Describe Hinsberg Reagent's reaction with Ethylamine.?

Question

Describe Hinsberg Reagent's reaction with Ethylamine.?

Answer 1

The Hinsberg test  is used to distinguish 3o, 2o and 1o amines.

The product from the 1o amine is soluble in base whereas the product from a 2o amine is insoluble. Secondary and tertiary amines may be distinguished on the basis of solubility in dilute HCl.  The unreacted 3o amine will be soluble in aqueous HCl whereas the benzenesulfonamide product from the 2o amine will be insoluble.

Procedure

Place 1 mL of 10% sodium hydroxide in a small test tube and dilute with 4 mL of water. Add five drops (use an equivalent amount if a solid) of amine and 9 drops of benzenesulfonyl chloride. Shake the mixture vigorously for 5 minutes. Warm it slightly and continue shaking, When the odor of benzenesulfonyl chloride has dissipated, cool the mixture. If an oil separates, try to induce crystallization by rubbing the inner wall of the teat tube with a glass rod and chilling in an ice bath, Any solid produced should be separated by filtration; it is the benzenesulfonamide derivative of the unknown. A portion of it should be tested in dilute sodium hydroxide solution, while another portion tested using dilute HCl solution.

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