This reaction is very close to my heart, as Kurt Alder (the Alder in Diels-Alder) was born in my hometown. There is a memorial plaque on the house he was born in, and whenever I show somebody around, I always take them there.
@@rickster255 Chorzów in the south of modern-day Poland. Neighbouring Katowice had their own Nobel Prize winner in Maria Goeppert-Mayer (Physics, 1963).
Even though I learned about this years ago, I still love your delivery in the IOC series! It's a good refresher, imo similar to a lot of Michael Penn's content, even if it was from my early undergrad it's nice to watch in the background and/or as a refresher on topics I'm rusty on. I understand you have a lot of projects on your plate and you've got a vicious algorithm to keep up with, but you definitely have viewers who appreciate this content, and I *do* hope you make more lectures in the future! I would also love to hear more in particular about YOUR research, whenever you make a new video about your experience in sulfur/fluorine chemistry. ~Perfluorocubane girl
I hope we get to see more of your lecture videos soon! Eventhough I've already passed Orgo and generally understood these topics, you always bring in some more advanced examples. Like I never learned about normal and inverse DA reactions and the electronics of the substitutants, only the stereo chem. So its great that you expand on these topics! So keep up the great work!
Legends spoke of the day this video would finally be released! I was but a young lad when I first heard about it. Now all these decades later, I feared I would not live long enough to see it. But now that it is here, I can die peacefully.
Always been my favourite puzzle piece of organic chemistry. Understanding the resultant chemistry, cycloadditions that have occurred in sequence etc. Drawing the orbital overlap and all of Woodward Hofmanns rules. Good fun
I've always thought about getting a diels alder reaction tattoo... my first research project was on the (retro) diels alder reaction, so it holds a spot of affection in my heart and well, i just think it's neat
omg i got so excited when i realized you make these videos, a lot of them cover topics ive been confused about and haven't found clear explanations for and getting the information from a youtuber i like makes it even better, thank you for making as many as you have!
I knew Diels-Alder but I always had a problem with these reactions of different cyclic compounds. Now I finaly understand It. Merry Chemsmas to you too 🧪🎄
These are the best of your videos. Not the funniest, true, but the best. Maybe you should tag team with NileRed or E&I/E&F, giving the reaction overview while they demo it.
At some point I want to do this myself - once the channel is bigger and I can afford to build a lab perhaps (also I think Nigel might do something similar)
Hi TC, I have added/embedded the video to the the Pericyclic Reaction Chemistry page of the Chemogenesis Web Book. The page discusses frontier molecular orbital symmetry in a little more detail. (UA-cam will not let me add a link.)
Yeah but I didn’t include it - if you imagine stabilizing a positive charge or a negative charge (e.g. vinyl ether -> oxonium + carbanion in a resonance structure); imagine an electronegative diene like a carbonyl then draw the enolate and a positive charge on the carbon -> partial charges predict reaction outcome
I am gonna put my funny chemistry story in here: This is not really yikes but kinda funny. We learned about saponification and made some soap in class. For this we used good ol NaOH and some frying oil. I still remember that I had to stir the mixture with a glass rod and took turns with my lab mate. Since the whole thing solidifies at some point so a stir bar is not really viable for this. All good everything worked out as it should and someone in the class tested it and washed his hands with our self made soap. Needless to say the guy was smelling like he worked a 12 hour shift at maccies.
if they don't bring in a sufficient amount of revenue, they are unsustainable for me to make; while I think they are valuable, and I want to make them (eventually), I am prioritizing developing skills, building the channel, and making videos that are interesting to a wider audience, as this is sustainable for the business long-term
Now sure if its just me the volume tends to be a bit low on your videos. Love to watch them so i thpught I'd mention it. I am a undergraduate chem student. Love the content
9:19 why is it that for the first reaction they had to employ very high pressures and run the reaction for 15 days just to get a 67% yield while only 30min was enough to achieve an 80% yield for the second reaction
Is it okay to think in normal demand Diels-Alder reaction, there's a flow of electron towards the alkene or charge separation at the beginning of the reaction which significantly increases the potential of the complex-which can be stabilized by EDG on diene and EWG of dienophile, thus stabilizing the activated complex in transition state? I've been always trying to understand the MO description of Diels-Alder reaction, but it was always too confusing for me to understand.
I think viewing it in terms of charge separation makes the most sense - it can be viewed as concerted or stepwise, and whether or not a Lewis Acid is involved can impact this. (ignore this next part unless you don't mind having your theory destabilized a bit) We ignore the role of solvents in almost every reaction from a mechanistic perspective, and most mechanisms function as 'chemical narratives' that help explain reactions to human brains, with the chemicals fulfilling the roles of actors.
@@That_Chemist You were always providing some examples of reaction with condition including solvent, temperature and catalyst, and now I noticed that. Sorry for my crappy english. Thank you so much.
Ahhh. Not a chemist but I've been dabbling into the subject I have the PDF There Logic Of Chemical Synthesis by E.J Corey & Xue-Min Cheng 1989. The first examples are the Diels Alder reaction it's very interesting. PDFs are very tricky to use on a phone which makes the books almost unreadable to me. Does anyone know of any open license chemistry books that aren't PDF?
