1-Methylcyclohexene is subjected to hydroboration with BH3/THF and then H2O2/NaOH. The major product (racemic) is

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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap012

1-Methylcyclohexene is subjected to hydroboration with $BH X_{3}$ /THF and then $H X_{2} O X_{2}$ / $NaOH$ . The major product (racemic) is

A1-methylcyclohexan-1-ol
Bcis-2-methylcyclohexan-1-ol
Ctrans-2-methylcyclohexan-1-ol
D2-methylcyclohexan-1-one

Answer: C

Boron adds to the less substituted ring carbon (C-2) and hydrogen to C-1, both on the same face (syn addition). Oxidation replaces B by OH with retention, so OH at C-2 and H at C-1 are cis, which puts the methyl group on the opposite face from OH: trans-2-methylcyclohexan-1-ol.

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1-Methylcyclohexene is subjected to hydroboration with BHX3​/THF and then HX2​OX2​/NaOH. The major product (racemic) is

Answer: C

More questions on Preparation of alcohols including from carbonyls and Grignard

1-Methylcyclohexene is subjected to hydroboration with $BH X_{3}$ /THF and then $H X_{2} O X_{2}$ / $NaOH$ . The major product (racemic) is