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13.15 : Carboxylic Acids to Primary Alcohols: Hydride Reduction

Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols.

Figure1

Weaker reducing agents like lithium tri-tert-butoxyaluminum hydride or diisobutylaluminum hydride cannot reduce carboxylic acids to primary alcohols.

Carboxylic acids can also be reduced to primary alcohols by using borane in thetetrahydrofuran solvent. The main advantage of using borane in reducing a carboxylic acid is that this reagent can selectively reduce carboxylic acid to primary alcohol in the presence of other reducible functional groups, such as a ketone or a nitro group.

Figure2

Tags
Carboxylic AcidsPrimary AlcoholsHydride ReductionLithium Aluminum HydrideLithium Tri tert butoxyaluminum HydrideDiisobutylaluminum HydrideBoraneTetrahydrofuranSelective ReductionKetoneNitro Group

From Chapter 13:

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13.15 : Carboxylic Acids to Primary Alcohols: Hydride Reduction

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13.1 : IUPAC Nomenclature of Carboxylic Acids

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13.2 : Physical Properties of Carboxylic Acids

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13.3 : Acidity of Carboxylic Acids

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13.4 : Substituent Effects on Acidity of Carboxylic Acids

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13.5 : IR and UV–Vis Spectroscopy of Carboxylic Acids

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13.6 : NMR and Mass Spectroscopy of Carboxylic Acids

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13.7 : Preparation of Carboxylic Acids: Overview

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13.8 : Preparation of Carboxylic Acids: Hydrolysis of Nitriles

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13.9 : Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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13.10 : Reactions of Carboxylic Acids: Introduction

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13.11 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

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13.12 : Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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13.13 : Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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13.14 : Carboxylic Acids to Acid Chlorides

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