Diels-Alder Reactions | 16.5 Organic Chemistry

Chad provides a comprehensive lesson on Diels-Alder reactions, a concerted 4 + 2 cycloaddition reaction. He covers the reaction mechanism and shows how to predict the relative reactivities of dienes and dienophiles. He then describes and demonstrates both the stereoselectivity and regioselectivity observed in Diels-Alder reactions. Chad then shows examples of how Diels-Alder reactions with cyclic dienes result in bicyclic compounds and how the Endo Rule describes the stereoselectivity in such examples. Finally, Chad covers the conservation of orbital symmetry, showing how the symmetry of the HOMO of the diene and the LUMO of the dienophile match which makes Diels-Alder reactions symmetry allowed.

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00:00 Lesson Introduction
00:43 Introduction to Pericyclic Reactions
02:18 Introduction to Diels-Alder Reactions
04:50 Relative Reactivities of Dienes
11:29 Relative Reactivities of Dienophiles
13:04 Stereoselectivity in Diels-Alder Reactions
19:06 Regioselectivity in Diels-Alder Reactions
29:19 Diels-Alder Reactions with Cyclic Dienes
41:24 Conservation of Orbital Symmetry

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