this is scientific and precise. we only are precise when talking about the stuff we are interested in. everything else would be overkill. even organic chemistry profs say "well good luck getting the crap out of the flask". we only care about what we want and the mechanism we are exploring. so if we don´t precisely want to check out side reactions. left over crap is left over crap.
Profs and even on papers xD I saw a bit of papers reffering to that kind of mixtures as «oils», «masses», «aggregates» etc xD so yeah, not as graphic as «crap» but i feel between them they called it «crap»... when your product is kept inside the «crap» xD my favourite was my PI calling a mass i got «gosma» meaning «goop».. less funny was treating it to get my product out of it...
@@AlldaylongRock i think i read "leftovers" in a few papers or "waste" so yeah in a paper you try to keep polite language. so "masses" "aggregates" "undefined chunks" "undefined substances" "leftovers" "remaining side products" but when talking to each other crap is the tamest description. The harder it is to clean up, the more vulgar the language in the lab
Agreed, benzyl alcohol is stupidly soluble in water. To get the most out of an extraction approach use a saturated bicarbonate aq wash and extract with a ton of extractions of solvent, also not sure, ether may be better than dcm for this approach. You could also potentially do a direct distillation of the benzoate and alcohol solution without extraction then work up the benzoate residue in the boiling flask
I'm not sure why I'm even watching these videos so often. Chemistry is kinda interesting, but I don't know too much about it and I don't "do" it. I guess this is my way to say your videos are fun to watch even for someone who isn't even that into chemistry. Also thank you for all the effort, really appreaciated =)
Literally I've only read about cannizzaro reaction in chemistry books when I was in my senior year( plus two in India ) almost an year ago , cool to see the practical version.
I love this old videos, and i love to realize that you have grown and gained confidence, but still loving chemistry. I'm 19 and I'm studying a science career, and you inspire me a lot.
Yeah people are fussy about calling it a "hydride transfer". I think it's more of a conceptual abstraction of what happens: a proton and pair of electrons are transferred from one to the other (often a useful way to look at reductions in organic chemistry, btw). Also, nice you could use thiamine ^^ The more infamous catalyst is cyanide! If you can avoid cyanide, that's probably a good idea :D
I'm guessing you lost so much of the benzylalcohol due to the extraction from the mixture with benzoic acid. For extractions, it's better to use *many* extractions with little liquid each time, than all the liquid in one go. You used 3x20 mL (for a total of 60 mL). Going for something like 4x15 mL, or even the adventurous 6x10 mL, would make you end up with the same amount of total volume of DCM/benzylalcohol mixture, but with a lot more of the alcohol extracted from the water-layer. Though mainly unpolar, benzylalcohol can hydrogen-bond to the water or the benzoic acid, making it somewhat more soluble (at least I would think), and therefore some would probably stay behind in the water layer. This is just a guess though, and I would probably not think that this would account for all the 19% that you were missing.
NileRed I would just have bubbled o2 through the solution to oxidize all aldehydes present in the presence of some copper(II)oxide powder for a few hours. Then proceed directly with the steam distillation. Discard everything that comes over below 95*C - it's garbage and water vapors. Water forms an azeotrope with benzyl alcohol at 99.9*C. The azeotrope has 9% alcohol in it (by mass). Keep distilling until no more alcohol comes over (you can determine this by the smell of the steam ). There is enough water to start with anyway so distill until sodium benzoate crushes out of the solution. The alcohol water solution that has been distilled can be separated by salting the water alcohol solution with calcium chloride up to saturation then do a diethyl ether solvent extraction. Do several extractions using 25ml ether batches. After you have finished, dry everything using CaCl2, distill the ether over, collect everything up to 50*C(if you used diethyl ether) , discard everything up to 200*C and the remaining alcohol in the flask should be the pure benzyl alcohol. If you want, you can distill over the benzyl alcohol again but it should be pure already. Now, the water remaining in the first flask (one with the benzoate salt and some orange organic goo polymer from the aldehyde). Be sure all salts are dissolved, filter it to get rid of the solid stuff and the little copper oxide added. Add salt until saturation. Try to extract the soluble orange goo with some benzil methyl cetone, but what is left is left forever in there. Acidify it with concentrated HCl, filter the raw benzoic acid obtained, wash it with a bit of water, recristalilze it from hot water and it should be pure.
