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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.

Figure1

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.

Tags
Nitrile ReductionLiAlH4 ReductionNucleophilic Acyl SubstitutionHydride IonPrimary AmineDiisobutylaluminum HydrideAldehyde

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14.28 : Nitriles to Amines: LiAlH4 Reduction

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14.1 : Carboxylic Acid Derivatives: Overview

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14.2 : Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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14.3 : Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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14.4 : Structures of Carboxylic Acid Derivatives

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14.5 : Physical Properties of Carboxylic Acid Derivatives

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14.6 : Acidity and Basicity of Carboxylic Acid Derivatives

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14.7 : Spectroscopy of Carboxylic Acid Derivatives

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14.8 : Relative Reactivity of Carboxylic Acid Derivatives

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14.9 : Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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14.10 : Acid Halides to Carboxylic Acids: Hydrolysis

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14.11 : Acid Halides to Esters: Alcoholysis

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14.12 : Acid Halides to Amides: Aminolysis

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14.13 : Acid Halides to Alcohols: LiAlH4 Reduction

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14.14 : Acid Halides to Alcohols: Grignard Reaction

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