JEE Main 2020 · 3 September · evening · Single correct · +4 / −1
The decreasing order of reactivity of the following compounds towards nucleophilic substitution (S N 2) is :

- (a) (IV) > (II) > (III) > (I)
- (b) (II) > (III) > (IV) > (I)
- (c) (II) > (III) > (I) > (IV)
- (d) (III) > (II) > (IV) > (I)
Answer and solution
Answer (b) (II) > (III) > (IV) > (I)
Solution
Chemistry ma’am · 3 steps
Check where each nitro group sits: the more it pulls from CH₂Cl, the faster S_N2 attack.
- What speeds SN2. In S_N2 the nucleophile attacks the CH₂ carbon that carries Cl. Electron-withdrawing groups on the ring make that carbon more electron-poor (more δ+), so the nucleophile is drawn in faster.
- Position matters. From the ortho or para position, NO₂ withdraws by both -M (resonance) and -I (inductive). From the meta position it withdraws by -I only. Since -I fades with distance, an ortho NO₂ pulls hardest, then para, then meta.
Compound NO₂ positions Withdrawal felt at CH₂Cl Rank (II) ortho + meta -M and the strongest -I (ortho is closest), plus -I from meta 1 (III) para + meta -M and a weaker -I from para, plus -I from meta 2 (IV) meta + meta -I only, from both groups 3 (I) none no extra withdrawal 4 - So. The order of S_N2 reactivity is (II) > (III) > (IV) > (I), which is option (b).
The idea to keep. For substituted benzyl halides, rank S_N2 rate by how strongly the ring groups pull electrons from CH₂X: ortho beats para (closer, stronger -I), and both beat meta (no -M).
Answer from the NTA final answer key. Solution by PrepWiser.