JEE Main 2023 · 30 January · evening · Single correct · +4 / −1
The most stable carbocation for the following is:
- (a) b
- (b) d
- (c) c
- (d) a
Answer and solution
Answer (c) c
Solution
Chemistry ma’am · 3 steps
Walk the + charge around the ring and check whether it ever lands on the carbon holding NH₂.
- Spread the charge. In each ion the C⁺ is conjugated with two ring double bonds, so the positive charge is shared by three alternate carbons. What decides stability is where the NH₂ group sits relative to those three carbons.
- What NH2 can do. Nitrogen's lone pair helps only when the NH₂ is on a carbon that carries the + charge in some resonance form. Then it forms a C=N⁺ bond, and every atom has a full octet. Anywhere else, NH₂ gives only its electron-withdrawing -I effect, which destabilises the cation.
C(+)-N̈H₂ ↔ C=N(+)H₂
Ion Where NH₂ sits Lone pair reaches the + charge? Net effect a on the sp³ carbon, cut off from the π system no only -I, destabilised b on the sp³ carbon, cut off from the π system no only -I, destabilised c on a ring carbon that carries the + charge in one resonance form yes, forms C=N⁺ strongly stabilised d on a π carbon next to C⁺, but the charge never lands there no only -I, destabilised - So. Only in c can the nitrogen lone pair share the positive charge, so c is the most stable carbocation, which is option (c).
The idea to keep. A lone-pair donor stabilises a carbocation by resonance only if it is on a carbon where the + charge actually lands. Push the charge through every resonance form first, then check where the donor sits.
Answer from the NTA final answer key. Solution by PrepWiser.