Identify the reactants required for each named reaction in List-I

• Etard reaction: oxidation of toluene to benzaldehyde.
• Gattermann reaction: conversion of benzene diazonium chloride to chlorobenzene/bromobenzene.
• Gattermann-Koch reaction: formylation of benzene to give benzaldehyde.
• Rosenmund reduction: reduction of acid chloride to aldehyde.

Find the major products in List-II

(1) Acetophenone $\xrightarrow[\mathrm{HCl}]{\mathrm{Zn-Hg}}$

This is Clemmensen reduction: $\mathrm{C_6H_5COCH_3} \rightarrow \mathrm{C_6H_5CH_2CH_3}$ Product = ethylbenzene.

(2) Toluene $\xrightarrow[(ii)\ \mathrm{SOCl_2}]{(i)\ \mathrm{KMnO_4},\ \mathrm{KOH},\ \Delta}$

First, toluene is oxidized to benzoic acid (or benzoate), then converted by $\mathrm{SOCl_2}$ to benzoyl chloride. Product = benzoyl chloride.

(3) Benzene $\xrightarrow[\text{anhyd. }\mathrm{AlCl_3}]{\mathrm{CH_3Cl}}$

Friedel-Crafts alkylation gives toluene.

(4) Aniline $\xrightarrow[273-278\ \mathrm{K}]{\mathrm{NaNO_2/HCl}}$

This gives benzene diazonium chloride.

(5) Phenol $\xrightarrow{\mathrm{Zn},\ \Delta}$

Phenol is reduced to benzene.

Match each named reaction

(P) Etard reaction requires toluene as reactant. From List-II, (3) gives toluene. $P \rightarrow 3$

(Q) Gattermann reaction requires benzene diazonium chloride as reactant. From List-II, (4) gives benzene diazonium chloride. $Q \rightarrow 4$

(R) Gattermann-Koch reaction requires benzene as reactant. From List-II, (5) gives benzene. $R \rightarrow 5$

(S) Rosenmund reduction requires acid chloride as reactant. From List-II, (2) gives benzoyl chloride. $S \rightarrow 2$

Final matching

$P \rightarrow 3,\quad Q \rightarrow 4,\quad R \rightarrow 5,\quad S \rightarrow 2$

Compare with options

This corresponds to Option D.

Compare with stored correct answer

Stored correct answer = D, which matches our derived answer.