Answered: CH3 COCH,CH3 Hagemann's ester

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter15: Carboxylic Acids And Esters

Section: Chapter Questions

Problem 15.33E

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Question

A compound known as Hagemann’s ester can be prepared by treating a mixture of formaldehyde and ethyl acetoacetate first with base and then with acid and heat. Write the structure for the product of each of the steps.
a. The first step is an aldol-like condensation.
b. The second step is a Michael addition.
c. The third step is an intramolecular aldol addition.
d. The final transformation includes a dehydration and a hydrolysis followed by a decarboxylation.

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