honestly i really enjoy these videos, but the more i watch them, the more i realize just how much i enjoy chemistry in practice, but actually understanding terminology and the definitions of stuff make me feel like my brain cant keep up
In exactly the same, I've always been interested in practical stuff like this, but the verbal and theory based stuff confuses me so I don't pay attention to it
I'm an italian student and my high school is actually named after Stanislao Cannizzaro; as I was scrolling down the recommended page I saw this video and absolutely had to take a look at it - just to support my country, you get it! After watching it (and liking a whole bunch) I actually went to check your channel out, and binge watched probably every single video that you posted since 4 years ago. I've just found out that I'm a sucker for chemistry. Absolutely great channel!!!!!!
whereas most chemistry classes tend to dismiss real world applications, nilered does a great job in explaining how practically these chemicals are used. I think this is why I enjoy his content so much.
I got confused at 14:45 - there were steps in the process where he removes water but he chooses a process where he has to add ice cubes...just a tip, they have freeze-able gel-filled cubes so you don't have to contaminate your chemicals with water.
My uni legit included this video to explain the Canizzaro reaction for our aldol condensation lab rather than just making their own video about it. I was super excited to see it was a NileRed video but then I got to thinking...do you allow universities to use your content for teaching purposes?
@Øivin Fjeldstad maybe you should watch the movie dark waters and do some reading. its a pretty interesting topic on a whole. it certainly is controversial. no doubt about it//.
@Øivin Fjeldstad no its about the chemicals, its properties, the company producing it and everything else. Tainted water supplies leading to mutations and cancer with full knowledge it was having that kind of impact is my definition of controversy. Ongoing court cases, to this day and probably for years to come. We all likely have it in our bloodstream due to the fact it is in many house hold products, around the world. Non-stick pans primarily. We eat shit from that dude. trace amounts or no, its far from safe for human consumption. Theres a reason its a little known or talked about topic. Theres a reason the movie was seen by so few people. Only a certain amount theatres were able to show it. The fact that im having to explain this now and that it isnt common knowledge should tell you a lot.
@@shellshockedbros4458 so either you're trolling or didnt read about it or watch the movie, because its explained in laymans terms, with plenty of detail in the movie, and there are literally hundreds of articles that explain it in even easier to comprehend ways. What about cancer and birth mutations doesnt seem like a problem to you? Or maybe the fact that the company directly responsible is one of the most profitable of all time? none of that is an issue to you? idk, try watching the movie again with the sound on this time ?
Seeing the other suggestions of filtering and what not in the comments is cool, I especially like when everyone’s friendly in their suggestions because as scientists we know we make mistakes and there is sometimes a better way to do something. Coming from an Astronomy and Astrophysics grad student this stuff is way beyond my chem 2 and thermodynamics knowledge but some of things I can put together and it’s really cool to see all the different ways there is to do certain reactions. We in my major tend to forget how dynamic and fun chemistry can be in this aspect
Pro tip: After the water washings, wash with a solution of saturated sodium chloride. This pulls out a lot of water. Then you'll need less drying salt (magnesium or sodium sulfate). Because a lot of solvent will stay in the sulfate, which you'll need to wash out will more solvent while filtering.
For anyone who is confused, an anhydride is a compound that absorbs lots of water since it does not contain any sort of water molecules. In the process, it also absorbs impurities almost like a solute would.
I'm not sure but maybe the benzyl alcohol formed some azeotropes with water or with some side products so you lost some of it. Also if you want to maximize yield when extracting with dcm you can make more washings (for example you get 85% with 3 washings but you could get 95% with 5)
Yes, benzyl alcohol forms a low boiling azeotrope with water that boils at 99.9˚C. To prevent this, you could use a solvent other than DCM that is less soluble in water such as chloroform.
I recently did this experiment in my ochem 1 lab. We used methylene chloride instead of DCM as our organic solvent. After extraction, we performed a sodium bicarbonate washing in the organic layer. The aqueous washings were discarded and the organic layer was dried using anhydrous sodium sulfate. Instead of distillation, the organic solvent was evaporated off (bp. 39.6C) and the crude benzyl alcohol solid was recrystallized using xylene. Our yield was still fairly low, but this is just another method.
Here in Germany I would have trouble getting CH2Cl2.... ;-) Its use is restricted to labs and industry and not for private use! ;-) Nicely demonstrated! Check the water solubility of your alcohol! And during the destillation you should have added a solvent that has a higher boiling point than your desired alcohol!
