How to distinguish between amines, amides and nitriles?

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purplefrog
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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
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illusionz
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Amines are bases so can be detected with indicator, leaving the last one to be the nitrile.
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EierVonSatan
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Any equipment? An IR spectrometer would make quick work of it
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illusionz
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(Original post by EierVonSatan)
Any equipment? An IR spectrometer would make quick work of it
Yeah I thought that but you don't see them very often in schools!!
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EierVonSatan
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(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:
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illusionz
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(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.
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Osamabinbenzene
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Buy me one and I'll use it, £2000000 should suffice
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