used in the treatment of excessive daytime sleepiness (narcolepsy), but when mixed with alcohol, it can cause loss of consciousness, which explains why it is sometim...

Q: Identify the alkyne you would use to prepare each of the following

Identify the alkyne you would use to prepare each of the following compounds via hydroboration-oxidation:

Q: Identify reagents that you could use to achieve each of the following

Identify reagents that you could use to achieve each of the following transformations:

Q: Proteases are enzymes that can break covalent bonds in proteins. Proteases

Proteases are enzymes that can break covalent bonds in proteins. Proteases play major roles in the regulation of biological processes, so compounds that inhibit their function, called protease inhibit...

Q: Draw the major products that are expected when each of the following

Draw the major products that are expected when each of the following alkynes is treated with O3 followed by H2O:

Q: An alkyne with the molecular formula C6H10 was treated with ozone followed

An alkyne with the molecular formula C6H10 was treated with ozone followed by water to produce only one type of carboxylic acid. Draw the structure of the starting alkyne and the product of ozonolysis...

Q: An alkyne with the molecular formula C4H6 was treated with ozone followed

An alkyne with the molecular formula C4H6 was treated with ozone followed by water to produce a carboxylic acid and carbon dioxide. Draw the expected product when the alkyne is treated with aqueous ac...

Q: Starting with acetylene, show reagents that you would use to prepare

Starting with acetylene, show reagents that you would use to prepare each of the following compounds: a. 1-Butyne b. 2-Butyne c. 3-Hexyne d. 2-Hexyne e. 1-Hexyne f. 2-Heptyne g. 3-Heptyne h. 2-O...

Q: (−)-Lepadiformine A, isolated from the marine organism Clavelina lepadiformis,

(−)-Lepadiformine A, isolated from the marine organism Clavelina lepadiformis, is observed to be toxic to several tumor cell lines. During a recent synthesis of (−)...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Using ethylene (H2C=CH2) as your only source of

Using ethylene (H2C=CH2) as your only source of carbon atoms, outline a synthesis for 3-hexanone (CH3CH2COCH2CH2CH3).

Q: How would you use 1H NMR spectroscopy to distinguish between the following

How would you use 1H NMR spectroscopy to distinguish between the following compounds?

Q: Metabolism refers to all of the chemical reactions that occur in living

Metabolism refers to all of the chemical reactions that occur in living organisms. During studies to understand metabolic pathways in yeast cells, various compounds were made and fed to the cells. In...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: a. 2-Heptyne b. 2,2-Dimethyl-4-octyne c. 3,3-Diethylcyclodecyne

Q: Predict the product for each of the following reactions: /

Predict the product for each of the following reactions:

Q: Draw the products of each of the following acid-base reactions

Draw the products of each of the following acid-base reactions and then predict the position of equilibrium in each case:

Q: Predict the products obtained when 1-pentyne reacts with each of

Predict the products obtained when 1-pentyne reacts with each of the following reagents: a. H2SO4, H2O, HgSO4 b. R2BH followed by H2O2, NaOH c. Two equivalents of HBr d. One equivalent of HCl e....

Q: Identify the reagents you would use to achieve each of the following

Identify the reagents you would use to achieve each of the following transformations:

Q: Identify which of the following bases can be used to deprotonate a

Identify which of the following bases can be used to deprotonate a terminal alkyne: a. NaOCH3 b. NaH c. BuLi d. NaOH e. NaNH2

Q: Determine whether or not the following compounds represent a pair of keto

Determine whether or not the following compounds represent a pair of keto-enol tautomers:

Q: Oleic acid and elaidic acid are isomeric alkenes: /

Oleic acid and elaidic acid are isomeric alkenes: Oleic acid, a major component of butter fat, is a colorless liquid at room temperature. Elaidic acid, a major component of partially hydrogenated ve...

Q: The familiar odor produced when rain falls on dry soil is called

The familiar odor produced when rain falls on dry soil is called petrichor. One principal component of petrichor is a compound called geosmin (derived from the Greek words for “earth...

Q: Predict the final product(s) for each sequence of reactions

Predict the final product(s) for each sequence of reactions:

Q: When (R)-4-bromohept-2-yne is

When (R)-4-bromohept-2-yne is treated with H2 in the presence of Pt, the product is optically inactive. Yet, when (R)-4-bromohex-2-yne is treated with the same conditions, the product is optically act...

Q: Draw the structure of an alkyne that can be converted into 3

Draw the structure of an alkyne that can be converted into 3-ethylpentane upon hydrogenation. Provide a systematic name for the alkyne.

Q: Propose a mechanism for each of the following transformations: /

Propose a mechanism for each of the following transformations:

Q: Draw the expected product of each of the following reactions, showing

Draw the expected product of each of the following reactions, showing stereochemistry where appropriate:

Q: Compound A is an alkyne that reacts with two equivalents of H2

Compound A is an alkyne that reacts with two equivalents of H2 in the presence of Pd to give 2,4,6-trimethyloctane. a. Draw the structure of compound A. b. How many chiral centers are present in com...

Q: Compound A has the molecular formula C7H12. Hydrogenation of compound A

Compound A has the molecular formula C7H12. Hydrogenation of compound A produces 2-methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A and draw t...

Q: Propose a plausible synthesis for each of the following transformations:

Propose a plausible synthesis for each of the following transformations:

Q: 1,2-Dichloropentane reacts with excess sodium amide in liquid

1,2-Dichloropentane reacts with excess sodium amide in liquid ammonia (followed by water workup) to produce compound X. Compound X undergoes acid-catalyzed hydration to produce a ketone. Draw the stru...

Q: An unknown alkyne is treated with ozone (followed by hydrolysis)

An unknown alkyne is treated with ozone (followed by hydrolysis) to yield acetic acid and carbon dioxide. What is the structure of the alkyne?

Q: Propose a structure that is consistent with each of the following 1H

Propose a structure that is consistent with each of the following 1H NMR spectra. In each case, the molecular formula is provided.

Q: Compound A is an alkyne with the molecular formula C5H8. When

Compound A is an alkyne with the molecular formula C5H8. When treated with aqueous sulfuric acid and mercuric sulfate, two different products with the molecular formula C5H10O are obtained in equal am...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Draw the structure of each possible dichloride that can be used to

Draw the structure of each possible dichloride that can be used to prepare the following alkyne via elimination:

Q: Draw the structures of compounds A to D: /

Draw the structures of compounds A to D:

Q: Identify reagents that you would use to achieve the following transformation:

Identify reagents that you would use to achieve the following transformation:

Q: In the upcoming chapters, we will learn a two-step

In the upcoming chapters, we will learn a two-step method for achieving the following transformation. In the meantime, we have already learned reactions that can be used to accomplish this transformat...

Q: A terminal alkyne was treated with NaNH2 followed by propyl iodide.

A terminal alkyne was treated with NaNH2 followed by propyl iodide. The resulting internal alkyne was treated with ozone followed by water, giving only one type of carboxylic acid. Provide a systemati...

Q: The following reaction does not produce the desired product but does produce

The following reaction does not produce the desired product but does produce a product that is a constitutional isomer of the desired product. Draw the product that is obtained and propose a mechanism...

Q: Rank the following radicals in order of stability: /

Rank the following radicals in order of stability:

Q: Draw resonance structures for each of the following radicals: /

Draw resonance structures for each of the following radicals:

Q: A compound with the molecular formula C10H10O4 produces a 1H NMR spectrum

A compound with the molecular formula C10H10O4 produces a 1H NMR spectrum that exhibits only two signals, both singlets. One signal appears at 3.9 ppm with a relative integration value of 79. The othe...

Q: 5-Methylcyclopentadiene undergoes homolytic bond cleavage of a C−H

5-Methylcyclopentadiene undergoes homolytic bond cleavage of a C−H bond to form a radical that exhibits five resonance structures. Determine which hydrogen atom is abstracted and dra...

Q: Stable radicals have been used as biosensors to monitor cellular oxygen levels

Stable radicals have been used as biosensors to monitor cellular oxygen levels. One of the first stable radicals to be reported was the triphenylmethyl radical, shown at right. More recently, similar...

Q: Identify the weakest C−H bond in each of the following

Identify the weakest C−H bond in each of the following compounds:

Q: The C−H bonds shown in red exhibit very similar BDEs

The C−H bonds shown in red exhibit very similar BDEs, because homolytic cleavage of either bond results in a resonance-stabilized radical. Nevertheless, one of these Câˆ&#...

Q: The naturally occurring compound (S)-limonene (compound 1 on

The naturally occurring compound (S)-limonene (compound 1 on the right) can be synthetically transformed with radical chemistry into compound 2, which has potent antimalarial activity. 2 Identify the...

Q: Draw the appropriate fishhook arrows for each of the following radical processes

Draw the appropriate fishhook arrows for each of the following radical processes.

Q: The genus Aspergillus includes several hundred species of mold, which collectively

The genus Aspergillus includes several hundred species of mold, which collectively produce a large number of natural products. Many of these natural products have been found to possess interesting bio...

Q: Draw a mechanism for each of the following reactions: a

Draw a mechanism for each of the following reactions: a. Chlorination of methylene chloride to produce chloroform b. Chlorination of chloroform to produce carbon tetrachloride c. Chlorination of et...

Q: Methyl bromide is widely used as a fumigant to prevent the spread

Methyl bromide is widely used as a fumigant to prevent the spread of diseases and pests in agricultural products, and it can be prepared from methane via radical bromination. Recently, a new method fo...

Q: Predict the major product obtained upon radical bromination of each of the

Predict the major product obtained upon radical bromination of each of the following compounds:

Q: Neurotransmitters are small molecules that are produced by the body to send

Neurotransmitters are small molecules that are produced by the body to send messages from one neuron to another. Noradrenaline (also called norepinephrine) and serotonin are neurotransmitters that act...

Q: A synthesis of the antibiotic natural product γ-indomycinone involved the

A synthesis of the antibiotic natural product γ-indomycinone involved the halogenation reaction shown below. The major product of the reaction is a monobrominated compound, and a significa...

Q: Predict the stereochemical outcome of radical bromination of the following alkanes:

Predict the stereochemical outcome of radical bromination of the following alkanes:

Q: Carbohydrates such as the glucose derivative shown below can serve as useful

Carbohydrates such as the glucose derivative shown below can serve as useful chiral starting materials for biopolymers and natural product synthesis. Radical bromination of this compound occurs at C1...

Q: Predict the products when each of the following compounds is treated with

Predict the products when each of the following compounds is treated with NBS and irradiated with UV light:

Q: When 2-methyl-2-butene is treated with NBS

When 2-methyl-2-butene is treated with NBS and irradiated with UV light, five different monobromination products are obtained, one of which is a racemic mixture of enantiomers. Draw all five monobromi...

Q: GABA, or gamma (γ)-amino butyric acid, is

GABA, or gamma (γ)-amino butyric acid, is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to under...

Q: Most supersonic planes produce exhaust of hot gases containing many compounds,

Most supersonic planes produce exhaust of hot gases containing many compounds, including nitric oxide (NO). Nitric oxide is a radical that is believed to play a role in ozone depletion. Propose propag...

Q: Compare the structure of vitamin E with the structures of BHT and

Compare the structure of vitamin E with the structures of BHT and BHA, and then determine which hydrogen atom is most easily abstracted from vitamin E.

Q: Predict the products for each reaction. In each case, be

Predict the products for each reaction. In each case, be sure to consider whether a chiral center is being generated, and then draw all expected stereoisomers.

Q: There are 20 commonly occurring amino acids from which all proteins are

There are 20 commonly occurring amino acids from which all proteins are derived (as will be discussed in Chapter 25), although many other less common amino acids have been isolated from natural source...

Q: For each of the following compounds, predict the number of signals

For each of the following compounds, predict the number of signals and location of each signal in a 13C NMR spectrum:

Q: Draw all resonance structures for each of the following radicals:

Draw all resonance structures for each of the following radicals:

Q: Consider all of the different types of C−H bonds in

Consider all of the different types of C−H bonds in cyclopentene and rank them in order of increasing bond strength:

Q: Compound A has the molecular formula C5H12 and undergoes monochlorination to produce

Compound A has the molecular formula C5H12 and undergoes monochlorination to produce four different constitutional isomers. a. Draw the structure of compound A. b. Draw all four monochlorination pro...

Q: Draw all resonance structures of the radical produced when a hydrogen atom

Draw all resonance structures of the radical produced when a hydrogen atom is abstracted from the OH group in BHT:

Q: When isopropylbenzene (cumene) is treated with NBS and irradiated with

When isopropylbenzene (cumene) is treated with NBS and irradiated with UV light, only one product is obtained. Propose a mechanism and explain why only one product is formed.

Q: There are three constitutional isomers with the molecular formula C5H12. Chlorination

There are three constitutional isomers with the molecular formula C5H12. Chlorination of one of these isomers yields only one product. Identify the isomer and draw the product of chlorination.

Q: When ethylbenzene is treated with one equivalent of NBS and irradiated with

When ethylbenzene is treated with one equivalent of NBS and irradiated with UV light, two stereoisomeric compounds are obtained in equal amounts. Draw the products and explain why they are obtained in...

Q: AIBN is an azo compound (a compound with a N=

AIBN is an azo compound (a compound with a N=N double bond) that is often used as a radical initiator. Upon heating, AIBN liberates nitrogen gas to produce two identical radicals: a. Give two reasons...

Q: Triphenylmethane readily undergoes autooxidation to produce a hydroperoxide: /

Triphenylmethane readily undergoes autooxidation to produce a hydroperoxide: a. Draw the expected hydroperoxide. b. Explain why triphenylmethane is so susceptible to autooxidation. c. In the presen...

Q: For each of the products shown in the following reaction, propose

For each of the products shown in the following reaction, propose a mechanism that explains its formation:

Q: The hydronaphthacene ring system consists of five fused six-membered rings

The hydronaphthacene ring system consists of five fused six-membered rings, as shown below in compounds 3 and 4. One method for construction of this ring system involves treatment of compound 1 with a...

Q: Identify the major product(s) for each of the following

Identify the major product(s) for each of the following reactions. If any of the reactions do not yield a product, indicate “no reaction.”

Q: Predict the major product(s) obtained upon bromination of (

Predict the major product(s) obtained upon bromination of (S)-3-methylhexane.

Q: Draw the products obtained when 3,3,6-trimethylcyclohexene

Draw the products obtained when 3,3,6-trimethylcyclohexene is treated with NBS and irradiated with UV light.

Q: When 2-methylpropane is treated with bromine in the presence of

When 2-methylpropane is treated with bromine in the presence of UV light, one product predominates. a. Identify the structure of the product. b. Draw the structure of the expected minor product. c....

Q: Consider the structure of the following compound: /

Consider the structure of the following compound: a. When this compound is treated with bromine under conditions that favor monobromination, two stereoisomeric products are obtained. Draw them and i...

Q: The rate at which two methyl radicals couple to form ethane is

The rate at which two methyl radicals couple to form ethane is significantly faster than the rate at which two tert-butyl radicals couple. Offer two explanations for this observation.

Q: How many constitutional isomers are obtained when each of the following compounds

How many constitutional isomers are obtained when each of the following compounds undergoes monochlorination?

Q: Using acetylene and 2-methylpropane as your only sources of carbon

Using acetylene and 2-methylpropane as your only sources of carbon atoms, propose a plausible synthesis for CH3COCH2CH(CH3)2. You will need to utilize many reactions from previous chapters.

Q: Compound X has the molecular formula C5H10. In the presence of

Compound X has the molecular formula C5H10. In the presence of a metal catalyst, compound X reacts with one equivalent of molecular hydrogen to yield 2-methylbutane. a. Suggest three possible structu...

Q: Suggest an efficient synthesis for the following transformation: /

Suggest an efficient synthesis for the following transformation:

Q: Determine the structure of a compound with the molecular formula C5H10O that

Determine the structure of a compound with the molecular formula C5H10O that exhibits the following broadband-decoupled and DEPT-135 spectra. The DEPT-90 spectrum has no signals.

Q: Compound X has the molecular formula C7H14. Hydrogenation of compound X

Compound X has the molecular formula C7H14. Hydrogenation of compound X produces 2,4-dimethylpentane. Hydroborationoxidation of compound X produces a racemic mixture of 2,4-dimethyl1-pentanol (shown b...

Q: Roquefortine C belongs to a class of natural products, called roquefortines

Roquefortine C belongs to a class of natural products, called roquefortines, first isolated from cultures of the fungus Penicillium roqueforti. Roquefortine C, which is also present in blue cheese, ex...

Q: Natural products that contain the N-1,1-dimethyl

Natural products that contain the N-1,1-dimethyl-2-propenyl group (called an N-reverse prenyl group) often exhibit antitumor or antifungal activity. The synthesis of a particular N-reverse prenylated...

Q: Identify reagents that can be used to accomplish each of the transformations

Identify reagents that can be used to accomplish each of the transformations shown below. If you are having trouble, the reagents for these transformations appear in the review of reactions at the end...

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations. If you are having trouble, the reagents for these transformations appear in the review of reactions at the end o...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: The isocoumarins are a class of natural products that are structurally related

The isocoumarins are a class of natural products that are structurally related to isocoumarin, shown below. They have been isolated from many sources, including bacteria, fungi, and plants. Artemidin...

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: As we will see in Chapter 26, steroids are a class

As we will see in Chapter 26, steroids are a class of organic compounds containing a specific tetracyclic skeleton (four rings), as seen in the compounds shown below. During efforts2 to synthesize a s...

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: Determine the structure of an alcohol with the molecular formula C5H12O that

Determine the structure of an alcohol with the molecular formula C5H12O that exhibits the following signals in its 13C NMR spectra: a. Broadband decoupled: 73.8 δ, 29.1 δ, and 9.5 δ b. DEPT-90: 73.8...

Q: Latrunculin B is a marine natural product that was first isolated from

Latrunculin B is a marine natural product that was first isolated from the Red Sea sponge Latrunculia magnifica. Latrunculins are toxic to eukaryotic cells (cells that have a welldefined nucleus) by d...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: A study of compounds contained in the gas phase above a range

A study of compounds contained in the gas phase above a range of bacterial strains revealed the presence of 254 unique volatile organic compounds representing a broad range of structural classes. The...

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: Using acetylene as your only source of carbon atoms, identify a

Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 2-bromobutane.

Q: Using acetylene as your only source of carbon atoms, identify a

Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 1-bromobutane.

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Using any reagents you like, show a way to convert 1

Using any reagents you like, show a way to convert 1-methylcyclopentene into 3-methylcyclopentene.

Q: Identify reagents that you could use to convert 2-bromo2-

Identify reagents that you could use to convert 2-bromo2-methylbutane into 3-methyl-1-butyne.

Q: Identify the structure of a compound with the molecular formula C5H12 that

Identify the structure of a compound with the molecular formula C5H12 that exhibits only one kind of proton. That is, all 12 protons are chemically equivalent.

Q: A compound with the molecular formula C7H14O exhibits the following 13C NMR

A compound with the molecular formula C7H14O exhibits the following 13C NMR spectra: Several structures are consistent with these spectra. To determine which structure is correct, a 1H NMR spectrum w...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Using any compounds that contain two carbon atoms or fewer, show

Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R,3R)-2,3- dihydroxypentane and (2S,3S)-2,3-dihydroxypentane.

Q: Using any compounds that contain two carbon atoms or fewer, show

Using any compounds that contain two carbon atoms or fewer, show a way to prepare a racemic mixture of (2R,3S)- and (2S,3R)-2,3- dihydroxypentane.

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Using acetylene as your only source of carbon atoms, design a

Using acetylene as your only source of carbon atoms, design a synthesis of trans-5-decene:

Q: Using acetylene as your only source of carbon atoms, design a

Using acetylene as your only source of carbon atoms, design a synthesis of cis-3-decene:

Q: Using acetylene as your only source of carbon atoms, design a

Using acetylene as your only source of carbon atoms, design a synthesis of pentanal (Note: pentanal has an odd number of carbon atoms, while acetylene has an even number of carbon atoms):

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Propose an efficient synthesis for the following transformation (many steps are

Propose an efficient synthesis for the following transformation (many steps are required):

Q: In this chapter, we have seen that an acetylide ion can

In this chapter, we have seen that an acetylide ion can function as a nucleophile and attack an alkyl halide in an SN2 process. More generally speaking, the acetylide ion can attack other electrophile...

Q: Small organic molecules known as plasticizers are added to polymers to make

Small organic molecules known as plasticizers are added to polymers to make them soft and flexible. Many phthalates commonly used as plasticizers have been banned from use in childrenâ€...

Q: In the previous problem, we saw that an acetylide ion can

In the previous problem, we saw that an acetylide ion can attack a variety of electrophiles. In Chapter 19, we will see that a C=O bond can also function as an electrophile. Consider the following rea...

Q: Identify reagents that you could use to achieve the following transformation:

Identify reagents that you could use to achieve the following transformation:

Q: Starting with acetylene as your only source of carbon atoms, identify

Starting with acetylene as your only source of carbon atoms, identify how you would prepare each member of the following homologous series of aldehydes: a. CH3CHO b. CH3CH2CHO c. CH3CH2CH2CHO d. C...

Q: Starting with acetylene as your only source of carbon atoms, propose

Starting with acetylene as your only source of carbon atoms, propose a plausible synthesis for 1,4-dioxane:

Q: In a study of volatile compounds extracted from cinnamon trees native to

In a study of volatile compounds extracted from cinnamon trees native to Sri Lanka, 27 compounds were identified, including3-phenylpropyl acetate. Propose a multiple-step synthesis of this compound us...

Q: Kakkon is the root of an Asian plant that has traditionally been

Kakkon is the root of an Asian plant that has traditionally been used in Chinese medicine. It smells fruity, winey, and medicinal. A study of the volatile components of kakkon (those responsible for t...

Q: Odor is one of the principal criteria used by consumers when purchasing

Odor is one of the principal criteria used by consumers when purchasing food products such as fish. Researchers thus compared relative amounts of various volatile substances present in samples of Euro...

Q: Identify all products expected for each of the following reactions. Take

Identify all products expected for each of the following reactions. Take stereochemistry into account and draw expected stereoisomer(s), if any:

Q: Draw the propagation steps that achieve the autooxidation of diethyl ether to

Draw the propagation steps that achieve the autooxidation of diethyl ether to form a hydroperoxide:

Q: Compound A has the molecular formula C5H12, and monobromination of compound

Compound A has the molecular formula C5H12, and monobromination of compound A produces only compound B. When compound B is treated with a strong base, a mixture is obtained containing compound C and c...

Q: A compound with the molecular formula shown below exhibits a 1H NMR

A compound with the molecular formula shown below exhibits a 1H NMR spectrum with only one signal. Deduce the structure in each case. a. C5H10 b. C5H8Cl4 c. C12H18

Q: The aroma, taste, and general quality of wine are tied

The aroma, taste, and general quality of wine are tied closely to the stage of development of the grapes from which it is made. In order to develop a molecular-level understanding of this phenomenon,...

Q: In a study measuring the volatile components of 150 pounds of fried

In a study measuring the volatile components of 150 pounds of fried chicken, a total of 130 distinct compounds were identified, including the linear alkane tetradecane. Propose a synthesis of this com...

Q: The compound (Z)-hexenyl acetate is one of several volatile

The compound (Z)-hexenyl acetate is one of several volatile organic signaling compounds released from Arabidopsis leaves when they are damaged. Propose a synthesis of this compound using ethylene (H2C...

Q: When a consumer purchases a tomato, smell is one of the

When a consumer purchases a tomato, smell is one of the factors affecting selection. Researchers in Japan have thus analyzed the volatile components of tomatoes using a novel method. Among the complex...

Q: Methyl 4-methylpentanoate is one of 120 volatile compounds identified in

Methyl 4-methylpentanoate is one of 120 volatile compounds identified in a study of metabolites from Streptomyces bacteria. Propose a synthesis of this ester starting from 2-methylbutane.

Q: The following sequence of reactions was employed during a synthesis of the

The following sequence of reactions was employed during a synthesis of the sex pheromone of the dermestid beetle. The conversion of compound 5 to compound 6 involves the removal of the THP group (ROTH...

Q: Propose an efficient synthesis for each of the following transformations. You

Propose an efficient synthesis for each of the following transformations. You might find it useful to review Section 10.13 before attempting to solve these problems.

Q: Consider the following two compounds. Monochlorination of one of these compounds

Consider the following two compounds. Monochlorination of one of these compounds produces twice as many stereoisomeric products as the other. Draw the products in each case and identify which compound...

Q: The initiation step for radical addition of HBr is highly endothermic:

The initiation step for radical addition of HBr is highly endothermic: a. Explain how this step can be thermodynamically favorable at high temperature even though it is endothermic. b. Explain why t...

Q: Compound A has the molecular formula C5H11Br. When compound A is

Compound A has the molecular formula C5H11Br. When compound A is treated with bromine in the presence of UV light, the major product is 2,2-dibromopentane. Treatment of compound A with NaSH (a strong...

Q: A compound with the molecular formula C12H24 exhibits a 1H NMR spectrum

A compound with the molecular formula C12H24 exhibits a 1H NMR spectrum with only one signal and a 13C NMR spectrum with two signals. Deduce the structure of this compound.

Q: When butane reacts with Br2 in the presence of Cl2, both

When butane reacts with Br2 in the presence of Cl2, both brominated and chlorinated products are obtained. Under such conditions, the usual selectivity of bromination is not observed. In other words,...

Q: When an acyl peroxide undergoes homolytic bond cleavage, the radicals produced

When an acyl peroxide undergoes homolytic bond cleavage, the radicals produced can liberate carbon dioxide to form alkyl radicals: Using this information, provide a mechanism of formation for each of...

Q: Consider the following radical process, called a thiol-ene coupling

Consider the following radical process, called a thiol-ene coupling reaction, in which an alkene is treated with a thiol (RSH) in the presence of a radical initiator: a. Draw a plausible mechanism fo...

Q: The alkyl halide 1-bromopropane is one of a number of

The alkyl halide 1-bromopropane is one of a number of compounds being considered as a replacement for chlorofluorocarbons as an industrial cleaning solvent. In a computational study of its atmospheric...

Q: Resveratrol is a naturally occurring antioxidant found in a broad range of

Resveratrol is a naturally occurring antioxidant found in a broad range of plants including grapes, mulberries, and peanuts. It demonstrates useful activity against heart disease and cancer. In the pr...

Q: In Chapter 2, we saw several patterns for drawing resonance structures

In Chapter 2, we saw several patterns for drawing resonance structures of ions or uncharged compounds. There are also several patterns for drawing resonance structures of radicals, although we have on...

Q: Compound 2 was used as a key intermediate in a synthesis of

Compound 2 was used as a key intermediate in a synthesis of oseltamivir, an anti-influenza agent. Propose a plausible mechanism for the conversion of 1 to 2, as shown, and explain the stereochemical o...

Q: Draw and name four terminal alkynes with the molecular formula C6H10.

Draw and name four terminal alkynes with the molecular formula C6H10.

Q: Preparation of 2,2-dimethyl-3-octyne cannot

Preparation of 2,2-dimethyl-3-octyne cannot be achieved via alkylation of acetylene. Explain.

Q: Identify the reagents necessary to achieve each transformation below. In each

Identify the reagents necessary to achieve each transformation below. In each case, you will need to use at least one reaction from this chapter and at least one reaction from the previous chapter. Th...

Q: A compound with the molecular formula C17H36 exhibits a 1H NMR spectrum

A compound with the molecular formula C17H36 exhibits a 1H NMR spectrum with only one signal. How many signals would you expect in the 13C NMR spectrum of this compound?

Q: One strategy for the synthesis of complicated polycyclic ring systems involves radical

One strategy for the synthesis of complicated polycyclic ring systems involves radical-mediated cyclization processes. For example, when the following radical is generated, it undergoes a spontaneous...

Q: Compounds with the structure ArN=NCON=NAr (where Ar

Compounds with the structure ArN=NCON=NAr (where Ar represents an aromatic group) are used in liquid crystal formulations for LCDs (liquid crystal displays) as well as for optical switches and image s...

Q: As seen in this chapter, hydrocarbons typically do not undergo radical

As seen in this chapter, hydrocarbons typically do not undergo radical iodination in the presence of 2 (compound 2a). Furthermore, radical halogenation (even chlorination) of strained hydrocarbons, li...

Q: The Kharasch reaction is a radical process in which carbon tetrachloride is

The Kharasch reaction is a radical process in which carbon tetrachloride is added across an alkene: a. Draw a mechanism showing initiation and propagation steps for this reaction and explain the obse...

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Propose a plausible mechanism for the following tautomerization process: /

Propose a plausible mechanism for the following tautomerization process:

Q: Using acetylene and methyl bromide as your only sources of carbon atoms

Using acetylene and methyl bromide as your only sources of carbon atoms, propose a synthesis for each of the following compounds:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: A small class of natural products, called α,α-

A small class of natural products, called α,α-disubstituted α-amino acids (Chapter 25), have been the targets of several synthetic techniques, because these c...

Q: 35. What are the best reagents to accomplish this transformation?

35. What are the best reagents to accomplish this transformation? a. t-BuOK b. NaC≡CH, followed by H2 and Pt c. NaC≡CH, followed by H2 and Lindlarâ€...

Q: The following compounds exhibit tautomerism, with a particularly high enol concentration

The following compounds exhibit tautomerism, with a particularly high enol concentration. Compound 1 exhibits an enol concentration of 9.1%, as compared with the enol concentration of 0.014% for (CH3)...

Q: Upon treatment with aqueous acid, compound 1 is converted into compound

Upon treatment with aqueous acid, compound 1 is converted into compound 2. a. In the first step of the accepted mechanism, one of the triple bonds is protonated to give a vinyl carbocation. Generally...

Q: Provide an IUPAC name for each of the following alcohols:

Provide an IUPAC name for each of the following alcohols:

Q: Safer alternatives to existing insecticides and mosquito repellants might be found in

Safer alternatives to existing insecticides and mosquito repellants might be found in the essential oils of plants. Phytol is one such isolated compound that has promising pest-fighting potential. Pro...

Q: Mandelate esters exhibit spasmolytic activity (they act as muscle relaxants).

Mandelate esters exhibit spasmolytic activity (they act as muscle relaxants). The nature of the alkyl group (R) greatly affects potency. Research indicates that the optimal potency is achieved when R...

Q: Draw the alkoxide ion that is formed in each of the following

Draw the alkoxide ion that is formed in each of the following cases:

Q: For each of the following pairs of alcohols, identify the one

For each of the following pairs of alcohols, identify the one that is more acidic and explain your choice:

Q: Flavonoids are a class of naturally occurring compounds with promising medicinal uses

Flavonoids are a class of naturally occurring compounds with promising medicinal uses due to their anti-inflammatory, anti-cancer and anti-HIV properties. Much of this biological activity is due to th...

Q: Identify the reagents that you would use to accomplish each of the

Identify the reagents that you would use to accomplish each of the following transformations:

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations: a. To convert 1-hexene into a primary alcohol b. To convert 3,3-dimethyl-1-hexene into a secondary alcohol c. T...

Q: How many signals would you expect in the 1H NMR spectrum of

How many signals would you expect in the 1H NMR spectrum of each of the following compounds:

Q: In each of the following transformations, identify whether the starting material

In each of the following transformations, identify whether the starting material has been oxidized, reduced, or neither. Try to determine the answer without calculating oxidation states and then use t...

Q: Compound 1 was converted into compound 2 and both compounds were evaluated

Compound 1 was converted into compound 2 and both compounds were evaluated for their cytotoxicity (ability to kill cells). It was observed that compound 2 was four to ten times less cytotoxic than com...

Q: Draw a mechanism and predict the major product for each reaction:

Draw a mechanism and predict the major product for each reaction:

Q: Ambuic acid has been isolated from fungi that are frequently found associated

Ambuic acid has been isolated from fungi that are frequently found associated with economically important rain forest plant species. Ambuic acid is active against several other fungi that are harmful...

Q: Show how you would use a Grignard reaction to prepare each compound

Show how you would use a Grignard reaction to prepare each compound below:

Q: Two of the compounds from Problem 12.13 can be prepared

Two of the compounds from Problem 12.13 can be prepared from the reaction between a Grignard reagent and an ester. Identify those two compounds and explain why the other four compounds cannot be prepa...

Q: Extracts from the flowering plants of Asteraceae have been used to produce

Extracts from the flowering plants of Asteraceae have been used to produce medicine, rubber, and pesticides. (+)-Carissone, a compound isolated from such extracts, has been found to have antibacterial...

Q: Identify the reagents you would use to achieve each of the following

Identify the reagents you would use to achieve each of the following transformations:

Q: Identify reagents that you could use to accomplish each of the following

Identify reagents that you could use to accomplish each of the following transformations:

Q: Lepadiformine is a cytotoxic agent (toxic to cells) isolated from

Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (...

Q: How many signals would you expect in the 13C NMR spectrum of

How many signals would you expect in the 13C NMR spectrum of each of the compounds in Problem 15.35?

Q: Predict the products for each of the following transformations: /

Predict the products for each of the following transformations:

Q: Predict the major organic product for each of the following reactions:

Predict the major organic product for each of the following reactions:

Q: Galanthamine, a natural product produced by the amaryllis family of flowering

Galanthamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer’s disease. In a synthesis of galanthamine and...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Lithium borohydride (LiBH4) is a useful reducing agent, as

Lithium borohydride (LiBH4) is a useful reducing agent, as it is more selective than LiAlH4 but less selective than NaBH4. Specifically, LiBH4 will reduce esters, but it will not reduce amides. This s...

