Ireland-Claisen Rearrangement Mechanism | Organic Chemistry @OrganicMechanismsChannel

Uploaded October 2021 | Updated September 2026, 1 week ago

The mechanism for an Ireland-Claisen Rearrangement reaction in which an allyl ester is converted to an unsaturated carboxylic acid using LDA, TMSCl, and NaOH. The first step of the reaction involves a deprotonation to form an enolate which can then attack the TMSCl and produce an LiCl salt. Deprotection of the TMS group with base and subsequent protonation will result in the carboxylic acid product.

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Ireland-Claisen Rearrangement Mechanism | Organic Chemistry