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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc036

In which of the following reactions is the major product formed with a rearranged carbon skeleton (compared with the starting alkene)?

  1. A3,3-dimethylbut-1-ene with followed by
  2. B3-methylbut-1-ene with and dilute
  3. C3,3-dimethylbut-1-ene with followed by
  4. D3,3-dimethylbut-1-ene with (no peroxide)

Answer: B, D

Free carbocations rearrange. 3,3-Dimethylbut-1-ene with HCl forms a secondary cation, then a methyl shift gives the tertiary cation and 2-chloro-2,3-dimethylbutane. 3-Methylbut-1-ene on acid hydration undergoes a hydride shift to give 2-methylbutan-2-ol. Oxymercuration and hydroboration involve no free carbocation, so the skeleton is retained.
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