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Diels-Alder Reaction

HOMO of
Cyclopentadiene

Keyboard Commands
for controling the models

 

Arrangement that leads to endo product.

endo-5-norbornene-2,3-dicarboxylic anhydride

LUMO of
Maleic anhydride

Arrangement that leads to exo product.

exo-5-norbornene-2,3-dicarboxylic anhydride

Lining up the models on the left so that they resemble the arrangements (the models in the center) that lead to the endo or to the exo product reveals that there is better orbital overlap between the HOMO and LUMO when forming the endo product. Better interaction between the orbitals implies a lower energy transition state. Thus, the endo product will be produced in excess when the reaction is under kinetic control.

Java Chemical Sample 3D Structure Viewer
provided by
John Purvis, Pomona College, Claremont, CA

ChemApplet@worldnet.att.net

Please forward any suggestions or corrections to Christopher Masi