Predict the major product of the following reaction sequence: [figure]
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Answer
(2) [figure]
Solution
Step (1): Br2/h brominates through the most stable free radical, the 3 radical, so Br goes to the ring carbon carrying CH3 (1-bromo-1-methylcyclohexane).
Step (2): alcoholic KOH, causes dehydrohalogenation; by Saytzeff rule the more substituted alkene, 1-methylcyclohexene, is the major product.
Step (3): HBr in the presence of peroxide adds by a free-radical path (peroxide effect, Kharasch effect): Br adds to the less substituted carbon to give the more stable 3 radical, so Br ends on the ring carbon next to the one carrying CH3 (anti-Markovnikov addition).
[figure]
The major product is 1-bromo-2-methylcyclohexane.
Answer: (2)