Extractions&Ire - 2020-11-23
In preparation of the bromination step, we make some more bromine and 1,4-dioxane, and achieve yields so high that might actually be negative numbers. Subreddit: https://www.reddit.com/r/ExplosionsAndFire/ Join the Discord!! https://discord.gg/VR6Fz9g Twitter: https://twitter.com/Explosions_Fire Patreon: https://www.patreon.com/ExplosionsandFire Music is as usual from the Aphex Twin soundcloud dump, track names are: - 13HighHatsTuneTamclapOrig - Sams Car References: 1997 Lab scale paper: https://www.researchgate.net/publication/244572672_Dimethyl_Cubane-14-dicarboxylate_A_Practical_Laboratory_Scale_Synthesis 2013 Pilot Scale: https://pubs.acs.org/doi/abs/10.1021/op400181g
"And over here we have some concentrated sulfuric acid"
pans to half broken cylinder
Glad I'm not the only one that noticed
I genuinely do not know how you've done it but you've been pumping up the content quality while simultaneously upping your shitpost game, highly impressive.
Neglecting my day job
@Extractions&Ire mood
@Extractions&Ire That's the fucking spirit.
@vaderdudenator1 @Extractions&Ire mood
The only chemistry channel on youtube where we take a tangent to focus on latex and sweaty men
@[Whatever name goes here] ok but have you seen nile blue
@baha altamimi Ah yes, the NR deepfakes. He clearly is an alien
Waiting for Nile to breakout the catsuit
Latex and sweaty people really come into their own when combined 😏
imagine having him as ya science teacher , would be sick mate
You'd learn all the things that you should know better than not to do, then have the reason demonstrated later by ignoring that fact completely and fucking up your product. :D
@Extractions&Ire i had awesome teachers but your stuff is on another lvl of funny enough to make me remember it and have a great time learning you rock man
@Extractions&Ire does failing means death? As it might be one and the same
That's what said about many people. But school is still school, the pressure, the confinement. It's not that the teachers are particularly disinterested, dull and unjust. It's the system and what it turns them into -- both teachers and students.
@Edward Gentle HEATHEN
Tom: does chemistry.
Chemistry:"And I took that personally"
:D
Filter paper struggle and the glove sweats. This is my kinda content
I love how efficient your home lab is! You have so many unique multi purpose tools, like a graduated cylinder that doubles as a murder weapon from Clue.
“Let’s dry this dioxane by adding a huge amount of water” XD
@Grak70 yeah ofc
The good ole chemistry chuckle
@Grak70 um you can dry ethanol or isopropanol whith it and they are very soluble
@chu Harry only because those solutions with water are non-ideal and have very strong hydrogen bonding effects. Dioxane does not, so it won’t reject extra water based on ionic effects.
Is it me or has Tom been replaced by a better more successful, talented and smarter alien ?
bro I got negative yields here
@Extractions&Ire Aah it's good to know nothing has changed over the years !😆😆😆
@Extractions&Ire Just take the compliment.
@Extractions&Ire it’s dry though!
Greetings from the Isle of Man. I haven't been involved with chemistry since high school 35 years ago. Been watching your very entertaining content for years now though and find it fascinating. Keep up the good work.
Thanks mate!! Appreciate it
I was really hoping for some chocolate ice cream chemistry, but then he said its just KOH 😢
@ALockworkOrange while I'm apprehensive about supporting their cause, I am grateful for health nuts. Because of them I can get concentrated peroxide 😂
@Electra Flarefire wellll considering that Sodium Nitrite has E250 that puts E numbers into perspective lol xD
@almani maxim Not a fan of fermented meats? :)
And yes, we are moving away from them, but when the choice was almost definitely botulinum or maybe cancer? It was great stuff!
There are lots of crazy things in the E number series and even crazier things that people drink and eat on top of that!
@Electra Flarefire hmm fair ,fair! did not think about botulism that can appear in non-treated meat! well, compared to the that the nitrite is even, like healthy XD *nods*. still very crazy what happens to be a certified food additive XD
"That I acquired somewhere," was the shadiest thing he could have said.
Then he followed with "I don't really remember,"
I have no idea why I feel this in my bones but your last distillation is wrong, I feel it is against nature to distill from right to left.
The original simmetry breaking? 😅
The GameCubane was my favorite console.
Same lol
I love the octanitro-GameCubane - but it will explode here and there.
That intro is just... chef's kiss
my name chef
If you want to make absolutely sure you remove all traces of acids from your bromine, even HBr, you can add a small amount of anhydrous disodium sulfate or trisodium phosphate to it, before the distillation. That way, you'll make sodium bisulfate and/or disodium phosphate, which are entirely non-volatile, and absolutely cannot be carried over in your distillation.
It's a little trick I used when I had to remove HCl from TiCl4 and VOCl3. ^^
Dude I'm not a chemist, I have a small amount of knowledge and a fair amount of your stuff does kinda go over my head lol. however I love your videos my guy I cant get enough
You’ll be a chemist just keep watching :)
You're not alone, mate
Haha I do the exact same thing. I don't know what's going on but I like the way he does it
Best thumbnail i've ever seen in my lifetime, I think i probably reached the peak of my lifetime where I see the perfect and unbeatable thumbnail, really, thanks Tom
That into made me laugh way more than it should have
with the reaction, how do you control where the bromine attaches onto the molecule? and dose it matter?
