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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Figure 23.4 - Mechanism of the Claisen
Condensation Reaction
1 Base abstracts an acidic alpha hydrogen
atom from an ester molecule, yielding an
ester enolate ion.
2 The enolate ion adds in a nucleophilic
addition reaction to a second ester
molecule, giving a tetrahedral alkoxide
intermediate.
H.
EtO
FO:
C
C
A
HH
H.
H3C-
OEt
нн
Eto
30:
1
H.
2
ICIH
HH
OEt
010
C.
OEt
OEt
Transcribed Image Text:Figure 23.4 - Mechanism of the Claisen Condensation Reaction 1 Base abstracts an acidic alpha hydrogen atom from an ester molecule, yielding an ester enolate ion. 2 The enolate ion adds in a nucleophilic addition reaction to a second ester molecule, giving a tetrahedral alkoxide intermediate. H. EtO FO: C C A HH H. H3C- OEt нн Eto 30: 1 H. 2 ICIH HH OEt 010 C. OEt OEt
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
H3C
O=U
O=C
HH
4
1:CIH
O=C
Η Η
OEt
OEt
5 H30+
OEt
+ EtO™
+ EtOH
Transcribed Image Text: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 H3C O=U O=C HH 4 1:CIH O=C Η Η OEt OEt 5 H30+ OEt + EtO™ + EtOH
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