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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4127

Pinacol, , is warmed with dilute . The main organic product is

  1. A2,3-dimethylbuta-1,3-diene
  2. B (3,3-dimethylbutan-2-one)
  3. C2,3-dimethylbut-2-ene
  4. D2,3-dimethylbutanal

Answer: B

Protonation and loss of water from one gives a tertiary cation. A methyl group migrates from the neighbouring carbinol carbon, giving an oxygen-stabilised cation. Loss of from this protonated ketone gives pinacolone, 3,3-dimethylbutan-2-one.
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