The Favorskii reaction involves treatment of an a-haloketone with base to yield a ring-contracted product. The mechanism involves the following 5 steps: 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction,d kaaction e FrpdtA draw the structure of tetrahedral intermediate 3 in the window, CO2H base
The Favorskii reaction involves treatment of an a-haloketone with base to yield a ring-contracted product. The mechanism involves the following 5 steps: 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction,d kaaction e FrpdtA draw the structure of tetrahedral intermediate 3 in the window, CO2H base
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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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:The Favorskii reaction involves treatment of an a-haloketone with base to yield a ring-contracted product.
The mechanism involves the following 5 steps:
1. Abstraction of a proton to form enolate anion 1;
2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion;
3. Addition of hydroxide ion to form tetrahedral intermediate 3;
4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4;
5. Proton transfer to form the rearranged carboxylic acid.
For the following reaction,d kaaction e
FrpdtA draw the structure of tetrahedral intermediate 3 in the window,
CO2H
base
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