Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume it is part of a racemic mixture.
The mechanism for the reaction is given below -
Another stable intermediate is also obtained from 1-phenylcyclohexene.
Benzylic carbocation is stable hence it is also formed. attacks to this intermediate to give cis-1,2-dichloro-1-phenylcyclohexane.