Chapter 22, Problem 22.44P

Interpretation Introduction

Interpretation:

Structures of dialkyl-substituted benzene, ${\text{C}}_{\text{14}}{\text{H}}_{\text{22}}$, which was recovered from the reaction mixture when it is treated with basic potassium permanganate followed by acid work up, are to be drawn.

Concept introduction:

The aromatic compound with carbon side chains on heating in the presence of basic ${\text{KMnO}}_{\text{4}}$, followed by acid workup oxidizes the side chains to a ${\text{CO}}_{\text{2}}\text{H}$ group.

A quaternary carbon chain is unreactive in the presence of basic potassium permanganate.