Give one chemical test to distinguish between the following pairs of compounds.
(i) Methylamine and dimethylamine
(ii) Secondary and tertiary amines
(iii) Ethylamine and aniline
(iv) Aniline and benzylamine
(v) Aniline and N-methylaniline
Give one chemical test to distinguish between the following pairs of compounds.
(i) Methylamine and dimethylamine
(ii) Secondary and tertiary amines
(iii) Ethylamine and aniline
(iv) Aniline and benzylamine
(v) Aniline and N-methylaniline
Solution and Explanation
(i) Methylamine and dimethylamine can be distinguished by the carbylamine test. Carbylamine test: Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium hydroxide form foul-smelling isocyanides or carbylamines. Methylamine (being an aliphatic primary amine) gives a positive carbylamine test, but dimethylamine does not.
(ii) Secondary and tertiary amines can be distinguished by allowing them to react with Hinsberg's reagent (benzenesulphonyl chloride, C6H5SO2Cl). Secondary amines react with Hinsberg's reagent to form a product that is insoluble in an alkali. For example, N, N - diethylamine reacts with Hinsberg's reagent to form N, N - diethylbenzenesulphonamide, which is insoluble in an alkali. Tertiary amines, however, do not react with Hinsberg's reagent.
(iii) Ethylamine and aniline can be distinguished using the azo-dye test. A dye is obtained when aromatic amines react with HNO2 (NaNO2 + dil.HCl) at 0-5°C, followed by a reaction with the alkaline solution of 2-naphthol. The dye is usually yellow, red, or orange in colour. Aliphatic amines give a brisk effervescence due (to the evolution of N2 gas) under similar conditions. ​
(iv) Aniline and benzylamine can be distinguished by their reactions with the help of nitrous acid, which is prepared in situ from a mineral acid and sodium nitrite. Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas.
On the other hand, aniline reacts with HNO2 at a low temperature to form stable diazonium salt. Thus, nitrogen gas is not evolved.
(v) Aniline and N-methylaniline can be distinguished using the Carbylamine test. Primary amines, on heating with chloroform and ethanolic potassium hydroxide, form foul-smelling isocyanides or carbylamines. Aniline, being an aromatic primary amine, gives positive carbylamine test. However, N-methylaniline, being a secondary amine does not.
Top Questions on Amines
Total number of molecules/species from the following which will be paramagnetic is ………. \[ O_2, O_2^+, O_2^-, NO, NO_2, CO, K_2[NiCl_4], [Co(NH_3)_6]Cl_3, K_2[Ni(CN)_4] \]
The total number of compounds from below when treated with hot KMnO4 giving benzoic acid is:
The major product of the following reaction is:
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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.