Chapter 21, Problem 21.7P

Interpretation Introduction

(a)

Interpretation:

The mechanism for the given reaction is to be drawn and the major product for the same reaction is to be predicted.

Concept introduction:

Amines are more nucleophilic than water and even alcohol, so they also react with acid chloride and acid anhydride to produce corresponding amides. Such type of reaction is called aminolysis. It also follows the nucleophilic addition-elimination mechanism. In the first step, amine adds to electrophilic carbon of acid chloride or acid anhydride followed by nucleophilic elimination of corresponding leaving group to form an amide as a product. The stoichiometry matters in the aminolysis reaction, it requires two equivalent of an amine. The second equivalent of an amine requires to deprotonate the positive charge on N atom which is formed in the first step.

Interpretation Introduction

(b)

Interpretation:

The mechanism for the given reaction is to be drawn and the major product for the same reaction is to be predicted.

Concept introduction:

Amines are more nucleophilic than water and even alcohol, so they also react with acid chloride and acid anhydride to produce corresponding amides. Such type of reaction is called aminolysis. It also follows the nucleophilic addition-elimination mechanism. In the first step, amine adds to electrophilic carbon of acid chloride or acid anhydride followed by nucleophilic elimination of corresponding leaving group to form an amide as a product. The stoichiometry matters in the aminolysis reaction, it requires two equivalent of an amine. The second equivalent of an amine requires to deprotonate the positive charge on N atom which is formed in the first step.