Q: Identify reagents that you could use to accomplish each of the following

Identify reagents that you could use to accomplish each of the following transformations:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: In a study of the chemical components of salted and pickled prunes

In a study of the chemical components of salted and pickled prunes, hexyl butanoate was identified as one of 181 detected compounds. Propose a synthesis of this compound using acetylene as your only s...

Q: Assign an IUPAC name for each of the following compounds:

Assign an IUPAC name for each of the following compounds:

Q: Draw the structure of each compound: a. cis-

Draw the structure of each compound: a. cis-1,2-Cyclohexanediol b. Isobutanol c. 2,4,6-Trinitrophenol d. (R)-2,2-Dimethyl-3-heptanol e. Ethylene glycol f. (S)-2-Methyl-1-butanol

Q: How would you distinguish between the following compounds using 13C NMR spectroscopy

How would you distinguish between the following compounds using 13C NMR spectroscopy?

Q: Draw and name all constitutionally isomeric alcohols with the molecular formula C4H10O

Draw and name all constitutionally isomeric alcohols with the molecular formula C4H10O.

Q: Rank each set of alcohols below in order of increasing acidity.

Rank each set of alcohols below in order of increasing acidity.

Q: Draw resonance structures for each of the following anions: /

Draw resonance structures for each of the following anions:

Q: Predict the major product of the reaction between 1-butanol and

Predict the major product of the reaction between 1-butanol and: a. PBr3 b. SOCl2, py c. HCl, ZnCl2 d. DMP, CH2Cl2 e. Na2Cr2O7, H2SO4, H2O f. Li g. NaH h. TMSCl, Et3N i. TsCl, pyridine j. Na...

Q: Acid-catalyzed hydration of 3,3-dimethyl-1

Acid-catalyzed hydration of 3,3-dimethyl-1-butene produces 2,3-dimethyl-2-butanol. Show a mechanism for this reaction.

Q: Starting with 1-butanol, show the reagents you would use

Starting with 1-butanol, show the reagents you would use to prepare each of the following compounds:

Q: Using a Grignard reaction, show how you could prepare each of

Using a Grignard reaction, show how you could prepare each of the following alcohols:

Q: Each of the following alcohols can be prepared via reduction of a

Each of the following alcohols can be prepared via reduction of a ketone or aldehyde. In each case, identify the aldehyde or ketone that would be required.

Q: What reagents would you use to perform each of the following transformations

What reagents would you use to perform each of the following transformations?

Q: Propose a mechanism for the following reaction: /

Propose a mechanism for the following reaction:

Q: Predict the multiplicity of each signal in the 1H NMR spectrum of

Predict the multiplicity of each signal in the 1H NMR spectrum of the following compound:

Q: In Chapter 8, we learned about addition of water across a

In Chapter 8, we learned about addition of water across a π bond. Identify whether the alkene has been oxidized, reduced, or neither. (Hint: First look at each carbon atom separately and th...

Q: Identify reactants that you would use to form a racemic mixture of

Identify reactants that you would use to form a racemic mixture of each of the following epoxides:

Q: Rank the signals of the following compound in terms of increasing chemical

Rank the signals of the following compound in terms of increasing chemical shift. Identify the proton(s) giving rise to each signal:

Q: Pheromones are chemicals that are used by members of the same species

Pheromones are chemicals that are used by members of the same species to communicate. During a study that involved preparing stereoisomers of the sex pheromone of the moth Lymantria bantaizana, alkyne...

Q: Predict the products for each of the following reactions: /

Predict the products for each of the following reactions:

Q: For each of the following reactions, predict the product and draw

For each of the following reactions, predict the product and draw a mechanism for its formation:

Q: Spirocyclic compounds, such as compound 3, are made and used

Spirocyclic compounds, such as compound 3, are made and used by insects for the purposes of communication. The first step of a synthesis of compound 3 involved treatment of (S)-1,2-epoxypropane (compo...

Q: For each reaction, predict the product and draw a mechanism for

For each reaction, predict the product and draw a mechanism for its formation:

Q: The sequence below shows an enantioselective synthesis of a diol that is

The sequence below shows an enantioselective synthesis of a diol that is achieved via two sequential reactions: 1. asymmetric biooxidation (in the presence of enzymes, nature’s cata...

Q: Identify reagents that you could use to prepare each of the following

Identify reagents that you could use to prepare each of the following thiols.

Q: Predict the products for each of the following reactions: /

Predict the products for each of the following reactions:

Q: In the following reaction, determine whether the alkyne has been oxidized

In the following reaction, determine whether the alkyne has been oxidized, reduced, or neither. Using the answer from the previous problem, try to determine the answer without calculating oxidation st...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Bongkrekic acid is an extremely potent toxin produced by the microorganism Pseudomonas

Bongkrekic acid is an extremely potent toxin produced by the microorganism Pseudomonas cocovenenans. Synthetic routes for preparing this compound have been sought in order to confirm its chemical stru...

Q: Predict the expected number of signals in the 13C NMR spectrum of

Predict the expected number of signals in the 13C NMR spectrum of each of the following compounds. For each signal, identify where you expect it to appear in the 13C NMR spectrum:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Decytospolides A and B are fungal natural products that are toxic to

Decytospolides A and B are fungal natural products that are toxic to some cancer cells. In a synthesis of these natural products, compound 3 was prepared via the reaction between an epoxide (compound...

Q: Assign an IUPAC name for each of the following compounds:

Assign an IUPAC name for each of the following compounds:

Q: Predict the products that are expected when each of the following compounds

Predict the products that are expected when each of the following compounds is heated with concentrated HBr:

Q: Draw all constitutionally isomeric ethers with the molecular formula C4H10O. Provide

Draw all constitutionally isomeric ethers with the molecular formula C4H10O. Provide a common name and a systematic name for each isomer.

Q: Starting with cyclohexene and using any other reagents of your choice,

Starting with cyclohexene and using any other reagents of your choice, show how you would prepare each of the following compounds:

Q: When 1,4-dioxane is heated in the presence of

When 1,4-dioxane is heated in the presence of HI, compound A is obtained: a. Draw the structure of compound A. b. If one mole of dioxane is used, how many moles of compound A are formed? c. Show a...

Q: In an effort to circumvent existing drug laws, novel psychoactive substances

In an effort to circumvent existing drug laws, novel psychoactive substances are continuously being developed. The stimulant benzylpiperazine (BZP) is one such “designerâ€...

Q: Tetrahydrofuran (THF) can be formed by treating 1,4

Tetrahydrofuran (THF) can be formed by treating 1,4-butanediol with sulfuric acid. Propose a mechanism for this transformation:

Q: When ethylene glycol is treated with sulfuric acid, 1,4

When ethylene glycol is treated with sulfuric acid, 1,4-dioxane is obtained. Propose a mechanism for this transformation:

Q: Methylmagnesium bromide reacts rapidly with ethylene oxide, it reacts slowly with

Methylmagnesium bromide reacts rapidly with ethylene oxide, it reacts slowly with oxetane, and it does not react at all with tetrahydrofuran. Explain this difference in reactivity.

Q: Identify the number of signals expected in the 1 H NMR spectrum

Identify the number of signals expected in the 1 H NMR spectrum of each of the following compounds:

Q: When 1-methylcyclohexene is treated with HCl, a Markovnikov addition

When 1-methylcyclohexene is treated with HCl, a Markovnikov addition is observed. How would you use 1H NMR spectroscopy to determine that the major product is indeed the Markovnikov product?

Q: Identify the reagents necessary to accomplish each of the following transformations:

Identify the reagents necessary to accomplish each of the following transformations:

Q: Identify the signals you would expect in the diagnostic region of the

Identify the signals you would expect in the diagnostic region of the IR spectrum for each of the following compounds:

Q: Identify how IR spectroscopy might be used to monitor the progress of

Identify how IR spectroscopy might be used to monitor the progress of each of the following reactions:

Q: Identify the characteristic signals that you would expect in the diagnostic region

Identify the characteristic signals that you would expect in the diagnostic region of an IR spectrum of each of the following compounds:

Q: Propose a molecular formula for a compound that has one degree of

Propose a molecular formula for a compound that has one degree of unsaturation and a mass spectrum that displays a molecular ion signal at m/z = 86.

Q: For each pair of compounds, identify how you would distinguish them

For each pair of compounds, identify how you would distinguish them using either 1H NMR spectroscopy or 13C NMR spectroscopy:

Q: The mass spectrum of an unknown hydrocarbon exhibits an (M+

The mass spectrum of an unknown hydrocarbon exhibits an (M+1)+• peak that is 10% as tall as the molecular ion peak. Identify the number of carbon atoms in the unknown compound.

Q: Match each compound with the appropriate spectrum. /

Match each compound with the appropriate spectrum.

Q: The sex attractant of the codling moth gives an IR spectrum with

The sex attractant of the codling moth gives an IR spectrum with a broad signal between 3200 and 3600 cm−1 and two signals between 1600 and 1700 cm−1. In the mass spectrum of this compound, the molecu...

Q: Compare the structures of cyclohexane and 2-methyl-2-

Compare the structures of cyclohexane and 2-methyl-2-pentene. a. What is the molecular formula of each compound? b. What is the HDI of each compound? c. Can high-resolution mass spectrometry be use...

Q: The mass spectrum of 1-ethyl-1-methylcyclohexane shows

The mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Identify the structure of each of t...

Q: How many signals are expected in the 1H NMR spectrum of each

How many signals are expected in the 1H NMR spectrum of each of the following compounds?

Q: The mass spectrum of 2-bromopentane shows many fragments.

The mass spectrum of 2-bromopentane shows many fragments. a. A fragment appears at M−15. Would you expect a signal at M−13 that is equal in height to the M−15 peak? Explain. b. One fragment appears...

Q: When treated with a strong base, 2-bromo-2

When treated with a strong base, 2-bromo-2,3-dimethylbutane will undergo an elimination reaction to produce two products. The choice of base (ethoxide vs. tert-butoxide) will determine which of the tw...

Q: Propose a molecular formula that fits the following data: a

Propose a molecular formula that fits the following data: a. A hydrocarbon (CxHy) with a molecular ion peak at m/z = 66. b. A compound that absorbs IR radiation at 1720 cm−1 and exhibits a molecular...

Q: The following is a mass spectrum of octane. a.

The following is a mass spectrum of octane. a. Which peak represents the molecular ion? b. Which peak is the base peak? c. Draw the structure of the fragment that produces the base peak.

Q: Draw a mechanism and predict the major product of the following reaction

Draw a mechanism and predict the major product of the following reaction:

Q: Calculate the HDI for each molecular formula. a. C4H6

Calculate the HDI for each molecular formula. a. C4H6 b. C5H8 c. C40H78 d. C72H74 e. C6H6O2 f. C7H9NO2 g. C8H10N2O h. C5H7Cl3 i. C6H5Br j. C6H12O6

Q: Propose two possible structures for a compound with the molecular formula C5H8

Propose two possible structures for a compound with the molecular formula C5H8 that produces an IR signal at 3300 cm−1.

Q: Limonene is a hydrocarbon found in the peels of lemons and contributes

Limonene is a hydrocarbon found in the peels of lemons and contributes significantly to the smell of lemons. Limonene has a molecular ion peak at m/z = 136 in its mass spectrum, and it has two double...

Q: Explain how you would use IR spectroscopy to distinguish between 1-

Explain how you would use IR spectroscopy to distinguish between 1-bromo-3-methyl-2-butene and 2-bromo-3-methyl-2-butene.

Q: A dilute solution of 1,3-pentanediol does not produce

A dilute solution of 1,3-pentanediol does not produce the characteristic IR signal for a dilute alcohol. Rather, it produces a signal that is characteristic of a concentrated alcohol. Explain.

Q: While13C is the main contributor to the (M+1)+•

While13C is the main contributor to the (M+1)+• peak, there are many other elements that can also contribute to the (M+1)+• peak. For example, there are two naturally occurring isotopes of nitrogen. T...

Q: Compare the structures of ethylene, acetylene, and benzene. Each

Compare the structures of ethylene, acetylene, and benzene. Each of these compounds produces only one signal in its 1H NMR spectrum. Arrange these signals in order of increasing chemical shift.

Q: Propose all possible structures for a compound with the molecular formula C4H8O

Propose all possible structures for a compound with the molecular formula C4H8O that exhibits a signal at 1720 cm−1 in its IR spectrum.

Q: Propose all possible structures for a compound with the molecular formula C4H8O

Propose all possible structures for a compound with the molecular formula C4H8O that exhibits a broad signal between 3200 and 3600 cm−1 in its IR spectrum and does not contain any signals between 1600...

Q: Draw the structure of a compound with the molecular formula C4H6 that

Draw the structure of a compound with the molecular formula C4H6 that exhibits a signal at 2200 cm−1 in its IR spectrum.

Q: Draw a mechanism and predict the product for the following reaction.

Draw a mechanism and predict the product for the following reaction. In this case, H3O+ must be used as a proton source instead of water. Explain why.

Q: The following are IR and mass spectra of an unknown compound.

The following are IR and mass spectra of an unknown compound. Propose at least two possible structures for the unknown compound.

Q: The following are IR and mass spectra of an unknown compound.

The following are IR and mass spectra of an unknown compound. Propose at least two possible structures for the unknown compound.

Q: Consider the following sequence of reactions: / a

Consider the following sequence of reactions: a. Explain how you could use IR spectroscopy to differentiate between compounds F and G. b. Explain how you could use IR spectroscopy to differentiate b...

Q: There are five constitutional isomers with the molecular formula C4H8. One

There are five constitutional isomers with the molecular formula C4H8. One of the isomers exhibits a particularly strong signal at M−15 in its mass spectrum. Identify this isomer and explain why the s...

Q: There are four isomers with the molecular formula C4H9Cl. Only one

There are four isomers with the molecular formula C4H9Cl. Only one of these isomers (compound A) has a chiral center. When compound A is treated with sodium ethoxide, three products are formed: compo...

Q: Chloramphenicol is an antibiotic agent isolated from the Streptomyces venezuelae bacterium.

Chloramphenicol is an antibiotic agent isolated from the Streptomyces venezuelae bacterium. Predict the expected isotope pattern in the mass spectrum of this compound (the relative heights of the mole...

Q: Ephedrine is a bronchodilator and decongestant obtained from the Chinese plant Ephedra

Ephedrine is a bronchodilator and decongestant obtained from the Chinese plant Ephedra sinica. A concentrated solution of ephedrine gives an IR spectrum with a broad signal between 3200 and 3600Â...

Q: Assuming a 300-MHz instrument is used, calculate the difference

Assuming a 300-MHz instrument is used, calculate the difference between the frequency of absorption (in hertz) of TMS and the frequency of absorption of a proton with a δ value of 1.2 ppm.

Q: Predict the expected isotope pattern in the mass spectrum of a compound

Predict the expected isotope pattern in the mass spectrum of a compound with the molecular formula C90H180Br2.

Q: Esters contain two C−O bonds and therefore will produce two

Esters contain two C−O bonds and therefore will produce two separate stretching signals in the fingerprint region of an IR spectrum. One of these signals typically appears at approximately 1000 cm−1,...

Q: Consider the following sequence of reactions and identify suitable reagents for a

Consider the following sequence of reactions and identify suitable reagents for a–h:

Q: Treating 1,2-cyclohexanediol with concentrated sulfuric acid yields a

Treating 1,2-cyclohexanediol with concentrated sulfuric acid yields a product with the molecular formula C6H10O. An IR spectrum of the product exhibits a strong signal at 1720 cm−1. Identify the struc...

Q: Draw the expected isotope pattern that would be observed in the mass

Draw the expected isotope pattern that would be observed in the mass spectrum of CH2BrCl. In other words, predict the relative heights of the peaks at M, M+2, and M+4.

Q: The following is the proposed structure of a blue fabric dye,

The following is the proposed structure of a blue fabric dye, based on high-resolution mass spectrometry data. The reported method employed a pulsed laser to desorb dye molecules directly from a sampl...

Q: Compound A exists in equilibrium with its tautomeric form, compound B

Compound A exists in equilibrium with its tautomeric form, compound B. An IR spectrum4 of a mixture of A and B exhibits four signals in the region 1600–1850 cm−1. T...

Q: The following two isomers were each subjected to mass spectrometric analysis.

The following two isomers were each subjected to mass spectrometric analysis. Some of the significant peaks from each of the two spectra are presented below. Match each isomer (A, B) to its correspond...

Q: Myosmine can be isolated from tobacco, along with several other structurally

Myosmine can be isolated from tobacco, along with several other structurally similar compounds, including nicotine. The originally accepted structure for myosmine was disproven with IR spectroscopy:...

Q: Compound 1 contains a tetrazole ring (a ring containing four nitrogen

Compound 1 contains a tetrazole ring (a ring containing four nitrogen atoms), while its constitutional isomer, compound 2, exhibits an azido group (—N3). Compounds 1 and 2 rapidly in...

Q: Oxymercuration-demercuration of compound 1 affords the expected hydration product 2

Oxymercuration-demercuration of compound 1 affords the expected hydration product 2 in 96% yield. In contrast, oxymercuration-demercuration of compound 3 results in only a minor amount of the normal h...

Q: A compound with the molecular formula C13H28 exhibits a 1H NMR spectrum

A compound with the molecular formula C13H28 exhibits a 1H NMR spectrum with two signals: a septet with an integration of 1 and a doublet with an integration of 6. Deduce the structure of this compoun...

Q: The following electrophile-induced, ether transfer reaction was utilized in

The following electrophile-induced, ether transfer reaction was utilized in the synthesis of several structurally related natural products. Provide a plausible mechanism for this transformation.

Q: Consider the structures of 2-nitrophenol and 3-nitrophenol.

Consider the structures of 2-nitrophenol and 3-nitrophenol. These compounds have very different pKa values. Predict which one has the lower pKa and explain why. (Hint: In order to solve this problem,...

Q: Pinolenic acid (C17H29CO2H) is an unbranched carboxylic acid with three

Pinolenic acid (C17H29CO2H) is an unbranched carboxylic acid with three cis alkene groups. It is found in pine nuts and is sometimes used in weight loss regimens as a hunger suppressant. Not every mas...

Q: The IR spectrum of a dilute solution of compound 1 (in

The IR spectrum of a dilute solution of compound 1 (in CS2) exhibits a signal at 3617 cm−1, while the IR spectrum of a dilute solution of compound 2 exhibits a signal at 3594 cm&acir...

Q: Phospholipids are a class of compounds largely responsible for the bilayer structure

Phospholipids are a class of compounds largely responsible for the bilayer structure of cell membranes of plants and animals (discussed in Chapter 26). The phospholipid shown here has two unbranched h...

Q: Propose a plausible mechanism for the following reaction: /

Propose a plausible mechanism for the following reaction:

Q: For each of the following compounds, rank the highlighted bonds in

For each of the following compounds, rank the highlighted bonds in terms of increasing wavenumber:

Q: For each of the following compounds, determine whether or not you

For each of the following compounds, determine whether or not you would expect its IR spectrum to exhibit a signal to the left of 3000 cm−1:

Q: Each of the following compounds contains two carbonyl groups. Identify which

Each of the following compounds contains two carbonyl groups. Identify which carbonyl group will exhibit a signal at lower wavenumber.

Q: Compare the wavenumber of absorption for the following two C=C

Compare the wavenumber of absorption for the following two C=C bonds. Use resonance structures to explain why the C=C bond in the conjugated compound produces a signal at lower wavenumber.

Q: For each pair of compounds, determine which C=C bond

For each pair of compounds, determine which C=C bond will produce a stronger signal.

Q: A compound with the molecular formula C8H10 produces three signals in its

A compound with the molecular formula C8H10 produces three signals in its 13C NMR spectrum and only two signals in its 1H NMR spectrum. Deduce the structure of the compound.

Q: Identify reagents that can be used to accomplish each of the transformations

Identify reagents that can be used to accomplish each of the transformations shown here:

Q: The C=C bond in 2-cyclohexenone produces an unusually

The C=C bond in 2-cyclohexenone produces an unusually strong signal. Explain using resonance structures.

Q: trans-2-Butene does not exhibit a signal in the

trans-2-Butene does not exhibit a signal in the double-bond region of the spectrum (1600–1850 cm−1); however, IR spectroscopy is still helpful in identifying the presence of the double bond. Identify...

Q: As explained previously, the concentration of an alcohol can be selected

As explained previously, the concentration of an alcohol can be selected such that both a broad signal and a narrow signal appear simultaneously. In such cases, the broad signal is always to the right...

Q: For each of the following IR spectra, identify whether it is

For each of the following IR spectra, identify whether it is consistent with the structure of an alcohol, a carboxylic acid, or neither:

Q: For each of the following IR spectra, determine whether it is

For each of the following IR spectra, determine whether it is consistent with the structure of a ketone, an alcohol, a carboxylic acid, a primary amine, or a secondary amine:

Q: Carefully consider the structure of 2,3-dimethyl-2

Carefully consider the structure of 2,3-dimethyl-2-butene. There are twelve Csp3−H bonds, and they are all identical. Nevertheless, there is more than one signal just to the right of 3000 cm−1 in the...

Q: Match each compound with the appropriate IR spectrum: /

Match each compound with the appropriate IR spectrum:

Q: Chrysanthemic acid is isolated from chrysanthemum flowers. The IR spectrum of

Chrysanthemic acid is isolated from chrysanthemum flowers. The IR spectrum of chrysanthemic acid exhibits five signals above 1500 cm−1. Identify the source for each of these signals....

Q: Describe how IR spectroscopy might be used to monitor the progress of

Describe how IR spectroscopy might be used to monitor the progress of each of the following reactions:

Q: In Chapter 20, we will explore how nitriles can be converted

In Chapter 20, we will explore how nitriles can be converted into carboxylic acids. How would you use IR spectroscopy to monitor the progress of this reaction?

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: 55. What is the major product of the following reaction?

55. What is the major product of the following reaction? 56. Determine which of the following reactions is expected to be thermodynamically favorable: a. I, II, III, and IV b. Only I, II, and III...

Q: Cyclopentanone was treated with lithium aluminum hydride followed by H3O+. Explain

Cyclopentanone was treated with lithium aluminum hydride followed by H3O+. Explain what you would look for in the IR spectrum of the product to verify that the expected reaction had occurred. Identify...

Q: When 1-chlorobutane is treated with sodium hydroxide, two products

When 1-chlorobutane is treated with sodium hydroxide, two products are formed. Identify the two products and explain how these products could be distinguished using IR spectroscopy

Q: How would you distinguish between each pair of compounds using mass spectrometry

How would you distinguish between each pair of compounds using mass spectrometry?

Q: For each of the following compounds, use the nitrogen rule to

For each of the following compounds, use the nitrogen rule to determine whether the molecular weight should be even or odd. Then calculate the expected m/z value for the molecular ion.

Q: Propose a molecular formula for a compound that exhibits the following peaks

Propose a molecular formula for a compound that exhibits the following peaks in its mass spectrum: a. (M)+• at m/z = 72, relative height = 38.3% of base peak (M+1)+• at m/z = 73, relative height = 1...

Q: Every time you stop to smell the roses, you are enjoying

Every time you stop to smell the roses, you are enjoying the odor of cis-rose oxide, a compound that also adds to the rich bouquet of wines. 1 In a mass spectrum of cis-rose oxide, the abundance of th...

Q: In the mass spectrum of bromobenzene (Figure 14.27),

In the mass spectrum of bromobenzene (Figure 14.27), the base peak appears at m/z = 77. a. Does this fragment contain Br? Explain your reasoning. b. Draw the cationic fragment that represents the ba...

Q: Below are mass spectra for four different compounds. Identify whether each

Below are mass spectra for four different compounds. Identify whether each of these compounds contains a bromine atom, a chlorine atom, or neither.

Q: Although 2,2-dimethylhexane has a molecular weight of 114

Although 2,2-dimethylhexane has a molecular weight of 114, no peak is observed at m/z = 114. The base peak in the mass spectrum occurs at M−57. a. Draw the fragmentation responsible for formation of...

Q: Acid-catalyzed hydration of 1-methylcyclohexene yields two alcohols.

Acid-catalyzed hydration of 1-methylcyclohexene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain.

Q: Show at least two different methods for preparing 1-methylcyclohexene from

Show at least two different methods for preparing 1-methylcyclohexene from 1-methylcyclohexanol.

Q: Identify two peaks that are expected to appear in the mass spectrum

Identify two peaks that are expected to appear in the mass spectrum of 3-pentanol. For each peak, identify the fragment associated with the peak.

Q: A compound with the molecular formula C3H8O produces a broad signal between

A compound with the molecular formula C3H8O produces a broad signal between 3200 and 3600 cm−1 in its IR spectrum and produces two signals in its 13C NMR spectrum. Deduce the structure of the compound...

Q: Identify the expected base peak in the mass spectrum of 2,

Identify the expected base peak in the mass spectrum of 2,2,3-trimethylbutane. Draw the fragment associated with this peak and explain why the base peak results from this fragment.

Q: The following are mass spectra for the constitutional isomers ethylcyclohexane and 1

The following are mass spectra for the constitutional isomers ethylcyclohexane and 1,1-dimethylcyclohexane. Based on likely fragmentation patterns, match the compound with its spectrum.

Q: How would you distinguish between each pair of compounds using high-

How would you distinguish between each pair of compounds using high-resolution mass spectrometry?

Q: How would you distinguish between each pair of compounds in Problem 14

How would you distinguish between each pair of compounds in Problem 14.28 using IR spectroscopy?

Q: Calculate the degree of unsaturation for each of the following molecular formulas

Calculate the degree of unsaturation for each of the following molecular formulas: a. C6H10 b. C5H10O2 c. C5H9N d. C3H5ClO e. C10H20 f. C4H6Br2 g. C6H6 h. C2Cl6 i. C2H4O2 j. C100H200Cl2O16

Q: Identify which two compounds shown here have the same degree of unsaturation

Identify which two compounds shown here have the same degree of unsaturation. C3H8O C3H5ClO2 C3H5NO2 C3H6

Q: Strigol is an important plant hormone that is released by crops such

Strigol is an important plant hormone that is released by crops such as rice and sugarcane. Unfortunately for these plants, strigol also activates the germination of any nearby witchweed seeds, result...

Q: All of the following compounds absorb IR radiation in the range between

All of the following compounds absorb IR radiation in the range between 1600 and 1850 cm−1. In each case, identify the specific bond(s) responsible for the absorption(s) and predict...

Q: Using any reagents of your choosing, show how you would convert

Using any reagents of your choosing, show how you would convert tert-butyl alcohol into 2-methyl-1-propanol.

Q: Rank each of the bonds identified in order of increasing wavenumber

Rank each of the bonds identified in order of increasing wavenumber

Q: A compound with the molecular formula C4H6O4 produces a broad signal between

A compound with the molecular formula C4H6O4 produces a broad signal between 2500 and 3600 cm−1 in its IR spectrum and produces two signals in its 1H NMR spectrum (a singlet at 12.1 ppm with a relativ...

Q: Propose the structure of a compound that exhibits the following 1H NMR

Propose the structure of a compound that exhibits the following 1H NMR data: a. C5H10O 1.09 δ (6H, doublet) 2.12 δ (3H, singlet) 2.58 δ (1H, septet) b. C5H12O 0.91 δ (3H, triplet) 1.19 δ (6H, si...

Q: We saw a general rule that the two protons of a CH2

We saw a general rule that the two protons of a CH2 group will be chemically equivalent if there are no chiral centers in the compound. An example of an exception is 3-bromopentane. This compound does...

Q: Deduce the structure of a compound with the molecular formula C9H12 that

Deduce the structure of a compound with the molecular formula C9H12 that produces the following 1H NMR spectrum:

Q: Deduce the structure of a compound with the molecular formula C9H10O2 that

Deduce the structure of a compound with the molecular formula C9H10O2 that produces the following 1H NMR spectrum and 13C NMR spectrum:

Q: Propose the structure of a compound consistent with the following data:

Propose the structure of a compound consistent with the following data: a. C5H10O, broadband-decoupled 13C NMR: 7.1, 34.6, 210.5 δ b. C6H10O, broadband-decoupled 13C NMR: 70.8, 115.2, 134.8 δ

Q: Determine the structure of an alcohol with the molecular formula C4H10O that

Determine the structure of an alcohol with the molecular formula C4H10O that exhibits the following signals in its 13C NMR spectra: a. Broadband decoupled: 69.3 δ, 32.1 δ, 22.8 δ, and 10.0 δ b. DEPT...

Q: Determine the structure of an alcohol with the molecular formula C6H14O that

Determine the structure of an alcohol with the molecular formula C6H14O that exhibits the following DEPT-135 spectrum:

Q: Deduce the structure of a compound with the molecular formula C6H14O2 that

Deduce the structure of a compound with the molecular formula C6H14O2 that exhibits the following IR, 1H NMR, and 13C NMR spectra:

Q: Using any compounds that have no more than two carbon atoms,

Using any compounds that have no more than two carbon atoms, identify a method for preparing each of the following compounds:

Q: Deduce the structure of a compound with the molecular formula C8H10O that

Deduce the structure of a compound with the molecular formula C8H10O that exhibits the following IR, 1H NMR, and 13C NMR spectra:

Q: Deduce the structure of a compound with the molecular formula C5H10O that

Deduce the structure of a compound with the molecular formula C5H10O that exhibits the following IR, 1H NMR, and 13C NMR spectra. Data from the mass spectrum are also provided.

Q: Deduce the structure of a compound with the molecular formula C8H14O3 that

Deduce the structure of a compound with the molecular formula C8H14O3 that exhibits the following IR, 1H NMR, and 13C NMR spectra:

Q: Deduce the structure of a compound with the molecular formula C6H10O4 that

Deduce the structure of a compound with the molecular formula C6H10O4 that exhibits the following IR, 1H NMR, and 13C NMR spectra:

Q: Carvone, a natural product isolated from plants, is used widely

Carvone, a natural product isolated from plants, is used widely in the flavor and fragrance industry; the (S) enantiomer smells and tastes like caraway seeds. Utilizing a process called bioremediation...

Q: 68. Which of the following methods can be used to prepare

68. Which of the following methods can be used to prepare this compound? 69. Which is an intermediate in the mechanism for the following reaction? 70. Which is a product of this reaction?

Q: Deduce the structure of a compound with the molecular formula C8H14O4 that

Deduce the structure of a compound with the molecular formula C8H14O4 that exhibits the following IR, 1H NMR, and 13C NMR spectra:

Q: 68. What are the best reagents to perform this transformation?

68. What are the best reagents to perform this transformation? a. Na2Cr2O7, H2SO4, H2O b. CrO3, H3O+, acetone c. PCC, CH2Cl2 d. KMnO4, NaOH, cold 69. Which of the following is NOT an efficient syn...

Q: Deduce the structure of a compound with the molecular formula C12H8Br2 that

Deduce the structure of a compound with the molecular formula C12H8Br2 that exhibits the following 1H NMR and 13C NMR spectra:

Q: An unknown compound exhibits the following IR, 1H NMR, and

An unknown compound exhibits the following IR, 1H NMR, and 13C NMR spectra. In a mass spectrum of this compound, the (M)+• peak appears at m/z = 104, and the (M+1)+•...

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Consider the structure of N,N-dimethylformamide (DMF):

Consider the structure of N,N-dimethylformamide (DMF): We might expect the two methyl groups to be equivalent; however, both the proton and carbon NMR spectra of DMF show two separate signals for the...

Q: Compare the following two constitutional isomers. The 13C NMR spectrum of

Compare the following two constitutional isomers. The 13C NMR spectrum of the first compound exhibits five signals, while the second compound exhibits six signals. Explain.

Q: 73. An unknown alcohol was treated with chromic acid to give

73. An unknown alcohol was treated with chromic acid to give a product with the following IR spectrum. Which of the following statements must be true? a. The unknown compound must be a primary alcoho...

Q: Draw the structure of a compound with the molecular formula C8H10 that

Draw the structure of a compound with the molecular formula C8H10 that exhibits five signals in its 13C NMR spectrum, four of which appear between 100 and 150 ppm.

Q: 73. Which of the following compounds is converted into carbon dioxide

73. Which of the following compounds is converted into carbon dioxide and acetic acid (CH3CO2H) upon ozonolysis? 74. All of the following methods can be used to prepare 2-butanone (CH3COCH2CH3) EXCEP...

Q: Predict the chemical shifts for the signals in the 1H NMR spectrum

Predict the chemical shifts for the signals in the 1H NMR spectrum of each of the following compounds:

Q: Consider the two methyl groups shown in the following compound. Explain

Consider the two methyl groups shown in the following compound. Explain why the methyl group on the right side appears at lower chemical shift.

Q: 75. Which compound gives the following 1H NMR spectrum?

75. Which compound gives the following 1H NMR spectrum? 76. A compound with the molecular formula C4H8O2 gives a 1H NMR spectrum with the following three signals. What is the structure of the compou...

Q: Artemisinin (also known as Qinghaosu) is a peroxide-containing

Artemisinin (also known as Qinghaosu) is a peroxide-containing compound that has been used in traditional Chinese medicine as a treatment for malaria. Today, synthetic derivatives of artemisinin are s...

Q: The base peak of a low-resolution spectrum of cyclohexanone is

The base peak of a low-resolution spectrum of cyclohexanone is at m/z = 55. A high-resolution spectrum reveals that this peak actually consists of two peaks at 55.0183 and 55.0546 with relative intens...

Q: A compound with the molecular formula C8H18 exhibits a 1H NMR spectrum

A compound with the molecular formula C8H18 exhibits a 1H NMR spectrum with only one signal. How many signals would you expect in the 13C NMR spectrum of this compound?

