JEE Main 2020 · 7 January · evening · Single correct · +4 / −1

The correct order of stability for the following alkoxides is :

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

Answer (a) (C) > (B) > (A)

Solution

Chemistry ma’am · 3 steps

Follow where the negative charge can go: the further it spreads, the more stable the alkoxide.

  1. What stabilises. An alkoxide is more stable when its negative charge is spread over more atoms. Resonance (−M) spreads the charge much better than the inductive effect (−I) alone.
    AlkoxideEffect on O⁻Where the charge can go
    (C) ⁻O-CH=CH-NO₂Resonance through C=C into NO₂ (−M), plus −IOnto the nitro oxygens, which are very electronegative
    (B) CH₂=C(NO₂)-O⁻Resonance with C=C, plus −I of NO₂ on the same carbonOnly onto the terminal CH₂ carbon
    (A) CH₃-CH(NO₂)-O⁻−I of NO₂ onlyStays on oxygen, no resonance
  2. Why C beats B. In (C) the O⁻, the C=C and the NO₂ form one conjugated chain, so the charge reaches the nitro oxygens. In (B) the NO₂ sits on the same carbon as O⁻, so it is cross-conjugated: resonance pushes the charge only onto CH₂, a carbon, and the NO₂ helps only by −I.
  3. So. (B) still has some resonance and an sp² carbon next to O⁻, so it beats (A), which has only −I. The order is (C) > (B) > (A), option (a).

The idea to keep. For anion stability, check resonance first and induction second. A group stabilises by −M only if it lies in conjugation with the charge, not just close to it.

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

Study General Organic Chemistry (GOC)

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