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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
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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
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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