Q: As part of a study on cyclopropane derivatives of fatty acids,

As part of a study on cyclopropane derivatives of fatty acids, the following amide was subjected to mass spectrometric analysis. The most abundant peak in the spectrum was found at m/z = 113. Suggest...

Q: Brevianamide S, a potent antitubercular natural product, was recently isolated

Brevianamide S, a potent antitubercular natural product, was recently isolated from a marine sediment collected off the coast of China. Predict the chemical shift and determine the multiplicity of eac...

Q: Treatment of 1,3,6-cyclononatriene (compound 1

Treatment of 1,3,6-cyclononatriene (compound 1), or its dimethyl derivative (compound 2), with potassium amide (KNH2) in liquid ammonia results in the formation of anion 1a or 2a, respectively: a. Dr...

Q: Compound 1 can serve as a precursor in the synthesis of flutamide

Compound 1 can serve as a precursor in the synthesis of flutamide (2), a drug used in the treatment of prostate cancer: a. Compound 1 has three distinct aromatic protons, labeled Ha, Hb, and Hc. Iden...

Q: Coumarin (1) and its derivatives exhibit a broad array of

Coumarin (1) and its derivatives exhibit a broad array of industrial applications, including, but not limited to, cosmetics, food preservatives, and fluorescent laser dyes. In the 1H NMR spectrum of c...

Q: Propose a plausible mechanism for the following process, called iodolactonization:

Propose a plausible mechanism for the following process, called iodolactonization:

Q: Ethyl 3-ethoxypropanoate is a solvent used in the preparation of

Ethyl 3-ethoxypropanoate is a solvent used in the preparation of polymers, and it has been detected in the gaseous emissions at some industrial sites. One study showed that it can be decomposed by sev...

Q: When 3-bromocyclopentene is treated with HBr, the observed product

When 3-bromocyclopentene is treated with HBr, the observed product is a racemic mixture of trans-1,2-dibromocyclopentane. None of the corresponding cis-dibromide is observed. Propose a mechanism that...

Q: Progesterone is a hormone that helps prepare a woman’s body for pregnancy

Progesterone is a hormone that helps prepare a woman’s body for pregnancy and regulates menstrual cycles. In a synthesis of progesterone, an alkene with the molecular formula C21H32O...

Q: Taxol (compound 3) can be isolated from the bark of

Taxol (compound 3) can be isolated from the bark of the Pacific yew tree, Taxus brevifolia, and is currently used in the treatment of several kinds of cancer, including breast cancer. Each yew tree co...

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: When adamantylideneadamantane, shown below, is treated with bromine, the

When adamantylideneadamantane, shown below, is treated with bromine, the corresponding bromonium ion forms in high yield. This intermediate is stable and does not undergo further nucleophilic attack b...

Q: Diisopinocampheylborane (Ipc2BH) is a chiral organoborane, readily employed for

Diisopinocampheylborane (Ipc2BH) is a chiral organoborane, readily employed for the production of many asymmetric products used in total synthesis. It is a crystalline material that can be prepared as...

Q: Zaragozic acids are a group of structurally related, natural products that

Zaragozic acids are a group of structurally related, natural products that were first isolated from fungal cultures in 1992. These compounds have been shown to reduce cholesterol levels in primates, a...

Q: Monensin is a potent antibiotic compound isolated from Streptomyces cinnamonensis. The

Monensin is a potent antibiotic compound isolated from Streptomyces cinnamonensis. The following reaction was employed during W. C. Still’s synthesis of monensin. Sodium bicarbonate...

Q: Which of the following compounds is NOT a product of this ozonolysis

Which of the following compounds is NOT a product of this ozonolysis reaction?

Q: Which of the following represents an efficient method for preparing the alcohol

Which of the following represents an efficient method for preparing the alcohol shown?

Q: Consider the following acid-catalyzed hydration reaction: /

Consider the following acid-catalyzed hydration reaction: Which of the following ions are intermediates in the accepted mechanism for this process? a. I, II, and III b. I and II c. None of the abo...

Q: Show reagents that can be used to achieve the following transformation:

Show reagents that can be used to achieve the following transformation:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: A carbocation is resonance stabilized when it is adjacent to an oxygen

A carbocation is resonance stabilized when it is adjacent to an oxygen atom: Such a carbocation is even more stable than a tertiary carbocation. Using this information, propose a mechanism for the fo...

Q: Determine whether the pinacol rearrangement, shown in the previous problem,

Determine whether the pinacol rearrangement, shown in the previous problem, is a reduction, an oxidation, or neither.

Q: Consider the following sequence of reactions and identify the structures of compounds

Consider the following sequence of reactions and identify the structures of compounds A, B, and C:

Q: (S)-Gizzerosine is an amino acid that is believed to

(S)-Gizzerosine is an amino acid that is believed to be responsible for a serious disease called “black vomit” in chickens. However, the same compound is a potentia...

Q: Briarellin E (compound 3) is produced by coral in the

Briarellin E (compound 3) is produced by coral in the Caribbean and Mediterranean seas and belongs to a larger family of marine natural products that are currently being investigated as potential anti...

Q: The compound duryne was one of several structurally related compounds isolated from

The compound duryne was one of several structurally related compounds isolated from a marine sponge. Propose an efficient synthesis of duryne starting with any compounds containing eleven or fewer car...

Q: Estragole is an insect repellant that has been isolated from the leaves

Estragole is an insect repellant that has been isolated from the leaves of the Clausena anisata tree. Propose a synthesis of estragole starting from 4-methylphenol.

Q: Propose a structure for a compound with the molecular formula C10H14O that

Propose a structure for a compound with the molecular formula C10H14O that exhibits the following 1 H NMR spectrum:

Q: For each of the following compounds, compare the two indicated protons

For each of the following compounds, compare the two indicated protons and determine whether they are enantiotopic, homotopic, or diastereotopic:

Q: Propose a structure for a compound with the molecular formula C3H8O that

Propose a structure for a compound with the molecular formula C3H8O that exhibits the following 1H NMR and 13C NMR spectra:

Q: Propose two possible structures for a compound with the molecular formula C5H12O

Propose two possible structures for a compound with the molecular formula C5H12O that exhibits the following 13C NMR and IR spectra:

Q: Propose a structure for a compound with the molecular formula C8H10O that

Propose a structure for a compound with the molecular formula C8H10O that exhibits the following 1H NMR spectrum:

Q: The following two isomeric ketones were among the 68 compounds isolated from

The following two isomeric ketones were among the 68 compounds isolated from the steam-distilled volatile oil of fresh and air-dried marijuana buds. Propose a separate synthesis for each of these two...

Q: Using 2-propanol as your only source of carbon, show

Using 2-propanol as your only source of carbon, show how you would prepare 2-methyl-2-pentanol.

Q: When 5-bromo-2,2-dimethyl-1

When 5-bromo-2,2-dimethyl-1-pentanol is treated with sodium hydride, a compound with the molecular formula C7H14O is obtained. Identify the structure of this compound.

Q: Problem 13.34 outlines a general method for the preparation of

Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify reagents that you could use to prepare a racemic mixture of each of the...

Q: Predict the products for each of the following: /

Predict the products for each of the following:

Q: Propose a plausible mechanism for each of the following transformations:

Propose a plausible mechanism for each of the following transformations:

Q: What product do you expect when tetrahydrofuran is heated in the presence

What product do you expect when tetrahydrofuran is heated in the presence of excess HBr?

Q: Compound B has the molecular formula C6H10O and does not possess any

Compound B has the molecular formula C6H10O and does not possess any π bonds. When treated with concentrated HBr, cis-1, 4-dibromocyclohexane is produced. Identify the structure of compound B.

Q: Draw the expected 1H NMR spectrum of the following compound:

Draw the expected 1H NMR spectrum of the following compound:

Q: Propose a stepwise mechanism for the following transformation: /

Propose a stepwise mechanism for the following transformation:

Q: Predict the product for each of the following reaction sequences:

Predict the product for each of the following reaction sequences:

Q: Using acetylene and ethylene oxide as your only sources of carbon atoms

Using acetylene and ethylene oxide as your only sources of carbon atoms, propose a synthesis for each of the following compounds:

Q: Predict the product and draw a mechanism for each of the following

Predict the product and draw a mechanism for each of the following reactions:

Q: Fill in the missing reagents below. /

Fill in the missing reagents below.

Q: Fill in the missing products below /

Fill in the missing products below

Q: When the following chiral epoxide is treated with aqueous sodium hydroxide,

When the following chiral epoxide is treated with aqueous sodium hydroxide, only one product is obtained, and that product is achiral. Draw the product and explain why only one product is formed.

Q: When meso-2,3-epoxybutane is treated with aqueous

When meso-2,3-epoxybutane is treated with aqueous sodium hydroxide, two products are obtained. Draw both products and describe their relationship.

Q: Propose an efficient synthesis for 1,4-dioxane using acetylene

Propose an efficient synthesis for 1,4-dioxane using acetylene as your only source of carbon atoms.

Q: Dimethoxyethane (DME) is a polar aprotic solvent often used for

Dimethoxyethane (DME) is a polar aprotic solvent often used for SN2 reactions. Propose an efficient synthesis for DME using acetylene and methyl iodide as your only sources of carbon atoms.

Q: Using compounds that possess no more than two carbon atoms, propose

Using compounds that possess no more than two carbon atoms, propose an efficient synthesis for the following compound:

Q: Consider the following compound: / a. How

Consider the following compound: a. How many signals do you expect in the 1H NMR spectrum of this compound? b. Rank the protons in terms of increasing chemical shift. c. How many signals do you exp...

Q: Propose an efficient synthesis for each transformation. /

Propose an efficient synthesis for each transformation.

Q: Propose a structure for an ether with the molecular formula C7H8O that

Propose a structure for an ether with the molecular formula C7H8O that exhibits the following 13C NMR spectrum:

Q: Draw a mechanism for each of the following reactions: /

Draw a mechanism for each of the following reactions:

Q: Propose a structure for a compound with the molecular formula C8H18O that

Propose a structure for a compound with the molecular formula C8H18O that exhibits the following 1H NMR and 13C NMR spectra:

Q: Propose a structure for a compound with the molecular formula C4H8O that

Propose a structure for a compound with the molecular formula C4H8O that exhibits the following 13C NMR and FTIR spectra:

Q: Propose a structure for a compound with the molecular formula C4H10O that

Propose a structure for a compound with the molecular formula C4H10O that exhibits the following 1H NMR spectrum:

Q: Predict the product of the following reaction: /

Predict the product of the following reaction:

Q: Epoxides can be formed by treating α-haloketones with sodium borohydride

Epoxides can be formed by treating α-haloketones with sodium borohydride. Propose a mechanism for formation of the following epoxide:

Q: When methyloxirane is treated with HBr, the bromide ion attacks the

When methyloxirane is treated with HBr, the bromide ion attacks the less substituted position. However, when phenyloxirane is treated with HBr, the bromide ion attacks the more substituted position E...

Q: Consider the following two compounds. When treated with NaOH, one

Consider the following two compounds. When treated with NaOH, one of these compounds forms an epoxide quite rapidly, while the other forms an epoxide very slowly. Identify which compound reacts more r...

Q: Propose an efficient synthesis for the following transformation: /

Propose an efficient synthesis for the following transformation:

Q: A compound with the molecular formula C9H18 exhibits a 1H NMR spectrum

A compound with the molecular formula C9H18 exhibits a 1H NMR spectrum with only one signal and a 13C NMR spectrum with two signals. Deduce the structure of this compound.

Q: Using bromobenzene and ethylene oxide as your only sources of carbon,

Using bromobenzene and ethylene oxide as your only sources of carbon, show how you could prepare trans-2,3-diphenyloxirane (a racemic mixture of enantiomers).

Q: Identify the reagents you would use to accomplish each of the following

Identify the reagents you would use to accomplish each of the following transformations:

Q: The SN2 reaction between a Grignard reagent and an epoxide works reasonably

The SN2 reaction between a Grignard reagent and an epoxide works reasonably well when the epoxide is ethylene oxide. However, when the epoxide is substituted with groups that provide steric hindrance,...

Q: The following sequence of reactions was employed during synthetic studies on reidispongiolide

The following sequence of reactions was employed during synthetic studies on reidispongiolide A, a cytotoxic marine natural product.8 Draw the structures of compounds A, B, C, and D

Q: Sphingolipids are a class of compounds that play an important role in

Sphingolipids are a class of compounds that play an important role in signal transmission and cell recognition. Fumonisin B1 is a potent sphingolipid biosynthesis inhibitor. A recent synthesis of fum...

Q: Guggul is an herbal extract from the resin of the mukul myrrh

Guggul is an herbal extract from the resin of the mukul myrrh tree, and it shows potential for treating high cholesterol. In a recent synthesis of (+)-myrrhanol A (a compound present in guggul), compo...

Q: During a total synthesis of 2-methyl-d-erythritol

During a total synthesis of 2-methyl-d-erythritol (a sugar of importance to isoprenoid biosynthesis), epoxide 2 was required. a. Identify the reagents you would use to achieve a stereoselective synth...

Q: Reboxetine mesylate is used in the treatment of depression and is currently

Reboxetine mesylate is used in the treatment of depression and is currently marketed as the racemate. The (S,S)-enantiomer of reboxetine is being evaluated for the treatment of neuropathic pain. The f...

Q: Treatment of one mole of dimethyl sulfate (CH3OSO3CH3) with two

Treatment of one mole of dimethyl sulfate (CH3OSO3CH3) with two moles of sodium acetylide results in the formation of two moles of propyne as the major product: a. Draw the inorganic, ionic species t...

Q: Salvinorin A, isolated from the Mexican plant Salvia divinorum, is

Salvinorin A, isolated from the Mexican plant Salvia divinorum, is known to bind with opioid receptors, thereby generating a powerful hallucinogenic effect. It has been suggested that salvinorin A may...

Q: Halogenation of alkynes with Cl2 or Br2 can generally be achieved with

Halogenation of alkynes with Cl2 or Br2 can generally be achieved with high yields, while halogenation of alkynes with 2 typically gives low yields. However, the following reaction is successfully com...

Q: How many signals do you expect in the 1H NMR spectrum of

How many signals do you expect in the 1H NMR spectrum of each of the following compounds:

Q: Predict the products for each of the following: /

Predict the products for each of the following:

Q: The following procedure is part of a synthetic strategy for the enantioselective

The following procedure is part of a synthetic strategy for the enantioselective preparation of carbohydrates (Chapter 24): a. Under these strongly basic conditions (NaOH), the alcohol group is depr...

Q: Laureatin is a natural product isolated from the marine algae Laurencia nipponica

Laureatin is a natural product isolated from the marine algae Laurencia nipponica that exhibits potent insecticidal activity against mosquitos. During an investigation toward the synthesis of laureati...

Q: The compound 5,9,12,16-tetramethyleicosane was

The compound 5,9,12,16-tetramethyleicosane was synthesized as part of a study of the male sex pheromone of a Brazilian bug that feeds on the leaves and fruit of tomato plants. The synthesis of this al...

Q: Brevetoxin B (compound 2) is produced by Ptychodiscus brevis Davis

Brevetoxin B (compound 2) is produced by Ptychodiscus brevis Davis, a marine organism responsible for red tides. Brevetoxin B is a potent neurotoxin, as a result of its ability to bind to sodium chann...

Q: The two lowest energy conformations of pentane are the anti-anti

The two lowest energy conformations of pentane are the anti-anti and the anti-gauche forms, in terms of arrangements around the two central C−C bonds. A recent study analyzed the conformations of 3-he...

Q: A variety of phenyl-substituted acetylenes (1a–d)

A variety of phenyl-substituted acetylenes (1a–d) were treated with HCl to give a mixture of E and Z isomers, as shown below a. As we saw in Problem 9.72, vinyl carbocations can for...

Q: Suggest an efficient synthesis for the following transformation: /

Suggest an efficient synthesis for the following transformation:

Q: Provide an IUPAC name for each of the following compounds:

Provide an IUPAC name for each of the following compounds:

Q: Draw a structure for each of the following compounds: a

Draw a structure for each of the following compounds: a. (R)-2-Ethoxy-1,1-dimethylcyclobutane b. Cyclopropyl isopropyl ether

Q: Diethyl ether was commonly used as an anesthetic before its negative effects

Diethyl ether was commonly used as an anesthetic before its negative effects on the human nervous system were recognized. As part of a study to develop a method for predicting toxicity based on struct...

Q: Propose a plausible mechanism for each of the following transformations:

Propose a plausible mechanism for each of the following transformations:

Q: Identify the structure of a compound with the molecular formula C9H20 that

Identify the structure of a compound with the molecular formula C9H20 that exhibits four CH2 groups, all of which are chemically equivalent. How many total signals would you expect in the 1H NMR spect...

Q: Identify the missing reagent needed to achieve each of the following transformations

Identify the missing reagent needed to achieve each of the following transformations:

Q: Show reagents that you could use to prepare each of the following

Show reagents that you could use to prepare each of the following ethers via a Williamson ether synthesis and explain your reasoning:

Q: Compound 2 was made as a potential anti-HIV agent,

Compound 2 was made as a potential anti-HIV agent, based on its structural similarity to other reported anti-HIV compounds. One of the early steps in the synthesis involved the creation of an ether gr...

Q: Identify reagents that you could use to prepare each of the following

Identify reagents that you could use to prepare each of the following ethers via an alkoxymercuration-demercuration:

Q: How would you use an alkoxymercuration-demercuration to prepare dicyclopentyl ether

How would you use an alkoxymercuration-demercuration to prepare dicyclopentyl ether using cyclopentene as your only source of carbon?

Q: Show how you would use an alkoxymercuration-demercuration to prepare isopropyl

Show how you would use an alkoxymercuration-demercuration to prepare isopropyl propyl ether using propene as your only source of carbon and any other reagents of your choosing.

Q: Predict the products for each of the following reactions: /

Predict the products for each of the following reactions:

Q: Assign a name for each of the following compounds: /

Assign a name for each of the following compounds:

Q: Assign a name for each of the following compounds. Be sure

Assign a name for each of the following compounds. Be sure to assign the configuration of each chiral center and indicate the configuration(s) at the beginning of the name.

Q: Assign a systematic name for each of the following compounds:

Assign a systematic name for each of the following compounds:

Q: Choline is a compound involved in neurotransmission. The biosynthesis of choline

Choline is a compound involved in neurotransmission. The biosynthesis of choline involves the transfer of a methyl group from SAM. Draw a mechanism for this transformation:

Q: Thienamycin is a potent antibacterial agent isolated from the fermentation broth of

Thienamycin is a potent antibacterial agent isolated from the fermentation broth of the soil microorganism, Streptomyces cattleya. The following SN2 process was utilized in a synthesis of thienamycin....

Q: The optically pure octyl sulfonate shown below was treated with varying mixtures

The optically pure octyl sulfonate shown below was treated with varying mixtures of water and dioxane, and the optical purity of the resulting product (2-octanol) was found to vary with the ratio of w...

Q: Cyclopropyl chloride (1) cannot generally be converted into cyclopropanol (

Cyclopropyl chloride (1) cannot generally be converted into cyclopropanol (4) through a direct substitution reaction, because undesired, ring-opening reactions occur. The following represents an alter...

Q: Compound 1 is observed to undergo debromination upon treatment with DMF to

Compound 1 is observed to undergo debromination upon treatment with DMF to afford an alkene. The E-isomer (compound 2) is obtained exclusively (none of the Z-isomer is observed). A concerted mechanism...

Q: The following sequence of reactions was performed during a synthesis of (+)-

The following sequence of reactions was performed during a synthesis of (+)-coronafacic acid, a key component in the plant toxin coronatine. Predict the product of this reaction sequence, and justify...

Q: 99. For the following substitution reaction, which statement is FALSE

99. For the following substitution reaction, which statement is FALSE? a. The process is bimolecular. b. Increasing the concentration of hydroxide will cause an increase in the rate of reaction. c....

Q: The regions of δ+ in a compound are the regions most

The regions of δ+ in a compound are the regions most likely to be attacked by an anion, such as hydroxide (HO−). In the compound shown, identify the two carbon atoms tha...

Q: Plastics and synthetic fibers are examples of the many materials made from

Plastics and synthetic fibers are examples of the many materials made from repeating subunits of carbon-containing molecules called polymers. Although most synthetic polymers are prepared from fossil...

Q: Identify the electron configuration for each of the following atoms:

Identify the electron configuration for each of the following atoms: a. Carbon b. Oxygen c. Boron d. Fluorine e. Sodium f. Aluminum

Q: Compound 1 was prepared during a recent synthesis of 1-deoxynojirimycin

Compound 1 was prepared during a recent synthesis of 1-deoxynojirimycin, a compound with application to HIV chemotherapy. Upon formation, compound 1 rapidly undergoes ring contraction in the presence...

Q: The following reaction exhibits a second-order rate equation:

The following reaction exhibits a second-order rate equation: a. What happens to the rate if the concentration of chlorocyclopentane is tripled and the concentration of sodium hydroxide remains the s...

Q: Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process:

Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process: The rate of hydrolysis is dependent on two main factors: 1. the stability of the leaving group, and 2. the stability o...

Q: Biotin (compound 4) is an essential vitamin that plays a

Biotin (compound 4) is an essential vitamin that plays a vital role in several important physiological processes. A total synthesis of biotin, developed by scientists at Hoffmann-La Roche, involved th...

Q: Steroids and their derivatives are among the most widely used therapeutic agents

Steroids and their derivatives are among the most widely used therapeutic agents. They are used in birth control, hormone replacement therapy, and in the treatment of inflammatory conditions and cance...

Q: When 2-iodobutane is treated with a variety of bases in

When 2-iodobutane is treated with a variety of bases in DMSO at 50°C, the percentage of 1-butene formed among total butenes is found to be dependent on the choice of base, as seen in the ch...

Q: Determine the hybridization state of each carbon atom in the following compounds

Determine the hybridization state of each carbon atom in the following compounds.

Q: Nemotin is a compound that was first isolated from the fungi Poria

Nemotin is a compound that was first isolated from the fungi Poria tenuis and Poria corticola in the 1940s and was shown to possess potent antibacterial activity. However, its structure was not verifi...

Q: Rank the indicated bonds in terms of increasing bond length:

Rank the indicated bonds in terms of increasing bond length:

Q: Use VSEPR theory to predict the geometry for each of the following

Use VSEPR theory to predict the geometry for each of the following structures:

Q: Compare the structures of a carbocation and a carbanion: /

Compare the structures of a carbocation and a carbanion: In one of these ions, the central carbon atom is trigonal planar, while the other is trigonal pyramidal. Using VSEPR theory, assign the correc...

Q: Ammonia (NH3) will react with a strong acid, such

Ammonia (NH3) will react with a strong acid, such as hydronium (H3O+), to give an ammonium ion, as shown below. This type of process is an acid-base reaction, which will be the topic of Chapter 3. Usi...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: When sand is coated with a layer of trimethylhydroxysilane, (CH3

When sand is coated with a layer of trimethylhydroxysilane, (CH3)3SiOH, it repels water and can no longer get wet. Hydrophobic sand (aka, magic sand) is fun to play with, but it can also have useful a...

Q: Identify whether each of the following compounds exhibits a molecular dipole moment

Identify whether each of the following compounds exhibits a molecular dipole moment. For compounds that do, indicate the direction of the net molecular dipole moment:

Q: Volatile organic compounds (VOCs) contribute to the aroma of plants

Volatile organic compounds (VOCs) contribute to the aroma of plants and can also be used for communication between plants. Diphenyl ether was identified as a minor VOC found in tomato plants. Identify...

Q: For each of the following pairs of compounds, identify the higher

For each of the following pairs of compounds, identify the higher boiling compound and justify your choice:

Q: Epichlorohydrin (1) is an epoxide used in the production of

Epichlorohydrin (1) is an epoxide used in the production of plastic, epoxy glues, and resins (reactions of epoxides will be discussed in Chapter 13). When epichlorohydrin is treated with phenol (2), t...

Q: Draw structures for all constitutional isomers with the following molecular formulas:

Draw structures for all constitutional isomers with the following molecular formulas: a. C6H14 b. C2H5Cl c. C2H4Cl2 d. C2H3Cl3

Q: Draw structures for all constitutional isomers with the molecular formula C4H8 that

Draw structures for all constitutional isomers with the molecular formula C4H8 that have: a. Only single bonds b. One double bond

Q: For each compound below, identify any polar covalent bonds and indicate

For each compound below, identify any polar covalent bonds and indicate the direction of the dipole moment using the symbols δ+ and δ−: a. HBr b. HCl c. H2O d. CH4O

Q: For each pair of compounds below, identify the one that would

For each pair of compounds below, identify the one that would be expected to have more ionic character. Explain your choice. a. NaBr or HBr b. BrCl or FCl

Q: Draw a Lewis dot structure for each of the following compounds:

Draw a Lewis dot structure for each of the following compounds: a. CH3CH2OH b. CH3CN

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: a. 3-Isopropyl-2,4-dimethyl-2-pentene b. 4-Ethyl-2-methyl-2-hexene c. 1,2-Dimethylcyclobutene (The name of a cycloalkene will often n...

Q: Draw a Lewis structure for a compound with the molecular formula C4H11N

Draw a Lewis structure for a compound with the molecular formula C4H11N in which three of the carbon atoms are bonded to the nitrogen atom. What is the geometry of the nitrogen atom in this com pound...

Q: Draw a Lewis structure of the anion AlBr4− and determine its

Draw a Lewis structure of the anion AlBr4− and determine its geometry.

Q: Draw the structure for the only constitutional isomer of cyclopropane:

Draw the structure for the only constitutional isomer of cyclopropane:

Q: Determine whether each compound below exhibits a molecular dipole moment:

Determine whether each compound below exhibits a molecular dipole moment: a. CH4 b. NH3 c. H2O d. CO2 e. CCl4 f. CH2Br2

Q: Identify the neutral element that corresponds with each of the following electron

Identify the neutral element that corresponds with each of the following electron configurations: a. 1s2 2s2 2p4 b. 1s2 2s2 2p5 c. 1s2 2s2 2p2 d. 1s2 2s2 2p3 e. 1s2 2s2 2p6 3s2 3p5

Q: In the compounds below, classify each bond as covalent, polar

In the compounds below, classify each bond as covalent, polar covalent, or ionic: a. NaBr b. NaOH c. NaOCH3 d. CH3OH e. CH2O

Q: Draw structures for all constitutional isomers with the following molecular formulas:

Draw structures for all constitutional isomers with the following molecular formulas: a. C2H6O b. C2H6O2 c. C2H4Br2

Q: Draw structures for any five constitutional isomers with the molecular formula C2H6O3

Draw structures for any five constitutional isomers with the molecular formula C2H6O3.

Q: For each type of bond below, determine the direction of the

For each type of bond below, determine the direction of the expected dipole moment: a. C−O b. C−Mg c. C−N d. C−Li e. C−Cl f. C−H g. O−H h. N−H

Q: Predict the bond angles for all bonds in the following compounds:

Predict the bond angles for all bonds in the following compounds: a. CH3CH2OH b. CH2O c. C2H4 d. C2H2 e. CH3OCH3 f. CH3NH2 g. C3H8 h. CH3CN

Q: In Section 4.2, we learned how to name bicyclic

In Section 4.2, we learned how to name bicyclic compounds. Using those rules, together with the rules discussed in this section, provide a systematic name for the following bicyclic compound. In a cas...

Q: Identify the expected hybridization state and geometry for the central atom in

Identify the expected hybridization state and geometry for the central atom in each of the following compounds:

Q: Count the total number of σ bonds and π bonds in the

Count the total number of σ bonds and π bonds in the compound below:

Q: For each pair of compounds below, predict which compound will have

For each pair of compounds below, predict which compound will have the higher boiling point and explain your choice: a. CH3CH2CH2OCH3 or CH3CH2CH2CH2OH b. CH3CH2CH2CH3 or CH3CH2CH2CH2CH3

Q: Which of the following pure compounds will exhibit hydrogen bonding?

Which of the following pure compounds will exhibit hydrogen bonding? a. CH3CH2OH b. CH2O c. C2H4 d. C2H2 e. CH3OCH3 f. CH3NH2 g. C3H8 h. NH3

Q: For each case below, identify the most likely value for x

For each case below, identify the most likely value for x: a. BHx b. CHx c. NHx d. CH2Clx

Q: Identify the hybridization state and geometry of each carbon atom in the

Identify the hybridization state and geometry of each carbon atom in the following compounds:

Q: Ambien™ is a sedative used in the treatment of insomnia.

Ambienâ„¢ is a sedative used in the treatment of insomnia. It was discovered in 1982 and brought to market in 1992 (it takes a long time for new drugs to undergo the extensive testing...

Q: Identify the most electronegative element in each of the following compounds:

Identify the most electronegative element in each of the following compounds: a. CH3OCH2CH2NH2 b. CH2ClCH2F c. CH3Li

Q: Nicotine is an addictive substance found in tobacco. Identify the hybridization

Nicotine is an addictive substance found in tobacco. Identify the hybridization state and geometry of each of the nitrogen atoms in nicotine:

Q: Below is the structure of caffeine, but its lone pairs are

Below is the structure of caffeine, but its lone pairs are not shown. Identify the location of all lone pairs in this compound:

Q: Classify each of the following alkenes as monosubstituted, disubstituted, trisubstituted

Classify each of the following alkenes as monosubstituted, disubstituted, trisubstituted, or tetrasubstituted:

Q: There are two different compounds with the molecular formula C2H6O. One

There are two different compounds with the molecular formula C2H6O. One of these isomers has a much higher boiling point than the other. Explain why.

Q: Identify which compounds below possess a molecular dipole moment and indicate the

Identify which compounds below possess a molecular dipole moment and indicate the direction of that dipole moment:

Q: Methylene chloride (CH2Cl2) has fewer chlorine atoms than chloroform (

Methylene chloride (CH2Cl2) has fewer chlorine atoms than chloroform (CHCl3). Nevertheless, methylene chloride has a larger molecular dipole moment than chloroform. Explain.

Q: Which of the following compounds has the larger dipole moment? Explain

Which of the following compounds has the larger dipole moment? Explain your choice: CHCl3 or CBrCl

Q: Bonds between carbon and oxygen (C−O) are more

Bonds between carbon and oxygen (C−O) are more polar than bonds between sulfur and oxygen (S−O). Nevertheless, sulfur dioxide (SO2) exhibits a dipole moment while carbon dioxide (CO2) does not. Explai...

Q: Arrange the following compounds in order of increasing boiling point:

Arrange the following compounds in order of increasing boiling point:

Q: Consider the three compounds shown below and then answer the questions that

Consider the three compounds shown below and then answer the questions that follow: a. Which two compounds are constitutional isomers? b. Which compound contains a nitrogen atom with trigonal pyram...

Q: Propose at least two different structures for a compound with six carbon

Propose at least two different structures for a compound with six carbon atoms that exhibits the following features: a. All six carbon atoms are sp2 hybridized. b. Only one carbon atom is sp hybridi...

Q: Draw all constitutional isomers with the molecular formula C5H10 that possess one

Draw all constitutional isomers with the molecular formula C5H10 that possess one π bond.

Q: With current spectroscopic techniques, chemists are generally able to determine the

With current spectroscopic techniques, chemists are generally able to determine the structure of an unknown organic compound in just one day. These techniques have only been available for the last sev...

Q: Arrange each set of isomeric alkenes in order of stability:

Arrange each set of isomeric alkenes in order of stability:

Q: A compound with the molecular formula C5H11N has no π bonds.

A compound with the molecular formula C5H11N has no π bonds. Every carbon atom is connected to exactly two hydrogen atoms. Determine the structure of the compound.

Q: Isonitriles (A) are an important class of compounds because of

Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles ca...

Q: Consider the following table that provides bond lengths for a variety of

Consider the following table that provides bond lengths for a variety of C−X bonds (measured in Å). Two trends emerge when we compare these data. First, notice that th...

Q: Positron emission tomography (PET) is a medical imaging technique that

Positron emission tomography (PET) is a medical imaging technique that produces a threedimensional picture of functional processes in the body, such as the brain uptake of glucose. PET imaging require...

Q: The following structure shows promise for studying how enzymes (nature's catalysts

The following structure shows promise for studying how enzymes (nature's catalysts) coil up into very discrete shapes that endow them with catalytic function: a. This compound has two Nâˆ...

Q: Draw a Lewis structure for each of the compounds below:

Draw a Lewis structure for each of the compounds below: a. CH2=CHOCH2CH(CH3)2 b. (CH3CH2)2CHCH2CH2OH c. (CH3CH2)3COH d. (CH3)2C=CHCH2CH3 e. CH2=CHCH2OCH2CH(CH3)2 f. (CH3CH2)2C=CH2 g. (CH3)3CCH2C...

Q: Oxygenated hydrocarbons (compounds containing carbon, hydrogen, and oxygen)

Oxygenated hydrocarbons (compounds containing carbon, hydrogen, and oxygen) are common components of biofuels. The combustion of three isomers of C3H6O (shown below) were studied to investigate the ef...

Q: For each of the following molecules, determine the number of carbon

For each of the following molecules, determine the number of carbon atoms present and then determine the number of hydrogen atoms connected to each carbon atom:

Q: Initially approved to treat psoriasis (a skin disorder) and rheumatoid

Initially approved to treat psoriasis (a skin disorder) and rheumatoid arthritis, the drug tofacitinib has recently been found to also promote hair growth and restore hair loss. Identify the number of...

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: d. (CH3)3C−C(CH3)3 e. CH3CH2CH(CH3)2 f. (CH3CH2)3COH g. (CH3)2CHCH2OH h. CH3CH2CH2OCH3 i. (CH3CH2)2C=CH2 j. CH2...

