Write the frontier molecular orbital analysis for a [3,3]-sigmatropic shift in the analogous fashion as presented in the chapter except that you are using a geometry that would lead to a boatlike conformation for the transition state. As a hint, you should find that the reaction is allowed. However, why would this geometry be less favorable?
Write the frontier molecular orbital analysis for a [3,3]-sigmatropic shift in the analogous fashion as presented in the chapter except that you are using a geometry that would lead to a boatlike conformation for the transition state. As a hint, you should find that the reaction is allowed. However, why would this geometry be less favorable?
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 20.28P: Write the frontier molecular orbital analysis for the cycloaddition of butadiene with butadiene when...
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Question
Write the frontier molecular orbital analysis for a [3,3]-sigmatropic shift in the
analogous fashion as presented in the chapter except that you are using a geometry
that would lead to a boatlike conformation for the transition state. As a hint, you
should find that the reaction is allowed. However, why would this geometry be less favorable?
Expert Solution
Step 1
Chair conformation is more stable than the boat conformation. Boat conformation is less stable therefore the geometry is not favourable.
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