Extractions&Ire - 2021-01-06
We take on a textbook named reaction to work towards our cubane end goal. But will we get textbook results?? 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: - 7 ∂ƒ∆ - Luke Vibert Spiral Staircase future Music Competition afx Remix 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 "Cubane Derivatives for Propellant Applications" 1989 https://apps.dtic.mil/sti/pdfs/ADA210368.pdf
Me watching Nile: "only 80% yield??? bruh come on"
me watching Ex&F: "18% yield?!?!? I'm so proud <3"
@Unknownize I'm going to call this out. Tom and Nile skip ALL of the tedious math that goes into preparing reactions. We get time lapsed video that makes the preparations and clean ups look simple. They take care of all the tedious memorizing of chemicals, obscure rules and exceptions to rules, etc.
Chemistry is not as fun as what we see in chemistry videos, because chemistry videos purposefully skip all the boring unfun stuff. I mean don't get me wrong, it's still really cool. But if you really hate the boring stuff you can't DO chemistry, not without hating it.
@John Morrell what you consider boring and unfun is definitely fun for many of us. The whole working through the process is incredibly satisfying.
@Enrique Camacho-Rico th Prince and the Pauper: Chemistry Edition
@Jaqen H'Ghar I enjoy all the colors of Nile. I like my YouTube Chemists!
Welcome back to Tom tries to explain the 4th dimension using chalk
This is a very nice 👍👏😊 channel
@Extractions&Ire I am sure veritasium is doing a give away with chemistry model bonding kits. Look at his latest Q&A Vid he uploaded at around 9:55.
He said he only giving away to teachers. But I am sure a YouTube teacher of chemistry counts. Plus both are Aussies. Help a fellow fella out down under
@Extractions&Ire use vr
It is a 3d chalkboard... If you were actually seriously asking about it. Animating it is gonna be a bit out of my league but something for chemistry might exist?
This may be my favorite comment of all time. Well done DBX Labs.
@Extractions&Ire you should check out the guy who built a robot to cut his hair. He uses a program that allows him to easily illustrate complex systems involved with machining and engineering.
The reverb on "ribbed for her pleasure" made that line ribbed for my pleasure.
"If I was writing a paper, I'd call this 'off-white'."
Please let the editors of Tetrahedron and Synlett hear this lmao.
I was looking for that
What are we going to make today, Brain?
The same thing we make every day, Pinky: Tar and piss.
This comment is so underrated
It’s quite difficult to make urine and Tar is a very complex substance
I love the mix of chemistry and comedy, all those little offhand comments really crack me up.
Thanks for making this pandemic more bearable to someone who's lost almost everything to it.
Glad you like the videos man, all the best to you mate
Cheers to that dude that sent you his second-hand lube! Also happy new year, hope 2021 brings you good yields
Used lube....
"This brand new, never before used bottle of lube"
-NileRed
Idk why I wanted to quote this, it doesn't even make sense, but I did. Sorry for being a waste of space in this reply section
@Soham Sengupta you're not forgiven
@Soham Sengupta My senses never make as well.
I love these cubane videos
"coming on top" is used a few too many times in this synthesis
@Benjamin Bradshaw fug orgo 1 game lack. Sn2*
@PizzaBert_ Hey both are just consequences sometimes, you can't entirely get rid of Sn1
@Explosions&Fire and you know we all like it.
Sounds like a movie I watched last... ..
Me, not a chemist: I'm honestly just here to hear an aussie yell at chems
Im not sure whether im watching a meme or a chemistry channel
Yes
Yes.
No
That melting point test at the end was definitely a meme.
It's pretty much chemistry shitposting but that's why we love it and he gets his shit done!
You have ketones in your ethanol; probably Methyl isobutyl ketone. When you added the hydroxide, an Aldol Reaction/Condensation started. This resulted in polymers that give the yellow color you hate so much. Food for thought, cool video though
Yeah that seems a likely theory, as the ethanol is not 'food grade' so it can have whatever in it. Seems a strange colour to go, it starts out like a light green rather than the usual red of the typical condensation, but I think eventually it goes to more a red it you leave it for a few days
@Extractions&Ire I bought a liter of 99% lab grade ethanol on ebay for like 6 euros. Might be worth it, along with some ph strips and filter papers for that vacuum filter. Makes it much easier to collect your product. ;)
Diels Alder reactions are also very stereospecific, so they're very useful that regard to make 6 member rings with a high degree of specificity. I think that's a major reason for covering them. They can also serve to introduce kinetic/thermodynamic products in greater detail
yes these are all certainly words
@the_bw_trekkie hmm yes indeed 🧐
The endo product is thermodynamic, right? And would the exo product have the diene bromine on the other side or would it be the product where the double bond with the bromine on it acts as the dieneophile? That second one sound like it would be really unlikely but idk
@España Dorada Generally the exo product is the thermodynamic one as the exo product is less sterically hindered and therefore more energetically favourable, that is it has a lower overall energy.