The Cannizzarro is one of the lesser favourable name reactions. It's a disproportionation reaction converts a valuable compound (aldehyde) into a mixture of two less valuable (alcohol and carboxylic acid). It's like the acidic ether synthesis which is only favourable if you want to create symmetric ethers. For asymmetric, the Williamsen synthesis with the alcoholate of the on chain and the alkyl halide of the other chain is more favourable because it is a specific reaction. Likewise, you create esters by using an alcoholate and an acyl halide.
NileRed you should do a tour of your lab with all your crazy glassware, like is your house a lab? Im just super curious to see all your equipment and where you film and stuff
Hi NileRed, another solid video, thanks! Did you use a procedure you found or did you put it together yourself? I'm trying to plan an experiment for some visiting students to try but I haven't found a straightforward prep so far.
One factor that may have led to the loss of the benzylalcohol is that you used DCM to extract it. DCM has a high tendency of forming an emulsion with water, which is the cloudiness you spoke about. Since you had quite a bit of DCM still in the water after the separation some of the benzylalcohol may have been dissolved in the aqueous part. If you had used another solvent for the extraction, like chloroform that doesn't form emulsion with water as much as DCM, your yield would have been higher.
I don't know why but I felt this video was a lot of work (maybe a bit more than usual?) with the ton of details that you provide :D Looking forward for the next videos then :P
It's not illegal. Rather, it is on the DEA list of watched chemicals, which means manufacturers and sellers must file reports with the DEA for tracking purposes. Benzaldehyde is a common precursor for many drugs, both legal and illegal. www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm
That makes more sense. I went and looked at the Wikipedia page, curious why it was controlled, and it said the FDA lists it as Generally Regarded as Safe and even the EU approves it as a flavor additive (and they tend to quite aggressively ban anything with a hint of risk about it). It did mention that it was used as a precursor in some pharmaceutical production, though, so I guessed maybe it was something like that. The list you linked to has a bunch of things I am not surprised are watched (like pepiridine and several ephedrine-related things) but also some innocuous things like iodine. The 'List II' contains lots of stuff that I'm pretty sure aren't watched though, like sulfuric and hydrochloric acid. I bought concentrated hydrochloric acid off of Amazon no problem a couple years ago (best tub cleaner for hard water deposits around) and I'd be surprised if that was reported anywhere.
You could, using a rotary evaporator, evaporate the DCM which at lower pressure boils at about 30 to 45°C while the benzoyl alcohol boils at room temp at ~200°C so you are kind of fine.
I think the alcohol had such a lower yield because of your method of distillation, or rather, your equipment. I believe the best course of action would have been to have used a more complex heater, one that is capable oh holding a temperature automatically. That way you are not hoping that all the alcohol is evaporated by the time the temperature reaches and surpasses its maximum. I believe that the lost alcohol was unable to evaporate before the temperature reached too high and the distillation was stopped.
I suspect that the biggest issue was in the distillation process of the benzyl alcohol. When you cannot accurately control the temperature of the solution a great deal of the alcohol will be lost before and after the transfer of temperature from 200 to 206.
Hey Nile, love your videos! This is a very interesting process as usual, but I don't think I speak alone when I say I never quite fully understand your videos, even with the side explanations and sources. I'd love to get a better understanding of your videos by doing a crash course of sorts in Organic Chem, as that branch of chemistry seems to make up the larger portion of your videos. I assume you have a degree in Chemistry and likely learned most of what you know from getting it, but are there any particular helpful (and preferably free) sources of basic Organic Chem instruction that you've used in the past? If so it would be awesome if you could point me to them. And, if I could make a suggestion, I'd love to see a cholesterol extraction (or maybe even synthesis) in the future, with it being such an important chemical and all. Once again, love your videos and hope you continue to make them in the future!
NileRed Wow! Thanks for the prompt reply! I suppose the easiest to explain and most helpful generally would be a deeper understanding of organic structures and their models, which once that is understood should help make comprehending a process much smoother. I find this along with terminology for certain reactive processes (e.g. reduction, oxidation, and so on) to be a big blocker when trying to figure out what's going on at a deeper level. Explaining common processes/terminologies could be done by introducing and fleshing out a term or concept and then using an example reaction (perhaps an excerpt from a previous video) to supplement it. These videos could be short and palatable, possibly part of a series, and relatively easy to make (in comparison to your other videos) and help the viewer digest your content easier without taking too much attention away from your bigger projects. TL;DR - Short, sweet videos covering important processes, model comprehension, and terminology would be nice.
