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Reduction of Nitriles to Amines

OCR A-level Organic ChemistryCarbon-Carbon Bond FormationLesson 4 of 8

Nitriles contain the −C≡N group. Because a nitrile can be made from a haloalkane (adding one carbon atom to the chain), it is a useful intermediate: the nitrile group can then be converted into other functional groups.

Reduction of a nitrile forms a primary amine. The C≡N triple bond gains hydrogen and becomes a −CH2NH2 group. OCR uses hydrogen gas with a nickel catalyst (H2/Ni) for this reduction.

In a general equation, 4 hydrogen atoms (2 H2) are added:

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Key terms in this lesson

primary amine
An amine in which the nitrogen atom is bonded to one alkyl or aryl group and two hydrogen atoms.

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