Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.22P
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Question
why are dienophiles involved in the diels alder reaction ?
Expert Solution
Step 1
Diels-Alder reaction mechanism proceeds through the suprafacial (same-face involvement of the ? system or isolated orbital in the process) interaction between a 4? electron system with a 2? electron system. Diels-Alder reaction involves cycloaddition reactions result in the formation of a new ring from two reactants.
In Diels-Alder reaction, the 4? electron system refers to the diene structure whereas the 2? electron system refers to the dienophile structure. This interaction now leads to a transition state without any additional energy barrier from the imposition of orbital symmetry.
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