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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 : Derivados del ácido carboxílico: descripción general

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14.2 : Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos

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14.4 : Estructuras de los derivados del ácido carboxílico

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14.5 : Propiedades físicas de los derivados del ácido carboxílico

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14.6 : Acidez y basicidad de los derivados del ácido carboxílico

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14.7 : Espectroscopía de derivados del ácido carboxílico

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14.8 : Reactividad relativa de los derivados del ácido carboxílico

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14.9 : Sustitución nucleofílica de acilo de derivados del ácido carboxílico

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14.10 : Halogenuros ácidos a ácidos carboxílicos: hidrólisis

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14.11 : Halogenuros ácidos a ésteres: alcoholisis

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14.12 : Halogenuros ácidos a amidas: aminolis

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14.13 : Halogenuros ácidos a alcoholes: reducción de LiAlH4

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