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March 13, 2010, 08:38:28 AM *
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Author Topic: Organic chemistry help ASAP  (Read 317 times)
kika09
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« on: January 12, 2010, 09:53:22 AM »

Can you predict whether the endo or exo isomer is favored as the product for the Diels-Alder reaction of cyclopentadiene and maleic anhydride.

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kingchemist
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« Reply #1 on: January 12, 2010, 01:20:24 PM »

I would have predicted the exo product merely on energy terms but what do I know.

However, have a look at the link below - I think it includes your reaction

http://www.meta-synthesis.com/webbook/49_pericyclic/pericyclic.html
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kyle1990
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« Reply #2 on: January 13, 2010, 01:57:52 PM »

I would have predicted the exo product merely on energy terms but what do I know

Endo products result from Diels-Alder reactions. You can think about it like this: A Diels-Alder reaction occurs between a diene and a dienophile (diene-lover). So the diene and dienophile are naturally attracted to each other, and prefer to be on top of each other so that there is a greater degree of orbital overlap. Here's a picture I swiped out of Organic Chemistry 7th ED by John McMurry. Notice the diene and dieneophile are directly on top of each other

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