+NileRed For instance when you talked about acidic alpha hydrogens, I can see why non-chemists get lost. When such notions are encountered, maybe you can do an addendum where you explain the theory a bit more, like why a particular hydrogen atom in an organic compound is considered acidic and how to identify the most acidic hydrogen in a compound (you would need to explain resonance and inductive effect I suppose).
Other UA-camrs: Can't handle the slightest amount of constructive criticism. NileRed: "Feel free to criticise ANYTHING involving my technique, or the method that I used." - What a madlad. ^^ But in all honesty: I'm not a chemist, nor do I have any hobbies involving more than knowing the most basic reactions. But once in a while, I really enjoy watching this guy's content. He explains everything really good. (except for the times he just gives you a chemical structure instead of an explanation, but I'm sure this is explained in other/earlier videos of his making. xD) It's fascinating almost every time, and you still take some knowledge with you, every time you watch. Even if you don't remember every detail. The internet (and the youth of today, who tend to have access to it waaaaay earlier than my generation) need more people like him. ESPECIALLY with all that TikTok sh** going on.
Very nice demonstration. A problem with using DCM for workups from alkaline aquaeous solutions is that it forms an annoying emulsion. Either diethyl ether or a hexane/ethyl acetate mixture will give you a quicker, cleaner workup.
A wee tip that i use to dry DCM and Chloroform is to put the wet DCM in the sep. funnel along with some saturated NaCl (brine) solution. it pulls out some water from the DCM into the aqueous and will mean you need to use less magnesium or sodium sulfate :) (also makes filtering off the solids easier)
At 7:45, why not separate the two initially with filtration? The two could then be separated further as you specified; but it seems like less would be removed as waste from the process.
![Lp. Сердце Вселенной #60 РОЖДЕНИЕ ЛОЛОЛОШКИ [Финал] • Майнкрафт](http://i.ytimg.com/vi/YoR0pAV9FVQ/mqdefault.jpg)
It's so much more fun to watch this when you're not expected to memorize it for an exam with 200 other reactions.
Ugh tell me about it I gave up halfway through the semester and just cheated on the exam
Yep
Lul
Definitely it's jee
U r so right
13:49: "a bunch of red orange crap". Scientific and precise to crude in 5 seconds. This is my favorite part. :)
this is scientific and precise. we only are precise when talking about the stuff we are interested in. everything else would be overkill. even organic chemistry profs say "well good luck getting the crap out of the flask". we only care about what we want and the mechanism we are exploring. so if we don´t precisely want to check out side reactions. left over crap is left over crap.
Profs and even on papers xD I saw a bit of papers reffering to that kind of mixtures as «oils», «masses», «aggregates» etc xD so yeah, not as graphic as «crap» but i feel between them they called it «crap»... when your product is kept inside the «crap» xD my favourite was my PI calling a mass i got «gosma» meaning «goop».. less funny was treating it to get my product out of it...
@@AlldaylongRock i think i read "leftovers" in a few papers or "waste" so yeah in a paper you try to keep polite language. so "masses" "aggregates" "undefined chunks" "undefined substances" "leftovers" "remaining side products" but when talking to each other crap is the tamest description. The harder it is to clean up, the more vulgar the language in the lab
obpinkslip when he says “damp” it sounds like “dam” so it sounds like “the dam crystals”
@@drsciencebj996 OMG SAME AND I WAS SO AMUSED
The crystallization timelapses are always awesome.
I love them too¡! 😊
U right
with some nice crystals
I am dumb and dont understand anything :D
I am here only for that :D :D :D
"Can also ,apparently, be used as a weak local anesthetic."
Did you find that out the hard way?
I was going to ask the same thing
According to the Handbook of Chemistry and Physics - 95th edition, benzyl alcohol is soluble in water. You lost a lot it in the washing step.
Gustavo Marzullo rip
Agreed, benzyl alcohol is stupidly soluble in water. To get the most out of an extraction approach use a saturated bicarbonate aq wash and extract with a ton of extractions of solvent, also not sure, ether may be better than dcm for this approach. You could also potentially do a direct distillation of the benzoate and alcohol solution without extraction then work up the benzoate residue in the boiling flask
@@spiderdude2099 but with smaller and multiple separations will improve the yield.
that was my first thought to. to much washing. could carbonate work? to wash. thT mite be a stupid question lol
@@christopherweaver9524 too
I'm not sure why I'm even watching these videos so often. Chemistry is kinda interesting, but I don't know too much about it and I don't "do" it. I guess this is my way to say your videos are fun to watch even for someone who isn't even that into chemistry.
