Question 15

Let's identify the major product of each List-II reaction and then match to the named reaction whose reactant it is. **(1)** Toluene + CrO₂Cl₂/CS₂, then H₃O⁺ (Étard reaction) → benzaldehyde (C₆H₅CHO). Benzaldehyde has no α-hydrogen, so it undergoes the **Cannizzaro reaction** → S → 1. **(2)** Benzoic acid → (PCl₅) benzoyl chloride → (NH₃) benzamide → (P₄O₁₀, Δ, dehydration) benzonitrile (C₆H₅CN). Nitriles are reduced by SnCl₂/HCl then hydrolysed to aldehydes in the **Stephen reaction** → P → 2. **(3)** Nitrobenzene → (Fe/HCl) aniline → (NaNO₂/HCl, 273–278 K) benzenediazonium chloride. Diazonium salt + CuCl/HCl or CuBr/HBr is the **Sandmeyer reaction** → Q → 3. **(4)** Toluene → (Cl₂/hν, H₂O) benzaldehyde (via benzal chloride hydrolysis) → (Tollens' reagent) benzoic acid → (SO₂Cl₂) benzoyl chloride → (NH₃) benzamide. Amide + Br₂/NaOH is the **Hoffmann bromamide degradation** → R → 4. **(5)** Aniline → acetanilide → p-nitroacetanilide → (aq. NaOH) p-nitroaniline — not needed here. Matching: P → 2, Q → 3, R → 4, S → 1, which is option (B).

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