A mixture of isomeric amines is treated with Hinsberg's reagent followed by an excess of aqueous . One of the components forms a completely clear solution, which upon the addition of dilute , re-preci

Question

A mixture of isomeric amines is treated with Hinsberg's reagent followed by an excess of aqueous $KOH$. One of the components forms a completely clear solution, which upon the addition of dilute $HCl$, re-precipitates as an insoluble solid. What is the structural class of this specific component?

Prashant Kotian · Accepted Answer

Correct answer: A. Primary amines react with benzenesulphonyl chloride to form an N-alkylbenzenesulphonamide. This amide contains an acidic proton, which reacts with to form a soluble water-soluble potassium salt (clear solution). When dilute is added, the salt is protonated back to the water-insoluble N-alkylbenzenesulphonamide, re-precipitating the solid.

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