Also thank you for all the effort, really appreaciated =)
That's exactly me I see his videos everyday and I have no idea what is happening or what's the logic behind it.
It's pretty cool tho
@@bulgna same
Same here...
Same, I hated both Chemistry and Physics in school, I only liked Biology. But it is kind of interesting in this format.
This was me until I actually just started learning it. I love the videos even more and rewatch regularly.
Literally I've only read about cannizzaro reaction in chemistry books when I was in my senior year( plus two in India ) almost an year ago , cool to see the practical version.
Telugu person spotted.
im doing now hehe
@@linxuser897 every book has it 💀
@@vanjinathan5877 He said "plus two". I think that terminology is only used in Telugu states.
@@goos6005 o i c
The automatic subtitles said "candid sorrow reaction" and tbh, I really felt that...
AKZ can u sub to me??
I love this old videos, and i love to realize that you have grown and gained confidence, but still loving chemistry. I'm 19 and I'm studying a science career, and you inspire me a lot.
17:13 The crystals ! They're beautifuuuul !
holly shit im dying, we did a benzaldehyde to benzoine reaction last week with thiamine to prevent the cannizzaro, the timing is too good to be true
also i saw a mechanism that included a dimer intermediate, not requireing the Hydride to be kicked
so yea some of it might go toward benzoine
Yeah people are fussy about calling it a "hydride transfer". I think it's more of a conceptual abstraction of what happens: a proton and pair of electrons are transferred from one to the other (often a useful way to look at reductions in organic chemistry, btw). Also, nice you could use thiamine ^^ The more infamous catalyst is cyanide! If you can avoid cyanide, that's probably a good idea :D
we actually did both to compare the yield, but yeah, scary stuff
Barnesrino Kripperino oh snap! so which was better?
I'm guessing you lost so much of the benzylalcohol due to the extraction from the mixture with benzoic acid. For extractions, it's better to use *many* extractions with little liquid each time, than all the liquid in one go. You used 3x20 mL (for a total of 60 mL). Going for something like 4x15 mL, or even the adventurous 6x10 mL, would make you end up with the same amount of total volume of DCM/benzylalcohol mixture, but with a lot more of the alcohol extracted from the water-layer. Though mainly unpolar, benzylalcohol can hydrogen-bond to the water or the benzoic acid, making it somewhat more soluble (at least I would think), and therefore some would probably stay behind in the water layer. This is just a guess though, and I would probably not think that this would account for all the 19% that you were missing.
All good suggestions!
NileRed I would just have bubbled o2 through the solution to oxidize all aldehydes present in the presence of some copper(II)oxide powder for a few hours. Then proceed directly with the steam distillation. Discard everything that comes over below 95*C - it's garbage and water vapors. Water forms an azeotrope with benzyl alcohol at 99.9*C. The azeotrope has 9% alcohol in it (by mass). Keep distilling until no more alcohol comes over (you can determine this by the smell of the steam ). There is enough water to start with anyway so distill until sodium benzoate crushes out of the solution. The alcohol water solution that has been distilled can be separated by salting the water alcohol solution with calcium chloride up to saturation then do a diethyl ether solvent extraction. Do several extractions using 25ml ether batches. After you have finished, dry everything using CaCl2, distill the ether over, collect everything up to 50*C(if you used diethyl ether) , discard everything up to 200*C and the remaining alcohol in the flask should be the pure benzyl alcohol. If you want, you can distill over the benzyl alcohol again but it should be pure already. Now, the water remaining in the first flask (one with the benzoate salt and some orange organic goo polymer from the aldehyde). Be sure all salts are dissolved, filter it to get rid of the solid stuff and the little copper oxide added. Add salt until saturation. Try to extract the soluble orange goo with some benzil methyl cetone, but what is left is left forever in there. Acidify it with concentrated HCl, filter the raw benzoic acid obtained, wash it with a bit of water, recristalilze it from hot water and it should be pure.
ᏰĪᏝᏝ ՇÎρɧᏋƦ a little over kill i think...
This
@@jacogomez1093 this made me laugh out loud
"candid sorrow reaction". Gotta love those automatic subtitles.
That's quite a nice phrase as it goes
I thought this said aromatic subtitles
Damn going back to this after a few years you can tell much more energy/excitement he shows in newer videos
It seems like he was doing that for the university in the first place
Hes definitely gotten a lot more comfortable with his narrating
honestly i really enjoy these videos, but the more i watch them, the more i realize just how much i enjoy chemistry in practice, but actually understanding terminology and the definitions of stuff make me feel like my brain cant keep up
In exactly the same, I've always been interested in practical stuff like this, but the verbal and theory based stuff confuses me so I don't pay attention to it
How about extracting Nicotine from cigarettes?
