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How to distinguish between amines, amides and nitriles?

hi,

I'm struggling to answer a question my chemistry teacher set. He asked us to imagine we had any equipment needed but only the following chemicals to determine which of 3 unknown compounds is the nitrile, amine and amide.

NaOH, H2SO4, Sodium Carbonate, Indicators/Test Papers, Brady's, Tollen's, Triiodoform, Sodium Nitrite

so far I have got:

Amide: add NaOH --> nothing happens --> heat --> test gas with damp red litmus/indicator paper --> blue (due to ammonia given off)

not sure how to test for amines/nitriles as they both seem to do the same things chemically :s

any help is appreciated :smile:
Reply 1
Amines are bases so can be detected with indicator, leaving the last one to be the nitrile.
Any equipment? An IR spectrometer would make quick work of it :smile:
Reply 3
Original post by EierVonSatan
Any equipment? An IR spectrometer would make quick work of it :smile:


Yeah I thought that but you don't see them very often in schools!!
Original post by illusionz
Yeah I thought that but you don't see them very often in schools!!


No true, but I don't think it's an experiment that will actually be done. Chemical tests should be avoided where ever possible :p:
Reply 5
Original post by EierVonSatan
No true, but I don't think it's an experiment that will actually be done. Chemical tests should be avoided where ever possible :p:


Yeah, it's strange. 2 years of organic/inorganic work at university and also worked for about 6 months at an organic synthetic chemical company, I've only ever used nmr/IR to work out what I've got, never chemical tests. Seems rather pointless teaching it at schools.

The same applies to an extend with the iupac nomenclature.
Buy me one and I'll use it, £2000000 should suffice

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