Chapter 27: Amino Acids, Peptides and Proteins
Reaction type: Nucleophilic Addition then Nucleophilic Acyl Substitution
Reagents : NH
Cl / NaCN then aq. acid / heat with a basic work-up.
Nucleophilic cyanide ion normally adds to an aldehyde to give a
, an α-hydroxy nitrile.
However, in the presence of ammonium chloride, the analogous α-amino nitrile is obtained.
that aldehydes are electrophilic at the carbonyl
Hydrolysis converts the nitrile to the carboxylic acid converts so providing the α-amino acid (
The nitrile is hydrolysed to a carboxylic acid, what other functional groups does this remind you of ?
Hydrolysis of Nitriles
Nucleophilic substitution of α-halocarboxylic acids
Alkylation of an acetamidomalonate
Dr. Ian Hunt
, Department of Chemistry, University of Calgary