Question

An organic compound (A) with molecular formula C₃H₇NO on heating with Br₂ and KOH forms a compound (B). Compound (B) on heating with CHCl₃ and alcoholic KOH produces a foul-smelling compound (C) and on reacting with C₆H₅SO₂Cl forms a compound (D) which is soluble in alkali. Write the structure of (A), (B), (C) and (D).

Answer 1

$$\mathrm{CH}{\phantom{A}}_3\underset{(\mathrm{A})}{\mathrm{CH}{\phantom{A}}_2}\mathrm{CONH}{\phantom{A}}_2+\mathrm{Br}{\phantom{A}}_2+\mathrm{KOH}⟶\mathrm{CH}{\phantom{A}}_3\underset{(\mathrm{B})}{\mathrm{CH}{\phantom{A}}_2}\mathrm{NH}{\phantom{A}}_2$$

$$\mathrm{CH}{\phantom{A}}_3\underset{(\mathrm{B})}{\mathrm{CH}{\phantom{A}}_2}\mathrm{NH}{\phantom{A}}_2+\mathrm{CHCl}{\phantom{A}}_3+\mathrm{KOH}⟶\mathrm{CH}{\phantom{A}}_3\underset{(\mathrm{C})}{\mathrm{CH}{\phantom{A}}_2}\mathrm{NC}+\mathrm{KCl}+\mathrm{H}{\phantom{A}}_2\mathrm{O}$$

A = Propanaimde

B = Ethyl amine (1° amine)

C = Ethyl isocyanide

D = N-ethyl benzene sulphonamide