Q: Consider the following two isomeric alkenes. The first isomer is a

Consider the following two isomeric alkenes. The first isomer is a monosubstituted alkene, while the second isomer is a disubstituted alkene. We might expect the second isomer to be more stable, yet h...

Q: Certain compounds that are alternatives to fossil fuels can be produced by

Certain compounds that are alternatives to fossil fuels can be produced by engineered microbes. Bisabolane, an example of a renewable biofuel, is a synthetic alternative to diesel fuel. Draw a bond-li...

Q: Atenolol and enalapril are drugs used in the treatment of heart disease

Atenolol and enalapril are drugs used in the treatment of heart disease. Both of these drugs lower blood pressure (albeit in different ways) and reduce the risk of heart attack. Using Table 2.1, ident...

Q: Draw all lone pairs on each of the oxygen atoms in the

Draw all lone pairs on each of the oxygen atoms in the following structures. Before doing this, review Table 2.2 and then come back to these problems. Try to identify all lone pairs without having to...

Q: The rich and varied flavors of toasted bread, roasted coffee,

The rich and varied flavors of toasted bread, roasted coffee, and seared meat are a result of a process known as the Maillard reaction. This reaction creates hundreds of new flavorful compounds, inclu...

Q: Draw all lone pairs on each of the nitrogen atoms in the

Draw all lone pairs on each of the nitrogen atoms in the following structures. First, review Table 2.3 and then come back to these problems. Try to identify all lone pairs without having to count. The...

Q: Glue adhesion usually requires a dry surface, so studying the chemistry

Glue adhesion usually requires a dry surface, so studying the chemistry behind the attachment of mussels to wet rocks can lead to the development of new adhesive materials. Chemists used the compound...

Q: In each of the following cases, determine whether the curved arrow

In each of the following cases, determine whether the curved arrow violates either of the two rules and describe the violation, if any. (Don’t forget to count all hydrogen atoms and...

Q: Drawing the resonance structure of the following compound requires one curved arrow

Drawing the resonance structure of the following compound requires one curved arrow. The head of this curved arrow is placed on the oxygen atom, and the tail of the curved arrow can only be placed in...

Q: Polyhydroxybutyric acid (PHB) is a component of biodegradable plastics that

Polyhydroxybutyric acid (PHB) is a component of biodegradable plastics that can be used in dissolving sutures or as a scaffold for skin regeneration. PHB is synthesized by linking together hydroxybuty...

Q: For each of the structures below, draw the resonance structure that

For each of the structures below, draw the resonance structure that is indicated by the curved arrows. Be sure to include formal charges.

Q: Predict the major and minor products for each of the following E2

Predict the major and minor products for each of the following E2 reactions:

Q: In each case below, draw the curved arrow(s)

In each case below, draw the curved arrow(s) required in order to convert the first resonance structure into the second resonance structure. In each case, begin by drawing all lone pairs and then use...

Q: The cation 1 has been shown to lose a proton (H

The cation 1 has been shown to lose a proton (H+) to produce a compound represented by resonance structures 2a, 2b, and 2c. a. Draw the curved arrows needed to convert resonance structure 2a into res...

Q: For each of the compounds below, locate the pattern we just

For each of the compounds below, locate the pattern we just learned (lone pair next to a π bond) and draw the appropriate resonance structure:

Q: Draw the resonance structure(s) for each of the compounds

Draw the resonance structure(s) for each of the compounds below:

Q: For each of the compounds below, locate the lone pair adjacent

For each of the compounds below, locate the lone pair adjacent to a positive charge and draw the resonance structure:

Q: Draw a resonance structure for each of the compounds below.

Draw a resonance structure for each of the compounds below.

Q: Draw a resonance structure of the following compound, which was isolated

Draw a resonance structure of the following compound, which was isolated from the fruits of Ocotea corymbosa, a native plant of the Brazilian Cerrado.

Q: Draw a resonance structure of the compound shown below, called 2

Draw a resonance structure of the compound shown below, called 2-heptanone, which is found in some kinds of cheese.

Q: Fingolimod is a novel drug that has been developed for the treatment

Fingolimod is a novel drug that has been developed for the treatment of multiple sclerosis. In 2008, researchers reported the results of phase III clinical trials of fingolimod, in which 70% of patien...

Q: Draw resonance structures for each of the following compounds: /

Draw resonance structures for each of the following compounds:

Q: For each of the following reactions, identify whether you would use

For each of the following reactions, identify whether you would use hydroxide or tertbutoxide to accomplish the desired transformation:

Q: For each of the following, draw all significant resonance forms and

For each of the following, draw all significant resonance forms and rank them from most significant to least significant. Briefly explain the rankings.

Q: In the compounds shown below, the six-membered rings are

In the compounds shown below, the six-membered rings are called benzene rings. Such rings are commonly found in natural products, and we will learn more about the remarkable stability of these ring sy...

Q: Valderramenol A, a natural product that was isolated from the leaves

Valderramenol A, a natural product that was isolated from the leaves of a plant native to the Philippines, was found to be antitubercular (can be used to treat tuberculosis). The structure of valderra...

Q: Draw a resonance hybrid for each of the following. /

Draw a resonance hybrid for each of the following.

Q: The dragmacidin class of natural products has been isolated from various marine

The dragmacidin class of natural products has been isolated from various marine sponges. They have been shown to have many interesting biological properties, including anti-viral, anti-fungal, and ant...

Q: For each compound below, identify all lone pairs and indicate whether

For each compound below, identify all lone pairs and indicate whether each lone pair is localized or delocalized. Then, use that information to predict the geometry for each atom that exhibits a lone...

Q: Nicotine is a toxic substance present in tobacco leaves. There are

Nicotine is a toxic substance present in tobacco leaves. There are two lone pairs in the structure of nicotine. In general, localized lone pairs are much more reactive than delocalized lone pairs. Wit...

Q: Isoniazid is used in the treatment of tuberculosis and multiple sclerosis.

Isoniazid is used in the treatment of tuberculosis and multiple sclerosis. Identify each lone pair as either localized or delocalized. Justify your answer in each case.

Q: Draw all carbon atoms, hydrogen atoms, and lone pairs for

Draw all carbon atoms, hydrogen atoms, and lone pairs for the following compounds:

Q: Draw bond-line structures for all constitutional isomers of C4H10.

Draw bond-line structures for all constitutional isomers of C4H10.

Q: The following substitution reaction exhibits second-order kinetics, and is

The following substitution reaction exhibits second-order kinetics, and is therefore presumed to occur via an SN2 process: a. What happens to the rate if the concentration of 1-iodopropane is tripled...

Q: Adamantane, a tricyclic alkane consisting of fused cyclohexane rings, has

Adamantane, a tricyclic alkane consisting of fused cyclohexane rings, has an intriguing structure that was first proposed as a theoretical structure in 1924. Chemists set out to synthesize the molecul...

Q: Draw bond-line structures for all constitutional isomers of C5H12.

Draw bond-line structures for all constitutional isomers of C5H12.

Q: Draw bond-line structures for vitamin A and vitamin C:

Draw bond-line structures for vitamin A and vitamin C:

Q: How many lone pairs are found in the structure of vitamin C

How many lone pairs are found in the structure of vitamin C?

Q: A carbene is a highly reactive intermediate in which a carbon atom

A carbene is a highly reactive intermediate in which a carbon atom bears a lone pair and no formal charge: How many hydrogen atoms are attached to the central carbon atom above?

Q: Draw the missing formal charge in each case below: /

Draw the missing formal charge in each case below:

Q: Draw significant resonance structures for the following compound: /

Draw significant resonance structures for the following compound:

Q: Draw bond-line structures for all constitutional isomers of the following

Draw bond-line structures for all constitutional isomers of the following compound: CH3CH2CH(CH3)2

Q: Identify which two compounds below are constitutional isomers: /

Identify which two compounds below are constitutional isomers:

Q: Identify the number of sp3 -hybridized carbon atoms in the following

Identify the number of sp3 -hybridized carbon atoms in the following compound: (CH3)2C=CHC(CH3)3

Q: Amino acids are biological compounds with the following structure, where the

Amino acids are biological compounds with the following structure, where the R group can vary. The structure and biological function of amino acids will be discussed in Chapter 25. Identify the total...

Q: Identify the major and minor products for the E2 reaction that occurs

Identify the major and minor products for the E2 reaction that occurs when each of the following substrates is treated with a strong base:

Q: Each structure below exhibits one lone pair. In each case,

Each structure below exhibits one lone pair. In each case, identify the type of atomic orbital that the lone pair occupies.

Q: Draw all significant resonance structures for each of the following:

Draw all significant resonance structures for each of the following:

Q: Write a condensed structural formula for each of the following compounds:

Write a condensed structural formula for each of the following compounds:

Q: What is the molecular formula for each compound in the previous problem

What is the molecular formula for each compound in the previous problem?

Q: Identify the number of carbon atoms and hydrogen atoms in the compound

Identify the number of carbon atoms and hydrogen atoms in the compound below:

Q: Draw bond-line structures for all constitutional isomers with the molecular

Draw bond-line structures for all constitutional isomers with the molecular formula C4H9Cl.

Q: Draw resonance structures for each of the following: /

Draw resonance structures for each of the following:

Q: Determine the relationship between the two structures below. Are they resonance

Determine the relationship between the two structures below. Are they resonance structures or are they constitutional isomers?

Q: Consider each pair of compounds below and determine whether the pair represents

Consider each pair of compounds below and determine whether the pair represents the same compound, constitutional isomers, or different compounds that are not isomeric at all:

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: a. CH2=CHCH2C(CH3)3 b. (CH3CH2)2CHCH2CH2OH c. CH≡COCH2CH(CH3)2 d. CH3CH2OCH2CH2OCH2CH3 e. (CH3CH2)3CBr f. (CH3)2C=CHCH3

Q: Retinol, one of the forms of vitamin A, is found

Retinol, one of the forms of vitamin A, is found in animal food sources and is essential for good vision. Below are two organohalides that were used to make synthetic forms of vitamin A. Upon treatmen...

Q: A mixture of sulfuric acid and nitric acid will produce small quantities

A mixture of sulfuric acid and nitric acid will produce small quantities of the nitronium ion (NO2+): Does the nitronium ion have any significant resonance structures? Why or why not?

Q: Consider the structure of ozone: / Ozone is

Consider the structure of ozone: Ozone is formed in the upper atmosphere, where it absorbs short wavelength UV radiation emitted by the sun, thereby protecting us from harmful radiation. Draw all sig...

Q: Melatonin is an animal hormone believed to have a role in regulating

Melatonin is an animal hormone believed to have a role in regulating the sleep cycle: The structure of melatonin incorporates two nitrogen atoms. What is the hybridization state and geometry of each...

Q: Draw all significant resonance structures for each of the following compounds:

Draw all significant resonance structures for each of the following compounds:

Q: Use resonance structures to help you identify all sites of low electron

Use resonance structures to help you identify all sites of low electron density (δ+) in the following compound:

Q: Use resonance structures to help you identify all sites of high electron

Use resonance structures to help you identify all sites of high electron density (δ−) in the following compound:

Q: Draw and rank all significant resonance forms for the following compound.

Draw and rank all significant resonance forms for the following compound. Briefly explain your rankings.

Q: Enamines, compounds with an amino group attached to a double bond

Enamines, compounds with an amino group attached to a double bond, are electron-rich alkenes that have important synthetic applications. Draw the major resonance contributors for the enamine shown and...

Q: Cycloserineis anantibiotic isolated from the microbe Streptomyces orchidaceous. It is used

Cycloserineis anantibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis. a. What is the molecular formula of this...

Q: Ramelteon is a hypnotic agent used in the treatment of insomnia:

Ramelteon is a hypnotic agent used in the treatment of insomnia: a. What is the molecular formula of this compound? b. How many sp3 -hybridized carbon atoms are present in this structure...

Q: When menthyl chloride is treated with a strong base, only one

When menthyl chloride is treated with a strong base, only one elimination product is observed. Yet, when neomenthyl chloride is treated with a strong base, two elimination products are observed. Draw...

Q: Compound 2 is produced by the fungus Exserohilum rostratum and has been

Compound 2 is produced by the fungus Exserohilum rostratum and has been shown to fight inflammation and block/prevent tissue scarring. Compound 2 was made in the laboratory from compound 1, as shown....

Q: CL-20 and HMX are both powerful explosives. CL-

CL-20 and HMX are both powerful explosives. CL-20 produces a more powerful blast but is generally considered too shock-sensitive for practical use. HMX is significantly less sensitive and is used as a...

Q: Progesterone is a female hormone that plays a critical role in the

Progesterone is a female hormone that plays a critical role in the menstrual cycle by preparing the lining of the uterus for implantation of an egg. During W. S. Johnson’s biomimetic...

Q: Many compounds with desirable medicinal properties are isolated from natural sources and

Many compounds with desirable medicinal properties are isolated from natural sources and are thus referred to as natural products. However, a compound’s medicinal properties are ofte...

Q: Polymers are very large compounds, assembled from smaller units, called

Polymers are very large compounds, assembled from smaller units, called monomers. For example, polymer 2, called poly(vinyl acetate), is made from vinyl acetate (1). Polymer 2 can be converted to poly...

Q: Coumarin and its derivatives exhibit a broad array of industrial applications,

Coumarin and its derivatives exhibit a broad array of industrial applications, including, but not limited to, cosmetics, food preservatives, and fluorescent laser dyes. Some derivatives of coumarin, s...

Q: Draw all constitutional isomers with the following molecular formula. a

Draw all constitutional isomers with the following molecular formula. a. C3H7Cl b. C4H10 c. C5H12 d. C4H10O e. C3H6Cl2

Q: All of the following acid-base reactions are reactions that we

All of the following acid-base reactions are reactions that we will study in greater detail in the chapters to follow. For each one, draw a mechanism and then clearly label the acid, base, conjugate a...

Q: In an intramolecular proton transfer reaction, the acidic site and the

In an intramolecular proton transfer reaction, the acidic site and the basic site are tethered together in the same structure, and a proton is passed from the acidic region of the structure to the bas...

Q: Dextromethorphan is a commonly used cough suppressant (antitussive) that is

Dextromethorphan is a commonly used cough suppressant (antitussive) that is under investigation for other therapeutic uses, including treatment of bipolar disorder.1 To increase its shelf-life, the dr...

Q: Predict which of the following two compounds will undergo an E2 reaction

Predict which of the following two compounds will undergo an E2 reaction more rapidly:

Q: For each pair of compounds below, identify the more acidic compound

For each pair of compounds below, identify the more acidic compound:

Q: Propranolol is an antihypertensive agent (used to treat high blood pressure

Propranolol is an antihypertensive agent (used to treat high blood pressure). Using Table 3.1, identify the most acidic proton in the compound and indicate the approximate expected pKa. From Table 3....

Q: L-dopa is used in the treatment of Parkinson’s disease.

L-dopa is used in the treatment of Parkinson’s disease. Using Table 3.1, identify the four most acidic protons in the compound and then arrange them in order of increasing acidity (t...

Q: Identify the stronger base in each of the following cases:

Identify the stronger base in each of the following cases:

Q: Compound 1 was isolated from a species of Streptomyces bacteria and has

Compound 1 was isolated from a species of Streptomyces bacteria and has been shown to have antibacterial and anticonvulsant properties. Compound 1 has also been made in the laboratory; however, it was...

Q: Nicotine is an addictive natural product found in tobacco. It has

Nicotine is an addictive natural product found in tobacco. It has been proposed that the amount of nicotine taken in by the body may depend on the relative proportions of the free base 1, as compared...

Q: Determine the position of equilibrium for each acid-base reaction below

Determine the position of equilibrium for each acid-base reaction below:

Q: Polyether ether ketone (PEEK) is a biocompatible polymer material that

Polyether ether ketone (PEEK) is a biocompatible polymer material that is used to make medical implants. The conjugate base of hydroquinone is used in the synthesis of PEEK. Is hydroxide a strong eno...

Q: Amino acids, such as glycine, are the key building blocks

Amino acids, such as glycine, are the key building blocks of proteins and will be discussed in greater detail in Chapter 25. At the pH of the stomach, glycine exists predominantly in a protonated form...

Q: In each compound below, two protons are color-coded (

In each compound below, two protons are color-coded (red and blue). Determine which of the two protons is more acidic:

Q: Predict the major and minor products for each of the following E2

Predict the major and minor products for each of the following E2 reactions:

Q: Arsenic is an element that can cause a variety of cancers.

Arsenic is an element that can cause a variety of cancers. The Environmental Protection Agency (EPA) and the World Health Organization (WHO) have thus set limits on acceptable levels of arsenic in dri...

Q: In each compound below, two protons are color-coded (

In each compound below, two protons are color-coded (red and blue). Determine which of the two protons is more acidic:

Q: Ascorbic acid (vitamin C) does not contain a traditional carboxylic

Ascorbic acid (vitamin C) does not contain a traditional carboxylic acid group, but it is, nevertheless, still fairly acidic (pKa = 4.2). Identify the acidic proton and explain your choice using reson...

Q: In the following compound, two protons are clearly identified. Determine

In the following compound, two protons are clearly identified. Determine which of the two is more acidic. After comparing the conjugate bases, you should get stuck on the following question: Is it mor...

Q: Identify the most acidic proton in each of the following compounds and

Identify the most acidic proton in each of the following compounds and explain your choice:

Q: For each pair of compounds below, identify which compound is more

For each pair of compounds below, identify which compound is more acidic and explain your choice:

Q: Water disinfection has greatly reduced the incidence of waterborne infectious diseases;

Water disinfection has greatly reduced the incidence of waterborne infectious diseases; however, disinfectants also lead to the unintended formation of drinking water disinfection by-products (DBPs) f...

Q: Identify the most acidic proton in each of the following compounds:

Identify the most acidic proton in each of the following compounds:

Q: Methods used in organic synthesis — the process of making new organic

Methods used in organic synthesis — the process of making new organic molecules — are continuously being developed.7 The following proton transfer react...

Q: In each compound below, two protons are color-coded (

In each compound below, two protons are color-coded (red and blue). Determine which of the two protons is more acidic:

Q: Compound 2 was prepared as part of an effort to determine the

Compound 2 was prepared as part of an effort to determine the absolute stereochemistry of compound 3, which was isolated from the liverwort plant. The synthesis of compound 2 involved the formation of...

Q: For each pair of compounds below, predict which will be more

For each pair of compounds below, predict which will be more acidic:

Q: The following compound is one of the strongest known acids:

The following compound is one of the strongest known acids: a. Explain why it is such a strong acid. b. Suggest a modification to the structure that would render the compound even more acidic.

Q: Amphotericin B is a powerful antifungal agent used for intravenous treatment of

Amphotericin B is a powerful antifungal agent used for intravenous treatment of severe fungal infections. Identify the most acidic proton in this compound:

Q: Predict the position of equilibrium for each of the following reactions:

Predict the position of equilibrium for each of the following reactions:

Q: The development of chemical sensors that can detect harmful contaminants, like

The development of chemical sensors that can detect harmful contaminants, like the toxic cyanide anion, is a prevalent line of research. Compound 1 was explored as a chemical sensor for cyanide in wat...

Q: In each of the following cases, identify whether the reagent shown

In each of the following cases, identify whether the reagent shown is suitable to accomplish the task described. Explain why or why not:

Q: We will learn the following reactions in upcoming chapters. For each

We will learn the following reactions in upcoming chapters. For each of these reactions, notice that the product is an anion (ignore the positively charged ion in each case). In order to obtain a neut...

Q: Predict which of the following compounds is more acidic: /

Predict which of the following compounds is more acidic: After making your prediction, use the pKa values from Table 3.1 to determine whether your prediction was correct.

Q: In each case below, identify the Lewis acid and the Lewis

In each case below, identify the Lewis acid and the Lewis base:

Q: The Nazarov cyclization is a versatile method for making five-membered

The Nazarov cyclization is a versatile method for making five-membered rings, a common feature in many natural products. This process has been used successfully in the preparation of many complex stru...

Q: Draw the carbocation intermediate that is expected when each of the following

Draw the carbocation intermediate that is expected when each of the following alkyl chlorides undergoes ionization. In each case, if the carbocation is resonance-stabilized, make sure to draw the reso...

Q: Draw the conjugate base for each of the following acids:

Draw the conjugate base for each of the following acids:

Q: Draw the conjugate acid for each of the following bases:

Draw the conjugate acid for each of the following bases:

Q: Compound A has a pKa of 7 and compound B has a

Compound A has a pKa of 7 and compound B has a pKa of 10. Compound A is how many times more acidic than compound B? a. 3 b. 3000 c. 1000

Q: In each reaction, identify the Lewis acid and the Lewis base

In each reaction, identify the Lewis acid and the Lewis base:

Q: What reaction will take place if H2O is added to a mixture

What reaction will take place if H2O is added to a mixture of NaNH2/NH3?

Q: Would ethanol (CH3CH2OH) be a suitable solvent in which to

Would ethanol (CH3CH2OH) be a suitable solvent in which to perform the following proton transfer? Explain your answer:

Q: Would water be a suitable proton source to protonate the following compound

Would water be a suitable proton source to protonate the following compound?

Q: Write an equation for the proton transfer reaction that occurs when each

Write an equation for the proton transfer reaction that occurs when each of the following acids reacts with water. In each case, draw curved arrows that show a mechanism for the proton transfer:

Q: Write an equation for the proton transfer reaction that occurs when each

Write an equation for the proton transfer reaction that occurs when each of the following bases reacts with water. In each case, draw curved arrows that show a mechanism for the proton transfer:

Q: In each case, identify the more stable anion. Explain why

In each case, identify the more stable anion. Explain why it is more stable:

Q: Later in this chapter (Section 7.12), we will

Later in this chapter (Section 7.12), we will see that a carbocation can be formed from an alcohol substrate in the presence of an acid, and an example of such a reaction is given below. This reaction...

Q: For each pair of compounds below, identify the more acidic compound

For each pair of compounds below, identify the more acidic compound:

Q: HA has a pKa of 15, while HB has a pKa

HA has a pKa of 15, while HB has a pKa of 5. Draw the equilibrium that would result upon mixing HB with NaA. Does the equilibrium favor formation of HA or formation of HB?

Q: For each reaction below, draw a mechanism (curved arrows)

For each reaction below, draw a mechanism (curved arrows) and then predict which side of the reaction is favored under equilibrium conditions:

Q: Rank the following anions in terms of increasing basicity: /

Rank the following anions in terms of increasing basicity:

Q: For each compound below, identify the most acidic proton in the

For each compound below, identify the most acidic proton in the compound:

Q: In each case below, identify the acid and the base.

In each case below, identify the acid and the base. Then draw the curved arrows showing a proton transfer reaction. Draw the products of that proton transfer and then predict the position of equilibri...

Q: Draw all constitutional isomers with the molecular formula C2H6S and rank them

Draw all constitutional isomers with the molecular formula C2H6S and rank them in terms of increasing acidity.

Q: Draw all constitutional isomers with the molecular formula C3H8O and rank them

Draw all constitutional isomers with the molecular formula C3H8O and rank them in terms of increasing acidity.

Q: Consider the structure of cyclopentadiene and then answer the following questions:

Consider the structure of cyclopentadiene and then answer the following questions: a. How many sp3 -hybridized carbon atoms are present in the structure of cyclopentadiene? b. Identify the most acid...

Q: In Section 3.4, we learned four factors (ARIO

In Section 3.4, we learned four factors (ARIO) for comparing the relative acidity of compounds. When two of these factors are in competition, the order of priority is the order in which these factors...

Q: a. Draw the products that are expected when tert-butyl

a. Draw the products that are expected when tert-butyl bromide undergoes solvolysis in isopropanol, (CH3)2CHOH. b. The dielectric constant of isopropanol is 18. Would you expect the solvolysis of ter...

Q: As we will learn in Chapter 20, treating a lactone (

As we will learn in Chapter 20, treating a lactone (a cyclic ester) with sodium hydroxide will initially produce an anion: This anion rapidly undergoes an intramolecular proton transfer (see Problem...

Q: Consider the pKa values of the following constitutional isomers: /

Consider the pKa values of the following constitutional isomers: Using the rules that we developed in this chapter (ARIO), we might have expected these two compounds to have the same pKa. Nevertheles...

Q: Consider the following compound with the molecular formula C4H8O2: /

Consider the following compound with the molecular formula C4H8O2: a. Draw a constitutional isomer that you expect will be approximately one trillion (1012) times more acidic than the compound above....

Q: There are only four constitutional isomers with the molecular formula C4H9NO2 that

There are only four constitutional isomers with the molecular formula C4H9NO2 that contain a nitro group (−NO2). Three of these isomers have similar pKa values, while the fourth isomer has a much high...

Q: Predict which of the following compounds is more acidic and explain your

Predict which of the following compounds is more acidic and explain your choice:

Q: Below is the structure of rilpivirine, a promising new anti-

Below is the structure of rilpivirine, a promising new anti-HIV drug that combats resistant strains of HIV. Its ability to side-step resistance will be discussed in the upcoming chapter. a. Identify...

Q: Most common amines (RNH2) exhibit pKa values between 35 and

Most common amines (RNH2) exhibit pKa values between 35 and 45. R represents the rest of the compound (generally carbon and hydrogen atoms). However, when R is a cyano group, the pKa is found to be dr...

Q: In one step of a recent total synthesis of (−)-seimatopolide A

In one step of a recent total synthesis of (−)-seimatopolide A, a potential antidiabetic drug, the following two structures reacted with each other in an acid-base reaction. a. Iden...

Q: The following compound has been designed to allow for labeling of a

The following compound has been designed to allow for labeling of a specific site of a protein. Identify the four most acidic protons in this compound, and rank them in order of increasing acidity.

Q: Asteltoxin, isolated from the cultures of Aspergillus stellatus, exhibits a

Asteltoxin, isolated from the cultures of Aspergillus stellatus, exhibits a potent inhibitory effect on the activity of E. coli BF1-ATPase. During S. L. Schreiber’s synthesis of aste...

Q: Draw the product for each of the following SN2 reactions:

Draw the product for each of the following SN2 reactions: a. (S)-2-Chloropentane and NaSH b. (R)-3-Iodohexane and NaCl c. (R)-2-Bromohexane and NaCN d. 1-Bromoheptane and NaOH

Q: For each pair of compounds, identify which is expected to undergo

For each pair of compounds, identify which is expected to undergo solvolysis more rapidly in water, and explain your choice in each case:

Q: Deuterium (D) is an isotope of hydrogen, in which

Deuterium (D) is an isotope of hydrogen, in which the nucleus has one proton and one neutron. This nucleus, called a deuteron, behaves very much like a proton, although there are observed differences...

Q: The bengamides are a series of natural products that have shown inhibitory

The bengamides are a series of natural products that have shown inhibitory effects on the enzyme methionine aminopeptidase, which plays a key role in the growth of new blood vessels, a necessary proce...

Q: In each of the following compounds, identify all carbon atoms that

In each of the following compounds, identify all carbon atoms that you expect will be deficient in electron density (δ+). If you need help, refer to Section 1.5.

Q: In the compound below, identify all carbon atoms that are electron

In the compound below, identify all carbon atoms that are electron deficient (δ+) and all carbon atoms that are electron rich (δ−). Justify your answer with...

Q: Consider the following two compounds: / a.

Consider the following two compounds: a. Identify which of these two compounds has greater resonance stabilization. b. Would you expect compound C (below) to have a resonance stabilization that is m...

Q: The natural products 3 and 4 have similar core structures even though

The natural products 3 and 4 have similar core structures even though they have been isolated from different plants. This allowed both of them to be made in the laboratory from a common precursor 2, w...

Q: During a synthesis of (+)-coronafacic acid, a key component in

During a synthesis of (+)-coronafacic acid, a key component in the plant toxin coronatine, the following reaction was performed, in which a ketone was converted into an acetal (the acetal functional g...

Q: Compounds 1 and 2 were prepared, and the difference in their

Compounds 1 and 2 were prepared, and the difference in their respective heats of combustion was found to be 17.2 kJ/mol. a. Redraw compounds 1 and 2 showing chair conformations for the six-membered r...

Q: Phenalamide A2 belongs to a class of natural products that are of

Phenalamide A2 belongs to a class of natural products that are of interest because of their antibiotic, antifungal, and antiviral activity. In the first total synthesis of this compound, the following...

Q: The formation of a variety of compounds called oxazolidinones is important for

The formation of a variety of compounds called oxazolidinones is important for the synthesis of many different natural products and other compounds that have potential use as future medicines. One met...

Q: Draw the expected products of the following solvolysis process: /

Draw the expected products of the following solvolysis process:

Q: The following compound belongs to a class of compounds, called estradiol

The following compound belongs to a class of compounds, called estradiol derivatives, which show promise in the treatment of breast cancer: a. Determine the hybridization state of Ca, Cb, and Cc. b...

Q: Identify and name the parent in each of the following compounds:

Identify and name the parent in each of the following compounds:

Q: Identify the two compounds below that have the same parent:

Identify the two compounds below that have the same parent:

Q: Under strongly acidic conditions, hexane is observed to undergo an isomerization

Under strongly acidic conditions, hexane is observed to undergo an isomerization process, during which it is converted into branched alkanes having the same molecular formula as hexane (C6H14). The ra...

Q: For each of the following compounds, identify all groups that would

For each of the following compounds, identify all groups that would be considered substituents and then indicate how you would name each substituent:

Q: The following compound is found in the urine of male mice and

The following compound is found in the urine of male mice and is believed to play a role both in attracting females and inducing aggression toward other males. Identify and name all substituents in th...

Q: For each of the following compounds, identify all groups that would

For each of the following compounds, identify all groups that would be considered substituents and then indicate the systematic name as well as the common name for each substituent:

Q: Bile acids, such as compound 1, are made from cholesterol

Bile acids, such as compound 1, are made from cholesterol in the liver through a series of reactions that are catalyzed by enzymes. Compound 2 is an important intermediate in this pathway. Compound 2...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: Draw a bond-line drawing for each of the following compounds

Draw a bond-line drawing for each of the following compounds: a. 3-Isopropyl-2,4-dimethylpentane   b. 4-Ethyl-2-methylhexane c. 1,1,2,2-Tetramethylcyclopropane

Q: Traditional medicines derived from the roots of nut-grass (Cyperus

Traditional medicines derived from the roots of nut-grass (Cyperus rotundus) have been used to treat a variety of ailments, including blood disorders and leprosy. Compound 2 is the active component in...

Q: When crude oil is distilled, the fraction collected in the boiling

When crude oil is distilled, the fraction collected in the boiling point range of 150–275°C is known as kerosene. Kerosene has a wide range of uses, from lamp oil to jet f...

Q: Name each of the following compounds: /

Name each of the following compounds:

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds: a. 2,2,3,3-Tetramethylbicyclo[2.2.1]heptane b. 8,8-Diethylbicyclo[3.2.1]octane c. 3-Isopropylbicyclo[3.2.0]heptane

Q: Vitamin D helps the body absorb calcium, iron, magnesium,

Vitamin D helps the body absorb calcium, iron, magnesium, phosphate, and zinc. Several compounds with the general structure below were synthesized and tested for their ability to mimic vitamin D activ...

Q: For each pair of compounds, identify whether they are constitutional isomers

For each pair of compounds, identify whether they are constitutional isomers or two representations of the same compound:

Q: As we will soon see in Section 4.5, gasoline

As we will soon see in Section 4.5, gasoline is a complex mixture of alkanes and other hydrocarbons, and the term “octane rating” is used as a standard measure of the performance of engine fuel. In th...

Q: In each case below, draw a Newman projection as viewed from

In each case below, draw a Newman projection as viewed from the angle indicated:

Q: Various Newman projections of the compound shown below were evaluated using computational

Various Newman projections of the compound shown below were evaluated using computational methods to determine its most stable three-dimensional shape. We will be learning more about such conformation...

Q: For each of the following compounds, predict the energy barrier to

For each of the following compounds, predict the energy barrier to rotation (looking down any one of the C−C bonds). Draw a Newman projection and then compare the staggered and eclipsed conformations....

Q: In each case below, identify the highest and lowest energy conformations

In each case below, identify the highest and lowest energy conformations. In cases where two or three conformations are degenerate, draw only one as your answer.

Q: Draw all of the expected products for each of the following solvolysis

Draw all of the expected products for each of the following solvolysis reactions:

Q: The conformations of (+)-epichlorohydrin (1), viewed along the Ca

The conformations of (+)-epichlorohydrin (1), viewed along the Ca−Cb bond, can be analyzed in exactly the same manner as the acyclic alkanes discussed in Chapter 4. a. Draw all stag...

Q: Practice drawing a chair several times using a blank piece of paper

Practice drawing a chair several times using a blank piece of paper. Repeat the procedure until you can do it without looking at the instructions above. For each of your chairs, make sure that it cont...

Q: Chemists have developed micron-sized, doughnut-shaped structures that

Chemists have developed micron-sized, doughnut-shaped structures that might be used someday to deliver drugs across cell membranes. During a procedure to prepare such micronsized structures, dioxane (...

Q: Practice drawing a chair conformation with all six axial positions and all

Practice drawing a chair conformation with all six axial positions and all six equatorial positions. Practice several times on a blank piece of paper. Repeat until you can draw all twelve positions wi...

Q: (−)-Cassioside, an anti-ulcer agent isolated from the dried

(−)-Cassioside, an anti-ulcer agent isolated from the dried stem bark of Chinese cinnamon, contains two six-membered rings, one of which adopts a chair conformation as shown. a. Ide...

