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

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SUMMARY

The reaction described involves the conversion of a secondary amine to a primary amine, specifically through an N-trityl deprotection reaction of the dipeptide N-(trityl)alanine-glycine. This process is not a free radical substitution but rather a deamination or dealkylation reaction, which can be facilitated by treatment with alcoholic acid. The addition of hydrogen indicates a reducing reaction, emphasizing the need for a stronger nucleophile than the ammonium species present.

PREREQUISITES
  • Understanding of amine classifications: primary, secondary, and tertiary amines.
  • Knowledge of deprotection reactions, specifically N-trityl deprotection.
  • Familiarity with nucleophilic substitution reactions and their mechanisms.
  • Basic principles of organic reaction types, including reduction and deamination.
NEXT STEPS
  • Research the mechanisms of N-trityl deprotection reactions in organic chemistry.
  • Study the principles of nucleophilic substitution reactions and their applications.
  • Explore the concept of deamination and its significance in organic synthesis.
  • Learn about the role of reducing agents in organic reactions, particularly in amine transformations.
USEFUL FOR

Chemistry students, organic chemists, and anyone studying reaction mechanisms involving amines and deprotection strategies in organic synthesis.

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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