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Question
What is the action of nitrous acid on the following compounds?
Isopropyl amine
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Solution
Isopropyl amine on reaction with nitrous acid form aliphatic diazonium salts as very unstable intermediates which decompose immediately by reaction with solvent water. Isopropyl alcohol is formed as the product of the reaction and nitrogen gas is liberated.
\[\begin{array}{cc}
\ce{CH3 - CH - CH3 + HNO2 ->[273 - 278K][(NaNO2 + HCl)] \underset{\text{Isopropyl diazonium chloride}}{[(CH3)2CH - N^+_2 Cl-]} ->[H2O] CH3 - CH - CH3 + N2 ^ + HCl}\\
\phantom{..............}|\phantom{..................................................................}|\phantom{.............................}\\
\phantom{..}\ce{\underset{\text{Isopropyl amine}}{NH2}}\phantom{......................................................}\ce{\underset{\text{Isopropyl alcohol}}{OH}}\phantom{...............}
\end{array}\]
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