JEE Main 2024 · 1 February · evening · Single correct · +4 / −1

The functional group that shows negative resonance effect is :

  1. (a) -OH
  2. (b) -OR
  3. (c) -COOH
  4. (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.

  1. 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.
    GroupAtom bonded to ringWhat it doesEffect
    -OHO with lone pairsdonates a lone pair+R
    -ORO with lone pairsdonates a lone pair+R
    -COOHC of C=O, no lone pairpulls π electrons towards O−R
    -NH₂N with a lone pairdonates a lone pair+R
  2. 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.
  3. 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.

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Asked about 180 times in JEE Main since 2020. This question is from 2024.