Chapter 22: Amines
Reduction of Nitriles
Reaction type : Oxidation - Reduction
or
Nucleophilic Addition
Summary
The nitrile,
RC
≡
N
, is reduced to the 1
o
amine by conversion of the
C≡N
to
R-CH
2
-NH
2
Reagents : either lithium aluminum hydride (LiAlH
4
) / ether solvent or catalytic hydrogenation (
e.g.
H
2
/Pd).
Alkyl nitriles are prepared by
nucleophilic substitution
(
S
N
2
) by cyanide ion, CN
-
, of
primary or secondary alkyl halides
.
Aryl nitriles can also be reduced to aryl amines.
QUESTIONS
What is the oxidation state of the nitrile C in acetonitrile, CH
3
CN ?
ANSWER
What is the oxidation of the same C atom in acetonitrile, CH
3
CN after reaction with LiAlH
4
?
ANSWER
Related reactions
Reduction of Azides
Reduction of Nitro compounds
Reduction of Amides
©
Dr. Ian Hunt
, Department of Chemistry
