CH3 CO₂Et Hagemann's ester The compound known as Hagemann's ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation. The reaction involves the following steps: 1. Deprotonation of ethyl acetoacetate to form enolate ion 1; 2. Reaction of the enolate ion with formaldehyde to form tetrahedral intermediate 2; 3. Protonation and dehydration to form unsaturated intermediate 3; 4. Michael reaction between a second ethyl acetoacetate enolate and the unsaturated intermediate to form enolate ion 4; 5. Proton transfer to form enolate ion 5; 6. Internal aldol cyclization to form cyclohexenone 6; 7. Acid-catalyzed ester hydrolysis to form carboxylic acid 7; 8. Decarboxylation to form the final product. Write out the mechanism on a sheet of paper and then draw the structure of enolate ion 4.

CH3 CO₂Et Hagemann's ester The compound known as Hagemann's ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation. The reaction involves the following steps: 1. Deprotonation of ethyl acetoacetate to form enolate ion 1; 2. Reaction of the enolate ion with formaldehyde to form tetrahedral intermediate 2; 3. Protonation and dehydration to form unsaturated intermediate 3; 4. Michael reaction between a second ethyl acetoacetate enolate and the unsaturated intermediate to form enolate ion 4; 5. Proton transfer to form enolate ion 5; 6. Internal aldol cyclization to form cyclohexenone 6; 7. Acid-catalyzed ester hydrolysis to form carboxylic acid 7; 8. Decarboxylation to form the final product. Write out the mechanism on a sheet of paper and then draw the structure of enolate ion 4.

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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