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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc069

1-Methylcyclohexene is subjected to (i) in THF; (ii) , . The major product (racemic) is

  1. Atrans-3-methylcyclohexan-1-ol
  2. B1-methylcyclohexan-1-ol
  3. Ctrans-2-methylcyclohexan-1-ol
  4. Dcis-2-methylcyclohexan-1-ol

Answer: C

Boron adds to the less substituted carbon (C-2) and H adds to C-1 on the same face (syn addition). Oxidation replaces B by OH with retention, so OH at C-2 and the new H at C-1 are cis, which puts the C-1 methyl and the C-2 OH trans. The product is trans-2-methylcyclohexan-1-ol. 1-Methylcyclohexan-1-ol would form by oxymercuration or acid hydration.
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