Year 12s: what will be the first way you research your future options? >>

Amino acid + acyl chloride reaction

splitter2017

Is it possible to react an amino acid with an acyl chloride.

e.g. Glycine + ethanoyl chloride
H2NCH2COOH + CH3COCl --> CH3CONHCH2COOH + HCL ?

On my practical sheet it says that there would be no reaction. Is this true? I know the COOH group will not react but surely the NH2 (amino group) end would react with the RCO to form an amide bond.

(edited 6 years ago)

Reply 1

alow

Original post by splitter2017

There would be a reaction. It even has a name: http://www.organic-chemistry.org/namedreactions/schotten-baumann-reaction.shtm

Reply 2

splitter2017

Original post by alow

There would be a reaction. It even has a name: http://www.organic-chemistry.org/namedreactions/schotten-baumann-reaction.shtm

Thanks, I guess the reaction (amino acid + acyl chloride) follows the same rules as an amine + acyl chloride as shown in your link.

p.s. What observations would you expect for such a reaction?
I would predict HCL vapour (white) would be seen and the solution would become strongly acidic.