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Which of the following reaction sequences CANNOT be used to prepare 2,3-dimethylbutan-2-ol as the major product?

Options

  1. AAcid-catalyzed hydration of 3,3-dimethylbut-1-ene
  2. BOxymercuration-demercuration of 3,3-dimethylbut-1-ene
  3. CReaction of 3-methylbutan-2-one with CH ₃ MgBr followed by acidic hydrolysis
  4. DReaction of propan-2-one with isopropylmagnesium bromide followed by acidic hydrolysis

Correct answer

B. Oxymercuration-demercuration of 3,3-dimethylbut-1-ene

Step-by-step solution

To determine which method cannot prepare 2,3-dimethylbutan-2-ol, we evaluate the major product of each reaction: 1) Acid-catalyzed hydration of 3,3-dimethylbut-1-ene initially forms a secondary carbocation, which undergoes a 1,2-methyl shift to form a more stable tertiary carbocation. The attack of water yields 2,3-dimethylbutan-2-ol. 2) Oxymercuration-demercuration of 3,3-dimethylbut-1-ene proceeds via Markovnikov addition without any carbocation rearrangement. The major product is 3,3-dimethylbutan-2-ol, not 2,3-

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