How will you distinguish between primary, secondary and tertiary amines by Hinsberg's test?

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Solution

The mixture of amines is treated with benzene sulphonyl chloride (Hinsberg's reagent) and shaken with alkali solution.
(1) Primary amine forms alkyl benzenesulphonamide which dissolves in alkali to form sodium or potassium salt of monoalkylbenzenesulphonamide.
$P h S O_{2} C l + H N H R \to P h S O_{2} N H R K O H - -- \to P h S O_{2} N K R (water soluble)$

(2) Secondary amine forms alkyl sulphonamide which does not form salt with alkali and hence remains insoluble (solid) in alkali solution.
$P h S O_{2} C l + H N R_{2} \to P h S O_{2} N R_{2} (water insoluble) \to no action$

(3) Tertiary amines does not react with Hinsberg's reagent.
$P h S O_{2} C l + N R_{3} \to no reaction$

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