Chapter 22, Problem 22.17P

Interpretation Introduction

Interpretation:

It is to be shown how to synthesize the given compound using benzene as the only aromatic starting compound.

Concept introduction:

When the aromatic species are treated with an acid chloride in the presence of a Lewis acid (e.g. ${\text{AlCl}}_{\text{3}}$), an acylation takes place at the aromatic ring; it is called a Friedel-Crafts acylation reaction. The limitations of a Friedel-Crafts alkylation reaction are carbocation rearrangement; thus it is not a much suitable method for alkylation. A Friedel-Crafts acylation reaction is used to circumvent this problem, which gives an aromatic ketone as the product instead of any carbocation rearrangement reaction. This carbonyl group is then reduced by the Clemmensen reduction to form an alkylbenzene.