Making [1.1.1]Propellane

[@Dolincek]

I love how everyone is talking about the cubane synthesis to make Tom finish it

[@darkmann12]

it's the fucking best

[@icandreamstream]

Tom’s fuckin GameCube intro gets me every time 😂

[@spiderdude2099]

I support chemistry based peer pressuring

[@visiblur]

We call it cheer pressure

[@DisorderedArray]

One of the PhDs in my lab did a lot of work on Propellane and similar molecules. After he defended our group made him a "doctor hat" which is a traditional thing here, and at the top of the hat I added a giant 3D printed propellane molecule powered by servos that would rise up and spin around when you pressed a button.

[@Tunkkis]

Mikä yliopisto?

[@pierreproudhon9008]

That's honestly so sweet

[@alialiyev6168]

WHERE IS THE VIDEO?????

[@adrianpip2000]

I love that you seem to invest in reagents and stuff. Like, I get the whole "only hardware store chemicals" concept, but sometimes you just wanna watch someone pop a fresh bottle of commercial methyllithium, y'know.

[@That_Chemist]

we get to chemistry vicariously through Sam :)

[@yougottrolledbythebest8117]

Your a fun guy I see .

[@That_Chemist]

@@yougottrolledbythebest8117 perhaps

[@Andy_M.S.c]

Things I absolutely love about this channel: -The subtle humour: text smileys, appropriate emoji/regular memes -The inclusion of mechanisms -"I can finally *propel* myself out of here -Yellow chem pain is not ignored -Many more to come

[@Lisa_Minci96]

C'mon man it's not a crack shed, it's a cocaine shed in the very least

[@charlesnathansmith]

Crack is higher purity, so that's definitely out of place there

[@thecountrychemist2561]

​@Nathan Smith what? Crack is diluted cocaine

[@kimtae858]

Tom's hydrazine cabin

[@charlesnathansmith]

@@thecountrychemist2561 no it is not. It is freebase cocaine, and usually separates out at a really high purity. Crack tends to be 90%+ while powder is rarely above 85% coming out of Mexico then gets cut further throughout the supply chain. Base extraction is an effective means of purifying most amines

[@Phapchamp]

​@@charlesnathansmith How do you know that (totally not a fed)

[@matiastripaldi406]

I love how your channel started as a "proper" chemistry vlog and then it slowly Chad-ified into what it is today. Please keep going this style is awesome Edit: OMG the 18-crown-6 has returned!!

[@BillAnt]

Ya that chemical really takes the crown. heh

[@neverfly5650]

I can't express how much I love this channel. High quality and exciting chemistry, good explanations and exactly my kind of humor. Keep doing what you do!

[@matiastripaldi406]

Cube: who are you Propellane: im the captain now

[@ErulianADRaghath]

I like the green highlight during the mechanism explainer phase, makes those of us not too familiar with chemical synthesis able to follow along.

[@derenjoy3r]

I love this kind of humor coupled with solid chemistry, AAA content my man also nice explanation of the mechanism!

[@xpxphidexpxp]

Love that you show the reaction mechanisms 🙏🏻 makes me really appreciate what I’ve learned in Orgo so far

[@I_XuMuK_I]

I live for E&F shade in chemistry youtube these days.

[@jimmychu7917]

I think it's amazing how Tom has single handedly entered "Yellow Chemistry BAD" into the collective subconscious of chemistry enthusiasts worldwide

[@420frankp]

Hope he drinks lots of fluids 😂

[@doctorsnakeoil]

Super cool, loved to see the mechanisms behind this, takes me back to OCHEM. Also, 69% yield. Nice.

[@ShouldOfStudiedForTheTest]

Just wanna say that I lovr your new green highlighting during mechanisms! Can't believe you still manage to improve.

[@robinpetersson5290]

A useful tip for doing those types of dihalocyclopropanations is to add the NaOH over a period of time, and not all at once. This helps to generate a fresh amount of carbene and will increase the yield.

[@wytototas4000]

I love how this guy is going more insane in every single video 😂

[@420frankp]

Where's the insane?

[@GerinoMorn]

I love your videos, because you're the person who DOES "in more detail..." bits. If it was boring, I can skip it, but if it wasn't there I couldn't just summon all that knowledge from ether xD

[@Sniperboy5551]

That’s a great final yield, it’s my favorite number

[@HapppyMann]

Love the little green circle in the reaction breakdowns, helps my small brain understand

[@Chevsilverado]

This is a great mix of Nile red and explosions and fire. The perfect mix of two extremes.

