Question

In Hinsberg‘s method, the amine mixtures are separated from each other. The reagent used in this process is p-toluenesulphonyl chloride. Amines form sulphonamide when treated with the reagent.

The sulphonamide of an amine(X) is insoluble in KOH. Therefore,(X) is:

(A) CH₃CH₂CH₂CH₂NH₂

(B) CH₃CH₂NHCH₂CH₃

(C) CH₃CH₂CH₂NH₂

(D) PhCH₂CH₂NH₂

Answer 1

Correct option is (B) CH₃CH₂NHCH₂CH₃

The sulphonamides of primary (1°) amines are soluble in KOH due to presence of α-hydrogen atoms. The sulphonamides of secondary or 2° amines are not soluble in KOH due to absence of α-H atoms. Tertiary alcohols do not react with Hinsberg reagent.