Question

A compound Z with molecular formula \[\ce{C3H9N}\] reacts with \[\ce{C6H5SO2Cl}\] 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 \[\ce{C6H5SO2Cl}\] 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.

\[\begin{array}{cc}
\ce{O}\phantom{.......}\\
||\phantom{.......}\\
\phantom{}\ce{CH3 - NH + C6H5 - S - Cl -> CH3N - SO2C6H5}\phantom{.}\\
\phantom{..}|\phantom{.............}||\phantom{...............}|\phantom{.......}\\
\phantom{.......}\ce{C2H5}\phantom{.........}\ce{O}\phantom{......}\ce{\underset{sulphonamide}{\underset{N-Ethyl-N-methyl benzene}{C2H5}}\phantom{.}}
\end{array}\]