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
Chapter23: Carbonyl Condensation Reactions
Section23.7: The Claisen Condensation Reaction
Problem 12P
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