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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2216

Which reactions involve a skeletal rearrangement (hydride or methyl shift) as the main pathway?

  1. A3,3-dimethylbut-1-ene with
  2. B3-methylbut-1-ene with dilute
  3. C3,3-dimethylbut-1-ene with then
  4. D3,3-dimethylbut-1-ene with then

Answer: A, B

The two ionic additions go through a secondary cation next to a tertiary-forming centre, so shifts occur. Oxymercuration uses a bridged mercurinium ion, and hydroboration is concerted, so neither rearranges.
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