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Organic, nitrogen compounds

  1. Sep 7, 2008 #1
    1. The problem statement, all variables and given/known data

    Part of a long question:

    suggest the type of reaction occuring:

    (C6H5)3C-NH-CH(CH3)-CO-NHCH2COOH -----> (C6H5)3C-H + NH2-CH(CH3)-CO-NHCH2COOH

    3. The attempt at a solution

    what i got in mind is that it could a free radical substitution reaction?! using H2....

    and i also realised that the reaction is converting a secondary amine to a primary amine... i don't know how it can be done... although converting a primary amine to a secondary one can easily be done by reacting the amine with an alkyl halide..... nucleophilic substitution reaction.

  2. jcsd
  3. Sep 8, 2008 #2


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    What element has been added to your compound in this reaction? Balance the equation and it will speak for itself.
  4. Sep 8, 2008 #3
    it seems that hydrogen has been added. but i can't find any type of reaction involving hydrogen like this.

    i would rather think of a species which is a stronger nucleophile than the 'ammonium stuff' since the carbon attached to the - NH - has a partial positive charge.

    but could it be a reducing reaction?!
  5. Sep 8, 2008 #4


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    You could also call it a deamination reaction (if you were interested in the alkyl/aryl group) or a dealkylation reaction (if you were interested in the amine fraction of the molecule).

    I would call it an N-trityl deprotection reaction of the dipeptide N-(trityl)alanine-glycine.
    Deprotection of trityl-substituted peptides can be accomplished by treatment with alcoholic acid. Not a free radical process.
  6. Sep 10, 2008 #5
    ooo ok..... the question is from a past past past exam paper...lol.... i guess we won't be getting such questions in the finals.... because i didn't find any deamination or dealkylation reaction in the syllabus...

    thnks again....:)
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