Type of Reaction for Organic, Nitrogen Compounds in Homework Question?

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Discussion Overview

The discussion revolves around identifying the type of reaction occurring in a specific organic transformation involving nitrogen compounds. Participants explore various reaction mechanisms and classifications, including free radical substitution, nucleophilic substitution, and potential reducing reactions. The context is homework-related, focusing on organic chemistry concepts.

Discussion Character

  • Homework-related
  • Debate/contested
  • Exploratory

Main Points Raised

  • One participant suggests that the reaction could be a free radical substitution reaction involving hydrogen.
  • Another participant questions the addition of hydrogen and proposes that a stronger nucleophile might be involved due to the partial positive charge on the carbon attached to the nitrogen.
  • A later reply introduces the idea of a reducing reaction and mentions the possibility of classifying the reaction as deamination or dealkylation, depending on the focus of interest.
  • One participant notes that the reaction could be viewed as an N-trityl deprotection reaction, which is not a free radical process.
  • Another participant expresses concern about the relevance of the reaction type to their syllabus, indicating that they did not find deamination or dealkylation reactions covered in their studies.

Areas of Agreement / Disagreement

Participants express differing views on the classification of the reaction, with no consensus reached on the exact type of reaction occurring. Multiple competing interpretations remain present throughout the discussion.

Contextual Notes

Participants highlight the complexity of the reaction and the potential for various interpretations, noting the absence of certain reaction types in their syllabus, which may limit their understanding.

Kushal
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Homework Statement



Part of a long question:

suggest the type of reaction occurring:

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


The Attempt at a Solution



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

and i also realized 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.


thnks
 
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What element has been added to your compound in this reaction? Balance the equation and it will speak for itself.
 
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?!
 
Kushal said:
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?!

Yes.

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.
 
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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