I'm assuming the reaction proceeds through a radical mechanism (unless the dioxane does anything fucky with it - a quick google search hasn't told me much about the reactivity of the dioxane-bromine complex, so there's probably no major change to the mechanism). This sort of radical substitution will tend to primarily proceed through whichever intermediate is the most stable. Generally, radicals are more stable in highly substituted positions due to an overlap of the radical electron orbital with neighboring σ* antibonding Orbitals (this is formally called hyperconjugation). Therefore, a radical will be more stable when it's right next to the fully substituted carbon rather than on the opposite side of the ring, hence radical bromination will prefer substituting this position.
Depending on how high the energy difference between the two transition states is, the reaction is either going to proceed cleanly (if there's a high transition state energy difference) or it's going to be a mess and require really tight temperature control / a selective catalyst (maybe dioxane does that, idk). I'd be more worried about not being able to selectively get 3 bromines on, because if the product is contaminated with significant amounts of mono-, di- or tetrasubstituted bromoacetal it's going to be a nightmare to isolate the product from that mixture (if not impossible without good chromatographic methods). Just using the impure stuff would fuck with subsequent reactions, as the following Diels-Alder step and the final closing reaction need bromine in the right position.
I've listened to too much Aphex my dude, every time a song comes on, I forget that you use his music and I'm like: "I swear I've heard this before...."
This gives me, a final year chem undergrad, hope that I too can successfully combine my passions for chemistry, tangents, being clumsy and memes.
Olive oil is quite good at neutralizing bromine, as well.
At least you're starting when the sun is still up. Round here it's like, "Hey, it's 8:30 pm, what little thing can I pull off in the next hour?" (No, not like that you dirty buggers!)
Next thing you know it's 11 and we're just getting underway...
Christ up where I’m at it’s like “8:30 PM? The suns been down for 4 hours!”
I love your videos man, they're the perfect blend of funny & interesting. You should do plant extractions, maybe with an ultrasound cleaner?
5:03 I was legit in tears laughing at this. omg. I couldn't stop laughing until I'd watched it four times. I can't breathe
edit: I can breathe again. That's the hardest I've laughed all year. Thank you so much, please pass on my condolences to glass-cleaning Tom.
This, I watch him distill some nasty tarring shit all the time and can't stop thinking "where the f* he finds patience to wash the glassware afterwards"
I love you and this show you're like the science teacher I never had. No bromo 😂😂
5:34 "Wouldn't be an Extractions & Ire video unless we committed at least 3 atrocities..."
Goes to get the white phosphorus and cyanide
Also 10/10 opening
Have you tried making ferrocene yet? That's very cool!
An iron atom sandwiched between two five-sided carbon rings!
No way. There’s just no way you played Aphex Twin at 5:44 . Bravo sir
I know there was a reasonable amount of shitposts in this, but the number of catastrophes is surprisingly small, excellent work bad science man!
I truly love the humor in these sick videos man, really brightens my day.
You may need to add an atrocity counter 😂 great work though as usual mate!
Watching that bromine neutralization was so fucking satisfying!
This guy feels like the MaxMoeFoe of chemistry
Thanks for yet another amazing video! Your struggles make these videos so much more human, and I absolutely love it. Keep making great content :)
So excited for this project! Even if we never get to see any cubane at the end, the reactions are really ineresting!
That intro tho... what a throwback and a good laugh as well
Love watching your videos! Can't wait to see more!
Me and my roommate's cat watched this video with equal interest.
Either you were very not interrested or you better start becoming your roommates cats favorite human
@Blutwind I have already succeeded at this don't worry. I am the only human he allows to lift him.
Cody Carpenter awwwwwwwe
Love your videos, keep up the great content!
the intro is top tier, good job!
about half the reason i watch this channel is so i can expect afx music while watching sped up chemistry
I know nothing to do with chemistry, but these videos are still very interesting and entertaining.
I don't know who added subtitles but thank you from the bottom of my heart <3
It'd be funny as hell if the gesticulations with one hand made it into two -- and then three -- hands, and nothing was said about it.
Haven't started vid already laughing at the intro, god this is great
Love your channel and can't wait to see nice fat cubane structure being made! Sorry to hear about your azeotrope blunder. I made dry dioxane several years ago learned about its miscibility with water hard way. Potassium hydroxide works really well. After multiple treatments with solid KOH it is already reasonably dry and peroxide free. You can go for Na when it stops forming dirty alkaline aqueous layer at the bottom. It takes around 24 h of reflux over sodium to remove the last traces of water. Hope it helps and you will be able to recover all the solvent in this jar.
Love your glassware. If it ain't broke... Er, well...
it only broke when it becomes unusable.... right?
That game cube intro got me, I was like wtf did I click on the wrong video. 😂
Meneltir - 2020-11-23
slaps blackboard This bad boy can fit so many reactions on it.
Extractions&Ire - 2020-11-23
so many terrible drawings
Ok Ok - 2020-12-01
slaps beaker ......fuck
spiderdude2099 - 2021-06-05
So many shitty hexagons…..
a smol bean - 2021-06-24
@spiderdude2099 *pentagons drawn believing they were hexagons and hexagons drawn believing they were pentagons