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Chapter 22: Amines
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Reduction of Nitriles
Reaction type : Oxidation - Reduction or Nucleophilic Addition
Summary
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The nitrile, RCºN, is reduced
to the 1o amine by conversion of the CºN
to R-CH2-NH2
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Reagents : either lithium aluminum hydride (LiAlH4) / ether
solvent or catalytic hydrogenation (e.g. H2/Pd).
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Alkyl nitriles are prepared by nucleophilic
substitution (SN2) by cyanide ion,
CN-, of primary or secondary alkyl
halides.
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Aryl nitriles can also be reduced to aryl amines.
Questions
What is the oxidation state of the nitrile C in acetonitrile, CH3CN
? 
What is the oxidation of the same C atom in acetonitrile, CH3CN
after reaction with LiAlH4 ?
Related reactions
