Chapter 15, Problem 62P

Interpretation Introduction

Interpretation:

To prove that a tetrahedral intermediate is formed in the given reaction.

Concept introduction:

The nucleophilic acyl substitution reaction in esters is an ${\text{S}}_{\text{N}}\text{1}$ reaction. It is a two-step reaction. In the first step, a tetrahedral intermediate is formed which then collapses in the second step to give the product.

For the formation of the tetrahedral intermediate, the nucleophilic acyl substitution reaction takes place on the carbonyl carbon in the first step of the reaction.

For the collapse of the tetrahedral intermediate, the group attached to the substituent attached to the acyl group leaves leading to the formation of carbonyl compound and a weaker base.