That Chemist forced me to make phenol in a Tim Horton's parking lot
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- Опубликовано: 2 янв 2024
- Joey over at That Chemist forced me to make phenol, but then gave me some. Guess it was worth the shady deal. Make sure to check him out on his channel: @That_Chemist
Sources:
-Thumbnail: ChatGPT (DALL-E)
-pubs.acs.org/doi/abs/10.1021/...
- Joey's mind
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I like the smell of phenol but Mrs. Chemist hates it
Are all the good chemists Canadian or you guys just come up here to party?
Women always spoil fun man times! 🙄😂😉🫶🍻
at least fennel doesn't smell like phenol
But what about the smell of Timmy's? Aphrodisiac or emetic?
Hell yeah phenol smells lovely
Chemdelic really does mix homogeneously with other chemtubers
Mr. Miscible
That moment when that chemist not just runs your reaction but even writes your script😂
Nile Red: Canadian
Nurd Rage: Canadian
That Chemist: Canadian
Chemdelic: Possibly Canadian
Explosions&Fire: Close enough.
Ex&F: went to Canadian Tire once
Calling Tom a Canadian is almost as bad as calling a kiwi an Australian
That’s probably because if you do home chemistry in the US, you get raided for being a meth lab
@@Sniperboy5551 Only if you are stupid about it, Ordering 2000ml sep funnels and round bottom flasks will get you noticed quicker than buying low volume stuff
Australians are just upside down Canadians.
This is an excellent way to start the year I love this collaboration 😌🔥
Man I love meme chemistry videos so much it’s legit the best genre (plus for some reason I learn better off of them)
Practice vs theory
FENNEL????
Great I wish you would make more vids with That Chemist!🔥
Yes
new channel called them chemists?
Call it" The Carbon Doms " .
You're welcome .
Was great to hang with you and Joey. Now to drink the forbidden solid alcohol 🤤
Stony lab glass is good quality imo! Great video you guys! Was really excited to see this one!
So stoked to see you and That Chemist together!!
Lol love the collab! your vids always informative and funny bro
When you walk into a tim hortons restroom and see chemdelic...
That would be hard! I live in the USA :)
@@chemdelic there are some Tim Horton's in the USA. seen 'em with my own eyes
So many maple donuts…
Tim Horton needs to come to Texas.
So he did the work and you filmed it. What a chad move
Buying shares in chemistry YT I feel a pump coming
That's what she said
1:58 looks like you surprised a friend and their just "oh" with a smile but you can see the slight irritation in his eyes (chemical symbol in the middle)
Fee-noll
...awesome
What a shit deal I’d rather have the nitromethane
Maybe there's a way to produce Sesamol from Phenol. Like synthesis of cathecol from phenol, then synthesis of SmH (Sesamyl Hydride; 1,2-Methylenedioxybenzene), then to Sesamol.
You'd be better off starting with commercially available Hydroxyquinol. It's possible to synthesize hydroxyquinol starting from hydroquinone, but it would be far from efficient, probably wouldn't be cheap, and would take a long time. Starting from phenol is extremely unnecessary, and overcomplicates things. I wouldn't start with catechol though either.
But, for the sake of discussion: Phenol would require the addition of two more hydroxyl groups to the ring with one being ortho- to the existing hydroxyl group, and the other being para-. You really only have two options for doing this unless you are capable of doing a Buchwald-Hartwig coupling. That would require the corresponding isomer of dichloro- or dibromo- phenol, a complex ligand, a base, and a palladium catalyst. Depending on the Pd catalyst used the reaction needs to be done under an inert atmosphere. For example, a common palladium catalyst used in many of these types of coupling reactions, tetrakis-triphenylphosphine palladium(0) is air sensitive, but air-free techniques possibly could be avoided by using Tris(dibenzylideneacetone) dipalladium(0). Anyway, I digress. First, a series of inefficient nitrations that will certainly produce many isomers (especially as you have more hydroxyl groups if you can even make it that far... you'll see why), reductions, and diazotizations, and reaction of the diazonium salts with water. This has a major problem though: azo-coupling. The ring has increasingly more hydroxyl groups on it which further activate the ring making the ring itself reactive towards the diazonium salts. The result is a bunch of hydroxybenzenes linked to each other by azo groups (R-N=N-R). Great way to make strongly colorful junk (think azo dyes). The other way (which could actually work) is by a series of phenolic formylations, and Dakin/Baeyer-Villiger oxidations similar to how catechol can be made just more complicated, and lengthy. Not worth the effort when you can get something that already has two hydroxyl groups present from the beginning like hydroquinone. Then you don't have to worry about regioselectivity, etc. as much.
If catechol were used as the starting material: nitration should give a mixture of 3-nitrocatechol, and 4-nitrocatechol. This would be inefficient, and difficult to separate the desired 4-nitro isomer from the other. Assuming it can be done well enough, the nitro group is reduced to an amine, and the amine converted to a hydroxyl group by diazotization followed by reaction of the diazonium salt with water giving hydroxyquinol (kind of --->). This suffers from the same draw back as with the similar method starting from phenol mentioned above (azo-coupling).
