Login-Verarbeitung ...

Trial ends in Request Full Access Tell Your Colleague About Jove

14.13: Acid Halides to Alcohols: LiAlH4 Reduction

JoVE Core
Organic Chemistry

Ein Abonnement für JoVE ist erforderlich, um diesen Inhalt ansehen zu können. Melden Sie sich an oder starten Sie Ihre kostenlose Testversion.

Acid Halides to Alcohols: LiAlH4 Reduction

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.


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.


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

Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter