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This document discusses Hinsberg's method and two alternative methods for differentiating between primary, secondary, and tertiary amines. Hinsberg's method uses a schematic diagram to show how the test distinguishes the amines. Reacting amines with nitrous acid or using IR spectroscopy can also differentiate the amines based on their chemical reactions and absorption bands.
This document discusses Hinsberg's method and two alternative methods for differentiating between primary, secondary, and tertiary amines. Hinsberg's method uses a schematic diagram to show how the test distinguishes the amines. Reacting amines with nitrous acid or using IR spectroscopy can also differentiate the amines based on their chemical reactions and absorption bands.
This document discusses Hinsberg's method and two alternative methods for differentiating between primary, secondary, and tertiary amines. Hinsberg's method uses a schematic diagram to show how the test distinguishes the amines. Reacting amines with nitrous acid or using IR spectroscopy can also differentiate the amines based on their chemical reactions and absorption bands.
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