JEE Main 2024 · 1 February · evening · Single correct · +4 / −1
The functional group that shows negative resonance effect is :
- (a) -OH
- (b) -OR
- (c) -COOH
- (d) -NH₂
Answer and solution
Answer (c) -COOH
Solution
Chemistry ma’am · 3 steps
Look at the atom attached to the ring: a lone pair gives +R, a C=O pulling electrons gives −R.
- What decides the sign. A group shows +R when the atom bonded to the ring has a lone pair it can push into the π system. It shows −R when it carries a multiple bond to a more electronegative atom, like C=O, that pulls π electrons out of the ring.
Group Atom bonded to ring What it does Effect -OH O with lone pairs donates a lone pair +R -OR O with lone pairs donates a lone pair +R -COOH C of C=O, no lone pair pulls π electrons towards O −R -NH₂ N with a lone pair donates a lone pair +R - Why COOH withdraws. In -COOH the carbonyl carbon is attached to the ring. The ring's π electrons can shift onto the electronegative carbonyl oxygen, which leaves a positive charge on the ring.
- So. Only -COOH withdraws electrons by resonance, so the answer is (c).
The idea to keep. Check the first atom of the group. A lone pair on it (O, N, halogen) means +R. A double or triple bond from it to O or N (C=O, C≡N, NO₂) means −R.
Answer from the NTA final answer key. Solution by PrepWiser.