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# A chemist has treated P-chloroaniline with acetic anhydride and wants to separate the amine product from any unreacted amine which reagent used for separation based on the basicities of the two compounds.

$\begin{array}{1 1}(a)\;HNO_3\;and\;H_2SO_4&(b)\;5\%\;aqueous\;HCl\\(c)\;5\%\;CH_3COOH&(d)\;\text{None}\end{array}$

Can you answer this question?

If the mixture is treated with 5% aqueous HCl,the amine will form the hydrochloride salt and dissolve in the aqueous solution.The amide however is not basic enough to be protonated in 5% HCl and therefore does not dissolve.
Hence (b) is the correct answer.
answered Mar 3, 2014