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...
See AnswerQ: 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.
See AnswerQ: 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...
See AnswerQ: 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...
See AnswerQ: 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...
See AnswerQ: 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.
See AnswerQ: 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...
See AnswerQ: 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...
See AnswerQ: 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...
See AnswerQ: 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...
See AnswerQ: Identify which of the following reagents is expected to be a stronger
Identify which of the following reagents is expected to be a stronger nucleophile and explain your choice:
See AnswerQ: The following compound has one aldehyde group and two OH groups.
The following compound has one aldehyde group and two OH groups. Under acidic conditions, either one of the OH groups can function as a nucleophile and attack the carbonyl group, giving rise to two po...
See AnswerQ: Nitriles undergo alkylation at the α position much like ketones undergo alkylation
Nitriles undergo alkylation at the α position much like ketones undergo alkylation at the α position. The α position of the nitrile is first deprotonated to...
See AnswerQ: The conjugate base of diethyl malonate can serve as a nucleophile to
The conjugate base of diethyl malonate can serve as a nucleophile to attack a wide range of electrophiles. Identify the product that is formed when the conjugate base of diethyl malonate reacts with e...
See AnswerQ: When ethylene oxide is treated with a strong nucleophile, the epoxide
When ethylene oxide is treated with a strong nucleophile, the epoxide ring is opened to form an alkoxide ion that can function as a nucleophile to attack another molecule of ethylene oxide. This proce...
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