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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g3048

Under acidic conditions, in which the carbocation rearranges fully to the most stable accessible cation, the alkene(s) that give the 2-methylbutan-2-yl cation on protonation are:

  1. A2-methylbut-1-ene
  2. B3-methylbut-1-ene
  3. C2-methylbut-2-ene
  4. Dpent-2-ene

Answer: A, B, C

2-Methylbut-1-ene and 2-methylbut-2-ene are protonated directly at the less substituted carbon, giving this tertiary cation. 3-Methylbut-1-ene gives a secondary cation which then undergoes a 1,2-hydride shift to the same tertiary cation. Pent-2-ene gives only straight-chain secondary cations, which cannot reach it by a simple 1,2-shift.
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