Q: Draw both chair conformations for each of the following compounds:

Draw both chair conformations for each of the following compounds:

Q: The following disubstituted cyclohexane, drawn in a Newman projection, was

The following disubstituted cyclohexane, drawn in a Newman projection, was shown to have moderate antiviral activity. a. As depicted above, is the adenine group (highlighted) occupying an axial or an...

Q: The most stable conformation of 5-hydroxy-1,3

The most stable conformation of 5-hydroxy-1,3-dioxane has the OH group in an axial position, rather than an equatorial position. Provide an explanation for this observation.

Q: Draw both conformations for each of the following compounds: /

Draw both conformations for each of the following compounds:

Q: Lindane (hexachlorocyclohexane) is an agricultural insecticide that can also be

Lindane (hexachlorocyclohexane) is an agricultural insecticide that can also be used in the treatment of head lice. Draw both chair conformations of lindane.

Q: The following tertiary alkyl halide was heated in ethanol for several days

The following tertiary alkyl halide was heated in ethanol for several days, and the resulting mixture of products contained five different elimination products and two substitution products: a. Draw...

Q: Draw the lowest energy conformation for each of the following compounds:

Draw the lowest energy conformation for each of the following compounds:

Q: In Problem 4.29, you drew the two chair conformations

In Problem 4.29, you drew the two chair conformations of lindane. Carefully inspect them and predict the difference in energy between them, if any.

Q: Compound A exists predominantly in a chair conformation, while compound B

Compound A exists predominantly in a chair conformation, while compound B exists predominantly in a twist boat conformation. Explain.

Q: Draw Haworth projections for cis-1,3-dimethylcyclohexane and

Draw Haworth projections for cis-1,3-dimethylcyclohexane and trans-1,3-dimethylcyclohexane. Then, for each compound, draw the two chair conformations. Use these conformations to determine whether the...

Q: Draw Haworth projections for cis-1,4-dimethylcyclohexane and

Draw Haworth projections for cis-1,4-dimethylcyclohexane and trans-1,4-dimethylcyclohexane. Then for each compound, draw the two chair conformations. Use these conformations to determine whether the c...

Q: Draw Haworth projections for cis-1,3-di-

Draw Haworth projections for cis-1,3-di-tert-butylcyclohexane and trans-1,3-di-tert-butylcyclohexane. One of these compounds exists in a chair conformation, while the other exists primarily in a twis...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: For each of the following pairs of compounds, identify whether the

For each of the following pairs of compounds, identify whether the compounds are constitutional isomers or different representations of the same compound:

Q: Use a Newman projection to draw the most stable conformation of 3

Use a Newman projection to draw the most stable conformation of 3-methylpentane, looking down the C2−C3 bond.

Q: Identify which of the following compounds is expected to have the larger

Identify which of the following compounds is expected to have the larger heat of combustion:

Q: For each pair of compounds below, identify which one is expected

For each pair of compounds below, identify which one is expected to undergo elimination more rapidly when treated with a strong base.

Q: Draw each of the following compounds: a. 2,

Draw each of the following compounds: a. 2,2,4-Trimethylpentane b. 1,2,3,4-Tetramethylcycloheptane c. 2,2,4,4-Tetraethylbicyclo[1.1.0]butane

Q: Sketch an energy diagram that shows a conformational analysis of 2,

Sketch an energy diagram that shows a conformational analysis of 2,2-dimethylpropane. Does the shape of this energy diagram more closely resemble the shape of the energy diagram for ethane or for buta...

Q: What are the relative energy levels of the three staggered conformations of

What are the relative energy levels of the three staggered conformations of 2,3-dimethylbutane when looking down the C2−C3 bond?

Q: Draw the ring flip for each of the following compounds:

Draw the ring flip for each of the following compounds:

Q: For each of the following pairs of compounds, identify the compound

For each of the following pairs of compounds, identify the compound that would have the higher heat of combustion:

Q: Draw a relative energy diagram showing a conformational analysis of 1,

Draw a relative energy diagram showing a conformational analysis of 1,2-dichloroethane. Clearly label all staggered conformations and all eclipsed conformations with the corresponding Newman projectio...

Q: In the following compound, identify the number of hydrogen atoms that

In the following compound, identify the number of hydrogen atoms that occupy axial positions as well as the number of hydrogen atoms that occupy equatorial positions:

Q: Draw a bond-line structure for each of the following compounds

Draw a bond-line structure for each of the following compounds:

Q: Assign IUPAC names for each of the following compounds: /

Assign IUPAC names for each of the following compounds:

Q: The barrier to rotation of bromoethane is 15 kJ/mol.

The barrier to rotation of bromoethane is 15 kJ/mol. Based on this information, determine the energy cost associated with the eclipsing interaction between a bromine atom and a hydrogen atom.

Q: Identify whether each of the following reactions is expected to exhibit a

Identify whether each of the following reactions is expected to exhibit a primary isotope effect if (CD3)3CBr is used instead of (CH3)3CBr. Explain your reasoning in each case.

Q: Menthol, isolated from various mint oils, is used in the

Menthol, isolated from various mint oils, is used in the treatment of minor throat irritation. Draw both chair conformations of menthol and indicate which conformation is lower in energy.

Q: Draw both chair conformations for each of the following compounds. In

Draw both chair conformations for each of the following compounds. In each case, identify the more stable chair conformation: a. Methylcyclohexane b. trans-1,2-Diisopropylcyclohexane c. cis-1,3-Dii...

Q: For each of the following pairs of compounds, determine which compound

For each of the following pairs of compounds, determine which compound is more stable (you may find it helpful to draw out the chair conformations):

Q: Draw a Newman projection of the following compound as viewed from the

Draw a Newman projection of the following compound as viewed from the angle indicated:

Q: Glucose (a sugar) is produced by photosynthesis and is used

Glucose (a sugar) is produced by photosynthesis and is used by cells to store energy. Draw the most stable conformation of glucose:

Q: Sketch an energy diagram showing a conformational analysis of 2,2

Sketch an energy diagram showing a conformational analysis of 2,2,3,3-tetramethylbutane. Use Table 4.6 to determine the energy difference between staggered and eclipsed conformations of this compound....

Q: Rank the following conformations in order of increasing energy: /

Rank the following conformations in order of increasing energy:

Q: Consider the following two conformations of 2,3-dimethylbutane.

Consider the following two conformations of 2,3-dimethylbutane. For each of these conformations, use Table 4.6 to determine the total energy cost associated with all torsional strain and steric strain...

Q: myo-Inositol is a polyol (a compound containing many OH

myo-Inositol is a polyol (a compound containing many OH groups) that serves as the structural basis for a number of secondary messengers in eukaryotic cells. Draw the more stable chair conformation of...

Q: Below is the numbered skeleton of trans-decalin: /

Below is the numbered skeleton of trans-decalin: Identify whether each of the following substituents would be in an equatorial position or an axial position: a. A group at the C-2 position, pointing...

Q: Identify the major and minor product(s) that are expected

Identify the major and minor product(s) that are expected for each of the following reactions.

Q: There are 18 constitutional isomers with the molecular formula C8H18. Without

There are 18 constitutional isomers with the molecular formula C8H18. Without drawing all 18 isomers, determine how many of the isomers will have a parent name of heptane.

Q: Derivatives of griselimycin, a natural product isolated in the 1960s,

Derivatives of griselimycin, a natural product isolated in the 1960s, are being investigated for the treatment of tuberculosis. For each of the highlighted substituents in the griselimycin derivative...

Q: trans-1,3-Dichlorocyclobutane has a measurable dipole moment

trans-1,3-Dichlorocyclobutane has a measurable dipole moment. Explain why the individual dipole moments of the C−Cl bonds do not cancel each other to produce a zero net dipole moment...

Q: For each pair of compounds below, determine whether they are identical

For each pair of compounds below, determine whether they are identical compounds, constitutional isomers, or stereoisomers:

Q: Consider the structures of cis-1,2-dimethylcyclopropane and

Consider the structures of cis-1,2-dimethylcyclopropane and trans-1,2-dimethylcyclopropane: a. Which compound would you expect to be more stable? Explain your choice. b. Predict the difference in en...

Q: Compare the three staggered conformations of ethylene glycol. The anti conformation

Compare the three staggered conformations of ethylene glycol. The anti conformation of ethylene glycol is not the lowest energy conformation. The other two staggered conformations are actually lower i...

Q: Determine whether the following compounds are constitutional isomers: /

Determine whether the following compounds are constitutional isomers:

Q: Consider the following tetra-substituted cyclohexane: /

Consider the following tetra-substituted cyclohexane: a. Draw both chair conformations of this compound. b. Determine which conformation is more stable. c. At equilibrium, would you expect the comp...

Q: Consider the structures of cis-decalin and trans-decalin:

Consider the structures of cis-decalin and trans-decalin: a. Which of these compounds would you expect to be more stable? b. One of these two compounds is incapable of ring flipping. Identify it and...

Q: The structural unit below has been incorporated into a synthetic polymer designed

The structural unit below has been incorporated into a synthetic polymer designed to mimic the skeletal muscle protein titin. In its most stable conformation (shown), it forms one intramolecular hydro...

Q: Compound A and compound B are constitutional isomers with the molecular formula

Compound A and compound B are constitutional isomers with the molecular formula C3H7Cl. When compound A is treated with sodium methoxide, a substitution reaction predominates. When compound B is treat...

Q: Aspernomine, a natural product isolated from the fungus Aspergillus nomius,

Aspernomine, a natural product isolated from the fungus Aspergillus nomius, was found to be an antiinsectan (it protects against predation by insects). a. Two of the six-membered rings are represente...

Q: Phakellin (3), a natural product isolated from marine organisms,

Phakellin (3), a natural product isolated from marine organisms, has been studied for its potential use as an antibiotic agent. During studies aimed at developing a strategy for the synthesis of phake...

Q: Crude extracts from the ginkgo tree, Ginkgo biloba, have been

Crude extracts from the ginkgo tree, Ginkgo biloba, have been used for centuries to alleviate symptoms associated with asthma. There are four principal components of Ginkgo extracts, called ginkgolide...

Q: The pKa of the most acidic CH2 group in each of the

The pKa of the most acidic CH2 group in each of the following compounds was measured in DMSO as solvent. Given the data above, determine which of the following two compounds (5 or 6) is more acidic b...

Q: In the following compound, identify each C=C unit as

In the following compound, identify each C=C unit as cis, trans, or not stereoisomeric.

Q: Identify the number of stereoisomers that are possible for a compound with

Identify the number of stereoisomers that are possible for a compound with the following constitution: H2C=CHCH2CH2CH2CH=CH2.

Q: Compound X and compound Y are constitutional isomers with the molecular formula

Compound X and compound Y are constitutional isomers with the molecular formula C5H10. Compound X possesses a carbon-carbon double bond in the trans configuration, while compound Y possesses a carbon-...

Q: Identify all chiral centers in each of the following compounds:

Identify all chiral centers in each of the following compounds:

Q: Draw all constitutional isomers with the molecular formula C4H9Br and identify the

Draw all constitutional isomers with the molecular formula C4H9Br and identify the isomer(s) that possess chiral centers.

Q: Do you expect the following compound to be chiral? Explain your

Do you expect the following compound to be chiral? Explain your answer (consider whether this compound is superimposable on its mirror image).

Q: Compound A and compound B are constitutional isomers with the molecular formula

Compound A and compound B are constitutional isomers with the molecular formula C4H9Cl. Treatment of compound A with sodium methoxide gives trans-2-butene as the major product, while treatment of comp...

Q: Draw the enantiomer of each of the following compounds: /

Draw the enantiomer of each of the following compounds:

Q: Ixabepilone is a cytotoxic compound approved by the FDA in 2007 for

Ixabepilone is a cytotoxic compound approved by the FDA in 2007 for the treatment of advanced breast cancer. Bristol-Myers Squibb is marketing this drug under the trade name Ixempra. Draw the enantiom...

Q: Each of the following compounds possesses carbon atoms that are chiral centers

Each of the following compounds possesses carbon atoms that are chiral centers. Locate each of these chiral centers and identify the configuration of each one:

Q: In Chapter 24, we will see that amino acids (like

In Chapter 24, we will see that amino acids (like the ones shown below) can be linked together to give short chains, called peptides, or longer chains (≈50–2000 ami...

Q: When 0.575 g of monosodium glutamate (MSG) is

When 0.575 g of monosodium glutamate (MSG) is dissolved in 10.0 mL of water and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is +1.47°. Calcula...

Q: When 0.095 g of cholesterol is dissolved in 1.

When 0.095 g of cholesterol is dissolved in 1.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is −2.99°. Calculate the specific...

Q: When 1.30 g of menthol is dissolved in 5.

When 1.30 g of menthol is dissolved in 5.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is +0.57°. Calculate the specific rota...

Q: Levetiracetam is used for the treatment of seizures in patients with epilepsy

Levetiracetam is used for the treatment of seizures in patients with epilepsy. For patients who have a hard time swallowing the needed pills twice daily, relief is in sight now that the FDA has grante...

Q: The specific rotation of l-dopa in water (at 15

The specific rotation of l-dopa in water (at 15°C) is −39.5. A chemist prepared a mixture of l-dopa and its enantiomer, and this mixture had a specific rotation of −37. Calculate the % ee of this mixt...

Q: The specific rotation of ephedrine in ethanol (at 20°C

The specific rotation of ephedrine in ethanol (at 20°C) is −6.3. A chemist prepared a mixture of ephedrine and its enantiomer, and this mixture had a specific rotation of −6.0. Calculate the % ee of t...

Q: A common method for confirming the proposed structure and stereochemistry of a

A common method for confirming the proposed structure and stereochemistry of a natural product is to synthesize the proposed structure and then compare its properties with those of the natural product...

Q: An unknown compound with the molecular formula C6H13Cl is treated with sodium

An unknown compound with the molecular formula C6H13Cl is treated with sodium ethoxide to produce 2,3-dimethyl-2-butene as the major product. Identify the structure of the unknown compound.

Q: The specific rotation of vitamin B7 in water (at 22°

The specific rotation of vitamin B7 in water (at 22°C) is +92. A chemist prepared a mixture of vitamin B7 and its enantiomer, and this mixture had a specific rotation of +85. Calculate the % ee of thi...

Q: Synthetic chemists often employ enzymes to conduct asymmetric syntheses that favor the

Synthetic chemists often employ enzymes to conduct asymmetric syntheses that favor the production of one enantiomer over another. Baker’s yeast was used to convert the diketone shown...

Q: Identify whether each of the following pairs of compounds are enantiomers or

Identify whether each of the following pairs of compounds are enantiomers or diastereomers:

Q: In the field of chemical research, one area of interest is

In the field of chemical research, one area of interest is the study of how variations in structure, including stereochemical variations, affect the biological activity of natural products. (â&#...

Q: For each of the following objects determine whether or not it possesses

For each of the following objects determine whether or not it possesses a plane of symmetry:

Q: In the previous problem, one object has three planes of symmetry

In the previous problem, one object has three planes of symmetry. Identify that object.

Q: Each of the following molecules has one plane of symmetry. Find

Each of the following molecules has one plane of symmetry. Find the plane of symmetry in each case: (Hint: A plane of symmetry can slice atoms in half.)

Q: Draw all possible stereoisomers for each of the following compounds. Each

Draw all possible stereoisomers for each of the following compounds. Each possible stereoisomer should be drawn only once:

Q: A racemic mixture with the constitution shown below was isolated from the

A racemic mixture with the constitution shown below was isolated from the Maytenus apurimacensis plant that is used in South American folk medicine. In an effort to find another source of these compou...

Q: Identify the configuration of the chiral center in each of the following

Identify the configuration of the chiral center in each of the following compounds:

Q: Predict the major and minor products for each of the following reactions

Predict the major and minor products for each of the following reactions.

Q: Protease inhibitors are a class of anti-viral drugs that have

Protease inhibitors are a class of anti-viral drugs that have had success in treating HIV/AIDS. The following molecules were synthesized as potential HIV protease inhibitors. Compound 1 was found to b...

Q: Determine whether each of the following allenes is chiral or achiral:

Determine whether each of the following allenes is chiral or achiral:

Q: For each of the following alkenes, assign the configuration of the

For each of the following alkenes, assign the configuration of the double bond as either E or Z:

Q: Bogorol A is a natural product with the potential to fight antibiotic

Bogorol A is a natural product with the potential to fight antibiotic-resistant bacteria. Shown below is an intermediate that was used in a synthesis of bogorol A. Assign the configuration of the alke...

Q: Atorvastatin is sold under the trade name Lipitor and is used for

Atorvastatin is sold under the trade name Lipitor and is used for lowering cholesterol. Annual global sales of this compound exceed $13 billion. Assign a configuration to each chiral center in atorvas...

Q: Atropine, extracted from the plant Atropa belladonna, has been used

Atropine, extracted from the plant Atropa belladonna, has been used in the treatment of bradycardia (low heart rate) and cardiac arrest. Draw the enantiomer of atropine:

Q: Paclitaxel (marketed under the trade name Taxol) is found in

Paclitaxel (marketed under the trade name Taxol) is found in the bark of the Pacific yew tree, Taxus brevifolia, and is used in the treatment of cancer: a. Draw the enantiomer of paclitaxel. b. How...

Q: Assign the configuration of the chiral center in the following compound:

Assign the configuration of the chiral center in the following compound:

Q: Carbon is not the only element that can function as a chiral

Carbon is not the only element that can function as a chiral center. In Problem 5.6 we saw an example in which a phosphorus atom is a chiral center. In such a case, the lone pair is always assigned th...

Q: For each of the following pairs of compounds, determine the relationship

For each of the following pairs of compounds, determine the relationship between the two compounds:

Q: Predict the major product for each of the following reactions.

Predict the major product for each of the following reactions.

Q: Identify the number of stereoisomers expected for each of the following:

Identify the number of stereoisomers expected for each of the following:

Q: Draw the enantiomer for each of the following compounds: /

Draw the enantiomer for each of the following compounds:

Q: Identify the configuration of each chiral center in the following compounds:

Identify the configuration of each chiral center in the following compounds:

Q: You are given a solution containing a pair of enantiomers (A

You are given a solution containing a pair of enantiomers (A and B). Careful measurements show that the solution contains 98% A and 2% B. What is the ee of this solution?

Q: Predict the value for the specific rotation of the following compound.

Predict the value for the specific rotation of the following compound. Explain your answer.

Q: The specific rotation of (S)-2-butanol is +

The specific rotation of (S)-2-butanol is +13.5. If 1.00 g of its enantiomer is dissolved in 10.0 mL of ethanol and placed in a sample cell with a length of 1.00 dm, what observed rotation do you expe...

Q: The specific rotation of l-alanine in water (at 25

The specific rotation of l-alanine in water (at 25°C) is +2.8. A chemist prepared a mixture of l-alanine and its enantiomer, and 3.50 g of the mixture was dissolved in 10.0 mL of water. This solution...

Q: For each of the following pairs of compounds, determine the relationship

For each of the following pairs of compounds, determine the relationship between the two compounds:

Q: For each of the following pairs of compounds, determine the relationship

For each of the following pairs of compounds, determine the relationship between the two compounds:

Q: Determine whether each statement is true or false: a.

Determine whether each statement is true or false: a. A racemic mixture of enantiomers is optically inactive. b. A meso compound will have exactly one nonsuperimposable mirror image. c. Rotating th...

Q: Draw a plausible mechanism for each of the following transformations /

Draw a plausible mechanism for each of the following transformations

Q: Determine the configuration for every chiral center in each of the following

Determine the configuration for every chiral center in each of the following compounds:

Q: Draw the enantiomer of each compound in the previous problem.

Draw the enantiomer of each compound in the previous problem.

Q: When 0.075 g of penicillamine is dissolved in 10.

When 0.075 g of penicillamine is dissolved in 10.0 mL of pyridine and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is −0.47°. Calculate the spe...

Q: (R)-Limonene is found in many citrus fruits, including

(R)-Limonene is found in many citrus fruits, including oranges and lemons: For each of the following compounds identify whether it is (R)-limonene or its enantiomer, (S)-limonene:

Q: Each of the following compounds possesses a plane of symmetry. Find

Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformati...

Q: cis-1,3-Dimethylcyclobutane has two planes of symmetry

cis-1,3-Dimethylcyclobutane has two planes of symmetry. Draw the compound and identify both planes of symmetry.

Q: For each of the following pairs of compounds, determine the relationship

For each of the following pairs of compounds, determine the relationship between the two compounds:

Q: Determine whether each of the following compounds is optically active or optically

Determine whether each of the following compounds is optically active or optically inactive:

Q: Draw bond-line structures using wedges and dashes for the following

Draw bond-line structures using wedges and dashes for the following compounds:

Q: The following questions apply to the five compounds in the previous problem

The following questions apply to the five compounds in the previous problem. a. Which compound is meso? b. Would an equal mixture of compounds b and c be optically active? c. Would an equal mixture...

Q: Provide a synthesis for the target molecule shown below, starting with

Provide a synthesis for the target molecule shown below, starting with an alkyl halide of your choice. Show your retrosynthetic analysis, and then provide a complete synthesis, showing all necessary r...

Q: Triphenylmethane dyes are among the first synthetic dyes developed for commercial use

Triphenylmethane dyes are among the first synthetic dyes developed for commercial use. A comparison of the structures of these compounds reveals that even small differences in structure can lead to la...

Q: Draw all three staggered conformations for the following compound, viewed along

Draw all three staggered conformations for the following compound, viewed along the C2−C3 bond. Determine which conformation is the most stable, taking into account gauche interactio...

Q: The all-trans-1,2,3,4

The all-trans-1,2,3,4,5,6-hexaethylcyclohexane (1) prefers the allequatorial conformation while the all-trans-1,2,3,4,5,6-hexaisopropylcyclohexane (2) possesses a severely destabilized all-equatorial...

Q: When a toluene solution of the sugar-derived compound below is

When a toluene solution of the sugar-derived compound below is cooled, the molecules self-assemble into fibrous aggregates which work in concert with the surface tension of the solvent to form a stabl...

Q: Consider the structure of the following ketone: /

Consider the structure of the following ketone: a. Does this compound exhibit rotational symmetry? b. Does this compound exhibit reflectional symmetry? c. Is the compound chiral? If so, draw its en...

Q: The natural product meloscine can be prepared via a 19-step

The natural product meloscine can be prepared via a 19-step synthesis, featuring the following allene as a key intermediate: a. Draw a Newman projection of the allene when viewed from the leftÂ...

Q: Each of 10 stereoisomeric sugar derivatives can be prepared via a multiple

Each of 10 stereoisomeric sugar derivatives can be prepared via a multiple-step synthesis starting from either glucuronolactone 1D or its enantiomer 1L. Depending on the specific series of reactions u...

Q: The following compound is an intermediate in the synthesis of a gelator

The following compound is an intermediate in the synthesis of a gelator, which is a compound capable of self-assembling to form a gel in an organic liquid. a. Identify each functional group in the mo...

Q: The following compound is an amino acid derivative (Chapter 25).

The following compound is an amino acid derivative (Chapter 25). In solution, molecules of this compound show a tendency to “stick” together, or self-as...

Q: In Chapter 3, we will explore the factors that render compounds

In Chapter 3, we will explore the factors that render compounds acidic or basic. Tropolone (1) is a compound that is both fairly acidic and fairly basic. It is acidic because it is capable of losing a...

Q: Which is the better retrosynthesis for the given target molecule? Explain

Which is the better retrosynthesis for the given target molecule? Explain, and provide a one-step synthesis of the target molecule.

Q: Chlorofluorocarbons (CFCs) are gases that were once widely used as

Chlorofluorocarbons (CFCs) are gases that were once widely used as refrigerants and propellants. When it was discovered that these molecules contributed to the depletion of the ozone layer, their use...

Q: Each of the following compounds can be prepared with an alkyl iodide

Each of the following compounds can be prepared with an alkyl iodide and a suitable nucleophile. In each case, identify the alkyl iodide and the nucleophile that you would use.

Q: For each of the following reactions identify the arrow-pushing pattern

For each of the following reactions identify the arrow-pushing pattern that is being utilized:

Q: Rank the three carbocations shown in terms of increasing stability:

Rank the three carbocations shown in terms of increasing stability:

Q: The following hypothetical compound cannot be prepared or isolated, because it

The following hypothetical compound cannot be prepared or isolated, because it has a very reactive nucleophilic center and a very reactive electrophilic center, and the two sites would react with each...

Q: Each of the following compounds exhibits two electrophilic centers. Identify both

Each of the following compounds exhibits two electrophilic centers. Identify both centers in each compound. (Hint: You will need to draw resonance structures in each case.)

Q: Draw the transition state for each of the following SN2 reactions:

Draw the transition state for each of the following SN2 reactions:

Q: Draw all constitutional isomers with the molecular formula C4H9Br, and then

Draw all constitutional isomers with the molecular formula C4H9Br, and then arrange them in order of: a. increasing reactivity toward an SN2 reaction. b. increasing reactivity toward an E2 reaction....

Q: For the following mechanism, identify the sequence of arrowpushing patterns:

For the following mechanism, identify the sequence of arrowpushing patterns:

Q: For the following mechanism, identify the sequence of arrow-pushing

For the following mechanism, identify the sequence of arrow-pushing patterns:

Q: The following two reactions will be explored in different chapters. Yet

The following two reactions will be explored in different chapters. Yet, they are very similar. Identify and compare the sequences of arrowpushing patterns for the two reactions.

Q: For the following mechanism, identify the sequence of arrow-pushing

For the following mechanism, identify the sequence of arrow-pushing patterns:

Q: Below are two potential methods for preparing the same ether, but

Below are two potential methods for preparing the same ether, but only one of them is successful. Identify the successful approach and explain your choice.

Q: Lithium salts have been used for decades to treat mental illnesses,

Lithium salts have been used for decades to treat mental illnesses, including depression and bipolar disorder. Although the treatment is effective, researchers are still trying to determine how lithiu...

Q: For the following mechanism, identify the sequence of arrow-pushing

For the following mechanism, identify the sequence of arrow-pushing patterns:

Q: For the following mechanism, identify the sequence of arrow-pushing

For the following mechanism, identify the sequence of arrow-pushing patterns:

Q: Draw curved arrows for each step of the following mechanism:

Draw curved arrows for each step of the following mechanism:

Q: Draw curved arrows for each step of the following mechanism:

Draw curved arrows for each step of the following mechanism:

Q: Draw curved arrows for each step of the following mechanism:

Draw curved arrows for each step of the following mechanism:

Q: Draw curved arrows for each step of the following mechanism:

Draw curved arrows for each step of the following mechanism:

Q: Draw the transition state for the substitution reaction that occurs between ethyl

Draw the transition state for the substitution reaction that occurs between ethyl iodide and sodium acetate (CH3CO2Na).

Q: Predict whether each of the following carbocations will rearrange. If so

Predict whether each of the following carbocations will rearrange. If so, draw the expected rearrangement using curved arrows.

Q: Consider the following reaction: / The following rate

Consider the following reaction: The following rate equation has been experimentally established for this process Rate = k[HO−][CH3CH2Br] An energy diagram for this process is show...

Q: When (R)-3-bromo-2,3-

When (R)-3-bromo-2,3-dimethylpentane is treated with sodium hydroxide, four different alkenes are formed. Draw all four products and rank them in terms of stability. Which do you expect to be the majo...

Q: Identify whether each of the following factors will affect the rate of

Identify whether each of the following factors will affect the rate of a reaction: a. Keq   b. ΔG   c. Temperature d. ΔH   e. Ea   f. ΔS

Q: Draw a Lewis structure for each of the following compounds:

Draw a Lewis structure for each of the following compounds: a. C2H6 b. C2H4 c. C2H2 d. C3H8 e. C3H6 f. CH3OH

Q: In the presence of a special type of catalyst, hydrogen gas

In the presence of a special type of catalyst, hydrogen gas will add across a triple bond to produce a double bond: The process is exothermic. Do you expect a high temperature to favor products or re...

Q: Consider the following reaction. Predict whether an increase in temperature will

Consider the following reaction. Predict whether an increase in temperature will favor reactants or products. Justify your prediction.

Q: When an amine is protonated, the resulting ammonium ion is not

When an amine is protonated, the resulting ammonium ion is not electrophilic: However, when an imine is protonated, the resulting iminium ion is highly electrophilic: Explain this difference in reac...

Q: Draw the curved arrows that accomplish the following transformation: /

Draw the curved arrows that accomplish the following transformation:

Q: As seen in Problem 6.18, carbocation rearrangements can occur

As seen in Problem 6.18, carbocation rearrangements can occur via the migration of a carbon atom other than a methyl group. For example, carbocation 1 was observed to rearrange to give carbocation 2....

Q: Under basic conditions (catalytic MeO− in MeOH), compound 1

Under basic conditions (catalytic MeO− in MeOH), compound 1 rearranges through the mechanistic sequence shown below to a propellane-type isomer 5. Note that MeO− is...

Q: Compound 1 has been prepared and studied to investigate a novel type

Compound 1 has been prepared and studied to investigate a novel type of intramolecular elimination mechanism. The proposed mechanistic pathway for this transformation is presented below. Complete the...

Q: (S)-2-Iodopentane undergoes racemization in a solution of

(S)-2-Iodopentane undergoes racemization in a solution of sodium iodide in DMSO. Explain.

Q: Smoking tobacco with a water pipe, or hookah, is often

Smoking tobacco with a water pipe, or hookah, is often perceived as being less dangerous than smoking cigarettes, but hookah smoke has been found to contain the same variety of toxins and carcinogens...

Q: The following sequence was utilized in a biosynthetically inspired synthesis of preussomerin

The following sequence was utilized in a biosynthetically inspired synthesis of preussomerin, an antifungal agent isolated from a coprophilous (dung-loving) fungus. a. Draw curved arrows for each ste...

Q: (+)-Aureol is a natural product that shows selective anticancer activity against

(+)-Aureol is a natural product that shows selective anticancer activity against certain strains of lung cancer and colon cancer. A key step in the biosynthesis of (+)-aureol (how nature makes the mol...

Q: Borane (BH3) is very unstable and quite reactive. Draw

Borane (BH3) is very unstable and quite reactive. Draw a Lewis structure of borane and explain the source of the instability.

Q: Strychnine (6), a notorious poison isolated from the strychnos genus

Strychnine (6), a notorious poison isolated from the strychnos genus, is commonly used as a pesticide in the treatment of rodent infestations. The sophisticated structure of strychnine, first elucidat...

Q: The specific rotation of (S)-carvone (at +20

The specific rotation of (S)-carvone (at +20°C) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of −55°. a. What is the specific rota...

Q: Identify whether each of the following compounds is chiral or achiral:

Identify whether each of the following compounds is chiral or achiral:

Q: The specific rotation of vitamin C (using the D line of

The specific rotation of vitamin C (using the D line of sodium, at 20°C) is +24. Predict what the observed rotation would be for a solution containing 0.100 g of vitamin C dissolved in 10.0 mL of etha...

Q: There are many examples of carbocation rearrangements that cannot be classified as

There are many examples of carbocation rearrangements that cannot be classified as a methyl shift or hydride shift. For example, consider the following rearrangement that was employed in the synthesis...

Q: Compound 1 undergoes a thermal elimination of nitrogen at 250°C

Compound 1 undergoes a thermal elimination of nitrogen at 250°C to form nitrile 4. One proposed (and subsequently refuted) mechanism for this transformation involves intermediates 2 and 3:...

Q: In the presence of a Lewis acid, compound 1 rearranges,

In the presence of a Lewis acid, compound 1 rearranges, via intermediate 2, to afford compound 3. a. Draw curved arrows showing how 1 is transformed into 2. Note that the Lewis acid has been left out...

Q: A total synthesis of the marine natural product aldingenin C in the

A total synthesis of the marine natural product aldingenin C in the laboratory resulted in a significant revision of its proposed structure. The synthesis involved the conversion of compound 1 to comp...

Q: Draw a Fischer projection for each of the following compounds, placing

Draw a Fischer projection for each of the following compounds, placing the −CO2H group at the top:

Q: In Chapter 9, we will see that an acetylide ion (

In Chapter 9, we will see that an acetylide ion (formed by treatment of acetylene with a strong base) can serve as a nucleophile in an SN2 reaction: This reaction provides a useful method for making...

Q: There are only two stereoisomers of 1,4-dimethylcyclohexane.

There are only two stereoisomers of 1,4-dimethylcyclohexane. Draw them and explain why only two stereoisomers are observed.

Q: There are four constitutional isomers with the molecular formula C3H9N. Draw

There are four constitutional isomers with the molecular formula C3H9N. Draw a Lewis structure for each isomer and determine the number of lone pairs on the nitrogen atom in each case.

Q: How many stereoisomers do you expect for the following compound? Draw

How many stereoisomers do you expect for the following compound? Draw all of the stereoisomers.

Q: For each of the following pairs of compounds, determine the relationship

For each of the following pairs of compounds, determine the relationship between the two compounds:

Q: The following compound is known to be chiral. Draw its enantiomer

The following compound is known to be chiral. Draw its enantiomer and explain the source of chirality.

Q: The following compound is optically inactive. Explain why /

The following compound is optically inactive. Explain why

Q: The following compound, whose central ring is referred to as a

The following compound, whose central ring is referred to as a 1,2,4-trioxane, is an anticancer agent that demonstrates activity against canine osteosarcoma. Assign the configuration of each chiral ce...

Q: Coibacin B is a natural product that exhibits potent antiinflammatory activity and

Coibacin B is a natural product that exhibits potent antiinflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites: a. Assign the configura...

Q: When 3-bromo-2,4-dimethylpentane is treated

When 3-bromo-2,4-dimethylpentane is treated with sodium hydroxide (NaOH), only one alkene is formed. Draw the product and explain why this reaction has only one regiochemical outcome.

