Chapter 23 lecture notes

Chapter 23 lecture notes - Chemistry 0320 - Spring 2008 Ch...

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Chemistry 0320 — Spring 2008 Ch 23 — Ester Enolates and Claisen Condensation page 1 Chapter 23: Ester Enolates and Claisen Condensation 23-1 Claisen Condensation Mechanism Wrong match-up between the base and substrate:
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Chemistry 0320 — Spring 2008 Ch 23 — Ester Enolates and Claisen Condensation page 2 Low-yielding Claisen condensation: Mechanism of Retro-Claisen Mixed Claisen condensation R O R' O OEt R O R' O OEt OEt + NaOEt EtOH no ! -H Example
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Chemistry 0320 — Spring 2008 Ch 23 — Ester Enolates and Claisen Condensation page 3 Dieckmann condensation — Intramolecular Claisen condensation Ex1 Ex2 Claisen condensation with ketones Ex1 Ex2 Claisen condensation in biology O S CoA + CO 2 O S CoA HO O acetyl CoA malonyl CoA O S CoA O O H O RS acetyl ACP O S CoA RS O H O S CoA O steroids
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Chemistry 0320 — Spring 2008 Ch 23 — Ester Enolates and Claisen Condensation page 4 23-2 β -Dicarbonyl Compounds in Synthesis Alkylations Decarboxylations of β -ketocarboxylic acids O R OEt O R' hydrolysis O R OH O R' heat O R R' + CO 2 Mechanism
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This note was uploaded on 04/13/2008 for the course CHEM 320 taught by Professor Koide during the Spring '08 term at Pittsburgh.

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Chapter 23 lecture notes - Chemistry 0320 - Spring 2008 Ch...

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