9. Diels-Alder(DA) reactions tend to be reversible. While some heat is needed to catalyze the Diels-Alder reaction, excess amounts of heat will cause the reverse, retro Diels-Alder reaction. The products of a retro Diels-Alder reaction are a diene and a dienophile. + Pyrone 50 °C Diels-Alder Pyrone is a diene that is locked into s-cis conformation, setting it up as a good diene to use in Diels-Alder reactions. When reacted with the following alkyne, a bicyclic DA product is made. When this DA product is heated further, a retro DA reaction occurs, but it forms two new molecules: carbon dioxide and an aromatic ring. This retro DA is not reversible as carbon dioxide is a gas and is lost from the reaction flask. Draw the mechanism for both the DA and retro DA reactions. X- & CO₂Me CO₂Me 200 °C retro Diels-Alder A + CO₂Me CO₂Me + CO₂

9. Diels-Alder(DA) reactions tend to be reversible. While some heat is needed to catalyze the Diels-Alder reaction, excess amounts of heat will cause the reverse, retro Diels-Alder reaction. The products of a retro Diels-Alder reaction are a diene and a dienophile. + Pyrone 50 °C Diels-Alder Pyrone is a diene that is locked into s-cis conformation, setting it up as a good diene to use in Diels-Alder reactions. When reacted with the following alkyne, a bicyclic DA product is made. When this DA product is heated further, a retro DA reaction occurs, but it forms two new molecules: carbon dioxide and an aromatic ring. This retro DA is not reversible as carbon dioxide is a gas and is lost from the reaction flask. Draw the mechanism for both the DA and retro DA reactions. X- & CO₂Me CO₂Me 200 °C retro Diels-Alder A + CO₂Me CO₂Me + CO₂

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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