Q: There are many forms of cancer, all of which involve abnormal

There are many forms of cancer, all of which involve abnormal cell growth. The growth and production of cells, called cell proliferation, is known to involve an enzyme called protein farnesyltransfera...

Q: Over 100 cannabinoid compounds, including the one shown below, have

Over 100 cannabinoid compounds, including the one shown below, have been isolated from the marijuana plant in order to explore the plant’s medicinal properties. Identify the chiral c...

Q: One class of anti-viral drugs, called protease inhibitors,

One class of anti-viral drugs, called protease inhibitors, has been studied for the treatment of hepatitis C. A series of related compounds, represented by structure 2 (with varying R groups) were pre...

Q: 54. For a reaction with ΔG < 0, which of

54. For a reaction with ΔG a. The reaction must be exothermic b. The reaction must be endothermic c. Keq > 1 d. None of the above 55. Which of the following can serve as a nucleophi...

Q: How many different alkenes will be produced when each of the following

How many different alkenes will be produced when each of the following substrates is treated with a strong base? a. 1-Chloropentane b. 2-Chloropentane c. 3-Chloropentane d. 2-Chloro-2-methylpentan...

Q: Draw the major product that is obtained when (2S,3S

Draw the major product that is obtained when (2S,3S)-2-Bromo3-phenylbutane is treated with sodium ethoxide, and explain the stereochemical outcome of this reaction.

Q: Predict the stereochemical outcome for each of the following E2 reactions.

Predict the stereochemical outcome for each of the following E2 reactions. In each case, draw only the major product of the reaction.

Q: Identify the sole product of the following reaction: /

Identify the sole product of the following reaction:

Q: In an effort to develop molecular surfaces with interesting electronic properties,

In an effort to develop molecular surfaces with interesting electronic properties, compounds such as the one below were prepared. Consider the possibilities for preparation of this c...

Q: Predict the major product for each of the following reactions:

Predict the major product for each of the following reactions:

Q: In each of the following cases, draw the structure of an

In each of the following cases, draw the structure of an alkyl halide that will undergo an E2 elimination to yield only the indicated alkene.

Q: 66. What is the strongest base that is present after methyl

66. What is the strongest base that is present after methyl magnesium bromide (CH3MgBr) is treated with water? 67. Which side of the following equilibrium is favored? a. The right side. b. The left...

Q: Draw the transition state for the reaction between tert-butyl chloride

Draw the transition state for the reaction between tert-butyl chloride and sodium hydroxide.

Q: Identify any formal charges in the structures below: /

Identify any formal charges in the structures below:

Q: Indicate whether you would use sodium ethoxide or potassium tert-butoxide

Indicate whether you would use sodium ethoxide or potassium tert-butoxide to achieve each of the following transformations.

Q: Melphalan is a chemotherapy drug used in the treatment of multiple myeloma

Melphalan is a chemotherapy drug used in the treatment of multiple myeloma and ovarian cancer. Melphalan is an alkylating agent belonging to the nitrogen mustard family. Draw a likely mechanism for th...

Q: 1-Bromobicyclo[2.2.2]octane does

1-Bromobicyclo[2.2.2]octane does not undergo an E2 reaction when treated with a strong base. Explain why not.

Q: Explain why the following reaction yields the Hofmann product exclusively (no

Explain why the following reaction yields the Hofmann product exclusively (no Zaitsev product at all) even though the base is not sterically hindered:

Q: Draw a plausible mechanism for each of the following transformations:

Draw a plausible mechanism for each of the following transformations:

Q: Chiral catalysts can be designed to favor the formation of a single

Chiral catalysts can be designed to favor the formation of a single enantiomer in reactions where a new chiral center is formed. Recently, a novel type of chiral copper catalyst was developed that is...

Q: 71. All of the following are representations of cis-1

71. All of the following are representations of cis-1,2-dimethylcyclohexane, EXCEPT: 72. All of the following are representations of 2-methylpentane, EXCEPT 73. Which of the following is expected to...

Q: When the following optically active alcohol is treated with HBr, a

When the following optically active alcohol is treated with HBr, a racemic mixture of alkyl bromides is obtained. Draw a mechanism for this process, and explain the stereochemical outcome.

Q: Identify the reagents you would use to achieve each of the following

Identify the reagents you would use to achieve each of the following transformations:

Q: Predict which of the following substrates will undergo a solvolysis reaction more

Predict which of the following substrates will undergo a solvolysis reaction more quickly. Explain your choice.

Q: 74. Which is the correct hybridization state and geometry for the

74. Which is the correct hybridization state and geometry for the carbon atom in HCN? a. sp, linear b. sp2, trigonal planar c. sp3, tetrahedral d. None of the above 75. Which of the following is...

Q: Draw a structure for each of the following ions; in each

Draw a structure for each of the following ions; in each case, indicate which atom possesses the formal charge: a. BH4– b. NH2– c. C2H5+

Q: 74. What is the configuration of the stereocenter in the following

74. What is the configuration of the stereocenter in the following compound? a. R b. S c. Z d. Depends on T 75. What is the relationship between the following two compounds? a. Enantiomers b. D...

Q: (S)-1-Bromo-1,2-diphenylethane

(S)-1-Bromo-1,2-diphenylethane reacts with a strong base to produce cis-stilbene and trans-stilbene: a. This reaction is stereoselective, and the major product is transstilbene. Explain why the trans...

Q: Which of the following reactions is expected to produce 1-propanol

Which of the following reactions is expected to produce 1-propanol (CH3CH2CH2OH) at a faster rate? Explain.

Q: Therearetwostereoisomersof1-tert-butyl-4-chloro-cyclohexane.

Therearetwostereoisomersof1-tert-butyl-4-chloro-cyclohexane. One of these isomers reacts with sodium ethoxide in an E2 reaction that is 500 times faster than the reaction of the other isomer. Identify...

Q: In 2010 the structure of the compound (+)-trigonoliimine A (isolated

In 2010 the structure of the compound (+)-trigonoliimine A (isolated from the leaves of a plant in the Yunnan province of China) was reported as shown below. In 2011, a synthesis of the reported struc...

Q: Substitution vs. Elimination: Identify the major and minor product(

Substitution vs. Elimination: Identify the major and minor product(s) for each of the following reactions:

Q: 77. All of the following are significant resonance structures of the

77. All of the following are significant resonance structures of the phenyl carbocation, EXCEPT: 78. Which of the following resonance structures is the greatest contributor to the resonance hybrid?...

Q: Predict the major product for each of the following reactions.

Predict the major product for each of the following reactions.

Q: Consider the following substitution reaction: / a.

Consider the following substitution reaction: a. Determine whether this reaction proceeds via an SN2 or SN1 process, and draw a complete mechanism. b. What is the expected rate equation for this pro...

Q: When 2-bromo-2-methylhexane is treated with sodium

When 2-bromo-2-methylhexane is treated with sodium ethoxide in ethanol, the major product is 2-methyl-2-hexene. a. Draw a mechanism for this process. b. What is the expected rate equation for this p...

Q: When the following ester is treated with lithium iodide in DMF,

When the following ester is treated with lithium iodide in DMF, a carboxylate ion is obtained: a. Draw a plausible mechanism for this reaction. b. When a methyl ester is used as the substrate (inste...

Q: If you are having trouble paying attention during a long lecture,

If you are having trouble paying attention during a long lecture, your levels of acetylcholine (a neurotransmitter) may be to blame. Identify any formal charges in acetylcholine.

Q: When (1R,2R)-2-bromocyclohexanol is treated with

When (1R,2R)-2-bromocyclohexanol is treated with a strong base, an epoxide (cyclic ether) is formed. Suggest a mechanism for formation of the epoxide:

Q: When butyl bromide is treated with sodium iodide in ethanol, the

When butyl bromide is treated with sodium iodide in ethanol, the concentration of iodide quickly decreases, but then slowly returns to its original concentration. Identify the major product of the r...

Q: The following compound can react rapidly via an SN1 process. Explain

The following compound can react rapidly via an SN1 process. Explain why this primary substrate will undergo an SN1 reaction so rapidly.

Q: Consider the reaction below, which involves both a dehydrogenation (removal

Consider the reaction below, which involves both a dehydrogenation (removal of two neighboring hydrogen atoms) and a Diels-Alder reaction (which we will learn about in Chapter 16). Utilizing a special...

Q: Which of the following reactions is expected to exhibit a faster rate

Which of the following reactions is expected to exhibit a faster rate? Explain

Q: Consider the reaction below. The rate of this reaction is markedly

Consider the reaction below. The rate of this reaction is markedly increased if a small amount of sodium iodide is added to the reaction mixture. The sodium iodide is not consumed by the reaction and...

Q: Propose a mechanism of formation for each of the following products:

Propose a mechanism of formation for each of the following products:

Q: When a new synthetic method is developed, it is applied to

When a new synthetic method is developed, it is applied to a series of compounds to explore its utility. 4-Fluorophenylacetonitrile was used as a substrate in a synthetic methodology research paper. P...

Q: Control of stereochemistry is always an important consideration when designing a synthesis

Control of stereochemistry is always an important consideration when designing a synthesis. Several techniques exist to invert the stereochemistry of secondary alcohols, and a newly developed method w...

Q: When you look up thermodynamic values in a table, such as

When you look up thermodynamic values in a table, such as bond dissociation energies or heats of combustion, did you ever wonder where all the numbers come from? You can thank the physical organic che...

Q: The following reaction sequence was part of a stereocontrolled synthesis of cyoctol

The following reaction sequence was part of a stereocontrolled synthesis of cyoctol, used in the treatment of male pattern baldness. The third step in this process employs an uncharged nucleophile, af...

Q: For each of the following compounds, identify any polar covalent bonds

For each of the following compounds, identify any polar covalent bonds by drawing δ+ and δ− symbols in the appropriate locations:

Q: Upon treatment with a strong base (such as NaOH), 2

Upon treatment with a strong base (such as NaOH), 2-naphthol (compound 1) is converted to its conjugate base (anion 2), which is then further converted into compound 3 upon treatment with butyl iodide...

Q: Bromotriphenylmethane (compound 1) can be converted to 2a or 2b

Bromotriphenylmethane (compound 1) can be converted to 2a or 2b or 2c upon treatment with the appropriate nucleophile. a. Draw a mechanism for the conversion of 1 to 2b. b. In all three cases, conve...

Q: Draw the curved arrows that accomplish each of the following transformations:

Draw the curved arrows that accomplish each of the following transformations:

Q: (−)-Cameroonanol has been isolated from the essential oil of Echinops giganteus

(−)-Cameroonanol has been isolated from the essential oil of Echinops giganteus (globe thistle) plants and it is associated with a strong woody fragrance. Its structure, including re...

Q: For each of the following processes predict the sign of ΔS for

For each of the following processes predict the sign of ΔS for the reaction. In other words, will ΔSsys be positive (an increase in entropy) or negative (a decrease in entropy)...

Q: For each of the following reactions determine whether ΔS for the reaction

For each of the following reactions determine whether ΔS for the reaction (ΔSsys) will be positive, negative, or approximately zero:

Q: For each of the following carbocations determine if it will rearrange,

For each of the following carbocations determine if it will rearrange, and if so, draw the carbocation rearrangement with a curved arrow:

Q: For each of the following reactions predict the sign of ΔG.

For each of the following reactions predict the sign of ΔG. If a prediction is not possible because the sign of ΔG will be temperature dependent, describe how ΔG will be affected by raising the temper...

Q: At room temperature, molecules spend most of their time in lower

At room temperature, molecules spend most of their time in lower energy conformations. In fact, there is a general tendency for any system to move toward lower energy. As another example, electrons fo...

Q: In each of the following cases, use the data given to

In each of the following cases, use the data given to determine whether the reaction favors reactants or products: a. A reaction for which ΔG = +1.52 kJ/mol b. A reaction for which Keq = 0.5 c. A re...

Q: Consider the relative energy diagrams for four different processes: /

Consider the relative energy diagrams for four different processes: a. Compare energy diagrams A and D. Assuming all other factors (such as concentrations and temperature) are identical for the two p...

Q: Identify all of the nucleophilic centers in each of the following compounds

Identify all of the nucleophilic centers in each of the following compounds:

Q: Compare the Lewis dot structure of nitrogen and phosphorus and explain why

Compare the Lewis dot structure of nitrogen and phosphorus and explain why you might expect these two atoms to exhibit similar bonding properties.

Q: For each of the following cases use the information given to determine

For each of the following cases use the information given to determine whether or not the equilibrium will favor products over reactants: a. A reaction with Keq = 1.2 b. A reaction with Keq = 0.2...

Q: Identify all of the electrophilic centers in each of the following compounds

Identify all of the electrophilic centers in each of the following compounds:

Q: (R)-(−)-Carvone is responsible for the characteristic minty odor and

(R)-(−)-Carvone is responsible for the characteristic minty odor and flavor of spearmint oil, and it can also serve as a useful chiral starting material for organic synthesis. A carb...

Q: Consider the following SN2 reaction: / a.

Consider the following SN2 reaction: a. Assign the configuration of the chiral center in the substrate. b. Assign the configuration of the chiral center in the product. c. Does this SN2 process proc...

Q: Draw an energy diagram of a reaction with the following characteristics:

Draw an energy diagram of a reaction with the following characteristics: a. A one-step reaction with a negative ΔG b. A one-step reaction with a positive ΔG c. A two-step reaction with an overall n...

Q: Assign a systematic (IUPAC) name for each of the following

Assign a systematic (IUPAC) name for each of the following compounds:

Q: Name one element that you would expect to exhibit bonding properties similar

Name one element that you would expect to exhibit bonding properties similar to boron. Explain.

Q: For each of the following cases, read the curved arrows and

For each of the following cases, read the curved arrows and identify which arrow-pushing pattern is utilized:

Q: Most fabrics do a good job at protecting skin from exposure to

Most fabrics do a good job at protecting skin from exposure to sunlight, but addition of UV-absorbing compounds to clothing can further reduce the amount of ultraviolet light that passes through the f...

Q: For each of the following multistep reactions, read the curved arrows

For each of the following multistep reactions, read the curved arrows and identify the sequence of arrow–pushing patterns:

Q: Several natural products have been isolated from the flowering plant Sarcostemma acidum

Several natural products have been isolated from the flowering plant Sarcostemma acidum, which has been used in folk medicine as a cough suppressant. During efforts to make these compounds in the labo...

Q: Which value of ΔG corresponds with Keq = 1? a

Which value of ΔG corresponds with Keq = 1? a. +1 kJ/mol b. 0 kJ/mol c. −1 kJ/mol

Q: George Olah was awarded the 1994 Nobel Prize in Chemistry for his

George Olah was awarded the 1994 Nobel Prize in Chemistry for his research involving carbocations. An interesting series of carbocation rearrangements studied by Olah is shown below. Each of these rea...

Q: The following reaction gives a product with the molecular formula C4H8O2.

The following reaction gives a product with the molecular formula C4H8O2. Draw the structure of the product.

Q: In each of the following cases compare the bonds identified in red

In each of the following cases compare the bonds identified in red, and determine which bond you would expect to have the largest bond dissociation energy

Q: Consider the following reaction: / a. Use

Consider the following reaction: a. Use Table 6.1 to estimate ΔH for this reaction. b. ΔS of this reaction is positive. Explain. c. Determine the sign of ΔG. d....

Q: Consider the following four energy diagrams: / a

Consider the following four energy diagrams: a. Which diagrams correspond with a two-step mechanism? b. Which diagrams correspond with a one-step mechanism? c. Compare energy diagrams A and C. Whic...

Q: Using E-Z designators, identify the configuration of each C

Using E-Z designators, identify the configuration of each C=C double bond in the following compound:

Q: Draw a Lewis structure of a carbon atom that is missing one

Draw a Lewis structure of a carbon atom that is missing one valence electron (and therefore bears a positive charge). Which second-row element does this carbon atom resemble in terms of the number of...

Q: Pladienolide B is a macrocyclic (large ring) natural product isolated

Pladienolide B is a macrocyclic (large ring) natural product isolated from an engineered strain of the bacterium Streptomyces platensis. An enantioselective, 31-step synthesis of it was reported18 in...

Q: a. Consider the figure shown in Problem 7.90.

a. Consider the figure shown in Problem 7.90. Compound 3 is most easily purified via recrystallization in water. As such, the product would have to be thoroughly dried in order to utilize IR spectral...

Q: Identify the electron configuration for each of the following ions:

Identify the electron configuration for each of the following ions: a. A carbon atom with a negative charge b. A carbon atom with a positive charge c. A nitrogen atom with a positive charge d. An o...

Q: Consider the structure of formaldehyde: / a.

Consider the structure of formaldehyde: a. Identify the type of bonds that form the C=O double bond. b. Identify the atomic orbitals that form each C−H bond. c. What type of atomi...

Q: Indolizomycin is a potent antibiotic agent produced by a microorganism, called

Indolizomycin is a potent antibiotic agent produced by a microorganism, called SK2-52. Of particular interest is the fact that SK2-52 is a mutant microorganism that was created in a laboratory from tw...

Q: Draw a Lewis dot structure for each of the following atoms:

Draw a Lewis dot structure for each of the following atoms: a. Carbon b. Oxygen c. Fluorine d. Hydrogen e. Bromine f. Sulfur g. Chlorine h. Iodine

Q: Sigma bonds experience free rotation at room temperature: /

Sigma bonds experience free rotation at room temperature: In contrast, π bonds do not experience free rotation. Explain. (Hint: Compare Figures 1.24 and 1.29, focusing on the orbitals used...

Q: Identify the systematic name as well as the common name for each

Identify the systematic name as well as the common name for each of the following compounds:

Q: Using the data in Table 6.1, predict the sign

Using the data in Table 6.1, predict the sign and magnitude of ΔH° for each of the following reactions. In each case, identify whether the reaction is expected to be endothermic...

Q: Draw a mechanism for the reverse process of the previous problem.

Draw a mechanism for the reverse process of the previous problem. In other words, draw the acid-catalyzed conversion of 1-cyclohexenol to cyclohexanone.

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations (you will also need to use reactions from previous chapters).

Q: Lactones can be prepared from diethyl malonate and epoxides. Diethyl malonate

Lactones can be prepared from diethyl malonate and epoxides. Diethyl malonate is treated with a base, followed by an epoxide, followed by heating in aqueous acid: Using this process, identify what re...

Q: Consider a process that attempts to prepare tyrosine using a Hell–

Consider a process that attempts to prepare tyrosine using a Hell–Volhard–Zelinsky reaction: a. Identify the necessary starting carboxylic acid. b. When treated with Br2, the starting carboxylic aci...

Q: Draw a mechanism for the acid-catalyzed conversion of cyclohexanone into

Draw a mechanism for the acid-catalyzed conversion of cyclohexanone into its tautomeric enol.

Q: 93. Which of the following is the strongest base?

93. Which of the following is the strongest base? // 94. What is the expected major product of this reaction? 95. Which reagents can be used to achieve this transformation?

Q: Predict the major product of the following transformation: /

Predict the major product of the following transformation:

Q: Using formaldehyde and acetaldehyde as your only sources of carbon atoms,

Using formaldehyde and acetaldehyde as your only sources of carbon atoms, show how you could make each of the following compounds. You may find it helpful to review acetal formation (Section 19.5).

Q: Consider the structures of the constitutional isomers, compound A and compound

Consider the structures of the constitutional isomers, compound A and compound B. When treated with aqueous acid, compound A undergoes isomerization to give a cis stereoisomer. In contrast, compound B...

Q: An alcohol with the molecular formula C4H10O was treated with PCC to

An alcohol with the molecular formula C4H10O was treated with PCC to produce an aldehyde that exhibits exactly three signals in its 1 H NMR spectrum. Predict the aldol addition product that is obtaine...

Q: Using acetaldehyde as your only source of carbon, show how you

Using acetaldehyde as your only source of carbon, show how you would prepare 1,3-butanediol.

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: This chapter covered many C−C bond-forming reactions,

This chapter covered many C−C bond-forming reactions, including aldol reactions, Claisen condensations, and Michael addition reactions. Two or more of these reactions are often perfo...

Q: Predict the major product obtained when each of the following compounds is

Predict the major product obtained when each of the following compounds is treated with bromine (Br2) together with sodium hydroxide (NaOH) followed by aqueous acid (H3O+):

Q: The following transformation cannot be accomplished by direct alkylation of an enolate

The following transformation cannot be accomplished by direct alkylation of an enolate. Explain why not and then devise an alternate synthesis for this transformation.

Q: The product of an aldol condensation is an α,β-

The product of an aldol condensation is an α,β-unsaturated ketone, which is capable of undergoing hydrogenation to yield a saturated ketone. Using this technique, identify th...

Q: Starting with diethyl malonate and using any other reagents of your choice

Starting with diethyl malonate and using any other reagents of your choice, propose an efficient synthesis for each of the following compounds:

Q: When a malonic ester synthesis is performed using excess base and 1

When a malonic ester synthesis is performed using excess base and 1,4-dibromobutane as the alkyl halide, an intramolecular reaction occurs, and the product contains a ring. Draw the product of this p...

Q: Starting with ethyl acetoacetate and using any other reagents of your choice

Starting with ethyl acetoacetate and using any other reagents of your choice, propose an efficient synthesis for each of the following compounds:

Q: The product of a Dieckmann cyclization can undergo alkylation, hydrolysis,

The product of a Dieckmann cyclization can undergo alkylation, hydrolysis, and decarboxylation. This sequence represents an efficient method for preparing 2-substituted cyclopentanones (below) and cyc...

Q: Using ethanol as your only source of carbon atoms, propose a

Using ethanol as your only source of carbon atoms, propose a synthesis for each of the following compounds:

Q: We have seen that the alpha carbon atom of an enamine can

We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For exampl...

Q: Consider the reaction between cyclohexanone and the optically pure amine shown (

Consider the reaction between cyclohexanone and the optically pure amine shown (next page). a. Draw the structure of the resulting enamine and discuss how many isomer(s), if any, form in this reactio...

Q: Predict the product of the following reaction sequence, which was recently

Predict the product of the following reaction sequence, which was recently used in a synthetic route toward a series of 1,3,6-substituted fulvenes:

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations (you will need to use reactions from previous chapters):

Q: The following synthetic step was utilized as part of a recent synthesis

The following synthetic step was utilized as part of a recent synthesis of the polycyclic natural product haouamine B. In this reaction, the function of the first reagent (triflic anhydride) is to act...

Q: In a recent effort to devise a new synthetic pathway for the

In a recent effort to devise a new synthetic pathway for the preparation of useful building blocks for the synthesis of natural products, compound 2 was prepared by treating compound 1 with diethylmal...

Q: 113. What enolate is formed in this reaction? /

113. What enolate is formed in this reaction? 114. Which compounds will react with each other in the presence of NaOH to give the following product? 115. Which set of reagents can be used to achie...

Q: Identify the structure of the conjugated diene that will react with one

Identify the structure of the conjugated diene that will react with one equivalent of HBr to yield a racemic mixture of 3-bromocyclohexene.

Q: Draw the major product expected when 1,3-butadiene is

Draw the major product expected when 1,3-butadiene is treated with one equivalent of HBr at 0ºC, and show a mechanism of its formation.

Q: Draw the major product expected when 1,3-butadiene is

Draw the major product expected when 1,3-butadiene is treated with one equivalent of HBr at 40ºC, and show a mechanism of its formation.

Q: The natural product (–)-N-methylwelwitindolinone C isothiocyanate is isolated from

The natural product (–)-N-methylwelwitindolinone C isothiocyanate is isolated from a blue-green algae and has been identified as a promising compound to treat drug-resistant tumors....

Q: The following sequence, beginning with a cyclic hemiacetal (compound A

The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of th...

Q: The compound fusarisetin A (isolated from a soil fungus) displays

The compound fusarisetin A (isolated from a soil fungus) displays significant anticancer activity without detectable cytotoxicity (toxicity to cells). A key step in a reported synthesis of the enantio...

Q: Rank the following dienophiles (from least reactive to most reactive)

Rank the following dienophiles (from least reactive to most reactive) in terms of reactivity in a Diels–Alder reaction:

Q: Predict the major product obtained when each of the following aldehydes is

Predict the major product obtained when each of the following aldehydes is treated with aqueous sodium hydroxide:

Q: The absorbance spectrum of 1,3-butadiene displays an absorption

The absorbance spectrum of 1,3-butadiene displays an absorption in the UV region (λmax=217 nm), while the absorption spectrum of 1,2-butadiene does not display a similar absorption. Explain.

Q: Predict the products for each of the following Diels–Alder reactions

Predict the products for each of the following Diels–Alder reactions:

Q: Identify the reagents you would use to prepare each of the following

Identify the reagents you would use to prepare each of the following compounds via a Diels–Alder reaction:

Q: The following triene reacts with excess maleic anhydride to produce a compound

The following triene reacts with excess maleic anhydride to produce a compound with the molecular formula C14H12O6. Draw the structure of this product (ignoring stereochemistry).

Q: Chlordane is a powerful insecticide that was used in the United States

Chlordane is a powerful insecticide that was used in the United States during the second half of the twentieth century. Its use was discontinued in 1988 in recognition of its persistence and accumulat...

Q: Cyclopentadiene reacts very rapidly in Diels–Alder reactions. In contrast

Cyclopentadiene reacts very rapidly in Diels–Alder reactions. In contrast, 1,3-cyclohexadiene reacts more slowly and 1,3-cycloheptadiene is practically unreactive. Can you offer an explanation for thi...

Q: Rank the following compounds in order of increasing λmax: /

Rank the following compounds in order of increasing λmax:

Q: Which of the following compounds do you expect to have a longer

Which of the following compounds do you expect to have a longer λmax?

Q: Predict the expected λmax of the following compound: /

Predict the expected λmax of the following compound:

Q: When 5-deutero-5-methyl-1,3

When 5-deutero-5-methyl-1,3-cyclopentadiene is warmed to room temperature, it rapidly rearranges, giving an equilibrium mixture containing the original compound as well as two others. Propose a plausi...

Q: When each of the following ketones is treated with aqueous sodium hydroxide

When each of the following ketones is treated with aqueous sodium hydroxide, the aldol product is obtained in poor yields. In these cases, special distillation techniques are used to increase the yiel...

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Predict the product for each of the following electrocyclic reactions:

Predict the product for each of the following electrocyclic reactions:

Q: Identify whether the product obtained from each of the following reactions is

Identify whether the product obtained from each of the following reactions is a meso compound or a pair of enantiomers: a. Irradiation of (2E,4Z,6Z )-4,5-dimethyl-2,4,6-octatriene with UV light. b....

Q: Predict which side of the following equilibrium is favored and explain your

Predict which side of the following equilibrium is favored and explain your choice.

Q: When trans-3,4-dimethylcyclobutene is heated, conrotatory

When trans-3,4-dimethylcyclobutene is heated, conrotatory ring opening can produce two different products, yet only one is formed. Draw both products, identify which product is formed, and then explai...

Q: Predict the major product for each of the following reactions:

Predict the major product for each of the following reactions:

Q: Predict the product(s) obtained when benzoquinone is treated with

Predict the product(s) obtained when benzoquinone is treated with excess butadiene:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Cholesta-4,6,8(14)-triene,

Cholesta-4,6,8(14)-triene, shown below, was isolated from the thigh gland secretion of the male Great Basin Collared Lizard Crotaphytus bicinctores and is believed to be used for communication.6 Using...

Q: α-Terpinene is a pleasant-smelling compound present in the

α-Terpinene is a pleasant-smelling compound present in the essential oil of marjoram, a perennial herb. Upon hydrogenation with a metal catalyst, α-terpinene reacts with tw...

Q: When conducted in a chiral environment (for example, by using

When conducted in a chiral environment (for example, by using a chiral catalyst or adding a chiral auxiliary), an asymmetric aldol reaction can occur that favors the production of a single stereoisome...

Q: Compound A (C7H10) exhibits a λmax of 230 nm in

Compound A (C7H10) exhibits a λmax of 230 nm in its UV absorption spectrum. Upon hydrogenation with a metal catalyst, compound A will react with two equivalents of hydrogen gas. Ozonolysi...

Q: Draw all possible conjugated dienes with the molecular formula C6H10, taking

Draw all possible conjugated dienes with the molecular formula C6H10, taking special care not to draw the same compound twice.

Q: Starting with 1,3-butadiene as your only source of

Starting with 1,3-butadiene as your only source of carbon atoms and using any other reagents of your choice, design a synthesis of the following compound:

Q: Would you expect nitroethylene to be more or less reactive than ethylene

Would you expect nitroethylene to be more or less reactive than ethylene in a Diels–Alder reaction? (Hint: Draw the resonance structures of nitroethylene.)

Q: Propose a plausible mechanism for the following transformation. (Hint:

Propose a plausible mechanism for the following transformation. (Hint: Only two sequential pericyclic reactions are required.)

Q: Predict the major product of the following Diels–Alder reaction,

Predict the major product of the following Diels–Alder reaction, making sure to consider the regiochemical outcome as well as the stereochemical outcome.

Q: During the first total synthesis of chelidonine, a cytotoxic natural product

During the first total synthesis of chelidonine, a cytotoxic natural product isolated from the root of Chelidonium majus, the investigators used only heat to achieve the following transformation.7 Thi...

Q: During studies directed toward the synthesis of atropurpuran, a diterpene with

During studies directed toward the synthesis of atropurpuran, a diterpene with interesting molecular architecture, the investigators used high temperature to convert an acyclic tetraene into a tricycl...

Q: The poison gelsemoxonine can be isolated from the leaves of a plant

The poison gelsemoxonine can be isolated from the leaves of a plant native to southeastern Asia (Gelsemium elegans). A key step in a synthesis of this natural product involves a thermally initiated (7...

Q: Upon irradiation, some organic compounds undergo a reversible change in molecular

Upon irradiation, some organic compounds undergo a reversible change in molecular structure, such as cis–trans isomerization or cyclization of π-conjugatedchromophores. Th...

Q: Draw the condensation product obtained when each of the following compounds is

Draw the condensation product obtained when each of the following compounds is heated in the presence of aqueous sodium hydroxide:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Based on your answer to Problem 16.67, propose a

Based on your answer to Problem 16.67, propose a mechanism for the following transformation:

Q: Compare the structures of 1,4-pentadiene and divinylamine:

Compare the structures of 1,4-pentadiene and divinylamine: The first compound does not absorb UV light in the region between 200 and 400 nm. The second compound does absorb light above 200Â&nbs...

Q: When the following cyclopentadiene-fused [14]annulene is treated

When the following cyclopentadiene-fused [14]annulene is treated with KH, a green solution of a stable cyclopentadiene anion results. This transformation causes a dramatic change in part of the 1H&Aci...

Q: The following compound, isolated from a New Zealand sea squirt,

The following compound, isolated from a New Zealand sea squirt, demonstrates activity against a malarial strain that is resistant to other treatments. Consider the relative basicity of each nitrogen a...

Q: In a mass spectrometric study of nitrogenous aromatic compounds, a peak

In a mass spectrometric study of nitrogenous aromatic compounds, a peak at m/z = 39 was found for 17 of the 20 compounds investigated, including the 4 compounds in the first row below, with a relative...

Q: Fluorenyldiene 1 is a highly conjugated, planar molecule that is readily

Fluorenyldiene 1 is a highly conjugated, planar molecule that is readily oxidized to dication 2. Draw at least four other resonance structures of dication 2 and identify why the resonance structure s...

Q: Numerous herbicides and fungicides are known to contain an acetylenic group.

Numerous herbicides and fungicides are known to contain an acetylenic group. For example, compound A is a pyrimidinone herbicide that functions by inhibiting the accumulation of both chlorophyll and &...

Q: For each of the following compounds, identify whether each C=

For each of the following compounds, identify whether each C=C π system is cumulated, conjugated, or isolated:

Q: Identify reagents necessary to convert cyclohexane into 1,3-cyclohexadiene

Identify reagents necessary to convert cyclohexane into 1,3-cyclohexadiene. Notice that the starting material has no leaving groups and cannot simply be treated with a strong base. You must first intr...

Q: Perhydroazulene derivatives have shown usefulness in electronic display applications. In a

Perhydroazulene derivatives have shown usefulness in electronic display applications. In a study to find an efficient route for the synthesis of the perhydroazulene skeleton, compound 1 was heated in...

Q: During a recent investigation into the chemistry of oligofurans (polymers of

During a recent investigation into the chemistry of oligofurans (polymers of the furan heterocycle, which show potential to be used in materials), the investigators observed an interesting reaction wi...

Q: When tricyclic cyclooctyne derivative A reacts with benzyl azide (C6H5CH2N3),

When tricyclic cyclooctyne derivative A reacts with benzyl azide (C6H5CH2N3), a [3+2] cycloaddition occurs between the alkyne and the azide (called a click reaction) to install a new five-membered het...

Q: Endiandric acids are a class of natural products isolated from the Australian

Endiandric acids are a class of natural products isolated from the Australian plant Endiandra introrsa. Natural products containing chiral centers are generally found in nature as a single enantiomeri...

Q: Roquefortine C belongs to a family of natural products first isolated from

Roquefortine C belongs to a family of natural products first isolated from cultures of the fungus Penicillium roqueforti in the mid-1970s. Since then, roquefortine C has also been found in other natur...

Q: As shown, compound 1 can be transformed to compound 2,

As shown, compound 1 can be transformed to compound 2, which undergoes a thio-Claisen rearrangement (similar to a Claisen rearrangement, but with sulfur instead of oxygen) to give compound ...

