Write the reactions of (i) aromatic and (ii) aliphatic primary amines with nitrous acid
Solution and Explanation
(i) Aromatic amines react with nitrous acid (prepared in situ from NaNO2 and a mineral acid such as HCl) at 273 - 278 K to form stable aromatic diazonium salts i.e., NaCl and H2O.
(ii) Aliphatic primary amines react with nitrous acid (prepared in situ from NaNO2 and a mineral acid such as HCl) to form unstable aliphatic diazonium salts, which further produce alcohol and HCl with the evolution of N2 gas.
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Concepts Used:
Amines - Chemical Properties
There are many chemical properties of amines.
The primary and secondary amines, including several amine derivatives, have a direct impact on their properties due to the presence of hydrogen bonding. The compounds containing phosphorus have a lower boiling point and the compounds containing amines and alcohol have a higher boiling point. The structure of alkanols is immensely similar to that of amine except the presence of the hydroxyl group. In such a case, oxygen has a higher electronegativity than that of nitrogen, so alkanol compounds are more acidic in nature in comparison to the amines.
On account of the ability to form hydrogen bonds, the amines have tendencies of high solubility in water. The amine molecules such as Ethyl, diethyl, triethyl, and Methyl are gaseous in nature. Whereas, higher weight amines have a solid structure and alkyl amines have a liquid structure. There is an ammonia smell to gaseous amines and a fishy smell to liquid amines. The solubility of amines entirely depends upon the number of carbon atoms in the molecule.