I know you’re not making these that often but could you maybe do one on hypervalent iodine next time I just can’t find any good stuff for it’s chemistry online and general reactive behaviors
Hi sir. Can you explain all chemistry in the movie That's Cunning! Shijo Saidai no Sakusen? (1996) .i have watched since im was a boy 17 years old till now 27 and don't understand detail chemistry react in that movie
Chiral enzymes which activate the molecules from a certain approach, or by forming a covalent intermediate, although I’m not sure about the main mechanism of diels alderases, as I am not a biochemist
Correct me if i'm wrong, but at 8:00, the shown product is the endo product, isn't it?
You are correct!
I'm a now-retired surveyor and not a chemist, but I have long found Diels-Alder to be the most fascinating reaction.
This reaction is very close to my heart, as Kurt Alder (the Alder in Diels-Alder) was born in my hometown. There is a memorial plaque on the house he was born in, and whenever I show somebody around, I always take them there.
That’s so cool, where is it?
@@rickster255
Chorzów in the south of modern-day Poland. Neighbouring Katowice had their own Nobel Prize winner in Maria Goeppert-Mayer (Physics, 1963).
Just learned about this in my organic chemistry class. Great video!
Even though I learned about this years ago, I still love your delivery in the IOC series! It's a good refresher, imo similar to a lot of Michael Penn's content, even if it was from my early undergrad it's nice to watch in the background and/or as a refresher on topics I'm rusty on. I understand you have a lot of projects on your plate and you've got a vicious algorithm to keep up with, but you definitely have viewers who appreciate this content, and I *do* hope you make more lectures in the future! I would also love to hear more in particular about YOUR research, whenever you make a new video about your experience in sulfur/fluorine chemistry.
~Perfluorocubane girl
I hope we get to see more of your lecture videos soon! Eventhough I've already passed Orgo and generally understood these topics, you always bring in some more advanced examples. Like I never learned about normal and inverse DA reactions and the electronics of the substitutants, only the stereo chem. So its great that you expand on these topics! So keep up the great work!
Legends spoke of the day this video would finally be released! I was but a young lad when I first heard about it. Now all these decades later, I feared I would not live long enough to see it. But now that it is here, I can die peacefully.
Always been my favourite puzzle piece of organic chemistry. Understanding the resultant chemistry, cycloadditions that have occurred in sequence etc. Drawing the orbital overlap and all of Woodward Hofmanns rules. Good fun
It is a very nice summary of DA reactions. Great work!
Thank you :)
I've always thought about getting a diels alder reaction tattoo... my first research project was on the (retro) diels alder reaction, so it holds a spot of affection in my heart and well, i just think it's neat
It’s pretty neat :)
Diels Alder reaction is one of my favourite reactions.
The long awaited return
omg i got so excited when i realized you make these videos, a lot of them cover topics ive been confused about and haven't found clear explanations for and getting the information from a youtuber i like makes it even better, thank you for making as many as you have!
I’m glad you find them helpful :)
I just finished up my lecture based organic chemistry classes, but goddamn this reaction is so cool
Hell yes, my favorite kind of video from your channel
Nice a new video in this series
Another IOC instalment! What a great day! (:
Thank you Marise, the video was great.
Great video. Merry Christmas to you too.
Excellent presentation!
These were my favorite reactions to do in orgo 2
I knew Diels-Alder but I always had a problem with these reactions of different cyclic compounds. Now I finaly understand It. Merry Chemsmas to you too 🧪🎄
Love your vids, keep it up! It’s always fun keeping up with the stuff we learn in university with videos like this :)
4:25 So this is an ALDERnative way to explain some organic chemistry?
Thank you, Mr. Chemist Man!
You're very welcome!
Show us some presentation from the works and papers you've done!
They just wouldn’t get enough views to be worth it - maybe one day
Hahaha I heard about it on Hamilton's podcast and all I know about it used to be that o-chem med students joke about hating it.
One of Diels - Alders’ highlights, the Strychnine molecule.
These are the best of your videos. Not the funniest, true, but the best.
Maybe you should tag team with NileRed or E&I/E&F, giving the reaction overview while they demo it.
At some point I want to do this myself - once the channel is bigger and I can afford to build a lab perhaps (also I think Nigel might do something similar)
This video is great, what do you think about making a series of lectures about other pericyclic reactions?
Please do more, radical, 1,3-dipolar and anything to help when reading total synthesis paper.
Great job! I’m a big fan of your lectures😍 But what do you think about more videos about MO theory?))
I’m not the best person to make them, but that doesn’t mean I won’t ever make one
Hey, a few months ago you talked about a dithiolane alternative that can be deprotected with silver salts alone, could you tell us about it?
Read my latest Chemistry a European Journal article - just use fresh, wet Ag2O or another silver salt with water, and acetonitrile or DCM
Stochiometric activated Raney nickel reduces it to a CH2
Also it can be lithiated with LDA, and the C-H can be converted to a carbocation using trityl BF4 via hydride abstraction
@@That_Chemist Thanks, what is the title/DOI?
