Questions from Organic Chemistry

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...