Chapter 18, Problem 18.31P

(a)

Interpretation Introduction

Interpretation:

Given reaction has to be draw completed.

Concept Introduction:

Acid anhydride can react with water, alcohol and  amine. When acid anhydride reacts with water it gives two equivalent of carboxylic acid, with alcohol it gives carboxylic acid and ester, with amine it gives carboxylate ion and amide.

Amine, water and alcohol acts as a nucleophile and gets attached to the carbonyl carbon of the acid anhydride. The base takes the proton from the from the tetrahedral intermediate. The carboxylate ion gets eliminated from the tetrahedral intermediate to form carboxylic acid derivative.

(b)

Interpretation Introduction

Interpretation:

Given reaction has to be completed.

Concept Introduction:

Reaction of acid chloride with ammonia or amines:

The reaction of acid chlorides with ammonia and primary and secondary amines will yield amide.

The nucleophilic addition of ammonia or amine to the carbonyl carbon occurs which is followed by a proton transfer forming an addition intermediate that will eliminate chloride and lose a proton to give the amide compound.

(c)

Interpretation Introduction

Interpretation:

Given reaction has to be draw and completed.

Concept Introduction:

Reaction of an ester with ammonia or an amine:

Treatment of an ester with ammonia or a primary or secondary amine gives an amide.

The nucleophilic addition of the ammonia or amine to the carbonyl carbon occurs followed by a proton transfer and a tetrahedral addition intermediate is formed. The intermediate can directly alkoxide and lose a proton to the alkoxide to give products.

(d)

Interpretation Introduction

Interpretation:

Given reaction has to be draw and completed.

Concept Introduction:

Reaction of an ester with ammonia or an amine:

Treatment of an ester with ammonia or a primary or secondary amine gives an amide.

The nucleophilic addition of the ammonia or amine to the carbonyl carbon occurs followed by a proton transfer and a tetrahedral addition intermediate is formed. The intermediate can directly alkoxide and lose a proton to the alkoxide to give products.