Question

A compound Z with molecular formula $$\mathrm{C}{\phantom{A}}_3\mathrm{H}{\phantom{A}}_9\mathrm{N}$$ reacts with $$\mathrm{C}{\phantom{A}}_6\mathrm{H}{\phantom{A}}_5\mathrm{SO}{\phantom{A}}_2\mathrm{Cl}$$ to give a solid, insoluble in alkali. Identify Z.

Answer 1

Z is an aliphatic amine which gives a solid insoluble in base. This implies that reaction with $$\mathrm{C}{\phantom{A}}_6\mathrm{H}{\phantom{A}}_5\mathrm{SO}{\phantom{A}}_2\mathrm{Cl}$$ must give a product without any replaceable hydrogen attached to nitrogen. In other words, the amine must be a secondary amine. i.e. Z is ethylmethylamine.

$$\begin{array}{c}\mathrm{O}\phantom{.......}\\ ||\phantom{.......}\\ \phantom{}\mathrm{CH}{\phantom{A}}_3-\mathrm{NH}+\mathrm{C}{\phantom{A}}_6\mathrm{H}{\phantom{A}}_5-\mathrm{S}-\mathrm{Cl}⟶\mathrm{CH}{\phantom{A}}_3\mathrm{N}-\mathrm{SO}{\phantom{A}}_2\mathrm{C}{\phantom{A}}_6\mathrm{H}{\phantom{A}}_5\phantom{.}\\ \phantom{..}|\phantom{.............}||\phantom{...............}|\phantom{.......}\\ \phantom{.......}\mathrm{C}{\phantom{A}}_2\mathrm{H}{\phantom{A}}_5\phantom{.........}\mathrm{O}\phantom{......}\underset{\mathrm{sulphonamide}}{\underset{\mathrm{N}-\mathrm{Ethyl}-\mathrm{N}-\mathrm{methyl}\mathrm{benzene}}{\mathrm{C}{\phantom{A}}_2\mathrm{H}{\phantom{A}}_5}}\phantom{.}\end{array}$$