For hydroquinone the route would consist of something like this: Reimer-Tiemann formylation of hydroquinone to give 5-hydroxy salicylaldehyde probably in low yield. Similar ortho-selective formylations of phenolic compounds like the Duff formylation, the magnesium methoxide promoted ortho-selective formylation of phenols (yes, that's actually what that reaction is called), and the Casnati-Skattebøl formylation (which is very similar to the previous one) can be used, and will probably work better. Fries rearrangement of the hydroquinone diacetate ester to give quinacetophenone also works, and gives decent yields (there's an OrgSyn procedure for both the acetylation, and the Fries rearrangement). Dakin oxidation of either should give hydroxyquinol, also probably in low yield. Oxidation of the product to the corresponding p-quinone is a concern since hydrogen peroxide is used in the Dakin oxidation which would polymerize under the alkaline conditions of the Dakin oxidation. Alternatively, Baeyer-Villiger oxidation with a peroxyacid like peroxyacetic acid might also work, but could suffer from the same problem on top of being more dangerous due to the potentially energetic instability of peroxyacids.
Like I said before, it's much easier, and more cost/time-efficient to just find a way to order hydroxyquinol rather than make it. These things do make for some interesting organic chemistry thought experiments though.
I just stumbled upon an MUCH better way starting from hydroquinone.
Hydroquinone is first oxidized to benzoquinone. The best way to do this is the iodine-catalyzed hydrogen peroxide oxidation in isopropanol. The benzoquinone is subsequently recrystallized from an alcohol; I successfully used methanol when I did this reaction, but I don’t know if that’s the best solvent. Next, the benzoquinone is reacted with a large excess (greater than three equivalents) of Ac2O in the presence of H2SO4 as a catalyst. This gives hydroxyquinol triacetate which can easily be hydrolyzed with hydrochloric acid to hydroxyquinol.
There’s an OrgSyn paper on the reaction of benzoquinone with Ac2O: hydroxyhydroquinone triacetate, Org. Synth. 1925, 4, 35
Ac2O is readily available from a couple small scientific companies. Hope that helps.
Wait, how many Canadian chemistry RUclipsrs are there?
All of them .
They were just switched at birth .
Chemdelic is actually American, he just lives really far north. Nurdrage, That Chemist, and NileRed are all Canadian tho!
@@LabCoatz_Sciencelab coatz ❤
I have the perfect spot within a 🙈 Playlist that bonds like ions
This doesn't look like a parking lot O_o. I may be drunk...but not THAT drunk. You swarmy PoS.
Doesn't benzoic acid undergo decarboxylation as well ? isn't that gonna mess with the whole catalytic process ?
Requires much higher temperatures and usually you use a metal catalyst. Also, lots of lovely tar scunge.
You're pronouncing it wrong. You're pronouncing it "FEN-el" (like phenyl) while it's actually "fen-OL" phonetically.
I always said it like fee-nole
😂 that the last time i show interest in something like this😂 science rules
Any one else see a smiley face @1:54?
Crunchy
Can i get what ratio of salicylic acid to sodium benzoate was used? And also how to replace sodium benzoate by benzoic acid?
Fun video btw
It doesn't matter, just use mostly the acid
I have some videos where I make Hydrogen gas from non-toxic Aluminum Galinstan amalgam in ethanol water. It needs more indium though to be a eutectic mixture. The trick is to melt the Galinstan and Aluminum foil that is ripped into pieces, and add it one by one while mixing it in the crucible with the back of a spoon (or ideally, a glass stir rod or graphite stir rod). I succeeded in making Hydrogen gas and even igniting some of it. The next step is making Isopropylamine freebase (2-Propylamine) from acetone and excess ammonia in ethanol water using a non-toxic Aluminum Galinstan amalgam to reduce the imine into an amine. Then turning it into 2-Propylamine HCl. Later on, making Norpropylhexedrine and Propylhexedrine from Cyclohexyl-2-Propanone and ammonia and methylamine in ethanol water, then making Norpropylhexedrine HCl and Propylhexedrine HCl. And then trying to make IsopropylAmphetamine freebase from Isopropylamine and Phenyl-2-Propanone, forming an imine intermediate and reducing it with Aluminum Galinstan amalgam (Al/GaInSn) in ethanol water. Then making Ethiopropamine and more from 1-(2-thienyl)-2-Propanone and ethylamine using non-toxic Aluminum Galinstan amalgam. Maybe make IndanylAminoPropane and IndanylMethylAminoPropane from Indanyl-2-Propanone and ammonia and methylamine in ethanol water using non-toxic Aluminum Galinstan amalgam (Al/GaInSn) alternative to toxic Aluminum Mercury (Al/Hg). 🧤🥼🥽⚗️🐀👽🤓🏋♂️🦾🐀☕️🥤😎👍🍺 Grab a beer!
