Diels-Alder Cycloaddition
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- Опубликовано: 3 янв 2015
- The mechanism and stereochemistry of the Diels-Alder reaction are examined here. This cycloaddition is one of the coolest reactions in organic chemistry. You'll see.
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This is great! Thanks for including the MO and explaining EVERYTHING to do with it instead of just the mechanism; it was so helpful.
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Thank you very much for this professor! I've been trying to understand the stereochemistry of this reaction for months and now everything is clear thanks to you!
PROFESSOR DAVE YOU'RE AWESOME! my professor at Colorado State tries explaining everything with resonance and partial charges but you made this so much simpler and comprehensive! READY TO CRUSH MY O CHEM FINAL. !!!!!! THANK YOU
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I have seen this done with the diene being labeled 1-4 and the dienophile being labeled A & B, it creates less confusion on big rings. Thanks for your videos!
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Finally a video with a cyclic diene and dienophile
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My O-chem book butchered and overcomplicated it's explanation of endo and exo. THANK YOU for knowing exactly how to explain it. I want to find whoever made my book and fight them.
2 pages! TWO FULL PAGES to explain endo and exo. Listen to this "In the Endo approach, the dienophile aligns with its electron withdrawing group substituent underneath the pi system or directly above it. When it reacts such that the pi electron orbitals of its electron withdrawing group align under (or above) the pi orbitals of the diene, the orientation of approach is called endo." and it carries on like this
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What is endo rule for (4+2) cycle explain with example sir please..
How does one convert benzene to diene's and dienophiles?
Good
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it should be known that the first two reactions shown would not actually work, unless under extreme conditions due to the diene and dienophile both having high electron density. An electron withdrawing group should be attached to on or the other.
also at the end of the video there were no electron withdrawing groups and this topic was not discussed even though it is extremely important to the reaction. The interaction between the forming pi bonds and the electron withdrawing group on the othe molecule is the reason that most reactions do proceed in an endo approach and is known as the endo rule. a great example of this is the reaction between anthracene and diethyl fumarate were these pi bond, EWG interactions actually determine regiospecificity of the product.
+david mastrippolito butadiene and ethene will go with some heat! but yes, it's true that withdrawing and donating groups are important to the kinetics of the reaction.
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Sir I want to know about reactivity of dienes when EWG or ERG is present across the double bond of dienes.
depends on whether it's reacting with a nucleophile or electrophile!
Professor Dave Explains
if the reaction happens with dienophile only
oh right this is on Diels Alder, i didn't check the context. as far as i'm aware the rate only increases if there is one of each present
Dienes must be in what particular geometry?
s-cis
👌🏼
Hi Professor. There is a new pi-bond forming in the diene. But, the p-orbital are not in the same phase. How is it possible ? Are they making a pi*-bond ? How is it energetically favorable ? Thanks a lot for your videos, you're helping me a lot :)
the orbitals do work out! there is a moment in this clip where i briefly depict the orbital interactions, the molecules must be parallel for the overlap to occur.
Professor Dave Explains Thanks for your answer ! But I'm actually speaking about the new pi-bond forming between the Carbon (2) and the Carbon (3) of the initial diene ! Right where the new (and the only) double bond is.
Oh I see, hmm, I don't recall actually! Maybe phases are changing in the transition state or something, as electrons from the HOMO of the diene go to the LUMO of the dienophile, maybe that changes the number of nodes or something and those two p orbitals become in phase. Haha honestly I don't remember at all!
No problem ! :-)
Is there any catalyst involved in all these rxn? and what is the name of the dienophile, and the product?
nope, none! you just put them together and it goes. sometimes you need a little heat but that's not a catalyst. the dienophile could be a variety of molecules, as can the product.
Professor Dave Explains Thank you sir!
hi.sir I want to know. steriochemistry especially confermers
+ubaid ullah i've got tutorials on that, check them out!
on your second example didn't you draw the exo reaktion but the endo product?
hmm at what time stamp? exo/endo only applies when the dienophile has a structure that can extend either under the diene or away from the diene
at around 5:40
@@pascalkoch953 You cannot tell if it is the endo or exo product unless you draw in the hydrogen atoms where the 2 rings connect.
Sir,do we need any reagents for diels alder cyclo addition??
not really, just the diene and dienophile! sometimes the reaction mixture needs to be heated considerably, depending on the favorability of the particular reaction.
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What is the difference between thermal and photochemical reaction
thermal = heat, photo = light!
I know this .... but when we say it is thermal or light reaction possible or not possible
Or what is the difference in terms of mechanism
I mean..thermal and photochemical cycloaddition reaction
yeesh i forget, probably has something to do with alignment of orbitals, the p orbitals that overlap have to be in phase with one another, when the diene and dienophile approach each other. with the light stuff, usually a photon excites an electron to a higher orbital and that affects which one is the HOMO and which is the LUMO, i'd have to dig into some old stuff to remember exactly
Okay, thank you very much for your response
anthracene + ethene → ?? in diels alder reaction
please answer
tq
+Manmeet Kundal just take four carbons from the edge of the anthracene (diene) and make a new six membered ring with ethene (dienophile), you'll get a bicyclic structure.
Can ethene react with the 2nd ring of anthracene to form the ring?
+Manmeet Kundal actually it seems like it is exclusively the middle ring that reacts.
+Professor Dave Explains thank u sir
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