Chapter 9, Problem 9.47P

Interpretation Introduction

Interpretation:

The structure of the product with the formula ${\text{C}}_{\text{9}}{\text{H}}_{\text{10}}{\text{O}}_{\text{2}}$ formed when acetic acid is treated with a strong base followed by benzoyl bromide is to be drawn. The mechanism leading to the formation of this product is to be drawn.

Concept introduction:

Acetic acid is a weak acid that is deprotonated by a strong base. Being a weak acid, its conjugate base, the carboxylate anion, is a relatively stronger base. With a negative charge on the oxygen atom, it is also a strong nucleophile. Strong nucleophiles favor an ${\text{S}}_{\text{N}}\text{2}$ reaction as the nucleophile is involved in the elementary step and facilitates the departure of the leaving group. The leaving group ability is relatively unimportant in an ${\text{S}}_{\text{N}}\text{2}$ reaction.