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.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter19: Carboxylic Anhydrides, Esters, And Amides
Section: Chapter Questions
Problem 19.47P
icon
Related questions
Question
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
Expert Solution
steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Alkanes and Cycloalkanes
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Introduction to General, Organic and Biochemistry
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:
9781285869759
Author:
Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning