Question

An organic compound [A] having molecular formula C₂H₇N on treatment with nitrous acid gives a compound [B] having molecular formula C₂H₆O. [B] on treatment with an organic compound [C] gives a carboxylic acid [D] and a sweet-smelling compound [E]. Oxidation of [B] with acidified potassium dichromate also gives [D].
(i) Identify [A], [B], [C], [D] and [E].
(ii) Write a balanced chemical equation of [D] with chlorine in the presence of red phosphorus and name the reaction.

Answer 1

(i)
A is C₂H₅NH₂ → Ethylamine
B is C₂H₅OH → Ethanol
C is CH₃COOCOCH₃ → Acetic anhydride
D is CH₃COOH → Acetic acid
E is CH₃COOC₂H₅ → Ethyl acetate

(ii) \[\ce{CH_3COOH + Cl_2 ->[Red P][-HCl] \underset{\text{Monochloro acetic acid}}{CH_2CICOOH}}\]

This reaction is called Hell - volhard - zelinsky (HUZ) reaction.