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14.28: Nitriles to Amines: LiAlH4 Reduction

JoVE Core
Organic Chemistry

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Nitriles to Amines: LiAlH4 Reduction

14.28: Nitriles to Amines: LiAlH4 Reduction

Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.

As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to generate a dianion. A final protonation of the dianion with water yields a primary amine as the final product.


A milder reducing agent like diisobutylaluminum hydride reduces nitriles to aldehydes. In this reaction, nitrile reacts with one equivalent of the reducing agent. This is followed by hydrolysis to yield aldehyde.


Keywords: Nitrile Reduction LiAlH4 Reduction Nucleophilic Acyl Substitution Hydride Ion Primary Amine Diisobutylaluminum Hydride Aldehyde

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