Chapter 18, Problem 18.35P

Interpretation Introduction

Interpretation:

The synthesis for DEET from 3-methylbenzoic acid has to be proposed.

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.