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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2210

1-Methylcyclohexene is treated with $BD X_{3} \cdot THF$ and then $H X_{2} O X_{2} / NaOH$ . The major product is

A1-methylcyclohexan-1-ol with D on the methyl group
B1-deuterio-2-methylcyclohexan-1-ol
C2-deuterio-2-methylcyclohexan-1-ol, with D and OH cis
D2-deuterio-2-methylcyclohexan-1-ol, with D and OH trans

Answer: C

Boron adds to the less substituted ring carbon (C1 of the alcohol) and D adds to the methyl-bearing carbon (C2) on the same face. Oxidation replaces B by OH with retention. So D is on C2, cis to OH, and

CH X_{3}

is trans to OH.

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