Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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The compound below can be produced through two different Diels-Alder reactions.
CO₂H
CO₂H
a. Draw the reactants that can be used in each of the two different Diels-Alder reactions.
b. Which route is better? Explain why in complete sentences.
Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in
lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The
following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both
reactions, paying particular attention to stereochemistry.
+
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Transcribed Image Text:The compound below can be produced through two different Diels-Alder reactions. CO₂H CO₂H a. Draw the reactants that can be used in each of the two different Diels-Alder reactions. b. Which route is better? Explain why in complete sentences. Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both reactions, paying particular attention to stereochemistry. +
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Solution:

We know Diels Alder reactions are stereospecific reaction, so the stereochemistry depends on the stereochemistry of the reactants.

Simply the stereochemistry of the reactants is preserved into product also. It means cis reactants gives cis product and vice versa.

Endo rule is Diels Alder reactions: Generally, endo products are comparatively more stable than exo product 

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