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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 sole product, draw structures of the possible intermediates, and then explain why only a single product is formed in the reaction of HBr with3-bromocyclohexene.
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