Chemiolis - 2023-04-11
In this video I'm making the cutest and best square, oxetane. Cyclobutane could never. Cubane nowhere to be found. Oxetane has taken the geometry throne. Support my channel with patreon: https://www.patreon.com/chemiolis Support my channel by becoming a member https://www.youtube.com/channel/UCoDmZirW1o9XSKSRM6YJ1rQ/join
Thats some high tier square chemistry here
Yellow Chem bad
Bars🔥
Shut up! It's just a fashion sector so, "everyone can participate".
Next project is making a microscopic Rubik's Cube out of Cubane and Oxetane. hehe
"ignites cutely" I love the vibe of these latest videos 😂
Dude this channel is insane. I've been watching YouTube my whole life, so I remember watching NurdRage and NileRed who got me into chemistry. Idk something about the way he describes everything
You know you now have to make cubane, right?
In the middle of a Ph.D thesis
MaxfieldMD is plowing through that synthesis, he's nearly done.
He might actually finish it and not fck around like SOMEONE we all know...
@@hesitant1757 a physics PhD thesis
@@drasiella ):
"You ever see a molecule and think... Wtf it's so cute... Cute"
Yes, Cubane.
That's the last thing you wanna from a chick in bed "Oh look at that little cute thing!!" ha-ha-ha
Thank you for including mechanisms, they are some of the best parts of your videos to me.💛
they are great, i dont understand a single thing from listening to the explanation but the mechanism really helps
Only humans would look at a little bundle of atoms in a square shape and call it cute, but I am HERE FOR IT.
Heterocyclic compounds are always cute, and have also cute names due to Hantszch-Widman (or something like that) nomenclature rules.
Imagine 1,2 diazete, Thiirane, Oxepine, or even Oxetane. So cute 😂
You: it's cute
Me: I can hear the constant internal screaming from the bond strain
same bro
“I put a label on it to match its cuteness”😂😂😂
oxetane is very cute! Personally, although much more common, I find furans very cute too. Especially 2,5-disubstituted furans. They look so happy.
In the 1970s I made an oxetane intermediate in the synthesis of a pheromone. I started with butyraldehyde and 1-pentene, and reacted them under UV light in acetonitrile solvent. This resulted in the formation of a longer molecule with an oxetane ring in its middle.
We got the square, now we need the cube.
0:28 “I add in 183 mills of stinky, fishy triethylamine” 😂
oooh look at those angles, imagine the explosivity
Babe wake up new chemiolis video just dropped
Why did you make Oxetane?
It looks cute.
😂
Nice video! Wondering why the first step is necessary since in theory you should generate the same alkoxide intermediate from 1-chloropropanol if you treat that with base.
Oxetanes are cool molecules, though they can be a pain to work with in pharmaceuticals. They tend to ring open under acidic conditions (ie stomach acid or even silica gel) due to their strain. However, they have interesting properties and can be used as ketone bioisosteres! 😊
This is why I love chem video comments
I was wondering the same thing, though I don't think cyclization would proceed with just Et3N as a base. Making the acetate and treating it with hydroxide liberates alkoxide readily. You could definitely just use NaH and use the chloroalcohol directly, can also prepare the iodide for even better reactivity via Finkelstein.
my gf if she was a molecule:
2:29 Forbidden fruit smoothie.
Nice! Finally, a square!
Oxetane: "uwu, I'm just a tiny widdle heterocycle in a big world"
burns cutely
Have you ever thought of making one of these thermochromic molecules?
It's quite a good idea for a video
I love all these exotic chemical synthesis, each time I discover something new ! :D
Thank you so much for showing the mechanisms! They make it so much easier to understand.
But theres no way that Oxetane is stable right? The first thing I thought when I saw the structure was steric hindrance. I kinda put this in the same catagory as cyclopropane.
The product burns cutely❤❤
Try polymerizing oxetane with Lewis acids - a rather interesting reaction, and if you pass acetylene through a polymerizing mass, you get an even more interesting product.
Very nicely done.
Thank you sir for your educational illustration. There is a question in my mind regarding the synthesis
Dose the oxatane molecule synthesize by [2.2] cycloaddation using Paterno-Buchi reaction
Could the started materials be formaldehyde with Ethene ?
Thank you sir
Thank you for this cute video.
How do you find the synthesis recipe for such an obscure molecule?!?! I’m intrigued. Love ur vids
Thankfully all these reactions are captured in databases and searchable by drawing the reaction. Ochem research would be brutal without it.
@@KakashiBallZ Thats dope
@@KakashiBallZ could you share some of the databases that allow search by structure?
