Aniline is treated separately with the reagents given in List-I. Matc…

The correct answer is Option (1) → A-III, B-IV, C-II, D-I

Aniline is a primary aromatic amine: it has two hydrogen atoms on nitrogen and an unshared electron pair, so it gives the carbylamine reaction, it is acylated, and as a base it forms salts with acids.

(A) Chloroform and ethanolic potassium hydroxide, on heating — This matches (III) Phenyl isocyanide. This is the carbylamine reaction of a primary amine:

    \( \displaystyle \ce{C6H5NH2 + CHCl3 + 3KOH} \xrightarrow{\text{Heat}} \ce{C6H5NC + 3KCl + 3H2O} \)

(B) Benzoyl chloride, in the presence of a base — This matches (IV) N-Phenylbenzamide. In benzoylation the benzoyl group, C₆H₅CO–, replaces a hydrogen on nitrogen:

    \( \displaystyle \ce{C6H5NH2 + C6H5COCl} \xrightarrow{\text{Base}} \ce{C6H5NHCOC6H5 + HCl} \)

(C) Ethanoic anhydride — This matches (II) N-Phenylethanamide (acetanilide). Here the acetyl group, CH₃CO–, goes on to nitrogen (acetylation):

    \( \displaystyle \ce{C6H5NH2 + (CH3CO)2O -> C6H5NHCOCH3 + CH3COOH} \)

(D) Dilute hydrochloric acid — This matches (I) Anilinium chloride. Aniline is basic and forms a salt with the acid:

    \( \displaystyle \ce{C6H5NH2 + HCl -> C6H5NH3^+Cl^-} \)

NCERT (2026-27 edition):
9.6 Chemical Reactions – “Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium hydroxide form isocyanides or carbylamines which are foul smelling substances.”

“Amines also react with benzoyl chloride (C₆H₅COCl). This reaction is known as benzoylation.”

“Aliphatic and aromatic primary and secondary amines react with acid chlorides, anhydrides and esters by nucleophilic substitution reaction. This reaction is known as acylation. … The products obtained by acylation reaction are known as amides.”

“Amines, being basic in nature, react with acids to form salts.”