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Question

Write the reactions of (i) aliphatic and (ii) aromatic primary amines with nitrous acid:

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Solution


(i) Aliphatic primary amines (except methylamine) react with nitrous acid in cold condition to form unstable aliphatic diazonium salt, which decomposes to give alcohol with liberation of nitrogen gas.
The reaction of ethylamine with nitrous acid is as shown.
C2H5NH2+HNO2NaNO2+HCl−−−−−−−273278KC2H5OH+H2O+N2
(ii) Aromatic primary amines react with nitrous acid in cold condition to give diazonium salts.
C6H5NH2+NaNO2+2HCl273278K−−−−−−C6H5N+2Cl+NaCl+2H2O

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