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14.13: Acid Halides to Alcohols: LiAlH4 Reduction

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Organic Chemistry

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Acid Halides to Alcohols: LiAlH4 Reduction
 
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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.

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Keywords: Acid Halides Alcohols LiAlH4 Reduction Nucleophilic Attack Tetrahedral Intermediate Aldehyde Alkoxide DIBAL-H Lithium Tri(t-butoxy)aluminum Hydride

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