Chapter 21, Problem 21.9P

Interpretation Introduction

Interpretation:

A synthesis that will carry out the transformation in Solved Problem 21.8 but does not involve benzoyl chloride an an intermediate is to be proposed.

Concept introduction:

Carboxylic acid derivatives can be relatively easily interconverted provided the product is more stable (lower in the stability ladder) than the susbtrate. Conversion of a substrate lower on the stability ladder (more stable) to one higher on the ladder (less stable) is usually not feasible. Such syntheses must be carried out in a number of reaction steps, generally involving inorganic reagents. The least stable acid derivative is acid chloride, so the first step would be conversion of the stable substrate to acid chloride using an inorganic reagent like ${\text{SOCl}}_{\text{2}}$. The acid chloride can then be relatively esily converted to any derivative, even one less stable than the starting compound.