Consider the compound 2-methyl-2-carboethoxycyclopentanone, whose structure is shown below, to answer the following question(s). CH3 OEt When 2-methyl-2-carboethoxycyclopentanone is treated with sodium ethoxide in ethanol solution followed by a mild aqueous acid work-up, 5-methyl-2-carboethoxycyclopentanone is isolated as the major product. This reaction proceeds by a reverse Claisen condensation mechanism followed by a recyclization. On the structures provided below, show electron flow with arrows in this interesting reaction.

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Question 24
Consider the compound 2-methyl-2-carboethoxycyclopentanone, whose structure is shown below, to answer the
following question(s).
CH3
When 2-methyl-2-carboethoxycyclopentanone is treated with sodium ethoxide in ethanol solution followed by a
mild aqueous acid work-up, 5-methyl-2-carboethoxycyclopentanone is isolated as the major product. This reaction
proceeds by a reverse Claisen condensation mechanism followed by a recyclization. On the structures provided
below, show electron flow with arrows in this interesting reaction.
OEt
0
Hfl
NaOEt H3O* H₂C
EtOH
CH3
OEt
OEt
Transcribed Image Text:Consider the compound 2-methyl-2-carboethoxycyclopentanone, whose structure is shown below, to answer the following question(s). CH3 When 2-methyl-2-carboethoxycyclopentanone is treated with sodium ethoxide in ethanol solution followed by a mild aqueous acid work-up, 5-methyl-2-carboethoxycyclopentanone is isolated as the major product. This reaction proceeds by a reverse Claisen condensation mechanism followed by a recyclization. On the structures provided below, show electron flow with arrows in this interesting reaction. OEt 0 Hfl NaOEt H3O* H₂C EtOH CH3 OEt OEt
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