JEE Main 2021 · 20 July · morning · Single correct · +4 / −1

Among the given species the Resonance stabilised carbocations are :

JEE Main PYQ figure
  1. (a) (C) and (D) only
  2. (b) (A), (B) and (D) only
  3. (c) (A) and (B) only
  4. (d) (A), (B) and (C) only
Answer and solution

Answer (c) (A) and (B) only

Solution

Chemistry ma’am · 2 steps

Check the carbon right next to the positive one: a π bond there means resonance.

  1. The test. A carbocation is resonance stabilised only if its empty p orbital lines up with a π bond on the directly attached carbon. The charge can then spread onto another carbon. If even one sp³ carbon sits in between, the π electrons cannot reach the empty orbital.
    SpeciesWhat is attached to the C⁺Resonance?
    (A) benzyla benzene ring carbon, part of the aromatic π systemyes, the charge spreads to the ortho and para carbons
    (B) allyl, CH₂=CH-CH₂⁺a C=C carbonyes, the charge is shared by both end carbons
    (C) cyclohexenylmethylan sp³ ring carbon, and the C=C starts one carbon further awayno, it is not conjugated
    (D) vinyl, CH₃COCH₂CH=CH⁺the charge sits on a doubly bonded carbon itself, and its empty orbital is perpendicular to the π bondno, and the C=O is cut off by a CH₂
  2. So. Only (A) and (B) have a π bond conjugated with the empty p orbital, so the answer is (c).

The idea to keep. For resonance in a carbocation, the π bond must be on the carbon directly bonded to C⁺. A double bond one carbon away gives no resonance, and a vinyl cation cannot use its own π bond.

Answer from the NTA final answer key. Solution by PrepWiser.

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Asked about 180 times in JEE Main since 2020. This question is from 2021.