Making primary amines from imines (by the reaction of ammonia with aldehydes/ketones) doesn't work very well. That reaction is an equilibrium reaction like all imine formation reactions, and that equilibrium lies towards the reactants rather than the products in this case (especially if water is present). Some imine is formed, but it does so very slowly. That is why hydroxylamine is used instead to prepare oximes which are reduced to the primary amine (usually with lithium aluminum hydride, but others can be used like NaBH4 with NiCl2). Alternatively, an imine made from benzyl amine, and the desired carbonyl compound can be used. After reduction of the imine to the secondary amine, the benzyl group can be cleaved with catalytic hydrogenolysis giving the primary amine.
Hay look theirs the phenol lol 😆
What’s your favorite chemical?
What is phenol used for? And why the disclaimer on the beginning?
Cheap circuit boards (as phenol formaldehyde resin), heat resistant handles, tons of other things
I can do a taste test for you
Fennel
What am I watching lmfao. Is this SA?
how does trinitro-phenol occur? It always seemed like organic black magic to me
The hydroxyl group of phenol is an election donating group which actives the benzene ring to electrophilic aromatic substitution reactions like nitration. Activating groups like the hydroxyl group are ortho-, para- directors meaning the group directs the electrophilic attack on the ring towards the 2 and 6 positions (ortho), and the 4 position (para). The result when a large excess of nitronium ions are present is 2,4,6-trinitrophenol.
If you’re wondering about the mechanism of nitration reactions in general: sulfuric acid donates a proton to the hydroxyl group of nitric acid (H2SO4 is the stronger acid). This forms an oxonium ion which is a good leaving group, and a bisulfate ion which acts as a spectator ion for now. The negatively charged oxygen present throughout donates a pair of electrons to the nitrogen forming a nitrogen-oxygen double bond (this oxygen anion has been present the entire time, and is also present in nitric acid; it’s stabilized by resonance). At the same time, the electrons in the bond connecting the nitrogen to the oxygen of the oxonium are transferred to the oxonium’s oxygen atom. Thus, it’s subsequently kicked off as water. This leaves the nitronium ion (O=N+=O) which has a positive charge on the nitrogen; this is a good electrophile. The benzene ring is a good nucleophile especially when activating groups are present on the ring. Basically, the ring donates a pair of elections to the nitrogen of the nitronium forming a bond between one of the carbons in the ring and the nitrogen. Simultaneously, a pair of electrons in one of the N=O bonds is transferred to the oxygen reforming the negative charge on the oxygen. This forms the nitro group, and a carbocation on an adjacent carbon in the ring (the carbocation is briefly somewhat stabilized by resonance; the resonance structures are determined by the substituents on the ring). This ring’s aromaticity is broken; and this intermediate (called a sigma complex) is still fairly unstable. To regain stability the aromaticity needs to be restored; finally, this happens when the bisulfate ion (formed in the protonation of the nitric acid) deprotonates the hydrogen atom attached to the same carbon the nitro group is attached to. Simultaneously, the hydrogen transfers its bond electron back to the ring reforming the aromaticity along with sulfuric acid. This process happens two more times to form the trinitro compound.
Lezgew
This is very tasty but nitrochlorform tastes better
What's phenol?
I would say amphetamines. But I´m not sure.
A benzene ring with an alcohol functional group attached, as seen in the thumbnail.
Phen - Prefix referring to the presence of a benzene ring
Ol - Suffix for anything containing the OH functional group
Pretty sure I'm wrong too
Nee joh, d'r zit toch helemaal geen stikstof in!@@Westhamsterdam
@@Westhamsterdam NO!
That was funny but in a contrived sort of way. It works better if you can make it feel less awkward, more funny, tell good jokes and cut down on the meme injections. I, for one, did not believe for one second that That Chemist has EVER been anywhere near a Timmy's. Prove me wrong!
Thank you for the advice!
F
What drugs is this for? Wiki doesn´t have it. A dangerous corrosive material.
It does a great job removing finger and toenails .
It was once used as an antiseptic as well .
Otherwise it's a precursor to many things , including quite a variety of OTC and prescription medicines .
It's also used to make plastics , explosives , etc ...
It's pretty versatile .
It is used to make meth precursor
@@krisha670 It appears to be a precursor for many, many pharmaceutical drugs. Most if not all pharmaceutical drugs are petroleum based.
@@krisha670yeah its in the name? Meth-and-fenell-mean? Duh
@@dyllan559 it's methamphetamine. So, no it is not in the name
Ngl it’s cursed how you pronounce phenol the same way phenyl is pronounced.
First one to comment
Ok this time you are 💀
Nuh uh
Wait how 17h ago
It came out 2 min ago
RUclipsr magic
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