MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Carbocations: formation, stability, rearrangements
JEE Advanced levelSingle correct optionDifficulty 3 of 3g3037

Match each cation in List I with the effect that is mainly responsible for its stability (or instability) in List II. List I: P: ; Q: ; R: ; S: cyclopenta-2,4-dien-1-ylium (cyclopentadienyl cation). List II: 1: lone-pair donation (); 2: hyperconjugation as the only delocalisation; 3: delocalisation into a benzene ring pi system; 4: antiaromatic destabilisation.

  1. AP-2, Q-1, R-3, S-4
  2. BP-3, Q-2, R-1, S-4
  3. CP-1, Q-2, R-3, S-4
  4. DP-1, Q-2, R-4, S-3

Answer: C

P has an oxygen lone pair next to the cation (1). Q has only alkyl groups, so only hyperconjugation operates (2). R is conjugated with the aromatic ring (3). S has a cyclic conjugated system with 4 pi electrons, so it is antiaromatic (4).
Practice General Organic Chemistry III: Reaction Intermediates More on Carbocations: formation, stability, rearrangements

More questions on Carbocations: formation, stability, rearrangements