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NEET levelSingle correct optionDifficulty 1 of 3o3235

The optically active tertiary bromide shown is shaken with water-acetone in the absence of base. What is the optical activity of the alcohol product?

  1. AOptically active with inverted configuration only
  2. BOptically inactive (racemic)
  3. COptically active with retained configuration only
  4. DOptically active, a meso compound

Answer: B

The compound is 3-bromo-3-methylhexane (one enantiomer drawn). Ionisation gives a planar tertiary carbocation and water attacks both faces almost equally, so the product alcohol, 3-methylhexan-3-ol, is racemic and optically inactive.
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