Chapter 13.6, Problem 9P

Interpretation Introduction

Interpretation:

The mechanism for the preparation of $\text{1-phenylcyclohexene}$ from the reaction of

benzene and cyclohexene is to be explained.

Concept introduction:

The reaction that involves the substitution of aromatic ring by alkyl group is called alkylation reaction.

The alkyl halide or the compound that forms stable carbocation can also be used for the alkylation of aromatic compounds.

The $\text{π}$ electrons of benzene attack the carbocation and cause it to undergo substitution followed by deprotonation of cyclohexadienyl cation.

The double bond at benzylic position can be introduced by the benzylic bromination with $\text{N-bromosuccinimide}\text{(NBS)}$ followed by dehydrohalogenation.