Q: Rank the three C−C bonds of 1-butene in

Rank the three C−C bonds of 1-butene in terms of bond length (from shortest to longest).

Q: Compare the following three isomeric dienes: / a

Compare the following three isomeric dienes: a. Which compound will liberate the least heat upon hydrogenation with 2 mol of hydrogen gas? Why? b. Which compound will liberate the most heat upon hy...

Q: Draw an energy diagram showing the relative energy levels of the MOs

Draw an energy diagram showing the relative energy levels of the MOs for 1,3,5,7-octatetraene and identify the HOMO and LUMO for both the ground state and the excited state.

Q: Predict the products for each of the following reactions and propose a

Predict the products for each of the following reactions and propose a mechanism that explains the formation of each product:

Q: Consider the following two dienes. When treated with HBr, one

Consider the following two dienes. When treated with HBr, one of these dienes yields four products, while the other diene yields only two products. Explain.

Q: Identify reagents that can be used to produce each of the following

Identify reagents that can be used to produce each of the following compounds via an aldol reaction.

Q: β-Damascenone belongs to a family of fragrant natural products called

β-Damascenone belongs to a family of fragrant natural products called rose ketones that have been used in the perfume industry. In one synthesis of β-damascenone, the reaction...

Q: What monomer should be used to make each of the following polymers

What monomer should be used to make each of the following polymers?

Q: Predict the products for each of the following reactions: /

Predict the products for each of the following reactions:

Q: A hetero Diels–Alder reaction is a variation of the Diels

A hetero Diels–Alder reaction is a variation of the Diels–Alder reaction in which one or more of the carbon atoms of the diene and/or the dienophile are replaced by...

Q: Consider the following two isomers of 2,4-hexadiene.

Consider the following two isomers of 2,4-hexadiene. One isomer reacts rapidly as a diene in a Diels–Alder reaction, and the other does not. Identify which isomer is more reactive an...

Q: Rank the following dienes in terms of reactivity in Diels– Alder

Rank the following dienes in terms of reactivity in Diels– Alder reactions (from least reactive to most reactive):

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: Aromatic compounds often have multiple names that are all accepted by IUPAC

Aromatic compounds often have multiple names that are all accepted by IUPAC. Provide three different systematic (IUPAC) names for the following compound.

Q: For each of the following compounds, draw its structure:

For each of the following compounds, draw its structure: a. 2,6-Dibromo-4-chloroanisole b. meta-Nitrophenol

Q: Provide at least five different acceptable IUPAC names for the following compound

Provide at least five different acceptable IUPAC names for the following compound.

Q: In an effort to make lasers more affordable and easier to make

In an effort to make lasers more affordable and easier to make, chemists are developing organic solid-state lasers (OSSLs) using small organic molecules that are capable of lasing (releasing laser lig...

Q: Aromatic compounds are commonly found in plant oils. For example,

Aromatic compounds are commonly found in plant oils. For example, an extract of rosemary, which shows anti-oxidant activity, was found to contain the compounds eugenol, thymol, and carvacrol.1 These n...

Q: Compound A is an aromatic compound with the molecular formula C8H8.

Compound A is an aromatic compound with the molecular formula C8H8. When treated with excess Br2, compound A is converted into compound B, with the molecular formula C8H8Br2. Identify the structures o...

Q: In some circumstances, dehydrogenation is observed. Dehydrogenation involves the loss

In some circumstances, dehydrogenation is observed. Dehydrogenation involves the loss of two hydrogen atoms (the reverse of hydrogenation). Analyze each of the following dehydrogenation reactions and...

Q: Predict whether each of the following compounds should be aromatic:

Predict whether each of the following compounds should be aromatic:

Q: The cyclopropenyl cation has a three-membered ring that contains a

The cyclopropenyl cation has a three-membered ring that contains a continuous system of overlapping p orbitals. This system contains a total of two π electrons. Using a Frost circle, draw a...

Q: Predict whether the following compound will be aromatic, nonaromatic, or

Predict whether the following compound will be aromatic, nonaromatic, or antiaromatic. Explain your reasoning.

Q: Determine whether each of the following ions is aromatic, nonaromatic,

Determine whether each of the following ions is aromatic, nonaromatic, or antiaromatic:

Q: In a pioneering study on the limits of aromaticity, the following

In a pioneering study on the limits of aromaticity, the following resonance-stabilized dianion was prepared and examined. Predict whether this dianion is aromatic, nonaromatic, or antiaromatic.

Q: For each of the following compounds determine which (if any)

For each of the following compounds determine which (if any) lone pairs are participating in aromaticity:

Q: Go to the beginning of Section 17.1 where the structures

Go to the beginning of Section 17.1 where the structures of several best-selling drugs were shown. Review the structures of those compounds and identify all of the aromatic rings that are not already...

Q: Draw the two possible enols that can be formed from 3-

Draw the two possible enols that can be formed from 3-methyl-2-butanone and show a mechanism of formation of each under base-catalyzed conditions.

Q: Draw a mechanism for the following transformation: /

Draw a mechanism for the following transformation:

Q: Identify which compound is expected to have a lower pKa. Justify

Identify which compound is expected to have a lower pKa. Justify your choice.

Q: Meclizine, shown below, is an antiemetic (prevents nausea and

Meclizine, shown below, is an antiemetic (prevents nausea and vomiting). a. Would you expect meclizine to be an antihistamine as well? Justify your answer. b. This drug is known to cause sedation. D...

Q: Draw the expected product when each of the following compounds is oxidized

Draw the expected product when each of the following compounds is oxidized with chromic acid:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Hamigeran B and several related natural products were isolated from a sponge

Hamigeran B and several related natural products were isolated from a sponge found off the coast of New Zealand. Hamigeran B has demonstrated strong activity against the viruses that cause polio and h...

Q: Predict the major product obtained when each of the following compounds is

Predict the major product obtained when each of the following compounds is treated with Birch conditions:

Q: Rippertenol is a compound made by termites and used by the insects

Rippertenol is a compound made by termites and used by the insects to defend themselves from predators. Due to its complexity, the first synthesis of rippertenol was not reported until more than 30 ye...

Q: A compound with the molecular formula C8H8O produces an IR spectrum with

A compound with the molecular formula C8H8O produces an IR spectrum with signals at 3063, 1686, and 1646 cm−1. The 1H NMR spectrum of this compound exhibits a singlet at 2.6 ppm (I=3H) and a multiplet...

Q: A compound with the molecular formula C8H10 produces an IR spectrum with

A compound with the molecular formula C8H10 produces an IR spectrum with many signals, including 3108, 3066, 3050, 3018, and 1608 cm−1. The 1 H NMR spectrum of this compound exhibits a singlet at 2.2...

Q: Provide a systematic name for each of the following compounds:

Provide a systematic name for each of the following compounds:

Q: The reaction in the previous problem is an equilibrium process. Draw

The reaction in the previous problem is an equilibrium process. Draw a mechanism of the reverse process. That is, draw a mechanism showing conversion of the conjugated, cyclic enone into the acyclic d...

Q: Draw a structure for each of the following compounds: a

Draw a structure for each of the following compounds: a. ortho-Dichlorobenzene b. Anisole c. meta-Nitrotoluene d. Aniline e. 2,4,6-Tribromophenol f. para-Xylene

Q: Draw structures for the eight constitutional isomers with the molecular formula C9H12

Draw structures for the eight constitutional isomers with the molecular formula C9H12 that contain a benzene ring.

Q: Draw structures for all constitutional isomers with the molecular formula C8H10 that

Draw structures for all constitutional isomers with the molecular formula C8H10 that contain an aromatic ring.

Q: Draw all aromatic compounds that have the molecular formula C8H9Cl.

Draw all aromatic compounds that have the molecular formula C8H9Cl.

Q: The systematic name of TNT, a well-known explosive,

The systematic name of TNT, a well-known explosive, is 2,4,6-trinitrotoluene (as seen in SkillBuilder 17.1). There are only five constitutional isomers of TNT that contain an aromatic ring, a methyl g...

Q: Identify the number of π electrons in each of the following compounds

Identify the number of π electrons in each of the following compounds:

Q: Consider the differences between cyclohexane and benzene: /

Consider the differences between cyclohexane and benzene: These compounds have different properties, different geometry, and different reactivity. Each of these compounds also has a unique set of ter...

Q: Identify which of the following are aromatic: /

Identify which of the following are aromatic:

Q: Firefly luciferin is the compound that enables fireflies to glow.

Firefly luciferin is the compound that enables fireflies to glow. a. The structure exhibits three rings. Identify which of the rings are aromatic. b. Identify which lone pairs are involved in establ...

Q: Identify each of the following as aromatic, nonaromatic, or antiaromatic

Identify each of the following as aromatic, nonaromatic, or antiaromatic. Explain your choice in each case.

Q: When 2,6-heptanedione is heated in the presence of

When 2,6-heptanedione is heated in the presence of aqueous sodium hydroxide, a condensation product with a sixmembered ring is obtained. Draw the product and show a mechanism for its formation.

Q: Consider the structures of the following alkyl chlorides: /

Consider the structures of the following alkyl chlorides: a. Which compound would you expect to undergo an SN1 process most readily? Justify your choice. b. Which compound would you expect to underg...

Q: Which of the following compounds would you expect to be most acidic

Which of the following compounds would you expect to be most acidic? Justify your choice.

Q: Identify which of the following compounds is expected to be a stronger

Identify which of the following compounds is expected to be a stronger base. Justify your choice.

Q: Draw a Frost circle for the following cation and explain the source

Draw a Frost circle for the following cation and explain the source of instability of this cation:

Q: Explain the vast difference in pKa values for the following two apparently

Explain the vast difference in pKa values for the following two apparently similar compounds:

Q: Would you expect the following compound to be aromatic? Justify your

Would you expect the following compound to be aromatic? Justify your answer.

Q: The following two drawings are resonance structures of one compound:

The following two drawings are resonance structures of one compound: But the following two drawings are not resonance structures: These two drawings represent two different compounds. Explain.

Q: Predict the major product for each of the following reactions.

Predict the major product for each of the following reactions.

Q: How many signals do you expect in the 13C NMR spectrum of

How many signals do you expect in the 13C NMR spectrum of each of the following compounds?

Q: Predict the product of the following reaction and propose a mechanism for

Predict the product of the following reaction and propose a mechanism for its formation:

Q: Identify the base you would use for each of the following transformations

Identify the base you would use for each of the following transformations:

Q: One of the constitutional isomers of xylene was treated with sodium,

One of the constitutional isomers of xylene was treated with sodium, methanol, and ammonia to yield a product that exhibited five signals in its 13C NMR spectrum. Identify which constitutional isomer...

Q: Consider the following two compounds: How would you distinguish between them

Consider the following two compounds: How would you distinguish between them using: a. IR spectroscopy? b. 1 H NMR spectroscopy? c. 13C NMR spectroscopy?

Q: Explain how the following two compounds can have the same conjugate base

Explain how the following two compounds can have the same conjugate base. Is this conjugate base aromatic?

Q: Compare the following electrostatic potential maps for cycloheptatrienone and cyclopentadienone.

Compare the following electrostatic potential maps for cycloheptatrienone and cyclopentadienone. Both of these maps were created using the same color scale so they can be compared. Notice the differe...

Q: Azulene exhibits an appreciable dipole moment, and an electrostatic potential map

Azulene exhibits an appreciable dipole moment, and an electrostatic potential map indicates that the five-membered ring is electron rich (at the expense of the seven-membered ring). a. In general, a...

Q: Propose an efficient synthesis for the following transformation: /

Propose an efficient synthesis for the following transformation:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Identify the structure of a compound with the molecular formula C9H10O2 that

Identify the structure of a compound with the molecular formula C9H10O2 that exhibits the following spectral data: a. IR: 3005 cm−1, 1676 cm−1, 1603 cm−1. b. 1 H NMR: 2.6 ppm (singlet, I = 3H), 3.9...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: A compound with the molecular formula C11H14O2 exhibits the following spectra (

A compound with the molecular formula C11H14O2 exhibits the following spectra (1H NMR, 13C NMR, and IR). Identify the structure of this compound.

Q: Predict the major product obtained when each of the following compounds undergoes

Predict the major product obtained when each of the following compounds undergoes a Claisen condensation:

Q: A compound with the molecular formula C9H10O exhibits the following spectra (

A compound with the molecular formula C9H10O exhibits the following spectra (1H NMR, 13C NMR, and IR). Identify the structure of this compound.

Q: Below are two hypothetical compounds. / a.

Below are two hypothetical compounds. a. Which compound would you expect to hold greater promise as a potential antihistamine? Explain your choice. b. Do you expect the compound you chose [in part (...

Q: Would you expect the following compound to be aromatic? Explain your

Would you expect the following compound to be aromatic? Explain your answer.

Q: Compounds A, B, C, and D are constitutionally isomeric

Compounds A, B, C, and D are constitutionally isomeric, aromatic compounds with the molecular formula C8H10. Deduce the structure of compound D using the following clues: • The 1 H NMR spectrum of co...

Q: Each of the following compounds contains two heteroatoms (one nitrogen atom

Each of the following compounds contains two heteroatoms (one nitrogen atom and one oxygen atom): In compound A, the lone pair on the nitrogen atom is more likely to function as a base. However, in c...

Q: Propose an efficient synthesis for the following transformation: /

Propose an efficient synthesis for the following transformation:

Q: Using toluene and acetylene as your only sources of carbon atoms,

Using toluene and acetylene as your only sources of carbon atoms, show how you would prepare the following compound:

Q: Due to their potential application in organic electronic devices, such as

Due to their potential application in organic electronic devices, such as television screens, a large number of compounds containing quinoidal pi systems (such as compound A) have been prepared. Reduc...

Q: Compound 1 contains a tetrazole ring (a five-membered ring

Compound 1 contains a tetrazole ring (a five-membered ring containing four nitrogen atoms), while its constitutional isomer, compound 2, exhibits an azido group (−N3). There is evide...

Q: Studies modeling chemical reactions in the atmosphere of Saturn’s moon Titan suggest

Studies modeling chemical reactions in the atmosphere of Saturn’s moon Titan suggest that the compound 1,2,5,6-tetracyanocyclooctatetraene can form through one of a series of gas-phase reactions media...

Q: Identify the reagents that you would use to produce each of the

Identify the reagents that you would use to produce each of the following compounds using a Claisen condensation:

Q: Consider the structures for naphthalene and phenanthrene. /

Consider the structures for naphthalene and phenanthrene. a. Draw all three resonance structures of naphthalene and then explain why the C2−C3 bond has a longer bond length (1.42 &A...

Q: Cyclobutadiene is not stable at room temperature. Upon formation, it

Cyclobutadiene is not stable at room temperature. Upon formation, it rapidly dimerizes via a Diels–Alder reaction. However, several derivatives of cyclobutadiene are known to be stab...

Q: Compound A has the molecular formula C8H8O. An IR spectrum of

Compound A has the molecular formula C8H8O. An IR spectrum of compound A exhibits a signal at 1680 cm−1. The 1 H NMR spectrum of compound A exhibits a group of signals between 7.5 an...

Q: Starting with benzene and using any other reagents of your choice,

Starting with benzene and using any other reagents of your choice, design a synthesis for each of the following compounds. Each compound has a Br and one other substituent that we did not learn how to...

Q: Benzene was treated with (R)-2-chlorobutane in the

Benzene was treated with (R)-2-chlorobutane in the presence of aluminum trichloride, and the resulting product mixture was found to be optically inactive. a. What products are expected, assuming that...

Q: The 1 H NMR spectrum of phenol exhibits three signals in the

The 1 H NMR spectrum of phenol exhibits three signals in the aromatic region of the spectrum. These signals appear at 6.7, 6.8, and 7.2 ppm. Use your understanding of shielding and deshielding effects...

Q: When toluene is treated with a mixture of excess sulfuric acid and

When toluene is treated with a mixture of excess sulfuric acid and nitric acid at high temperature, a compound is obtained that exhibits only two signals in its 1H NMR spectrum. One signal appears up...

Q: Each of the following compounds is an aromatic compound bearing a substituent

Each of the following compounds is an aromatic compound bearing a substituent that we did not discuss in this chapter. Using the principles that we discussed in this chapter, predict the major product...

Q: Predict the major product of the following reaction: /

Predict the major product of the following reaction:

Q: Bakelite is one of the first known synthetic polymers and was used

Bakelite is one of the first known synthetic polymers and was used to make radio and telephone casings as well as automobile parts in the early twentieth century. Bakelite is formed by treating phenol...

Q: Predict the product of the Dieckmann cyclization that occurs when each of

Predict the product of the Dieckmann cyclization that occurs when each of the following compounds is treated with sodium ethoxide, followed by acid work-up:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: When N,N-dimethylaniline is treated with bromine, ortho

When N,N-dimethylaniline is treated with bromine, ortho and para products are observed. Yet, when N,N-dimethylaniline is treated with a mixture of nitric acid and sulfuric acid, only the meta product...

Q: Aromatic heterocycles are also capable of undergoing electrophilic aromatic substitution. For

Aromatic heterocycles are also capable of undergoing electrophilic aromatic substitution. For example, when furan is treated with an electrophile, an electrophilic aromatic substitution reaction occur...

Q: The rate constants for the bromination of several disubstituted stilbenes are given

The rate constants for the bromination of several disubstituted stilbenes are given in the table below. Given that the double bond of stilbene acts as the nucleophile, provide a reasonable explanation...

Q: Compound 1 and compound 2 both contain tritium (T), which

Compound 1 and compound 2 both contain tritium (T), which is an isotope of hydrogen (tritium = 3 H). Both compounds are stable upon treatment with aqueous base. However, upon prolonged treatment with...

Q: Consider the following reaction, in which the product results from substitution

Consider the following reaction, in which the product results from substitution of fluorine and not from substitution of chlorine. a. Draw a mechanism for this reaction. b. Based on the observed reg...

Q: Predict the products for each of the following reactions, and in

Predict the products for each of the following reactions, and in each case, determine which product will predominate:

Q: When 1,4-dimethylcyclohepta-1,3-diene

When 1,4-dimethylcyclohepta-1,3-diene is treated with HBr at elevated temperature, the 1, 2-adduct predominates, rather than the 1,4-adduct. Explain this result.

Q: Electrophilic addition of HI proceeds with the same mechanism as HCl and

Electrophilic addition of HI proceeds with the same mechanism as HCl and HBr. New methods for the hydroiodination of dienes were studied and the reactions consistently produced the thermodynamic addit...

Q: Treatment of compound 1 with benzene in triflic acid (CF3SO3H)

Treatment of compound 1 with benzene in triflic acid (CF3SO3H) affords ammonium ion 3. Triflic acid is an extremely strong acid (pKa = −14), even more acidic than sulfuric acid; unde...

Q: When the following compound is treated with sodium ethoxide, followed by

When the following compound is treated with sodium ethoxide, followed by acid work-up, two condensation products are obtained, both of which are produced via Dieckmann cyclizations. Draw both products...

Q: The following synthesis was developed in an effort to prepare an analogue

The following synthesis was developed in an effort to prepare an analogue of a polycyclic aromatic hydrocarbon in which one of the C=C bonds was replaced with a B−N unit. Such deriva...

Q: Predict the products for each of the following reactions: /

Predict the products for each of the following reactions:

Q: When benzene is treated with 2 in the presence of CuCl2,

When benzene is treated with 2 in the presence of CuCl2, iodination of the ring is achieved with modest yields. It is believed that CuCl2 interacts with 2 to generate +, which is an excellent electrop...

Q: Draw a mechanism for the following reaction. Hint: This reaction

Draw a mechanism for the following reaction. Hint: This reaction is the reverse of sulfonation, so you should read the sulfonation mechanism backward. Your mechanism should involve a sigma complex (po...

Q: When benzene is treated with D2SO4, a deuterium atom replaces one

When benzene is treated with D2SO4, a deuterium atom replaces one of the hydrogen atoms. Propose a mechanism for this reaction. Once again, make sure that your mechanism involves a sigma complex.

Q: Draw a mechanism for the following reaction and make sure to draw

Draw a mechanism for the following reaction and make sure to draw all three resonance structures of the sigma complex:

Q: Predict the expected product(s) when benzene is treated with

Predict the expected product(s) when benzene is treated with each of the following alkyl halides in the presence of AlCl3. In each case, assume conditions have been controlled to favor monoalkylation....

Q: Draw a mechanism for the following reaction, which involves two consecutive

Draw a mechanism for the following reaction, which involves two consecutive Friedel–Crafts alkylations.

Q: A Friedel–Crafts alkylation is an electrophilic aromatic substitution in which

A Friedel–Crafts alkylation is an electrophilic aromatic substitution in which the electrophile (E+) is a carbocation. In previous chapters, we have seen other methods of forming car...

Q: Identify whether each of the following compounds can be made using a

Identify whether each of the following compounds can be made using a direct Friedel–Crafts alkylation or whether it is necessary to perform an acylation followed by a Clemmensen redu...

Q: For each of the following reactions, predict the major product and

For each of the following reactions, predict the major product and propose a mechanism for its formation:

Q: The following compound cannot be made with either a Friedel–Crafts

The following compound cannot be made with either a Friedel–Crafts alkylation or acylation. Explain.

Q: A Friedel–Crafts acylation is an electrophilic aromatic substitution in which

A Friedel–Crafts acylation is an electrophilic aromatic substitution in which the electrophile (E+) is an acylium ion. There are other methods of forming acylium ions, such as treatm...

Q: Draw the two major products obtained when toluene undergoes monobromination.

Draw the two major products obtained when toluene undergoes monobromination.

Q: When ethoxybenzene is treated with a mixture of nitric acid and sulfuric

When ethoxybenzene is treated with a mixture of nitric acid and sulfuric acid, two products are obtained, each of which has the molecular formula C8H9NO3. a. Draw the structure of each product. b. P...

Q: When 1,3-dinitrobenzene is treated with nitric acid and

When 1,3-dinitrobenzene is treated with nitric acid and sulfuric acid at elevated temperature, the product is 1,3,5-trinitrobenzene. Explain the regiochemical outcome of this reaction. In other words,...

Q: Does chlorination of chlorobenzene require the use of a Lewis acid?

Does chlorination of chlorobenzene require the use of a Lewis acid? Explain why or why not.

Q: Predict and explain the regiochemical outcome for chlorination of bromobenzene.

Predict and explain the regiochemical outcome for chlorination of bromobenzene.

Q: For each of the following compounds, predict whether the ring is

For each of the following compounds, predict whether the ring is activated or deactivated, then predict the strength of activation/deactivation, and finally predict the expected directing effects.

Q: Diazepam is a prescription medication first marketed under the trade name Vallium

Diazepam is a prescription medication first marketed under the trade name Vallium, and used to treat anxiety disorders. Predict whether the monosubstituted aromatic ring in diazepam is activated or de...

Q: For each compound below, identify which position(s) is

For each compound below, identify which position(s) is/are most likely to undergo an electrophilic aromatic substitution reaction.

Q: Identify reagents that can be used to achieve the following transformation:

Identify reagents that can be used to achieve the following transformation:

Q: 4-Fluoro-3-nitroaniline is a patented synthetic precursor

4-Fluoro-3-nitroaniline is a patented synthetic precursor used in the production of commercial hair dyes. Identify the position(s) on this compound most likely to undergo electrophilic aromatic substi...

Q: For each of the following compounds, determine the position that is

For each of the following compounds, determine the position that is most likely to be the site of an electrophilic aromatic substitution reaction:

Q: Sildenafil citrate was the first approved drug for treating male erectile dysfunction

Sildenafil citrate was the first approved drug for treating male erectile dysfunction, a condition affecting more than 30 million men in the U.S. The following reaction is part of a synthesis of silde...

Q: Determine whether a blocking group is necessary to accomplish each of the

Determine whether a blocking group is necessary to accomplish each of the following transformations:

Q: The flavor of beer can be tainted by a trace contaminant,

The flavor of beer can be tainted by a trace contaminant, called ortho-bromophenol. To reduce the incidents of contamination, beer manufacturers have used certified beer flavor standards to train prof...

Q: Identify reagents that can be used to convert benzene into each of

Identify reagents that can be used to convert benzene into each of the following compounds: a. Chlorobenzene b. Nitrobenzene c. Bromobenzene d. Ethylbenzene e. Propylbenzene f. Isopropylbenzene...

Q: Identify the product obtained when benzene is treated with each of the

Identify the product obtained when benzene is treated with each of the following reagents: a. Fuming sulfuric acid b. HNO3 /H2SO4 c. Cl2, AlCl3 d. Ethyl chloride, AlCl3 e. Br2, Fe f. HNO3 /H2SO4...

Q: Starting with benzene and using any other necessary reagents of your choice

Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. Note: some of these problems have more than one plausible answer....

Q: 2-Nitroaniline has been used as a precursor in the synthesis

2-Nitroaniline has been used as a precursor in the synthesis of the benzimidazole ring system (shown below), a structural feature that is present in many pharmaceuticals. A reliable method for synthes...

Q: Starting with benzene and using any other necessary reagents of your choice

Starting with benzene and using any other necessary reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible answer.

Q: Draw both resonance structures of the enolate formed when each of the

Draw both resonance structures of the enolate formed when each of the following ketones is treated with a strong base:

Q: Propose an efficient synthesis for each of the following compounds using the

Propose an efficient synthesis for each of the following compounds using the malonic ester synthesis:

Q: We will see in Chapter 20 that derivatives of aniline will react

We will see in Chapter 20 that derivatives of aniline will react with acyl chlorides (RCOCl) in the presence of pyridine (a base) to yield aromatic amides, as shown below for the parent aniline:

Q: Predict the product of the following reaction: /

Predict the product of the following reaction:

Q: Starting with benzene and using any other necessary reagents of your choice

Starting with benzene and using any other necessary reagents of your choice, design a synthesis for the following compound:

Q: The presence of additional nitro groups can have an impact on the

The presence of additional nitro groups can have an impact on the temperature at which a nucleophilic aromatic substitution will readily occur. Consider the following example: When both R groups are...

Q: Draw both products that are obtained when 4-chloro2-methyltoluene

Draw both products that are obtained when 4-chloro2-methyltoluene is treated with sodium amide followed by treatment with H3O+.

Q: Starting with benzene and using any other necessary reagents of your choice

Starting with benzene and using any other necessary reagents of your choice, design a synthesis for anisole (methoxybenzene).

Q: Draw the most likely mechanism for each of the following transformations:

Draw the most likely mechanism for each of the following transformations:

Q: When 2-ethyl-5-chlorotoluene was treated with sodium

When 2-ethyl-5-chlorotoluene was treated with sodium hydroxide at high temperature, followed by treatment with H3O+, three constitutional isomers with the molecular formula C9H12O were obtained. Draw...

Q: The welwitindolinones are a class of natural products that exhibit a host

The welwitindolinones are a class of natural products that exhibit a host of biological activities including insecticidal, fungicidal, and anti-cancer properties. The following reaction was performed...

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations:

Q: In a study to prepare new and more effective anti-inflammatory

In a study to prepare new and more effective anti-inflammatory agents, 2-fluoroloxoprofen was prepared from compound 2, which in turn was the product of a malonic ester synthesis. Starting with diethy...

Q: Rank the following compounds in order of increasing reactivity toward electrophilic aromatic

Rank the following compounds in order of increasing reactivity toward electrophilic aromatic substitution:

Q: Identify which of the following compounds is most activated toward electrophilic aromatic

Identify which of the following compounds is most activated toward electrophilic aromatic substitution. Which compound is least activated?

Q: Predict the product(s) obtained when each of the following

Predict the product(s) obtained when each of the following compounds is treated with a mixture of nitric acid and sulfuric acid:

Q: Predict the major product obtained when each of the following compounds is

Predict the major product obtained when each of the following compounds is treated with fuming sulfuric acid: a. Chlorobenzene b. Phenol c. Benzaldehyde d. ortho-Nitrophenol e. para-Bromotoluene...

Q: For each of the following groups, identify whether it is an

For each of the following groups, identify whether it is an activator or a deactivator, and determine its directing effects:

Q: The following compound has four aromatic rings. Rank them in terms

The following compound has four aromatic rings. Rank them in terms of increasing reactivity toward electrophilic aromatic substitution.

Q: Predict the product(s) obtained when each of the following

Predict the product(s) obtained when each of the following compounds is treated with chloromethane and aluminum trichloride. Some of the compounds might be unreactive. For those that are reactive, ass...

Q: Predict the major product obtained when each of the following compounds is

Predict the major product obtained when each of the following compounds is treated with bromine in the presence of iron tribromide: a. Bromobenzene b. Nitrobenzene c. ortho-Xylene d. tert-Butylben...

Q: When the following compound is treated with a mixture of nitric acid

When the following compound is treated with a mixture of nitric acid and sulfuric acid at 50°C, nitration occurs to afford a compound with two nitro groups. Draw the structure of this produ...

Q: When benzene is treated with 2-methylpropene and sulfuric acid,

When benzene is treated with 2-methylpropene and sulfuric acid, the product obtained is tert-butylbenzene. Propose a mechanism for this transformation.

Q: Propose an efficient synthesis for each of the following compounds using an

Propose an efficient synthesis for each of the following compounds using an acetoacetic ester synthesis:

Q: Draw a mechanism for each of the following transformations: /

Draw a mechanism for each of the following transformations:

Q: Propose a plausible mechanism for each of the following transformations:

Propose a plausible mechanism for each of the following transformations:

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Predict the product(s) of the following reactions:

Predict the product(s) of the following reactions:

Q: Starting with benzene and using any other reagents of your choice,

Starting with benzene and using any other reagents of your choice, design a synthesis for each of the following compounds:

Q: Each of the following syntheses will not produce the desired product.

Each of the following syntheses will not produce the desired product. In each case, identify the flaw in the synthesis.

Q: In each case, identify the most likely position at which monobromination

In each case, identify the most likely position at which monobromination would occur.

Q: When para-bromotoluene is treated with sodium amide, two products

When para-bromotoluene is treated with sodium amide, two products are obtained. Draw both products and propose a plausible mechanism for their formation.

Q: Picric acid is a military explosive formed via the nitration of phenol

Picric acid is a military explosive formed via the nitration of phenol under conditions that install three nitro groups. Draw the structure and provide an IUPAC name for picric acid.

Q: Propose a plausible mechanism forthe following transformation: /

Propose a plausible mechanism forthe following transformation:

Q: Compound 2, a pheromone of the honeybee queen, has been

Compound 2, a pheromone of the honeybee queen, has been shown to have antibacterial and anti-inflammatory properties. One laboratory synthesis of this pheromone involved the preparation of 1, followed...

Q: Benzene was treated with isopropyl chloride in the presence of aluminum trichloride

Benzene was treated with isopropyl chloride in the presence of aluminum trichloride under conditions that favor dialkylation. Draw the major product expected from this reaction.

Q: Draw all resonance structures of the sigma complex formed when toluene undergoes

Draw all resonance structures of the sigma complex formed when toluene undergoes chlorination at the para position.

Q: For each of the following groups of compounds, identify which compound

For each of the following groups of compounds, identify which compound will react most rapidly with ethyl chloride in the presence of aluminum trichloride. Explain your choice in each case and then pr...

Q: Compound A and compound B are both aromatic esters with the molecular

Compound A and compound B are both aromatic esters with the molecular formula C8H8O2. When treated with bromine in the presence of iron tribromide, compound A is converted into only one product, whil...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Predict the product(s) for each of the following reactions

Predict the product(s) for each of the following reactions:

Q: When 2,4-dibromo-3-methyltoluene is treated

When 2,4-dibromo-3-methyltoluene is treated with bromine in the presence of iron (Fe), a compound with the molecular formula C8H7Br3 is obtained. Identify the structure of this product.

Q: Each of the following compounds can be made with a Friedel–

Each of the following compounds can be made with a Friedel– Crafts acylation. Identify the acyl chloride and the aromatic compound you would use to produce each compound.

Q: Starting with benzene and using any other reagents of your choice,

Starting with benzene and using any other reagents of your choice, design a synthesis for each of the following compounds. In some cases, there may be more than one plausible answer.

Q: When benzene is treated with methyl chloride and aluminum trichloride under conditions

When benzene is treated with methyl chloride and aluminum trichloride under conditions that favor trialkylation, one major product is obtained. Draw this product and provide an IUPAC name.

Q: Identify the major product formed when each of the following compounds is

Identify the major product formed when each of the following compounds is treated with Et2CuLi followed by mild acid:

Q: The following compound is highly activated but nevertheless undergoes bromination very slowly

The following compound is highly activated but nevertheless undergoes bromination very slowly. Explain.

Q: When the following compound is treated with Br2 in the presence of

When the following compound is treated with Br2 in the presence of a Lewis acid, one product predominates. Determine the structure of that product.

Q: Predict the major product of the following reaction: /

Predict the major product of the following reaction:

Q: When ortho-bromonitrobenzene is treated with NaOH at elevated temperature,

When ortho-bromonitrobenzene is treated with NaOH at elevated temperature, only one product is formed. a. Draw the product. b. Identify the intermediate formed en route to the product. c. Would the...

Q: Historically, the nitroso group has been known as a strong deactivator

Historically, the nitroso group has been known as a strong deactivator, yet an ortho/para-director, in electrophilic aromatic substitution reactions. For example, nitration of nitrosobenzene affords m...

Q: Compound A has the molecular formula C7H14O and reacts with sodium borohydride

Compound A has the molecular formula C7H14O and reacts with sodium borohydride in methanol to form an alcohol. The 1H NMR spectrum of compound A exhibits only two signals: a doublet (I = 12) and a sep...

