22. Carboxylic Acid Derivatives: NAS

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

d.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

e.

Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following compounds?

f.

Write a mechanism for each of the following reactions:

b. the aminolysis of phenyl formate, using methylamine.

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.

Propose a mechanism for the reaction of acetic anhydride with water.

We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrahedral intermediate eliminate the carboxylate ion even if it does not lose a proton before the elimination step? Explain.

Propose a mechanism for the formation of succinic anhydride from succinic acid in the presence of acetic anhydride at neutral pH.

How does acetic anhydride make it easier to form the anhydride?

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

e. aqueous NaOH

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

f. cyclohexanol

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

i. isopropyl alcohol

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

k. potassium formate

What compounds are obtained from the following hydrolysis reactions?

d.

What products would you expect to obtain from the following reactions?

a. malonic acid + 2 acetyl chloride