[@spiderdude2099]

Always a good day when you can break out the Gigachad molecule 18-crown-6

[@philouzlouis2042]

Hi Chemiolis, Super nice video and synthesis; it furnished me ideas for some of my own synthesis that called for (Cl-CH2-)3C-CO2H and C(CH2Cl)4; and also for (ClCH2-)2C=CH2 so thank you for that all. Just as a side note; are you sure that (Cl-CH2-)3C-CO2H and (Cl-CH2-)4C are inert for their alkyl halide part towards NaOH solution? I imagine that the Cl atom can leave easily as Cl(-) replaced by a OH(-) thus yielding highly soluble alcohols ((poly-)methylol group(s)); this could remake some of your starting pentatetraerythritol aside with halides (mono-, di- and tri-) idem for your acetic acid related molecule of interest. Anyway nice job. PHZ (PHILOU Zrealone from the Science Madness forum)

[@colin351]

Drake shunning the cube dismissively, then smiling approvingly at weird propeller thing.

[@frankmercer7009]

Excellent work. Very easy to follow, thanks for showing the reaction mechanisms.

[@crabcrab2024]

Fantastic! That is what I call “good old chem”. You just nailed that propellane .

[@clovenbeast5183]

Right on I think I've only ever seen one other thing to do with pentaerythritol. Badass thank you

[@billbillson3129]

Pretty cool! I been watching the Cubane synthesis saga. This might've been the first time one of those lil chemical equation diagram thangs has made sense in my mind.... Thanks for sharing!

[@meitokenchop6037]

a yield of 69% reminds me of another type of Saga...

[@slyfoxchemistry]

You had a lot of fun with this one

[@me0101001000]

You really have to give him PROPs ... I'll see myself out

[@JRaiKetchum134]

Thank you for this organic tour de force! OChem is my absolute favorite and difficult synthetic schemes are even better.

[@jadentonkin466]

If you're in search of an extraordinary experience that combines the wonders of chemistry and the limitless creativity of Minecraft, look no further than the mesmerizing world of cubane! This mind-blowing molecule is sure to leave you utterly spellbound with its exceptional properties and jaw-dropping effects. Let's talk about cubane, the star of the show. This tiny molecular powerhouse is nothing short of a marvel. Its flawless cubic structure is a sight to behold, capturing the essence of symmetry and stability. The sheer elegance of this compact arrangement will leave you in awe, pondering the mysteries of the universe. But what truly sets cubane apart is its explosive nature. Brace yourself for an adventure like no other as you unlock the potential of this mighty molecule. Just a tiny spark can unleash a spectacular display of energy, captivating everyone around you. It's as if you hold the power of a supernova in the palm of your hand! And now, let's journey into the world of Minecraft, where cubane shines brighter than any diamond sword. Immerse yourself in a universe where the possibilities are as vast as the digital landscape before you. In this pixelated wonderland, cubane becomes the ultimate game-changer. With cubane as your ally, you can reshape the Minecraft world with unrivaled creativity. Watch in amazement as you effortlessly build towering structures, defying the laws of physics and gravity. But that's not all! Prepare for mind-bending explosions that will rock your virtual reality to its very core. The destructive power of cubane is at your fingertips, providing an adrenaline rush like no other. The synergy between cubane and Minecraft is a match made in gaming heaven. It's a thrilling fusion of science and imagination that propels your Minecraft experience to unparalleled heights. Every block you place, every explosion you trigger, becomes an exhilarating testament to the infinite possibilities that await. So, if you're seeking a game-changer that will revolutionize your Minecraft adventures, cubane is the secret ingredient you've been searching for. With its explosive energy and mind-bending capabilities, this remarkable molecule will redefine your virtual reality experience. Don't miss out on the opportunity to witness the awe-inspiring beauty of cubane and unleash your creativity like never before. Step into a world where chemistry meets gaming, and prepare to be blown away by the sheer brilliance of cubane in Minecraft.

[@ejkozan]

I love all puns in this video XD Who needs cube when you can propel yourself through chemistry XD Great work!

[@ChemicalEuphoria]

at this point youtube chem is starting to become just nano-scale solid geometry lmao

[@rosk860]

great video, i'm surprised during the MeLi step, that the major product isn't formed from MeLi doing NS on the carbons bearing chlorine. Also i would have expected some dimers and trimers forming during this step. Do you or the authors have any explaination of why the systems seems to prefer forming this creazy strained propellane ?

