Question: We have seen many examples where halogens add to alkenes with anti stereochemistry via the halonium ion mechanism.However, when 1-phenylcyclohexene reacts with chlorine in carbon

We have seen many examples where halogens add to alkenes with anti stereochemistry via the halonium ion mechanism.However, when 1-phenylcyclohexene reacts with chlorine in carbon tetrachloride, a mixture of the cis and trans isomers of the product is recovered. Propose a mechanism, and explain this lack of stereospecificity.

CI Ph Ph CI Ph Ci cCl, Cl Cl cis and trans- 1,2-dichloro-1-phenylcyclohexane 1-phenylcyclohexene

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