Reaction of HBr with 3-methylcyclohexene yields a mixture of four products cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1,2-dibromocyclohexane as the soul product. Required:
Draw structures of the possible intermediates and mechanismfor the latter reaction.