[@me0101001000]

That Chemist called. He says this is cursed.

[@christopherleubner6633]

Try microwave assisted chemistry for the carbene synthesis step. The crown catalysts work extremely well with microwaves

[@samiraperi467]

Pinacol is the pinnacle of compounds.

[@420frankp]

Its amazing what you can do with a proper budget

[@pierghiro]

E&F is going to make it, i believe it

[@TheBackyardChemist]

penta Er and hno3 are quite a spicy mix in other contexts If for some reason the chlorination does not go to completion, you might get some jumpy esters.

[@oitthegroit1297]

I love that intro lol! I'm also surprised at how relatively easy it is to synthesize such an unstable, strained compound. I assumed that, aside from the dibenzo 18 crown 6, it would require some weird exotic reagents and/or UV light, like with cubane. Edit: I read about it, and the propellane can undergo a polymerization reaction to form various staffanes. I wonder if these compounds have any energetic properties if they're combined with suitable oxidizers.

[@davidfetter]

Not an expert in this, but my understanding is that strain plays a pretty small role where things that really want to be gases play a much bigger one.

[@mduckernz]

@@davidfetter Ring strained hydrocarbons have been used as fuels in rocket propellant for liquid rocket engines. The ring strain does contribute to the ISP (efficiency). Many of them tend to have quite high density for hydrocarbons, and they have favourable melting points as well, tending to not require as much insulation to prevent them from freezing on the tank walls when exposed to the vacuum of space. You are right that they’re a bit rubbish for explosives, however. Ring strained nitrogen heterocycles are pretty great though! There are some interesting bicylic and tricyclic ones! They have quite high performance but tends to be quite friction sensitive - for both high performance and good handling characteristics you want aromatic nitrogen heterocycles instead as their aromaticity stabilises them, the whole molecule absorbing strain rather than just one or two bonds upon energy input

[@GAFUKIS]

Yeahhhh he uploaded!!!!

[@LFTRnow]

Wow. That looks like it takes at least a day between all of those steps.

[@samorakaos3695]

senin gibi bir yeteneğin 108k abonesi olması büyük haksızlık. harika işler yapıyorsun. takipteyim...

[@cipaisone]

This channel has to grow

[@jeffthechef69]

Am I the only one who absolutely fucking LOSES IT! Every time he says "I set the filtrate up for Short Path Vacuum Distillation."

[@thehyperscientist1961]

Nicely done. Tom (the guy with the crack shed) is probably gonna mention you in an upcoming video!

[@energytv3536]

Yes, now make all the different hydrocarbon cyclic molecules

[@petevenuti7355]

Sounds like you were smiling through most of the narration on this one 😁 Amazing work!

[@knivesnico8775]

YES FINALLY A PROPELLANE ENJOYER YEEES

[@bladdnun3016]

I wonder if the propellane can polymerize to form polypropellane.

[@bladdnun3016]

I see, the polymer is called staffane. Sure.

[@pelegsap]

This is incredible, and very enjoyable to watch (as always, actually 😊). I do have some constructive criticism about the handling of the MeLi in the video, if you're interested.

[@LunatyNFV]

Ok Senku😃

[@hyperbean1887]

I really enjoyed this one

[@RhoGamingYT]

You know what is better? Just do both :)

[@j_sum1]

Sweet 187 step synthesis.

[@giuliojuniorstroppiana3263]

All the amazing interesting knowledge about organic chemistry given in fun entertaining way

[@GURMEETSINGH-ke1xc]

@E&F cubane project was like a research he changed lots of things away from literature .Meanwhile pthers have been like industrial synthesis reaction fuelled by well optimized litrature. As researcher i know how painful it is to optimize a protocol.

[@chemistry-experiments78]

Neat! Now waiting for smt like tetrahedrane!

[@austintaylor1448]

I Officially love this channel

[@Nathan-gg2yj]

Is there a reason why you directly dry the liquids with MgSO4 and don't use a previous drying step with concentrated NaCl solution (in the seperatory funnel?) At least this was the way I was taught it back then 😅

[@backslash4571]

How do you have access to all of these chemicals? DCM is near impossible to obtain in the US, much less thionyl chloride, unless you’re a licensed lab.

