An organic compound (A) of molecular formula C_6H_5Cl on boiling with hot water gives (B) of molecular formula C_6H_6O.(B) on reaction with Zinc dust gives (C) a simplest aromatic hydrocarbon. (C) on reaction with methyl chloride in the presence of anhydrous AlCl_2 gives (D) of molecular formula C_7H_8. ldentify A, B, C, D and explain the reaction.

An organic compound (A) of molecular formula C_6H_5Cl on boiling with

1.	An organic compound (A) of molecular formula C_6H_5Cl on boiling with hot water gives (B) of molecular formula C_6H_6O.(B) on reaction with Zinc dust gives (C) a simplest aromatic hydrocarbon. (C) on reaction with methyl chloride in the presence of anhydrous AlCl_2 gives (D) of molecular formula C_7H_8. ldentify A, B, C, D and explain the reaction.
Answer» Solution :(i) A) is identified from the FORMULA as Benzene diazonium chloride `-C_6H_5N_2Cl` (ii) Benzene diazonium chloride when boiled with HOT water produces phenol as (B). `underset("Chloride(A)")underset("Benzene diazonium")(C_6H_5N_2Cl) + HOH overset(Delta)to underset("Phenol(B)")(C_6H_5OH) + N_2uarr + HCl` (ii) Phenol on reaction with Zinc dust gives Benzene as (C) which is simplest aromatic hydrocarbon. (iv) Benzene on treatment with (C) methyl chloride in the presence of anhydrous `AlCl_3`,Friedel Crafts reaction take PLACE and the PRODUCT formed is Toluene as (D).