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19.11: Reduction of Carboxylic Acids by Lithium Aluminum Hydride

Organic Chemistry · LibreTexts

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    From LibreTexts, under CC BY-NC-SA 4.0, as the source states it; its equations are written in TeX, which the PDF shows typeset. This page at LibreTexts.

    Carboxylic acids can be converted to 1o alcohols using Lithium aluminum hydride (LiAlH4). Note that NaBH4 is not strong enough to convert carboxylic acids or esters to alcohols. An aldehyde is produced as an intermediate during this reaction, but it cannot be isolated because it is more reactive than the original carboxylic acid.

    General reaction

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    Example

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    Possible Mechanism

    1) Deprotonation

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    2) Nucleophilic attack by the hydride anion

    supplement nuc attack hydride.svg

    3) Leaving group removal

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    4) Nucleophilic attack by the hydride anion

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    5) The alkoxide is protonated

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    Contributors

    19.11: Reduction of Carboxylic Acids by Lithium Aluminum Hydride is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.