An organic compound (A) of molecular formula C_(6)H_(7)N on reaction with sodium nitrite and hydrochloric acid at 0^(@)C gives (B) or formula C_(6)H_(5)N_(2)Cl (B) on treatment with cuprous cyanide give (C) of formula C_(7)H_(5)N. (C)on reaction with sodium and ethanol gives (D) of formula C_(7)H_(9)N. (D) on reaction with nitrous acid gives (E) of molecular formula C_(7)H_(8)O. Identify A,B,C,D and E and explain the reactions involved.

An organic compound (A) of molecular formula C_(6)H_(7)N on reaction w

1.	An organic compound (A) of molecular formula C_(6)H_(7)N on reaction with sodium nitrite and hydrochloric acid at 0^(@)C gives (B) or formula C_(6)H_(5)N_(2)Cl (B) on treatment with cuprous cyanide give (C) of formula C_(7)H_(5)N. (C)on reaction with sodium and ethanol gives (D) of formula C_(7)H_(9)N. (D) on reaction with nitrous acid gives (E) of molecular formula C_(7)H_(8)O. Identify A,B,C,D and E and explain the reactions involved.
Answer» Solution :(i) (A) is identified as Ailine from the molecular formula. (ii) Aniline on REACTION with sodium nitrite and hydrochloric acid at `0^(@)C` DIAZOTISATION take PLACE and the product (B) formed is benzene diazonium chloride. (iii) Benzene diazonium chloride on treatment with CuCN produces (C) as cyano benzene. (iv) Cyano benzene on reaction with Na and `C_(2)H_(5)OH` undergoes reduction reaction to give (D) as benzylamine. (v) BEnzylamine on treatment with nitrous acid gives benzyl alcohol as (E).