@@siiluviilu sci finder and reaxys are some of the most used for Ochem
wow i literally got a reaxys ad at the end and didn’t think anything of it until i read this comment
You sometimes fill your flask and separatory funnel too full. I think it make it hard to shake or mix the mixture effectively or to prevent overflow, when high exotherm reactions take place.
Great job
Unironically a pretty good review of my org 2 section on carboxylic acid derivatives
just a suggestion: when showing the structures of the compounds and blurring the background like at 1:35, try darkening the footage so that the white text is easier to make out. it's hard to see the small white lines on a background that is nearly the same color.
Nilered is like "these funny chemicals look similiar, wondering how you can turn each into another" and you are "oh i saw an interesting molecule model/graph in my textbook, wondering how it looks like in practice"
for a square molecule this is process surprisingly simple
1:27 looks like stick men rioting :)
Thanks for sharing
Can you use basic medium with 3 chloro 1 propanal and do some NGP type reaction?
hey why do you separate the organic layer and aqueous layer both through the bottom of the separatory funnel? the organic layer is gonna be contaminated from that and reduce yield.
My only comment is that the mechanism for the first reaction implies that the 3-chloro-1-propanol is still protonated in the presence of the triethylamine when the acetyl chloride is added. It's probably already a salt with the protonated triethylamine making the mechanism 1 step simpler. Good video!
I've been always curious how robust oxetane is.
Wholesome cute content
Nitpicky detail: the condenser at 4:52 is not a Dimroth condenser, but a Vigreux
the dimroth condenser is set up after the vigreux :-)
@@Chemiolis Ahh, I see!
Just a question, How come you cant just react 3-chloro propanol in basic conditions, causing the negative oxygen to preform a sn2 reaction with the 3 carbon and forming oxetane?
Good video! As always, thanks for the mechanism. I was wondering, why do you convert the alcohol to the acetate initially, if you are putting it in such highly basic conditions afterwards anyway? Couldn't you just put the alcohol into the potassium hydroxide directly?
It works with the alcohol directly, but it has poor yields. Acetate works better.
most kawaii chemical :3
Why cubes and squares are so cuuute XD
Heyy yaa what the fcuk broo ! 🤨😂 How is it possible ?!
@@archerszandala357 Magic XD
Why doesnt adding 3-bromopropanol to some strong base such as sodium t butoxide work? 3 bromo propanolate should always be in low concentration and depending on the amount of solvent t butoxide could also be?
Why don t you do a Williamson reaction ? Just bring the 1-chloro-propan-1-ol to a boil with some NaOH ? (Real question from a chemistry student)
Because you're more likely to polymerize imho.
Probably because the sp3-carbon bound to the chlorine gets closer to the collapsing ether bond, through the attraction of the chlorine to the carbonylcarbon
Reaction also works with 3-chloro-1-propanol and KOH directly, but is even lower yielding.
@@lukassorowka2672 Is this really a concerted reaction? I would assume it is a two step reaction, forming an alcoholate, which than reacts in an intramolecular SN2 reaction. This would be similar to the formation of oxetane using 3-chloro-propan-1-ol, but the reaction of the hydroxide as nucleophile with the carbonyl center is much more attractive in contrast to do a SN2 or E2 reaction at the C-3/C-2 Carbon directly. Therefore, the formation of undesired sideproducts is lower when using 3-chloropropyl acetate compared to 3-chloro-propan-1-ol.
@@a830485a I never said that its concerted. It is in fact as shown in the last third of the video a two step reaction. The coordination of the chloride to the carbonylcarbon is just my assumption on why the reaction with the 3-Chloroacetate rather takes place in an intramolecular fashion, while the williamson ethersynthesis probably leads to more polymerisation, as somebody already suggested as a reply here, because the sp3-carbon on the hydroxy-group isn't that electrophilic. But nevertheless I agree with you in that sense that the reaction with 3-Chloroacetate yields less side products because of the more electrophilic carbonylcarbon which avoids the E2/Sn2. Btw you can try all day long to yield Oxetane from 1-chloro-propan-1-ol, that won't work 😆. You need 3-Chloro-1-propanol as stated by chemiolis already
@ExtractionsAndIre - 2023-04-11
SQUARE
@darkmann12 - 2023-04-11
jahaha yhe flashbacks begin
@dankmemes3447 - 2023-04-11
When octanitrocubane? (Pls dont explode my car for this comment)
@JamesChurchill3 - 2023-04-11
Only 5 more of these and you'll have a cube!
@MrBradshawbenjamin - 2023-04-11
@@dankmemes3447 Heptanitrocubane has a more efficient crystal packing and consequently a higher density, might be a better explosive.
@SophTheLaunchTechnician - 2023-04-13
it's cubane man!