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JEE Advanced levelSingle correct optionDifficulty 3 of 3g1201

The alkene 3,3-dimethylbut-1-ene, , adds a proton at the terminal carbon to give a secondary cation, which then undergoes a single 1,2-shift to a more stable cation. The final cation is:

  1. A2,3-dimethylbutan-2-yl cation,
  2. B3,3-dimethylbutyl cation,
  3. C3,3-dimethylbutan-2-yl cation,
  4. D3-methylbutan-2-yl cation,

Answer: A

H+ adds to the CH2 end, giving (secondary). A methyl group on the neighbouring quaternary carbon shifts with its bonding pair to the cationic carbon, leaving a tertiary cation . Tertiary is more stable, so this is the final cation.
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