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JEE Main levelSingle correct optionDifficulty 2 of 3o3033

cis-1-Bromo-4-tert-butyl-1-methylcyclohexane (bromine and the tert-butyl group on the same face) is hydrolysed in aqueous acetone by SN1. The alcohol product is

  1. Aonly the trans alcohol, formed with complete inversion
  2. Ba mixture of two diastereomeric 4-tert-butyl-1-methylcyclohexan-1-ols (cis and trans)
  3. Conly the cis alcohol, formed with complete retention
  4. Da single optically active compound

Answer: B

The cation is planar at C-1 and has a plane of symmetry (it is achiral). Water can attack either face, giving the OH on the same side as the tert-butyl group (cis) or on the opposite side (trans). The two are diastereomers, formed in unequal amounts in general, and neither is optically active.
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