An organic aromatic compound ‘A’ with the molecular formula C₆H₇N is sparingly soluble in water. ‘A’ on treatment with dil HCI gives a water soluble compound ‘B’. ‘A’ also reacts with chloroform in presence of alcoholic KOH to form an obnoxious smelling compound ‘C’. ‘A’ reacts with benzene sulphonyl chloride to form an alkali soluble compound ‘D’.’A’ reacts with NaNO₂ and HCl to form a compound ‘E’ which on reaction with phenol forms an orange red dye ‘F’. Elucidate the structures of the organic compounds from ‘A’ to ‘F’.

⇒ Since compound A (C₆H₇N) is sparingly soluble in water and gives a water soluble compound (B), on treatment with dilute acid, therefore, compound A must be an amine.

⇒ Since compound A reacts C₆H₇N reacs with NaNO₂ and HCl to form a compound (E) which reacts with phenol in alkaline medium to give an orange red dye (F), therefore, compound (A) must be an aromatic primary amine, i.e., aniline C₆H₅NH₂

⇒ If A is aniline, then E must be benzenediazonium chloride and the orange red dye (F) must be p-hydroxyazobenzene.

⇒ Since compound A aniline reacts with CHCl₃ in the resence f alcoholic KOH o form a compound C having obnoxious smell, therefore, compound (C) must be benzene isonitrile.

⇒ Since compound (A) aniline reacts with benzenesulphonyl chloride to form compound (D) which is soluble in alkali, therefore (D) must be N- phenylbenzenesulphonamide.

⇒ Since compound (A) aniline reacts with mineral acid, HCl to form water soluble compound (B), therefore, (B) must be anilinium chloride.

Thus, compound A is aniline

Compound B is anilinium chloride

Compound C is benzene isonitrile

Compound D is N-phenylbenzenesulphonamide

Compound E is benezenediazonium chloride

Compound F is p-hydroxyazobenzene