NCERT Solutions

Class 12 Chemistry

Amines

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Q.2

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.?

(i) The best test for distinguishing methyl amine and dimethylamine is

the Carbylamines test.

Carbylamine Test: Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium hydroxide form foul smelling isocyanides or carbylamines.

In this case, Methylamine (which is an aliphatic primary amine) gives a positive carbylamine test while dimethylamine won’t.

Reaction:

                                       ∆

CH3-NH2+CHCl3 + 3KOH à CH3-NC-3KCl+ 3H2

Methylamine (10)             Methylisocyanide (foul smell)

                                       ∆

(CH3)2-NH2+CHCl3 + 3KOH à No reaction

 

(ii) Hinsberg’s reagent (benzenesulphonyl chloride, C 6H5SO2Cl);It can be

used to distinguish secondary and tertiary amines.

Hinsberg Test: 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.

Reaction:-

 

 

(iii) Ethylamine and aniline can be distinguished using the azo-dye test. A

dye is obtained when aromatic amines react with HNO 2 (NaNO2 + dilute 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 with the help of nitrous

acid.

Nitrous acid test: Benzylamine reacts with nitrous acid to form unstable diazonium salt, which in turn gives alcohol with the evolution of nitrogen gas, while aniline reacts with nitrous acid to form a stable diazonium salt without releasing nitrogen gas.

Reaction:

 

Carbylamine test can be used to distinguish between Aniline and N-

methylaniline.

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.

Reaction:

                                       ∆

C6H5-NH2+CHCl3 + 3KOH C6H5-NC-3KCl+ 3H2

Benzylamine (10)             Benzylisocyanide (foul smell)

                                       ∆

C6H5-NHCH3+CHCl3 + 3KOH No reaction

N-Methylaniline

Video solution:

Amines Class 12 Chemistry NCERT Chapter 9 NCERT Solutions

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