Chapter 27: Amino Acids, Peptides and Proteins
Strecker Synthesis
Reaction type: Nucleophilic Addition then Nucleophilic Acyl Substitution
Summary
Reagents : NH
4
Cl / NaCN then aq. acid / heat with a basic work-up.
Nucleophilic cyanide ion normally adds to an aldehyde to give a
cyanohydrin
, an α-hydroxy nitrile.
However, in the presence of ammonium chloride, the analogous α-amino nitrile is obtained.
Remember
that aldehydes are electrophilic at the carbonyl
C
atom.
Hydrolysis converts the nitrile to the carboxylic acid converts so providing the α-amino acid (
review
?)
QUESTION
:
The nitrile is hydrolysed to a carboxylic acid, what other functional groups does this remind you of ?
ANSWER
Related Reactions
Cyanohydrin formation
Hydrolysis of Nitriles
Nucleophilic substitution of α-halocarboxylic acids
Alkylation of an acetamidomalonate
©
Dr. Ian Hunt
, Department of Chemistry
