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

[crays]

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?

 

[chemisttree]

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?

 

[quicknote]

Great question! When glycine reacts with acyl chloride, it will react with both the -COOH group and the -NH2 group. This is because acyl chloride is a reactive compound that can form bonds with both the carboxylic acid group and the amino group of the amino acid. The reaction will result in the formation of an amide bond between the acyl chloride and the amino acid, producing an N-acylglycine compound. This type of reaction is commonly used in the synthesis of peptides and proteins, where amino acids are joined together through amide bonds. So, in summary, both the -COOH and -NH2 groups of glycine will react with acyl chloride. I hope this helps clarify your question!