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How to distinguish between amines, amides and nitriles?

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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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    Amines are bases so can be detected with indicator, leaving the last one to be the nitrile.
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    Any equipment? An IR spectrometer would make quick work of it
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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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    (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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    (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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