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Match each group attached to a phenyl ring in Column-I with the electronic effect(s) it shows in Column-II. Column-I (group on phenyl ring): (A) -N=O (B) -CH3 (C) -NH-C(=O)CH3 (D) -C(=O)OCH3 Column-II (effect shown): (P) +M (Q) -M (R) +H (hyperconjugation) (S) -I

1. A -> Q,S; B -> R; C -> P,S; D -> Q,S
2. A -> P,S; B -> R; C -> Q,S; D -> P,S
3. A -> Q,R; B -> P; C -> P,R; D -> Q,S
4. A -> P,R; B -> S; C -> Q,R; D -> P,R

Correct answer: A -> Q,S; B -> R; C -> P,S; D -> Q,S

Solution

-N=O (nitroso) is conjugated through N=O so it withdraws by resonance (-M) and is electronegative (-I). -CH3 donates by hyperconjugation (+H). -NH-C(=O)CH3 is bonded through N which has a lone pair to donate (+M) while the electronegative N gives -I. -C(=O)OCH3 is bonded through a carbonyl carbon so it withdraws by resonance (-M) and inductively (-I).

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