A mixture of isomeric amines is treated with Hinsberg's reagent followed by an excess of aqueous . O — Amines Chemistry Question
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?
💡 Solution & Explanation
Primary amines react with benzenesulphonyl chloride to form an N-alkylbenzenesulphonamide. This amide contains an acidic $N-H$ proton, which reacts with $KOH$ to form a soluble water-soluble potassium salt (clear solution). When dilute $HCl$ is added, the salt is protonated back to the water-insoluble N-alkylbenzenesulphonamide, re-precipitating the solid.