1.

A colourless substance (A) is sparingly soluble in water and gives (B) on heating with mineral acids. Compound (B) on reaction with CHCl_(3) and alcoholic potash produces an obnoxious smell of carbylamine due to the formation of (C). Compound (A) on reaction with chlorosulphonic acid gives (D) which on treatment with ammonia gives (E). Compound (E) on hydrolysis gives sulphanilamide, a well known drug. Give structures of (A) to (E) with proper reasoning.

Answer»

SOLUTION :The reaction of B with chloroform and alcoholic KOH gives carbylamine. This INDICATES that B is a primary aromatic amine. SINCE sulphanilamide is the final product, it means that B is aniline.
Now, B is formed by the ACIDIC hydrolysis of A, which is colourless and sparingly soluble in water, therefore, A is acetanilide. The reactions may be explained as:


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