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14.13 : Acid Halides to Alcohols: LiAlH4 Reduction

Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.

The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as the final product.

Figure1

However, it is possible to stop the reaction at the aldehyde by using a milder reducing agent like diisobutylaluminum hydride or lithium tri(t-butoxy)aluminum hydride.

Tags
Acid HalidesAlcoholsLiAlH4ReductionNucleophilic AttackTetrahedral IntermediateAldehydeAlkoxideDIBAL HLithium Tri t butoxy aluminum Hydride

From Chapter 14:

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14.13 : Acid Halides to Alcohols: LiAlH<sub>4</sub> 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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14.14 : Acid Halides to Alcohols: Grignard Reaction

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14.15 : Acid Halides to Ketones: Gilman Reagent

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