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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1164

Which of the following transformations are favoured because an aromatic ion is produced?

  1. ACyclopenta-1,3-diene treated with a strong base (sodium hydride) to give and the cyclopentadienide ion
  2. BCyclohepta-1,3,5-triene reacting with to give the tropylium ion
  3. CCyclopropene treated with a strong base to give the cyclopropenyl anion
  4. DCyclopenta-1,3-diene reacting with to give the cyclopentadienyl cation

Answer: A, B

Deprotonation of cyclopentadiene gives the aromatic 6 pi electron anion; hydride loss from cycloheptatriene gives the aromatic 6 pi electron tropylium cation. The cyclopropenyl anion (4 pi e) and the cyclopentadienyl cation (4 pi e) are antiaromatic, so the last two are disfavoured.
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