1-Methylcyclohexene can be converted into 1-methylcyclohexan-1-ol as the major product by which of the following? (More than one answer may be correct.)

A $Hg (OAc) X_{2}, H X_{2} O$ followed by $NaBH X_{4}$
Bdilute $H X_{2} SO X_{4}$ in water
C $BH X_{3} \cdot THF$ followed by $H X_{2} O X_{2} / NaOH$
D $Br X_{2}$ in water, followed by $Zn$

Answer: A, B

Oxymercuration-demercuration and acid-catalysed hydration are both Markovnikov and give the tertiary alcohol, with no rearrangement possible. Hydroboration-oxidation gives 2-methylcyclohexan-1-ol.

Br X_{2} / H X_{2} O

followed by

Zn

does not give this alcohol.

Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on Hydroboration, oxymercuration, halohydrin formation

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1-Methylcyclohexene can be converted into 1-methylcyclohexan-1-ol as the major product by which of the following? (More than one answer may be correct.)

Answer: A, B

More questions on Hydroboration, oxymercuration, halohydrin formation