ASUC chem 24

ASUC chem 24 - CHEMISTRY 3B Professor Peter Vollhardt...

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CHEMISTRY 3B Professor Peter Vollhardt 11/18/08 Lecture 24 ASUC Lecture Notes Online is the only authorized note-taking service at UC Berkeley. Do not share, copy or illegally distribute (electronically or otherwise) these notes. Our student-run program depends on your individual subscription for its continued existence. These notes are copyrighted by the University of California and are for your personal use only. D O N O T C O P Y Sharing or copying these notes is illegal and could end note taking for this course. LECTURE Chapter 23: Ester Enolates and the Claisen Condensation The mechanism of the Claisen condensation is driven by deprotonation of a beta-ketoester and involves addition-elimination. Step 1: Ester enolate formation Step 2: Nucleophilic addition Step 3: Elimination Step 4: Deprotonation of 3-oxoester Step 5: Protonation on aqueous work-up The products of the Claisen condensation are alkyl 3-oxoalkanoates (IUPAC), which have a common name of beta-ketoesters and generally as beta- dicarbonyl compounds. The hydrogens between the two carbonyls are unusually acidic due to inductive
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This note was uploaded on 10/07/2010 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at Berkeley.

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ASUC chem 24 - CHEMISTRY 3B Professor Peter Vollhardt...

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