Chapter 20, Problem 20.39P

Interpretation Introduction

(a)

Interpretation:

The transformation of the given reaction is to be determined.

Concept introduction:

Similar to esters that can undergo transesterification, an anhydride can be synthesized from another anhydride. To accomplish this transformation, the anhydride reactant is treated with excess sodium acetate. The leaving group is benzoate which leaves the molecule and the final product is formed.

Interpretation Introduction

(b)

Interpretation:

The transformation of the given reaction is to be determined.

Concept introduction:

The given reaction is acyl substitution involving other carboxylic acid derivatives reaction. The nucleophilic acyl substitution reactions take place in two steps. The first step involves the addition of the nucleophile to form a tetrahedral intermediate. In the second step, reformation of carbonyl and loss of leaving group takes place.

Interpretation Introduction

(c)

Interpretation:

The transformation of the given reaction is to be determined.

Concept introduction:

The given reaction is the synthesis of an amide from an ester. The reaction of the formation of an amide from an ester takes place in two steps. The first step involves the addition of the nucleophile to form a tetrahedral intermediate. In the second step, reformation of carbonyl and loss of leaving group takes place.

Interpretation Introduction

(d)

Interpretation:

The transformation of the given reaction is to be determined.

Concept introduction:

In the stability order, an amide is on a lower rung than a carboxylic acid. Therefore, the conversion of an amide to a carboxylic acid is energetically unfavorable. The transformation of an amide to the carboxylic acid is carried out by treating an amide with a hydroxyl group, followed by an acid workup. This reaction is termed as an amide hydrolysis reaction.