The endo product is generally the kinetic product product because even though it is more sterically hindered, pi orbital stacking stabilizes the transition state making it more likely to form, and form quickly, even though the end product had a higher energy.
Not to mention how drawing out the products is garunteed to take away any confidence you previously had drawing hexagons
I swear I wouldn’t be surprised if you couldn’t make a cup of tea without it tarring up or turning yellow. Maybe an 11% yield?
Wouldn’t have it any other way! One of my favorite channels. Keep it up!
Nothing like chemistry to distract me from the local coup
Meh they went home
@lolman533 not the ones in congress.
@lolman533 why did you mention me i have nothing to do with this
@meh Username checks out
r/beetlejuicing
Tom: what an ugly colour
Me: thats a nice color!
Also Me: * remembers that I painted my walls Pantone 448C, and that I might have a bad taste in colors *
Ok I looked it up and... that's certainly a choice. You do you
"Pantone 448 C, also referred to as "the ugliest colour in the world", is a colour in the Pantone colour system. Described as a "drab dark brown", it was selected in 2012 as the colour for plain tobacco and cigarette packaging in Australia, after market researchers determined that it was the least attractive colour."
Huh, TIL.
@Ian Grams I lost it at "The Australian Department of Health initially referred to the colour as "olive green", but the name was changed after concerns were expressed by the Australian Olive Association."
Dude, trying to accurately draw Diels-Alder reaction schemes in undergrad ochem almost BROKE ME.
Don't worry Tom, we don't watch this channel for the yields anyway.
Nope, we watch it for the re-use of broken glassware and nervous laughter! 🤣🤣
I don't even know what a good % yeild would be so when he says 18% I'm like hell yeah, you didn't fuck it all up and get nothing.
@Grandma's Underground Michigan Metal in undergrad i was upset when i got below 80% yield. now I'm happy if i get any
Next step involves 98% H2SO4? My money is on lots of tar.
There's no water in the molecule, so we really shouldn't get too tarry.
@Alex Besogonov You jinxed it :D
and a yield of about 15-20%
@philip verdross If you want to make a gram of product you first have to start with ingredients the size of the universe
@philip verdross that's honestly not that bad in a lab
"I just want to blow shit up, why do I have to learn all of this?"
-Tom, probably
I'm getting my revenge by using the things University taught me to actually blow things up
On the norhern hemisphere we grease the fittings with the finger spinning clockwise... so Australia is on the sth hemisphere... do you do it backwords? Or would chemistry turn yellow otherwise?
Maybe that's why everything is going yellow!!
this is a glorious comment
"It is very easy. We will just use hardware store chemicals directly from the shelve and have 100 % conversion with 100 % exo product"
Yeah... I don't think so
What could possibli go wrong
Minecraft, episode seven?
Ooo this is gonna be good… ⠀
Please forgive us.
We made the same joke again.
Oh yes, being unoriginal is a truly surreal attribute.
@Ꭼxpl๏sives Ꮮab๏rat๏rƴ do not worry, for it is an enigma we all possess
u n o r i g i n a l i t y
Tar is the bane of my existence. Once was running a transition metal reaction and it all tarred up and called my lecturer over... "What have you done? i have never seen that happen before for this reaction" and later "I dont think organometallic chemistry is your forte"
He was just jealous of your talent for discovery...You might have made crude oil out of abundant and cheap materials!
This reminds me of a time a professor looked over one groups work and was confused how the got to the proper outcome. As they combed over the report they uncovered it, the group had screwed up twice and magically screwed up in two ways that cancelled each other out.
Ah yes, one step closer to the inevitable ONC
Petition to get Tom one of the multi-layer glass marker boards so he can attempt to convey 3d models
Just buy him some of those model thingies with the springs and spheres with various holes in Them
@Garry Sekelli Maybe he could try marshmallows and toothpicks as a budget option?
