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  4. Identify the compound that will react with Hinsberg’s reagent to give a solid which dissolves in alkali.

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Q. Identify the compound that will react with Hinsberg’s reagent to give a solid which dissolves in alkali.

NEETNEET 2021Organic Chemistry – Some Basic Principles and Techniques

Solution:

$\underset{1^{\circ}\text{amine}}{R - NH - H } + \underset{\text{Hinsberg reagent}}{SO_2C_6H_5} \to \underset{\text{N - alkyl benzene Sulphonamide alkali soluble}}{R - NHSO_2C_6H_5} + HCl$
$H$ - atom attached to nitrogen is highly acidic because it is attached to strong electron withdrawing $- SO _{2} C _{6} H _{5}$ group