How to distinguish between amines, amides and nitriles?

Chemistry discussion, revision, exam and homework help.

Announcements Posted on
Please change your TSR password 23-05-2013
Enter our travel-writing competition for the chance to win a Nikon 1 J3 camera 20-05-2013
IMPORTANT: You must wait until midnight (morning exams)/4.30AM (afternoon exams) to discuss Edexcel exams and until 1pm/6pm the following day for STEP and IB exams. Please read before posting, including for rules for practical and oral exams. 28-04-2013
Sign in to Reply
  1. purplefrog's Avatar
    • PS Helper
    • Overlord in Training
    • Location: UCL
    • Posts: 2,603
    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
  2. illusionz's Avatar
    • Overlord in Training
    • Posts: 2,538
    Re: How to distinguish between amines, amides and nitriles?
    Amines are bases so can be detected with indicator, leaving the last one to be the nitrile.
  3. EierVonSatan's Avatar
    • PS Helper
    • TSR Royalty
    • Location: UK
    • Posts: 21,011
    Re: How to distinguish between amines, amides and nitriles?
    Any equipment? An IR spectrometer would make quick work of it
  4. illusionz's Avatar
    • Overlord in Training
    • Posts: 2,538
    Re: How to distinguish between amines, amides and nitriles?
    (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!!
  5. EierVonSatan's Avatar
    • PS Helper
    • TSR Royalty
    • Location: UK
    • Posts: 21,011
    Re: How to distinguish between amines, amides and nitriles?
    (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:
  6. illusionz's Avatar
    • Overlord in Training
    • Posts: 2,538
    Re: How to distinguish between amines, amides and nitriles?
    (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.
Sign in to Reply
Share this discussion:  
Article updates
Moderators

We have a brilliant team of more than 60 volunteers looking after discussions on The Student Room, helping to make it a fun, safe and useful place to hang out.

Reputation gems:
The Reputation gems seen here indicate how well reputed the user is, red gem indicate negative reputation and green indicates a good rep.
Post rating score:
These scores show if a post has been positively or negatively rated by our members.