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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2049

With HBr (no peroxide), which of the following alkenes give a major product that arises from a carbocation rearrangement?

  1. A3-methylbut-1-ene
  2. B3,3-dimethylbut-1-ene
  3. C2-methylbut-2-ene
  4. Dpent-1-ene

Answer: A, B

3-Methylbut-1-ene (hydride shift) and 3,3-dimethylbut-1-ene (methyl shift) form secondary cations that become tertiary by a 1,2-shift. 2-Methylbut-2-ene already forms a tertiary cation, and pent-1-ene forms a secondary cation with no better neighbour (a shift would give another secondary cation), so neither rearranges.
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