Q: Using the information provided below, deduce the structures of compounds A

Using the information provided below, deduce the structures of compounds A, B, C, and D:

Q: Identify the structures of compounds A to D below and then identify

Identify the structures of compounds A to D below and then identify reagents that can be used to convert cyclohexene into compound D in just one step.

Q: Identify the structures of compounds A to E below: /

Identify the structures of compounds A to E below:

Q: An aldehyde with the molecular formula C4H6O exhibits an IR signal at

An aldehyde with the molecular formula C4H6O exhibits an IR signal at 1715 cm−1. a. Propose two possible structures that are consistent with this information. b. Describe how you could use 13C NMR s...

Q: Predict the major product of the three following steps and show a

Predict the major product of the three following steps and show a mechanism for its formation:

Q: A compound with the molecular formula C9H10O exhibits a strong signal at

A compound with the molecular formula C9H10O exhibits a strong signal at 1687 cm−1 in its IR spectrum. The 1H and 13C NMR spectra for this compound are shown below. Identify the stru...

Q: A compound with the molecular formula C13H10O produces a strong signal at

A compound with the molecular formula C13H10O produces a strong signal at 1660 cm−1 in its IR spectrum. The 13C NMR spectrum for this compound is shown below. Identify the structure...

Q: A ketone with the molecular formula C9H18O exhibits only one signal in

A ketone with the molecular formula C9H18O exhibits only one signal in its 1H NMR spectrum. Provide a systematic (IUPAC) name for this compound.

Q: Using any compounds of your choosing, identify a method for preparing

Using any compounds of your choosing, identify a method for preparing each of the following compounds. Your only limitation is that the compounds you use can have no more than two carbon atoms. For pu...

Q: Draw a plausible mechanism for each of the following transformations:

Draw a plausible mechanism for each of the following transformations:

Q: Under acid-catalyzed conditions, formaldehyde polymerizes to produce a number

Under acid-catalyzed conditions, formaldehyde polymerizes to produce a number of compounds, including metaformaldehyde. Draw a plausible mechanism for this transformation:

Q: The following transformation was employed during synthetic studies toward the total synthesis

The following transformation was employed during synthetic studies toward the total synthesis of cyclodidemniserinol trisulfate, found to inhibit HIV-1 integrase. Propose a four-step synthesis to acco...

Q: Consider the following synthetic sequence: / a.

Consider the following synthetic sequence: a. Identify reagents that can be used to achieve each of the reactions shown. Note: Reagents have been shown for the conversion of 3 to 4, which involves se...

Q: Which of the following is the correct sequence of reactions needed to

Which of the following is the correct sequence of reactions needed to transform ketone 1 into aldehyde 2, or will all three routes produce the desired product? Explain your choice(s).

Q: Compare the indicated bonds (a and b) in the following

Compare the indicated bonds (a and b) in the following compound. Bond a has a bond length of 1.45 Ã…, while bond b has a bond length of 1.35 Ã…. Suggest a reason for this diffe...

Q: In the previous section, we learned how to use diethyl malonate

In the previous section, we learned how to use diethyl malonate as a starting material in the preparation of substituted carboxylic acids (the malonic ester synthesis). That method employed a step in...

Q: During a synthesis of a potential anticancer agent, 7-hydroxynitidine

During a synthesis of a potential anticancer agent, 7-hydroxynitidine, the investigators treated bromide 1 with two equivalents of a strong base to form compound 2. Propose a plausible mechanism to ac...

Q: In the following reaction, iodine monochloride (ICl) effectively serves

In the following reaction, iodine monochloride (ICl) effectively serves as a source of an electrophilic iodonium species, I+. a. Propose a mechanism for the formation of each of the two products, A a...

Q: Assign a systematic (IUPAC) name to each of the following

Assign a systematic (IUPAC) name to each of the following compounds:

Q: Draw the structure of each of the following compounds: a

Draw the structure of each of the following compounds: a. (S)-3,3-Dibromo-4-ethylcyclohexanone   b. 2,4-Dimethyl-3-pentanone c. (R)-3-Bromobutanal

Q: Compounds with two ketone groups are named as alkane diones; for

Compounds with two ketone groups are named as alkane diones; for example: The compound above is an artificial flavor added to microwave popcorn and movie- theater popcorn to simulate the butter flavo...

Q: Regular sunscreen use is an important part of keeping your skin healthy

Regular sunscreen use is an important part of keeping your skin healthy by protecting it from ultraviolet radiation, but some chemical agents in sunscreens may be harmful if absorbed into the skin. Re...

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: Draw a mechanism for each of the following reactions: /

Draw a mechanism for each of the following reactions:

Q: For most ketones, hydrate formation is unfavorable, because the equilibrium

For most ketones, hydrate formation is unfavorable, because the equilibrium favors the ketone rather than the hydrate. However, the equilibrium for hydration of hexafluoroacetone favors formation of t...

Q: Draw a plausible mechanism for each of the following transformations:

Draw a plausible mechanism for each of the following transformations:

Q: Using a Stork enamine synthesis, show how you might accomplish each

Using a Stork enamine synthesis, show how you might accomplish each of the following transformations:

Q: The natural product frontalin is a pheromone isolated from the pine beetle

The natural product frontalin is a pheromone isolated from the pine beetle Dendroctonus frontalis, a species that accounts for much of the diseased timber found in the northern hemisphere. The followi...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Predict the product(s) for each reaction below:

Predict the product(s) for each reaction below:

Q: Draw a plausible mechanism for the following transformation: /

Draw a plausible mechanism for the following transformation:

Q: Compound A has the molecular formula C8H14O2. Upon treatment with catalytic

Compound A has the molecular formula C8H14O2. Upon treatment with catalytic acid, compound A is converted into the cyclic hemiacetal shown below. Identify the structure of compound A.

Q: Draw a plausible mechanism for each of the following transformations:

Draw a plausible mechanism for each of the following transformations:

Q: Predict the major product for each of the following reactions:

Predict the major product for each of the following reactions:

Q: Pinnatoxin A is a marine natural product isolated from the shellfish Pinna

Pinnatoxin A is a marine natural product isolated from the shellfish Pinna muricata and has demonstrated dangerous toxic effects in humans. Pinnatoxin A has a remarkably intricate structure that inclu...

Q: Predict the product of each of the following reactions: /

Predict the product of each of the following reactions:

Q: Identify the reactants that you would use to make each of the

Identify the reactants that you would use to make each of the following compounds:

Q: Tricyclic ring structures, such as compound 6 shown below, are

Tricyclic ring structures, such as compound 6 shown below, are found in a large number of biologically active natural products. These fused rings are challenging to construct, so chemists are continuo...

Q: Draw a plausible mechanism for each of the following reactions:

Draw a plausible mechanism for each of the following reactions:

Q: Predict the major product for each of the following reactions:

Predict the major product for each of the following reactions:

Q: Chiral amines are used to catalyze a host of different enantioselective transformations

Chiral amines are used to catalyze a host of different enantioselective transformations. For instance, proline (explored further in Chapter 25) is a naturally occurring, chiral amino acid that can be...

Q: Predict the product of the following two-step procedure and draw

Predict the product of the following two-step procedure and draw a mechanism for its formation:

Q: Draw the products that are expected for each of the following reactions

Draw the products that are expected for each of the following reactions:

Q: The mechanism for acetal hydrolysis has been heavily investigated. In one

The mechanism for acetal hydrolysis has been heavily investigated. In one study, which explored rates as well as stereochemical aspects, compound 1 was treated with aqueous acid to afford compound 2....

Q: As described above, methenamine is hydrolyzed in aqueous acid to produce

As described above, methenamine is hydrolyzed in aqueous acid to produce formaldehyde and ammonia. Draw a mechanism showing formation of one molecule of formaldehyde (the remaining five molecules of f...

Q: Predict the major product for each of the following: /

Predict the major product for each of the following:

Q: Draw the structure of the cyclic compound that is produced when acetone

Draw the structure of the cyclic compound that is produced when acetone is treated with 1,3-propanedithiol in the presence of an acid catalyst.

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Draw a complete mechanism for the following transformation: /

Draw a complete mechanism for the following transformation:

Q: When 2 moles of benzaldehyde are treated with sodium hydroxide, a

When 2 moles of benzaldehyde are treated with sodium hydroxide, a reaction occurs in which 1 mole of benzaldehyde is oxidized (giving benzoic acid) while the other mole of benzaldehyde is reduced (giv...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following:

Q: Identify reagents that can be used to accomplish each of the transformations

Identify reagents that can be used to accomplish each of the transformations below:

Q: Predict the major product for each of the following reaction sequences:

Predict the major product for each of the following reaction sequences:

Q: Identify the reagents necessary to accomplish each of the transformations below:

Identify the reagents necessary to accomplish each of the transformations below:

Q: Predict the major product for each of the following reactions.

Predict the major product for each of the following reactions.

Q: In the following reaction, a Wittig reagent is generated in situ

In the following reaction, a Wittig reagent is generated in situ by mixing the phosphonium salt with a strong base, in the presence of an aldehyde (note that ester groups are generally not reactive to...

Q: The following reaction is from a synthesis of the natural product salinipyrone

The following reaction is from a synthesis of the natural product salinipyrone A. After being synthesized, salinipyrone A was then screened for antitumor activity. Predict the major product of this re...

Q: While developing the synthesis of a natural product, model systems are

While developing the synthesis of a natural product, model systems are commonly used to study new reactions. The product formed below was used to prepare such a model compound in the synthesis of the...

Q: Identify reagents that you would use to prepare each of the following

Identify reagents that you would use to prepare each of the following compounds via a Wittig reaction:

Q: As with aldehydes and ketones, the α position of esters can

As with aldehydes and ketones, the α position of esters can also be deprotonated. The enolate of ethyl diethoxyacetate was prepared in a synthesis of leustroducsin B, a natural product t...

Q: Identify reagents that can be used to prepare the following compound via

Identify reagents that can be used to prepare the following compound via a Robinson annulation:

Q: Predict the major product of each reaction below: /

Predict the major product of each reaction below:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: The anti-tumor compound maytansine was originally isolated from the Ethiopian

The anti-tumor compound maytansine was originally isolated from the Ethiopian shrub Maytenus serrata. Development of a multistep synthesis of maytansine involved compound 1 as a key precursor. Propose...

Q: Compound A has the molecular formula C10H10O and exhibits a strong signal

Compound A has the molecular formula C10H10O and exhibits a strong signal at 1720 cm−1 in its IR spectrum. Treatment with 1,2-ethanedithiol followed by Raney nickel affords the produ...

Q: Provide a systematic (IUPAC) name for each of the following

Provide a systematic (IUPAC) name for each of the following compounds:

Q: Draw the structure for each compound below: a. Propanedial

Draw the structure for each compound below: a. Propanedial b. 4-Phenylbutanal c. (S)-3-Phenylbutanal d. 3,3,5,5-Tetramethyl-4-heptanone e. (R)-3-Hydroxypentanal f. meta-Hydroxyacetophenone g. 2...

Q: Provide a systematic (IUPAC) name for the compound below.

Provide a systematic (IUPAC) name for the compound below. Be careful: This compound has two chiral centers (can you find them?).

Q: Draw all constitutionally isomeric aldehydes with the molecular formula C4H8O and provide

Draw all constitutionally isomeric aldehydes with the molecular formula C4H8O and provide a systematic (IUPAC) name for each isomer.

Q: Draw all constitutionally isomeric aldehydes with the molecular formula C5H10O and provide

Draw all constitutionally isomeric aldehydes with the molecular formula C5H10O and provide a systematic (IUPAC) name for each isomer. Which of these isomers possesses a chiral center?

Q: Draw all constitutionally isomeric ketones with the molecular formula C6H12O and provide

Draw all constitutionally isomeric ketones with the molecular formula C6H12O and provide a systematic (IUPAC) name for each isomer.

Q: Using cyclopentanone as your starting material and using any other reagents of

Using cyclopentanone as your starting material and using any other reagents of your choice, propose an efficient synthesis for each of the following compounds:

Q: For each pair of the following compounds, identify which compound would

For each pair of the following compounds, identify which compound would be expected to react more rapidly with a nucleophile:

Q: Draw the major product of each Wittig reaction below: /

Draw the major product of each Wittig reaction below:

Q: Draw the structure of the alkyl halide needed to prepare each of

Draw the structure of the alkyl halide needed to prepare each of the following Wittig reagents and then determine which Wittig reagent will be the more difficult to prepare. Explain your choice.

Q: Choose a Grignard reagent and a ketone that can be used to

Choose a Grignard reagent and a ketone that can be used to produce each of the following compounds: a. 3-Methyl-3-pentanol b. 1-Ethylcyclohexanol c. Triphenylmethanol d. 5-Phenyl-5-nonanol

Q: You are working in a laboratory, and you are given the

You are working in a laboratory, and you are given the task of converting cyclopentene into 1,5-pentanediol. Your first thought is simply to perform an ozonolysis followed by reduction with LiAlH4, bu...

Q: Predict the major product(s) from the treatment of acetone

Predict the major product(s) from the treatment of acetone with the following: a. [H+], NH3, (−H2O) b. [H+], CH3NH2, (−H2O) c. [H+], excess EtOH, (−H2O) d. [H+], (CH3)2NH, (−H2O) e. [H+], NH2NH2,...

Q: Propose a plausible mechanism for the following transformation: /

Propose a plausible mechanism for the following transformation:

Q: Treatment of catechol with formaldehyde in the presence of an acid catalyst

Treatment of catechol with formaldehyde in the presence of an acid catalyst produces a compound with the molecular formula C7H6O2. Draw the structure of this product.

Q: Starting with cyclopentanone and using any other reagents of your choosing,

Starting with cyclopentanone and using any other reagents of your choosing, identify how you would prepare each of the following compounds:

Q: Glutaraldehyde is a germicidal agent that is sometimes used to sterilize medical

Glutaraldehyde is a germicidal agent that is sometimes used to sterilize medical equipment too sensitive to be heated in an autoclave. In mildly acidic conditions, glutaraldehyde exists in a cyclic fo...

Q: Using 1-propanol as your only source of carbon, propose

Using 1-propanol as your only source of carbon, propose an efficient synthesis for each of the following compounds:

Q: Identify the reactants that you would use to make each of the

Identify the reactants that you would use to make each of the following imines:

Q: Identify the reactants that you would use to make each of the

Identify the reactants that you would use to make each of the following enamines:

Q: Predict the major product(s) obtained when each of the

Predict the major product(s) obtained when each of the following compounds undergoes hydrolysis in the presence of H3O+:

Q: Identify all of the expected products when the compound below is treated

Identify all of the expected products when the compound below is treated with aqueous acid:

Q: Draw a plausible mechanism for each of the following transformations:

Draw a plausible mechanism for each of the following transformations:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Identify the starting materials needed to make each of the following acetals

Identify the starting materials needed to make each of the following acetals:

Q: Using ethanol as your only source of carbon atoms, design a

Using ethanol as your only source of carbon atoms, design a synthesis for the following compound:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: The compound below is believed to be a wasp pheromone. Draw

The compound below is believed to be a wasp pheromone. Draw the major product formed when this compound is hydrolyzed in aqueous acid:

Q: The following reaction utilizes a Michael addition, followed by a Claisen

The following reaction utilizes a Michael addition, followed by a Claisen-type reaction to make chiral diketoester 3 as part of the total synthesis of dynemycin A, a natural product with promising ant...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: Draw a plausible mechanism for the following transformation: /

Draw a plausible mechanism for the following transformation:

Q: When cyclohexanone is treated with H2O, an equilibrium is established between

When cyclohexanone is treated with H2O, an equilibrium is established between cyclohexanone and its hydrate. This equilibrium greatly favors the ketone, and only trace amounts of the hydrate can be de...

Q: Consider the three constitutional isomers of dioxane (C4H8O2): /

Consider the three constitutional isomers of dioxane (C4H8O2): One of these constitutional isomers is stable under basic conditions as well as mildly acidic conditions and is therefore used as a comm...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: A compound with the molecular formula C10H10O4 exhibits only two signals in

A compound with the molecular formula C10H10O4 exhibits only two signals in its 1H NMR spectrum: a singlet at 4.0 (I = 3H) and a singlet at 8.1 (I = 2H). Identify the structure of this compound.

Q: Describe how you could use IR spectroscopy to distinguish between ethyl acetate

Describe how you could use IR spectroscopy to distinguish between ethyl acetate and butyric acid.

Q: Describe how you could use NMR spectroscopy to distinguish between benzoyl chloride

Describe how you could use NMR spectroscopy to distinguish between benzoyl chloride and para-chlorobenzaldehyde.

Q: A compound with the molecular formula C8H8O3 exhibits the following IR,

A compound with the molecular formula C8H8O3 exhibits the following IR, 1H NMR, and 13C NMR spectra. Deduce the structure of this compound.

Q: Propose a mechanism for the following transformation, and explain how you

Propose a mechanism for the following transformation, and explain how you could use an isotopic labeling experiment to verify your proposed mechanism:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: N-Acetylazoles undergo hydrolysis more readily than regular amides. Suggest

N-Acetylazoles undergo hydrolysis more readily than regular amides. Suggest a reason for the enhanced reactivity of N-acetylazoles toward nucleophilic acyl substitution.

Q: Dimethylformamide (DMF) is a common solvent: /

Dimethylformamide (DMF) is a common solvent: a. The 1 H NMR spectrum of DMF exhibits three signals. Upon treatment with excess LiAlH4 followed by water, DMF is converted into a new compound that exhi...

Q: Olefin metathesis (2005 Nobel Prize) using the Grubbs catalyst has

Olefin metathesis (2005 Nobel Prize) using the Grubbs catalyst has emerged as one of the most important tools for the organic chemist (e.g., 2 to 3). Metathesis substrate 2 can be prepared from 1 in t...

Q: Aminotetralins are a class of compounds currently being studied for their promise

Aminotetralins are a class of compounds currently being studied for their promise as antidepressant drugs. The following conversion was employed during a mechanistic study associated with a synthetic...

Q: Steroidal derivatives are important pharmacologically and biologically, and they continue to

Steroidal derivatives are important pharmacologically and biologically, and they continue to be a popular backbone in the search for new biologically active steroid hormone analogues. Propose a possib...

Q: Allylic bromide 2 was recently used as a key fragment in progress

Allylic bromide 2 was recently used as a key fragment in progress toward the total synthesis of an analogue of amphidinolide N, a potent cytotoxic agent isolated from the marine organism Amphidinium s...

Q: Compound 3 (below) was used as an intermediate in a

Compound 3 (below) was used as an intermediate in a recently reported synthesis of the γ-secretase inhibitor BMS-708163. Compound 3 was made from compound 1 via the two-step process shown....

Q: The m- and p-substituted methyl benzoates listed in the

The m- and p-substituted methyl benzoates listed in the table below were treated with NaOH in dioxane and water. The rate constants of saponification, k, are also listed in the table. Provide structur...

Q: The plant Thapsia villosa is so poisonous that it is known as

The plant Thapsia villosa is so poisonous that it is known as the deadly carrot! Despite the toxicity of this herb, its historical use in traditional medicine makes its extracted compounds attractive...

Q: Scorzocreticin (S)-1 was isolated from a plant that is

Scorzocreticin (S)-1 was isolated from a plant that is used for cooking traditional meat dishes on the Greek island of Crete. As part of a recent synthesis of scorzocreticin (S)-1, compound 1 was conv...

Q: 46. Which monomer can be used to prepare the following polymer

46. Which monomer can be used to prepare the following polymer under acidic conditions? 47. Which monomers are formed when the following polymer undergoes acid-catalyzed hydrolysis? 48. Which polym...

Q: (−)-Spongidepsin is a marine natural product that is toxic to some

(−)-Spongidepsin is a marine natural product that is toxic to some cancer cells. During a synthesis of (−)-spongidepsin, compound 1 was converted into compound 2. P...

Q: Prostaglandins (Section 26.7) are a group of structurally

Prostaglandins (Section 26.7) are a group of structurally related compounds that function as biochemical regulators and exhibit a wide array of activity, including the regulation of blood pressure, bl...

Q: The following two-step rearrangement was the cornerstone of the first

The following two-step rearrangement was the cornerstone of the first stereoselective total synthesis of quadrone, a biologically active natural product isolated from an Aspergillus fungus. Propose a...

Q: During recent studies to determine the absolute stereochemistry of a bromohydrin,

During recent studies to determine the absolute stereochemistry of a bromohydrin, the investigators observed an unexpected skeletal rearrangement. Provide a plausible mechanism for the formation of ep...

Q: During a recent total synthesis of englerin A, a potent cytotoxic

During a recent total synthesis of englerin A, a potent cytotoxic natural product isolated from the stem bark of a Tanzanian plant, the investigators observed the following (unusual) basecatalyzed rin...

Q: A convenient method for achieving the transformation below involves treatment of the

A convenient method for achieving the transformation below involves treatment of the ketone with Wittig reagent 1 followed by acid-catalyzed hydration: a. Predict the product of the Wittig reaction....

Q: During a recent synthesis of hispidospermidin, a fungal isolate and an

During a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed a novel, aliphatic Friedel–Crafts acylation. The follo...

Q: Treatment of the following ketone with LiAlH4 affords two products, A

Treatment of the following ketone with LiAlH4 affords two products, A and B. Compound B has the molecular formula C8H14O and exhibits strong signals at 3305 cm−1 (broad) and 2117 cm&...

Q: Predict the regiochemical outcome (major product) for each of the

Predict the regiochemical outcome (major product) for each of the following Diels–Alder reactions:

Q: Consider the following [4+4] cycloaddition process. Would

Consider the following [4+4] cycloaddition process. Would you expect this process to occur through a thermal or photochemical pathway? Justify your answer with MO theory.

Q: Diastereoselective transformations, including the one shown below, have been developed

Diastereoselective transformations, including the one shown below, have been developed during efforts toward the syntheses of antifungal and antibacterial natural products. Disregarding stereochemistr...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following thermal electrocyclic reactions:

Q: Predict the product(s) for each of the following reactions

Predict the product(s) for each of the following reactions:

Q: Inthomycin C, a natural product produced by Streptomyces bacteria, is

Inthomycin C, a natural product produced by Streptomyces bacteria, is known to inhibit the production of cellulose, an important component of the cell wall of plants. A recent synthesis of inthomycin...

Q: For each of the following reactions, use brackets and two numbers

For each of the following reactions, use brackets and two numbers to identify the type of sigmatropic rearrangement taking place:

Q: Consider the structure of cis-1,2-divinylcyclopropane:

Consider the structure of cis-1,2-divinylcyclopropane: This compound is stable at low temperature but rearranges at room temperature to produce 1,4-cycloheptadiene. a. Draw a mechanism for this tra...

Q: Predict the product for each of the following reactions: /

Predict the product for each of the following reactions:

Q: Draw a plausible mechanism for the following transformation: /

Draw a plausible mechanism for the following transformation:

Q: Use Woodward–Fieser rules to estimate the expected λmax for each

Use Woodward–Fieser rules to estimate the expected λmax for each of the following compounds:

Q: As seen at the end of Section 16.10, a

As seen at the end of Section 16.10, a deficiency in vitamin D can cause a bonesoftening disease called rickets, so many foods, including milk and cereals, are fortified with vitamin D. Our bodies syn...

Q: For each of the following tasks, use the color wheel in

For each of the following tasks, use the color wheel in Figure 16.37. a. Identify the color of a compound that absorbs orange light. b. Identify the color of a compound that absorbs blue-green light...

Q: Identify which of the following compounds are expected to have a pKa

Identify which of the following compounds are expected to have a pKa

Q: Draw the structure of each of the following compounds: a

Draw the structure of each of the following compounds: a. 1,4-Cyclohexadiene b. 1,3-Cyclohexadiene c. (Z)-1,3-Pentadiene d. (2Z,4E)-Hepta-2,4-diene e. 2,3-Dimethyl-1,3-butadiene

Q: Circle each compound that has a conjugated π system: /

Circle each compound that has a conjugated π system:

Q: Treatment of 1,2-dibromocycloheptane with excess potassium tert-

Treatment of 1,2-dibromocycloheptane with excess potassium tert-butoxide yields a product that absorbs UV light. Identify the product.

Q: In each of the following pairs of compounds identify the compound that

In each of the following pairs of compounds identify the compound that liberates the most heat upon hydrogenation:

Q: Draw all products that are expected when 2-ethyl-3

Draw all products that are expected when 2-ethyl-3-methyl 1,3-cyclohexadiene is treated with HBr at room temperature, and show a mechanism of their formation.

Q: After performing the reaction from Problem 16.37, the reaction

After performing the reaction from Problem 16.37, the reaction flask is heated to 40ºC and two of the products become the major products. When the flask is then cooled to 0ºC, no change occurs in the...

Q: Each of the following compounds does not participate as a diene in

Each of the following compounds does not participate as a diene in a Diels–Alder reaction. Explain why in each case.

Q: Provide both an IUPAC name and a common name for each of

Provide both an IUPAC name and a common name for each of the following compounds: a. HO2C(CH2)3CO2H b. CH3(CH2)2CO2H c. C6H5CO2H d. HO2C(CH2)2CO2H e. CH3COOH f. HCO2H

Q: Draw the structure of each of the following compounds: a

Draw the structure of each of the following compounds: a. Cyclobutanecarboxylic acid b. 3,3-Dichlorobutyric acid c. 3,3-Dimethylglutaric acid

Q: Provide an IUPAC name for each of the following compounds:

Provide an IUPAC name for each of the following compounds:

Q: One of the compounds from the previous problem has a pKa <

One of the compounds from the previous problem has a pKa < 10. Identify that compound and explain why it is so much more acidic than all of the other compounds.

Q: The following two compounds are constitutional isomers. Identify which of these

The following two compounds are constitutional isomers. Identify which of these is expected to be more acidic and explain your choice.

Q: Consider the structure of para-hydroxyacetophenone, which has a pKa

Consider the structure of para-hydroxyacetophenone, which has a pKa value in the same range as a carboxylic acid, despite the fact that it lacks a COOH group. Offer an explanation for the acidity of p...

Q: Based on your answer to the previous question, would you expect

Based on your answer to the previous question, would you expect meta-hydroxyacetophenone to be more or less acidic than para-hydroxyacetophenone? Explain your answer.

Q: When formic acid is treated with potassium hydroxide (KOH), an

When formic acid is treated with potassium hydroxide (KOH), an acid-base reaction occurs, forming a carboxylate ion. Draw a mechanism for this reaction and identify the name of the carboxylate salt.

Q: Acetic acid was dissolved in a solution buffered to a pH of

Acetic acid was dissolved in a solution buffered to a pH of 5.76. Determine the ratio of the concentrations of acetate ion and acetic acid in this solution. Which species predominates under these cond...

Q: Rank each set of compounds in order of increasing acidity:

Rank each set of compounds in order of increasing acidity: a. 2,4-Dichlorobutyric acid 2,3-Dichlorobutyric acid 3,4-Dimethylbutyric acid b. 3-Bromopropionic acid 2,2-Dibromopropionic acid 3,3-Di...

Q: Identify the reagents you would use to perform the following transformations:

Identify the reagents you would use to perform the following transformations: a. Ethanol → Acetic acid b. Toluene → Benzoic acid c. Benzene → Benzoic acid d. 1-Bromobutane → Pentanoic acid e. Eth...

Q: Identify the reagents you would use to achieve each of the following

Identify the reagents you would use to achieve each of the following transformations:

Q: Provide a name for each of the following compounds: /

Provide a name for each of the following compounds:

Q: Draw a structure for each of the following compounds: a

Draw a structure for each of the following compounds: a. Dimethyl oxalate b. Phenyl cyclopentanecarboxylate c. N-Methylpropionamide d. Propionyl chloride

Q: Draw resonance structures for the conjugate base that is produced when each

Draw resonance structures for the conjugate base that is produced when each of the following compounds is treated with sodium ethoxide:

Q: Propose a plausible mechanism for each of the following transformations. These

Propose a plausible mechanism for each of the following transformations. These reactions will all appear later in this chapter, so practicing their mechanisms now will serve as preparation for the res...

Q: Chlorocatechelin A was isolated from a bacterial culture, but it had

Chlorocatechelin A was isolated from a bacterial culture, but it had to be synthesized in the laboratory in order to obtain enough pure material for the study of its antimicrobial activity. Shown belo...

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Identify reagents that can be used to achieve the following transformation:

Identify reagents that can be used to achieve the following transformation:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: In this section, we have seen three ways to achieve the

In this section, we have seen three ways to achieve the following transformation. Identify the reagents necessary for all three methods.

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Draw the enolate ion that is formed when each of the following

Draw the enolate ion that is formed when each of the following compounds is treated with sodium ethoxide. In each case, draw all resonance structures of the enolate ion and predict whether a substanti...

Q: Rank the following compounds in terms of increasing acidity: /

Rank the following compounds in terms of increasing acidity:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Identify reagents that can be used to achieve the following transformation:

Identify reagents that can be used to achieve the following transformation:

Q: Propose a mechanism for each of the following transformations: /

Propose a mechanism for each of the following transformations:

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Identify reagents that can be used to achieve each of the following

Identify reagents that can be used to achieve each of the following transformations:

Q: Propose a mechanism for the following transformation: /

Propose a mechanism for the following transformation:

Q: Identify reagents that will accomplish each of the following transformations:

Identify reagents that will accomplish each of the following transformations:

Q: Juvabione is produced by fir trees of the genus Abies and is

Juvabione is produced by fir trees of the genus Abies and is known to inhibit insect reproduction and growth, thereby offering the trees some protection from insect infestations. One laboratory synthe...

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: α-Bisabolol is the primary constituent of the essential oil of

α-Bisabolol is the primary constituent of the essential oil of the chamomile plant. It has a long history of use in cosmetics due to its anti-inflammatory and skin-soothing properties. O...

Q: Draw the enol of each of the following compounds and identify whether

Draw the enol of each of the following compounds and identify whether the enol exhibits a significant presence at equilibrium. Explain.

Q: Compound A has the molecular formula C9H8O2 and exhibits a strong signal

Compound A has the molecular formula C9H8O2 and exhibits a strong signal at 1740 cm−1 in its IR spectrum. Treatment with two equivalents of LiAlH4 followed by water gives the followi...

Q: Rank each set of compounds in order of increasing acidity:

Rank each set of compounds in order of increasing acidity:

Q: Malonic acid has two acidic protons: / The

Malonic acid has two acidic protons: The pKa of the first proton (pK1) is measured to be 2.8, while the pKa of the second proton (pK2) is measured to be 5.7. a. Explain why the first proton is more...

Q: Identify a systematic (IUPAC) name for each of the following

Identify a systematic (IUPAC) name for each of the following compounds:

Q: Identify the common name for each of the following compounds:

Identify the common name for each of the following compounds:

Q: Draw the structures of eight different carboxylic acids with the molecular formula

Draw the structures of eight different carboxylic acids with the molecular formula C6H12O2. Then, provide a systematic name for each compound and identify which three isomers exhibit chiral centers.

Q: Draw and name all constitutionally isomeric acid chlorides with the molecular formula

Draw and name all constitutionally isomeric acid chlorides with the molecular formula C4H7ClO. Then provide a systematic name for each isomer.

Q: Identify the reagents you would use to convert pentanoic acid into each

Identify the reagents you would use to convert pentanoic acid into each of the following compounds: a. 1-Pentanol b. 1-Pentene c. Hexanoic acid

Q: Identify the reagents you would use to convert each of the following

Identify the reagents you would use to convert each of the following compounds into pentanoic acid: a. 1-Pentene b. 1-Bromobutane

Q: Careful measurements reveal that para-methoxybenzoic acid is less acidic than

Careful measurements reveal that para-methoxybenzoic acid is less acidic than benzoic acid, while meta-methoxybenzoic acid is more acidic than benzoic acid. Explain these observations.

Q: Ethyl acetoacetate has three enol isomers. Draw all three.

Ethyl acetoacetate has three enol isomers. Draw all three.

Q: Predict the major product(s) formed when hexanoyl chloride is

Predict the major product(s) formed when hexanoyl chloride is treated with each of the following reagents: a. CH3CH2NH2 (excess) b. LiAlH4 (excess), followed by H2O c. CH3CH2OH, pyridine d. H2O, p...

Q: Predict the major product(s) formed when cyclopentanecarboxylic acid is

Predict the major product(s) formed when cyclopentanecarboxylic acid is treated with each of the following reagents: a. SOCl2 b. LiAlH4 (excess), followed by H2O c. NaOH d. [H+], EtOH

Q: Predict the major product(s) for each of the following

Predict the major product(s) for each of the following reactions:

Q: Identify the carboxylic acid and the alcohol that are necessary in order

Identify the carboxylic acid and the alcohol that are necessary in order to make each of the following compounds via a Fischer esterification:

Q: Determine the structures of compounds A through F: /

Determine the structures of compounds A through F:

Q: Identify the reagents you would use to convert 1-bromopentane into

Identify the reagents you would use to convert 1-bromopentane into each of the following compounds: a. Pentanoic acid b. Hexanoic acid c. Pentanoyl chloride d. Hexanamide e. Pentanamide f. Ethyl...

Q: Starting with benzene and using any other reagents of your choice,

Starting with benzene and using any other reagents of your choice, show how you would prepare each of the following compounds:

Q: Propose an efficient synthesis for each of the following transformations:

Propose an efficient synthesis for each of the following transformations:

Q: When methyl benzoate bears a substituent at the para position, the

When methyl benzoate bears a substituent at the para position, the rate of hydrolysis of the ester group depends on the nature of the substituent at the para position. Apparently, a methoxy substituen...

Q: Identify reagents that can be used to accomplish each of the following

Identify reagents that can be used to accomplish each of the following transformations: