JEE Main 2021 · 20 July · morning · Single correct · +4 / −1
Among the given species the Resonance stabilised carbocations are :
- (a) (C) and (D) only
- (b) (A), (B) and (D) only
- (c) (A) and (B) only
- (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.
- 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.
Species What is attached to the C⁺ Resonance? (A) benzyl a benzene ring carbon, part of the aromatic π system yes, the charge spreads to the ortho and para carbons (B) allyl, CH₂=CH-CH₂⁺ a C=C carbon yes, the charge is shared by both end carbons (C) cyclohexenylmethyl an sp³ ring carbon, and the C=C starts one carbon further away no, 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 bond no, and the C=O is cut off by a CH₂ - 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.