Can Amino Acids React with Acyl Chloride on Both the -COOH and -NH2 Groups?

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SUMMARY

Amino acids, such as glycine, can react with acyl chlorides, but the reaction specificity depends on the functional groups involved. Ethyl chloride is not an acyl chloride, thus it does not participate in the same reactions as acyl chlorides. When an amino acid reacts with an acyl chloride, the -NH2 group typically reacts to form an amide, while the -COOH group can lead to the formation of an anhydride. This distinction is crucial for understanding the reactivity of amino acids in organic synthesis.

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  • Understanding of amino acid structure and functional groups
  • Knowledge of acyl chlorides and their reactivity
  • Familiarity with organic reaction mechanisms, specifically amide formation
  • Basic principles of organic synthesis and cyclization reactions
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  • Study the mechanism of amide formation from acyl chlorides
  • Research the properties and reactions of anhydrides in organic chemistry
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crays
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Hi guys, i am wondering when amino acid (let's take glycine as an example) reacts with acyl chloride say ethyl chloride. Would it react with both the -COOH group and -NH2 group or would it be considered as an acid and reacts only with the -NH2 group?
 
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Ethyl chloride is not an acyl chloride.

Your question is whether an acid chloride would react with a carboylic acid or a secondary amine? One would produce an amide (that would quickly cyclize to an azlactone) and the other would produce an anhydride.

What happens to amines in the presence of an anhydride?
 

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