Question

An organic compound (A) of molecular formula C₆HN₂Cl on boiling with hot water gives (B) of molecular formula C₆H₆O. (B) on reaction with Zinc dust gives (C) a simplest aromatic hydrocarbon. (C) on reaction with methyl chloride in the presence of anhydrous AICI₂ gives (D) of molecular formula C₇H₈ . Identify A, B, C, D and explain the reaction.

Answer 1

1. (A) is identified from the formula as Benzene diazonium chloride – C₆H₅N₂Cl

2. Benzene diazonium chloride when boiled with hot water produces phenol as (B).

3. Phenol on reaction with Zinc dust gives Benzene as (C) which is simplest aromatic hydrocarbon.

4. Benzene on treatment with (C) methyl chloride in the presence of anhydrous AlCl₃ , Friedel Crafts reaction take place and the product formed is Toluene as (D).