Chapter 15.16, Problem 44P

Interpretation Introduction

Interpretation:

To write the mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride.

Concept introduction:

The reaction of an acyl chloride with acetate ion is a nucleophilic substitution reaction. The acetate ion acts as a nucleophile and attacks the carbonyl carbon of the acyl chloride. The attack results in the formation of a tetrahedral intermediate. Some chloride group attached to the carbonyl carbon acts as a leaving group in the reaction and results in the collapse of the tetrahedral intermediate to form the corresponding anhydride.