Question

An organic compound (A) of molecular formula C₆H₇N on reaction with sodium nitrite and hydrochloric acid at 0°C gives (B) of formula C₆H₅N₂Cl. (B) on treatment with cuprous cyanide give (C) of formula C₇H₅N. (C) on reaction with sodium and ethanol gives (D) of formula C₇H₉N. (D) on reaction with nitrous acid gives (E) of molecular formula C₇H₈O. Identify A, B, C, D and E and explain the reactions involved.

Answer 1

1. (A) is identified as Aniline from the molecular formula. 

2. Aniline on reaction with sodium nitrite and hydrochloric acid at 0°C, diazotisation take place and the product (B) formed is benzene diazonium chloride.

3. Benzene diazonium chloride on treatment with CuCN produces (C) as cyano benzene.

4. Cyano benzene on reaction with Na and C₂H₅OH undergoes reduction reaction to give (D) as benzvlamine.

5. Benzylamine on treatment with nitrous acid gives benzyl alcohol as (E).