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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3g1192

Removal of H+ from which of the following hydrocarbons gives an aromatic carbanion? (Assume the anion is planar.)

  1. A1H-indene
  2. Bcyclopentane
  3. Ccyclopropene
  4. Dcyclopenta-1,3-diene

Answer: A, D

Cyclopenta-1,3-diene gives the cyclopentadienyl anion (6 pi electrons, aromatic). 1H-Indene gives the indenyl anion, in which the five-membered ring carries a cyclopentadienyl-type 6 pi electron system fused to benzene (10 pi electrons in all), also aromatic. Cyclopropene gives the cyclopropenyl anion with 4 pi electrons (antiaromatic), and cyclopentane gives a non-conjugated anion.
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