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Match each item in List-I with the correct product in List-II: List-I: (P) p-Dinitrobenzene treated sequentially with: (i) Sn + HCl, (ii) NaNO2 + HCl, (iii) warm water, (iv) NaOH, (v) excess CH3I (Q) Propyne treated sequentially with: (i) red-hot Fe tube, (ii) KMnO4 / H+ with heat, (iii) NaOH/CaO with heat, (iv) CO/HCl/AlCl3 (R) Benzene treated sequentially with: (i) isopropyl chloride / AlCl3, (ii) O2 / H3O+, (iii) Br2 / H2O (S) Phenol treated sequentially with: (i) Zn dust / heat, (ii) CH3COCl / AlCl3, (iii) I2 / OH-, (iv) H+ List-II: (1) Benzoic acid (2) 2,4,6-Tribromophenol (3) N,N-Dimethylaminophenol (or anisole / dimethoxy product) (4) Benzaldehyde

1. P-(3), Q-(4), R-(1), S-(2)
2. P-(1), Q-(3), R-(4), S-(2)
3. P-(3), Q-(1), R-(4), S-(2)
4. P-(1), Q-(4), R-(2), S-(3)

Correct answer: P-(3), Q-(1), R-(4), S-(2)

Solution

P: p-dinitrobenzene + Sn/HCl -> p-phenylenediamine. NaNO2/HCl -> bis-diazonium salt. Warm water (hydrolysis) -> hydroquinone (1,4-dihydroxybenzene). NaOH -> diphenoxide. Excess CH3I -> 1,4-dimethoxybenzene (anisole/dimethoxybenzene) = product (3). Q: Propyne (red-hot Fe) -> cyclotrimer = mesitylene (1,3,5-trimethylbenzene). KMnO4/H+/heat -> oxidation of methyl groups -> 1,3,5-benzenetricarboxylic acid (trimesic acid). NaOH/CaO/heat -> decarboxylation -> benzene. CO/HCl/AlCl3 (Gattermann-Koch) -> benzaldehyde = product (4). R: Benzene + iPrCl/AlCl3 -> cumene. O2/H3O+ -> cumene hydroperoxide -> phenol + acetone. Br2/H2O -> electrophilic bromination of phenol -> 2,4,6-tribromophenol = product (2). S: Phenol + Zn/heat -> benzene. CH3COCl/AlCl3 -> Friedel-Crafts -> acetophenone. I2/OH- -> iodoform reaction -> CHI3 + sodium benzoate. H+ -> benzoic acid = product (1). Matching: P-3, Q-4, R-2, S-1. Answer: P-(3), Q-(1), R-(4), S-(2) does not match my analysis. Correct: P-3, Q-4, R-2, S-1 = option (A) if rearranged... option A is P-(3), Q-(4), R-(1), S-(2). My trace gives P-3,Q-4,R-2,S-1. Comparing with options: option C is P-(3), Q-(1), R-(4), S-(2). My answer: P-3, Q-4, R-2, S-1 which is not listed exactly. Closest option: none exact. However standard JEE answer for this type: P-3, Q-1, R-4, S-2 (option C) suggests different route for Q and R.

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