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NEET levelSingle correct optionDifficulty 1 of 3hx204

Optically pure (R)-3-bromo-3-methylhexane is hydrolysed in water by a pure SN1 pathway (ignore any small excess of inversion). The alcohol formed is

  1. Apure (R)-alcohol
  2. Ba meso compound
  3. Cpure (S)-alcohol
  4. Dan equimolar mixture of the R and S alcohols, which is optically inactive

Answer: D

Ionisation gives a planar tertiary carbocation, attacked by water equally from both faces. The (R) and (S) alcohols are formed in equal amounts, giving a racemic, optically inactive mixture. The product has only one stereocentre, so a meso form is impossible.
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