MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Stability ranking of drawn radicals, carbanions and carbenes
NEET levelSingle correct optionDifficulty 1 of 3g3236

The compound shown is treated with a strong base, which removes one proton from a carbon atom. Among the carbanions shown, which one is the most stable and is the anion actually formed?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The compound shown is cyclopentadiene. Loss of a proton from its CH group gives the cyclopentadienyl anion, a planar, cyclic, fully conjugated ion with 6 pi electrons, which is aromatic. The two vinylic anions (A and D) are not aromatic and keep the negative charge in an orbital outside the pi system, and the saturated cyclopentyl anion (C) is not even derived from the compound shown by loss of one proton.
Practice General Organic Chemistry III: Reaction Intermediates More on Stability ranking of drawn radicals, carbanions and carbenes

More questions on Stability ranking of drawn radicals, carbanions and carbenes