Diels Alder Reaction Stereochemistry and Endo vs Exo Products

This video gives you tips and tricks on how to draw the stereochemistry for Diels Alder products when substituents are present on both the diene and dienophile including stereochemistry for a bicyclic product. You’ll also learn how to distinguish between endo and exo products for dienophiles with both cis and trans configurations.

↪ Links & Resources Mentioned In This Video ↩

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⏱ In this video:
[0:16] Diels Alder Reaction Overview
[0:56] Why the Product Needs Stereochemistry
[1:17] Diene Stereochemistry
[2:52] Cyclic Diene Example
[3:46] Dienophile Stereochemistry - Endo and Exo
[4:34] Dienophile Stereochemistry - Cis and Trans

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[SmokeyHooder]

The tricks for remembering or understand things that you present makes these videos invaluable for learning organic chemistry.
Like the close parable.
Brilliant.

[emmanuelletoussaint]

One of the topics for my quiz tomorrow is Diels-Alder rxns and this video was definitely very helpful! Thank you for all that you do!

[Sijo]

Your amazing!!! Every video watch, you make chemistry so easy to under stand. Thank you

[nate]

For the part at 2:40, I thought it does not matter if it’s in or out but more so if facing the same way or different directions they are cis or trans respectively

[saaniyahsajed]

you're the best. thank you so much for explaining these so well!

[pimpjuiceT]

concise and very clearly explained, thank you!

[诗舞翩翩]

than k you for your help! its even more helpful than my classes !

[shanemichael]

I am going to be tutoring a college student who is young and bright and she's sure to be a success in the near future. I find your videos refreshing as I brush up on my orgo. chem. I also told her about your entire you tube collection of videos which if she studies carefully, she won't even need tutoring. Chemistry might be one of my favorite subjects, but not for others, that's for sure. I didn't want to reach out to you on messenger, (as it has been a few years since I have) because I figured you're probably too busy and that's a little on the personal side anyway. I'm the guy who was studying just to learn more, but for no other reason. I had no deadlines to meet. I Hope this message finds you doing well. Thanks again !

[jayc]

your memory devices are really helpful: make-break-make, the endo/enter and exo/exit, and the rest are great

[oxychem-mdnaimurrahman]

Thanks for such a niche representation with tricks

[emilyandrews]

You’re carrying me through Ochem II rn😭

[loganblaskie]

This video is fine if you just want to pass your organic chemistry test and never think about organic chemistry again, but if you are interested in actually learning about organic chemistry on a deeper level I would not recommend this video. I would recommend taking the time to look at the transition state and how the diene and dienophile approach each other in the reactant complex, then consider how it would effect the resulting stereochemistry. This video fails to address the 'why' of the stereochemistry in favor of mnemonics that you will likely forget long before the geometric and mechanistic underpinnings of this reaction.

[andreifabre]

I believe all of this reactions are when the dienophile attacks from the bottom, but when it attach from the top does every thing is inverse?

[usernamehere]

Great video, thank you so much for sharing!

[NewWesternFront]

So you get enantiomers when all the chiral centers on a molecule are inverted in their absolute configuration. And we can see that those two structures become diastereomeric because that methyl configuration is retained. This is how I think to explain your “challenge”. I was having a little trouble finding a simpler answer in a plane/mirror of symmetry. What do you say?

[yusefsadik]

The Diels Alder reaction is so satisfactory, specially when you get cyclohexenes

[dlytykr]

in the beginning, did you say that they are sp2 (the diene and dienophile) because there is resonance? I have difficulty figuring out when it is sp2 or sp3

[amine_Raf]

Great explanation, but how about facial approaches, I always find that most Diels-Alder courses don't discuss their effect on stereochemistry despite their importance in organic synthesis involving DA reactions. How would you say the facial approach of a dienophile affects the stereochemistry and the number of theoretically possible stereoisomers?

[kewang]

Great video ! You should be my college professor!

[nate]

How do you choose endo/exo when the dienophile is trans