Hi TC, I have added/embedded the video to the the Pericyclic Reaction Chemistry page of the Chemogenesis Web Book. The page discusses frontier molecular orbital symmetry in a little more detail. (UA-cam will not let me add a link.)
2:10 Isn’t that a trihydropyridine?
Nice lecture!
Thanks :)
2:50 is there an explanation for the ortho-para rule
Yeah but I didn’t include it - if you imagine stabilizing a positive charge or a negative charge (e.g. vinyl ether -> oxonium + carbanion in a resonance structure); imagine an electronegative diene like a carbonyl then draw the enolate and a positive charge on the carbon -> partial charges predict reaction outcome
I am gonna put my funny chemistry story in here:
This is not really yikes but kinda funny. We learned about saponification and made some soap in class. For this we used good ol NaOH and some frying oil. I still remember that I had to stir the mixture with a glass rod and took turns with my lab mate. Since the whole thing solidifies at some point so a stir bar is not really viable for this. All good everything worked out as it should and someone in the class tested it and washed his hands with our self made soap. Needless to say the guy was smelling like he worked a 12 hour shift at maccies.
It’s been years since I’ve taken Orgo. I’m surprised that I still remember this reaction.
NO WAY. IT FINALLY HAPPENED
If you see a 5 membered ring with a conjugated ester, you can make it from a diels alder followed by ozonolysis and condensation.
The Diels-Alder video at last
You should have included the Woodward-Hoffman-Rules
This video would have been very helpful 2 weeks ago for my ochem 2 final
😔
holy ghost of caruthers its finally here
Just some advice, these videos are a perfect way to draw students to your channel…
you could say the viewers have been DIENE to see this video
@ThatChemist why are you not planning on doing anymore IOC videos? I think theyre of high quality and valuble content.
if they don't bring in a sufficient amount of revenue, they are unsustainable for me to make; while I think they are valuable, and I want to make them (eventually), I am prioritizing developing skills, building the channel, and making videos that are interesting to a wider audience, as this is sustainable for the business long-term
Now sure if its just me the volume tends to be a bit low on your videos. Love to watch them so i thpught I'd mention it. I am a undergraduate chem student. Love the content
I will fix it for a future video, if I don’t after 2 or 3, keep commenting about it and I’ll see it ;)
@@That_Chemist perfect! Bc i like to listen to it on my morning beach walks along the beautiful California Coast (;
Epic reaction
9:19 why is it that for the first reaction they had to employ very high pressures and run the reaction for 15 days just to get a 67% yield while only 30min was enough to achieve an 80% yield for the second reaction
Chemistry be like dat
Is it okay to think in normal demand Diels-Alder reaction, there's a flow of electron towards the alkene or charge separation at the beginning of the reaction which significantly increases the potential of the complex-which can be stabilized by EDG on diene and EWG of dienophile, thus stabilizing the activated complex in transition state? I've been always trying to understand the MO description of Diels-Alder reaction, but it was always too confusing for me to understand.
I think viewing it in terms of charge separation makes the most sense - it can be viewed as concerted or stepwise, and whether or not a Lewis Acid is involved can impact this.
(ignore this next part unless you don't mind having your theory destabilized a bit)
We ignore the role of solvents in almost every reaction from a mechanistic perspective, and most mechanisms function as 'chemical narratives' that help explain reactions to human brains, with the chemicals fulfilling the roles of actors.
@@That_Chemist You were always providing some examples of reaction with condition including solvent, temperature and catalyst, and now I noticed that. Sorry for my crappy english. Thank you so much.
can you do a video of {H5 - C5H5} NINO
Ahhh. Not a chemist but I've been dabbling into the subject I have the PDF There Logic Of Chemical Synthesis by E.J Corey & Xue-Min Cheng 1989. The first examples are the Diels Alder reaction it's very interesting. PDFs are very tricky to use on a phone which makes the books almost unreadable to me. Does anyone know of any open license chemistry books that aren't PDF?
I know you’re not making these that often but could you maybe do one on hypervalent iodine next time I just can’t find any good stuff for it’s chemistry online and general reactive behaviors
DM me on discord and I’ll tell you anything you want to know about them
Hi sir. Can you explain all chemistry in the movie That's Cunning! Shijo Saidai no Sakusen? (1996) .i have watched since im was a boy 17 years old till now 27 and don't understand detail chemistry react in that movie
woah thats a lot of big words
Diels alder S tier reaction
the best reaction ****
Why couldn't my previous lecturers here be like you? 😢
A tide of change is coming
@@That_Chemist looking forward to it!
This is triggering my PTSD
No one? Ok
DIELS NUTZ
Eeeaaaahhhh, great!
Diels nuts
This is wonderful, And I’m new. How would biochem be able define chirality?
Sorry; not define. Control
Chiral enzymes which activate the molecules from a certain approach, or by forming a covalent intermediate, although I’m not sure about the main mechanism of diels alderases, as I am not a biochemist