Question

The third and fourth steps in the synthesis of Hagemann's ester from ethyl acetoacetate and formaldehyde (Problem $23-71$ ) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.

Name: The third and fourth steps in the synthesis of Hagemann's ester from ethyl acetoacetate and formaldehyde (Problem 23-71 ) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.
Uploaded: 2022-06-24T19:47:50-08:00
Duration: 2 min 3 s
Channel: Grigoriy Sereda
Description: The third and fourth steps in the synthesis of Hagemann's ester from ethyl acetoacetate and formaldehyde (Problem 23-71 ) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.

          The third and fourth steps in the synthesis of Hagemann's ester from ethyl acetoacetate and formaldehyde (Problem $23-71$ ) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.

Added by Laura W.

Organic Chemistry

Janice Gorzynski Smith 4th Edition

Instant Answer

Solved by Expert Grigoriy Sereda

06/24/2022

Step 1

In this case, the substituted cyclohexenone is formed from the reaction between the carbonyl group of ethyl acetoacetate and the alpha carbon of the ester group. The reaction proceeds through an aldol condensation mechanism to form the cyclic compound. ** Show more…

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The third and fourth steps in the synthesis of Hagemann's ester from ethyl acetoacetate and formaldehyde (Problem $23-71$ ) are an intramolecular aldol cyclization to yield a substituted cyclohexenone, and a decarboxylation reaction. Write both reactions, and show the products of each step.