I'll just wave my hands around some more, I'm sure that'll help it out fine
Watching this series gives me the feeling that chemists exist only to make other chemists endure an incredible amount of suffering
That's definitely a valid interpretation
I think the most tedious part of this whole thing is that whenever you make a mistake that you can't fix, you need to re-make all the same chemicals again. It's a decently long synthesis route, and you're starting from the very beginning. So good luck. And thank you for the upload! Today was sucking, this will help make it better for sure.
Yeah absolutely. The plus side is that I'm usually a lot better the second time around, but hopefully it doesn't get to that because we have at the very least quite a bit of the non-brominated ketal to work with, so probably won't ever have to go back to the adipic acid assuming the ketal product stores okay
@Extractions&Ire Well that is good then :-)
And btw, I think the best descriptor is off-yellow.
That graduated cylinder must be a post-doc cylinder now 😅
Extractions and Ire:
Does taste test of all alkali salts and ranks them
Lets all organic reactions become yellow or tary somehow
Can't pronounce "Hydantoine"
All of sudden:
Cooks some Cubane and knows the Diels Alder reaction
That escalated quickly
im so happy i found this before you finished, the journey is amazing to see in real-time
I love the little tar celebrations that have been in recent videos! I only watch these videos for the tar, so it really plays to my interests
I've seen some very high temperature grease you can buy a tiny tube of for over $100. Stuff you'd use when purifying sulfuric acid drain cleaner
Yeah that's this sort of stuff. A tube this big is usually hundreds of dollars which is pretty ridiculous, for that price you'd hope it was good haha
3:25 75% Hoppy , 15% new and 10% year. That is quite the Hoppy yield you got there.
Must be making beer
I'm pretty sure that's the ratio for gun powder
I think the word was "happy", not "hoppy". As in "happy new year".
@Daniel Bickford 10% luck, 20% skill...
I love that you are turning chemisty into a meme lol, also, I cheered when it turned to tar. Joy at misfortune or something, but if it dosent turn to tar, somethings gone wrong
1:50 The Diels-Alder reaction is one of the most powerful reactions of organic synthesis. It not only is completely free of waste, it also allows to set up 4 stereocenters in a molecule IN ONE REACTION(!!). Look up Woodward's synthesis of reserpine. It was and still is a completel masterclass of Diels Alder chemistry.
i really like the aphex twin soundtrack, great choice !
Tons to learn from those types of reactions. Woodward -Hoffmann rules, MO theory, heat or light "forbidden" reactions. Good stuff.
I like the chemplayer reference 10:42
This is actually one of the most humorous and enternaining chemistry channels
i started following right when this synthesis first began, and i have to say, i get super excited when i see a new one!
I love that your chalk board looks part early human cave drawing , part middle school doodles but mostly chemistry.
I finished my organic chem lecture and lab with an A and got a 97 on my final, that was a little less than a month ago and I've already forgotten most of it 😬. Good thing I'm an Organismal Bio major and only had to take one class of orgo B)
This is my favorite thing in all of the internet and I'm so glad every time there's a new one.
I heard the moon was secretly yellow on the inside.
E&I 2021"This one is coming on top of this one"
My mind in the gutter: god bless this mess
Edit: 8000 greased joints of expensive lube
Dude, thank you. Seeing you upload a video makes my day every time.
Love this channel! I’m a microbio major so I love science and always thought Chem was super cool but the lab work always scared me😂(dropping a parafilmed Petri dish is a little more forgiving than a beaker of acid lol) but watching ur videos always makes me wanna try home chem myself! Hopefully one day I’ll have a lab shed of my own👌🏽😂 love the vids man keep doing the good work!
Diels Alder reactions are the reason I bought a model molecule kit. Shit's too freaky to understand in 2D. If you are studying chemistry I highly encourage you to buy one.
I however firmly believe that they are only taught to completely fuck with your ability to draw molecules in an exam. That's all.
Hell yeah man im loving this series. I hope you can make it to the end product!
Extractions&Ire - 2021-01-07
What's the nicest term you can use to describe the product colour? (without using the word brown)
Silly Sad - 2022-01-15
@DeadNeck90 it is never late to propose the correct answer
Dave Perry - 2022-01-22
@M Nice Technology Connection's reference.
M - 2022-01-23
@Dave Perry Thanks mate.
Yoh - 2022-02-07
Off-tan? :D
Trevor Day - 2022-03-31
Maybe..... beige?