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Draw the Major Organic Product Formed in the Reaction of 4-Methylcyclohexene with Bromine

Draw the anti-addition products of racemic 4-methylcyclohexene and Br2, explain the bromonium-ion mechanism, and count distinct stereoisomers.

Question

Racemic (±)(\pm)-4-methylcyclohexene reacts with Br2Br_2. Draw the major organic product structure(s), show a complete stepwise mechanism for one pathway, and state how many distinct stereoisomeric products are formed.

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Evidence boundary

The source specifies a racemate and Br2Br_2 but no reaction conditions or product ratio. The structure count follows stereochemical enumeration and anti addition; it does not assert four equal yields or a measured major/minor ratio. The diagram specifies connectivity and relative face orientation, not a preferred chair conformer.