[@backslash4571]

Also I’d suggest adding your solvent to dry ice already in a container, ideally a dewar rather than a glass container, it splashes and bubbles way less and comes down to temp much faster

[@Larken42]

Okay. Fish meets MeLi and becomes spaceship. Got it👍

[@7.12_am]

I'm new to this channel and I already love how water is called dihydrogen monoxide

[@ArturShvets-n2c]

I’m ending school chemistry soon. My life never will be the same after this video…

[@jhyland87]

This dude just casually glossing over using 73mL of thionyl chloride, like it's a reagent you can pick up from Home Depot. lol. Love your content :-)

[@MrBradshawbenjamin]

Interesting stuff - side quest completed

[@californium-2526]

Ring strain champion caught by Chemiolis.

[@kryall7637]

You earnt my sub with just that intro haha

[@michaelanderson4849]

That Aussie crack shed filled with yellow stuff going boom, is a bit sus... 🤨 😁

[@lolroflpmsl]

Damn this chemistry's getting good!

[@hellothere3163]

Absolute legend

[@olekmy1292]

I do wonder. How one can acquire so much knowledge about all of the proper procedures and how to set up the synthesis reactions to such perfection as I see it in this video? Also how to know what clean up steps are necessary?

[@yougottrolledbythebest8117]

Learning and shrooms lots of adderall too-Thomas Edison

[@rylandsmith8552]

I couldn't hear him, what does he add to the isopropyl to make that -70c bath in the last step?

[@rubenklobertanz4675]

dry ice (Adding isopropyl alcohol to dry ice makes the liquid cool very quickly ⏤ the mixture's temperature can reach -90°C (-130°F))

[@rylandsmith8552]

@@rubenklobertanz4675 thank you so much

[@soulreaper359]

Nice nice nice^^ needed to be sayed… that green dot is lit :) I like it

[@EbbeLoos]

4:20 I think it's better to pour your mixture into (ice) water. This should produce larger particles making the filtration easier

[@yougottrolledbythebest8117]

Using “heavy” water more interesting honestly . Try it out.

[@ahmadnaeem6722]

The best shape was already there i.e. shape of benzene because "Hexagons are Bestagons" - CGP Grey

[@matushonko7223]

Idea for a video: chloromethyl furfural chemistry (supposedly one of the most promising celllose-sourced raw materials, with the possibility of turning it into polymers, fuels etc)

[@viorp5267]

Most relatable chemical

[@Hamza-B3]

What about square based or triangular based pyramids?

[@Preinstallable]

LOL the “200ml dihydrogen monoxide” in the corner

[@erich.5326]

Nice final yield

[@lrvfb]

Great video dude!!

[@ГеоргийХромов-м3щ]

Poor molecule, it wants to get rid of the central bond as much as any woman wants to get rid of her bra at the end of the day.

[@WORTH-IT-MAN]

As much as women get rid of their bra when they see me 😎

[@ste0038]

As an avid viewer of explosions and fire, can confirm it is in fact a crack shed

[@cellina.starfire]

"This one is so strained, you can open her up real good. 😏" _moaning sound_ I hate you, lol.

[@АндрейКириллов-ш1ч]

Can you add link to the methodology, pls?

[@rocknrollmanic]

Shots fired I see

[@edoardobandieri2688]

Amazing. Very well done! Keep it up :)

[@slyfoxchemistry]

Amazing job well done how are you

[@LucDeLaat]

I noticed you were from the Netherlands, may I ask where you have studied?

[@mihirsanghvi9876]

5:11 put "the thing"back in 😱😱😭😭 it still has some stuck to it. Ohh and can to try to make dinitro acetylene

[@AJ-qv9yo]

Molecular origami. Love it.

[@spankyjeffro5320]

Man, chemists are crazy. "Today we are going to do a simple 300 step synthesis of this complicated molecule which requires at least 3000 obscure chemicals, 2000 of which we have to personally make which in turn adds 6500 more steps, during which if a single atom touches my skin I won't be able to taste colours any more." XD

[@christopherleubner6633]

Nitrate this and it would make an extremely potent energetic material.

[@LFTRnow]

I didn't quite have all the reagents and equipment, so after a few substitutions I wound up with banana bread. Help?

[@kiklul]

cube in his crack-shack lmfao

[@crabmansteve6844]

What is the composition of the tar?

[@tyt0uoff146]

Can we have a lab tour video ?

[@camj4631]

thiophenol has such a memorable smell... but its almost like meaty at really low concentration