Figure 23.4 - Mechanism of the Claisen Condensation Reaction. 3 The tetrahedral intermediate expels ethoxide ion to yield a new carbonyl compound, ethyl acetoacetate. 4 But ethoxide ion is a strong enough base to deprotonate ethyl acetoacetate, shift- ing the equilibrium and driving the overall reaction to completion. 5 Protonation of the enolate ion by addition of aqueous acid in a separate step yields the final 3-keto ester product. H3C H3C 17 H3C O=U O=C HH 4 1:CIH O=C Η Η OEt OEt 5 H30+ OEt + EtO™ + EtOH

Figure 23.4 - Mechanism of the Claisen Condensation Reaction. 3 The tetrahedral intermediate expels ethoxide ion to yield a new carbonyl compound, ethyl acetoacetate. 4 But ethoxide ion is a strong enough base to deprotonate ethyl acetoacetate, shift- ing the equilibrium and driving the overall reaction to completion. 5 Protonation of the enolate ion by addition of aqueous acid in a separate step yields the final 3-keto ester product. H3C H3C 17 H3C O=U O=C HH 4 1:CIH O=C Η Η OEt OEt 5 H30+ OEt + EtO™ + EtOH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Section21.SE: Something Extra

Problem 81AP

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