Synthesize 6-(4-tert-butylphenyl)cyclohex-3-enecarbonitrile using (Z)-3-phenylacrylonitrile as your starting material and any other reagents you wish.

Question

Please help and an explanation would be greatly appreciated.

Answer 1

First note the relative stereochemistry of the CN and the phenyl group are not specified in the question.

Retrosynthetically the cylohexene can be put together with a Diels Alder reaction between butadiene and (Z)-(4-tert-butylphenyl)acrylonitrile. The latter will need to be made from the (Z)-3-phenylacrylonitrile. My first thought would be an electrophilic substitution with t-butyl chloride using a mild Lewis acid catalyst, such as tin chloride rather than aluminium chloride.

Hope this helps.