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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx051

1-Bromo-1,4-dimethylcyclohexane (either cis or trans) is hydrolysed in aqueous acetone by an mechanism. Which statements are correct?

  1. AA planar carbocation is formed in the rate-determining step.
  2. BTwo stereoisomeric alcohols, cis- and trans-1,4-dimethylcyclohexan-1-ol, are obtained.
  3. CEach product is optically active.
  4. DThe product is a racemic mixture of enantiomers.

Answer: A, B

Ionisation gives a planar tertiary cation. Water can attack from either face, leading to the alcohol with cis or trans to the 4-methyl group, two diastereomers. Both have a plane of symmetry through C1 and C4 and are achiral, so no optically active product and no racemate is formed.
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