In Section 24.5, we learned how to use resonance OCH3 hybrids to understand the regiochemistry of Diels-Alder reactions. Frontier MO theory, on the other hand, explains the regiochemistry by taking into account the extent of orbital overlap between the frontier MOs. Consider the diene and dienophile shown here having the two different approaches indicated. In both cases, the p orbital contributions are shown for the pertinent frontier MOs. The relative contributions by the p AOs to the frontier MOs are indicated by the p AO sizes. Use this information to explain which approach is favored. CH30 LOCH3

In Section 24.5, we learned how to use resonance OCH3 hybrids to understand the regiochemistry of Diels-Alder reactions. Frontier MO theory, on the other hand, explains the regiochemistry by taking into account the extent of orbital overlap between the frontier MOs. Consider the diene and dienophile shown here having the two different approaches indicated. In both cases, the p orbital contributions are shown for the pertinent frontier MOs. The relative contributions by the p AOs to the frontier MOs are indicated by the p AO sizes. Use this information to explain which approach is favored. CH30 LOCH3

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 20.33P

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