Hinsbergs Method For Characterizing Primary, Secondary, And Tertiary Amines

1. Show by means of a schematic diagram how Hinsbergs test distinguishes primary, secondary, and tertiary
amines.

2. Suggest another method of differentiating primary, secondary, and tertiary amines.

- The Hinsbergs test has its limitations. It cannot be employed to distinguish amphiprotic amines because the
carboxylic acid will be deprotonated thus resulting in soluble sulfonamide. Another method that can be used
to differentiate primary, secondary, and tertiary amines would be reacting amines with nitrous acid. Primary
amines, when reacted with nitrous acid, give off an emission of nitrogen gas. Secondary amines, when
reacted with nitrous acids, result in the production of nitrosamine-yellow oil which is a powerful carcinogen
and is the reason why the nitrous acid test is not quite commonly used. Tertiary amines, when reacted with
nitrous acids, seem to have no observable reaction-it actually results in a colorless solution. The colorless
solution is actually the result of the tertiary amine reacting with the acid thus forming an ion.
- Another method applicable is the IR spectroscopy. The amines are differentiated by the IR absorption bands
they give off from their NH stretching vibrations. Tertiary amines lack NH groups therefore they do not
give off absorption bands in this area. Primary amines give off two while secondary amines give off one.
References:
[1] Owen, T. (1969). Characterization of Organic Compounds By Chemical Methods. USA: Marcel Dekker, Inc.
[2] Solomons TW, Fryhle C. (2011). Organic Chemistry. 10th ed. NJ: John Wiley & Sons Inc.
s