Match List I with List II: List I (Reaction) List II (Product...

(A) Oxidation of $p$-methoxytoluene with acidic $\text{KMnO}_4$ yields $p$-methoxybenzoic acid. The $-\text{OCH}_3$ group has a strong $+M$ effect which outweighs its $-I$ effect, making the product a weaker acid than benzoic acid. (Matches II)

(B) Oxidation of $p$-chlorotoluene yields $p$-chlorobenzoic acid. For halogens, the $-I$ effect outweighs the $+M$ effect, making the product a stronger acid than benzoic acid. (Matches I)

(C) Reduction of $p$-nitroanisole with $\text{Sn}/\text{HCl}$ yields $p$-anisidine. The $+M$ effect of the $-\text{OCH}_3$ group increases electron density on the nitrogen, making the product a stronger base than aniline. (Matches III)

(D) Reduction of $p$-chloronitrobenzene yields $p$-chloroaniline. The net electron-withdrawing nature of chlorine ($-I > +M$) decreases electron density on the nitrogen, making the product a weaker base than aniline. (Matches IV)

The correct matching is (A)-(II), (B)-(I), (C)-(III), (D)-(IV).

Answer: (A)-(II), (B)-(I), (C)-(III), (D)-(IV)