JEE Main 2020 · 7 January · evening · Single correct · +4 / −1
The correct order of stability for the following alkoxides is :
- (a) (C) > (B) > (A)
- (b) (C) > (A) > (B)
- (c) (B) > (C) > (A)
- (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.
- 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.
Alkoxide Effect on O⁻ Where the charge can go (C) ⁻O-CH=CH-NO₂ Resonance through C=C into NO₂ (−M), plus −I Onto the nitro oxygens, which are very electronegative (B) CH₂=C(NO₂)-O⁻ Resonance with C=C, plus −I of NO₂ on the same carbon Only onto the terminal CH₂ carbon (A) CH₃-CH(NO₂)-O⁻ −I of NO₂ only Stays on oxygen, no resonance - 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.
- 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.