Is that legal?
I will eventually!
Thank you! I'm looking forward to it!
It should be legal... I mean, I buy bottles of nicotine mixed into vegetable glycerin all the time for vaping.
I agree
man, every time he mentions redox reactions i'm reminded of the hell on earth that was high school ap chemistry
Sarah cN u sub to me plzz ??
@@Wishingweezy no. No one is going to sub to you
@@XevianLight I know 😢 😖
I'm an italian student and my high school is actually named after Stanislao Cannizzaro; as I was scrolling down the recommended page I saw this video and absolutely had to take a look at it - just to support my country, you get it!
After watching it (and liking a whole bunch) I actually went to check your channel out, and binge watched probably every single video that you posted since 4 years ago. I've just found out that I'm a sucker for chemistry.
Absolutely great channel!!!!!!
whereas most chemistry classes tend to dismiss real world applications, nilered does a great job in explaining how practically these chemicals are used. I think this is why I enjoy his content so much.
Benzyl makes everything sound so happy.
It sounds like Denzel.
Benzene is one of the things that make gasoline smell like it does
@@pacificcoastpiper3949 in Dutch the common name for gasoline is ‘benzine’
@@guillomeke interesting 🤔
@@guillomeke in most languages in Europe people use this word for gasoline including German, Russian, Italian, Czech, Estonian, etc
When you have no idea what's going on but enjoy the videos: Yea, science!
You hear that Mr white?! Yeah since!
I got confused at 14:45 - there were steps in the process where he removes water but he chooses a process where he has to add ice cubes...just a tip, they have freeze-able gel-filled cubes so you don't have to contaminate your chemicals with water.
This has to be one of the most beautiful recrystalizations I have ever seen.
Hearing Nile say "crap" really just warms my cold dark soul.
My uni legit included this video to explain the Canizzaro reaction for our aldol condensation lab rather than just making their own video about it. I was super excited to see it was a NileRed video but then I got to thinking...do you allow universities to use your content for teaching purposes?
Since it is being used for educational purposes it falls under fair use as far as I am aware of. I'm not sure what the laws are in Canada.
@@anchopanchorancho oh I figured as well, I just didn't know what he was comfortable with!
This guy doesn't even ask for likes or subscribers, he just does this out of curiosity and for fun and the wonder, this guy is amazing!
if you produce quality content then asking is not needed unlike the youtubers we have today.
Awesome vid as always. I can't wait for the molecule keychains I saw on your site.
I am trying to get them made as soon as possible!
Where did you get the mixer in the beaker?
@@unizero_ ahhh Teflon. That good old not at all controversial substance.
@Øivin Fjeldstad maybe you should watch the movie dark waters and do some reading. its a pretty interesting topic on a whole. it certainly is controversial. no doubt about it//.
@@idrinkmilk282 I still don't see the problem after reading and watching the movie.
Do elaborate more please.
@Øivin Fjeldstad no its about the chemicals, its properties, the company producing it and everything else. Tainted water supplies leading to mutations and cancer with full knowledge it was having that kind of impact is my definition of controversy.
Ongoing court cases, to this day and probably for years to come. We all likely have it in our bloodstream due to the fact it is in many house hold products, around the world. Non-stick pans primarily. We eat shit from that dude. trace amounts or no, its far from safe for human consumption.
Theres a reason its a little known or talked about topic. Theres a reason the movie was seen by so few people. Only a certain amount theatres were able to show it. The fact that im having to explain this now and that it isnt common knowledge should tell you a lot.
@@shellshockedbros4458 so either you're trolling or didnt read about it or watch the movie, because its explained in laymans terms, with plenty of detail in the movie, and there are literally hundreds of articles that explain it in even easier to comprehend ways.
What about cancer and birth mutations doesnt seem like a problem to you? Or maybe the fact that the company directly responsible is one of the most profitable of all time? none of that is an issue to you?
idk, try watching the movie again with the sound on this time ?
Any idea what the orange-brown crap might be? My first thought is alkoxide-promoted polymerization of the benzaldehyde.
Was wondering the same thing
Hi professor Evans just started watching this after your lecture!
Seeing the other suggestions of filtering and what not in the comments is cool, I especially like when everyone’s friendly in their suggestions because as scientists we know we make mistakes and there is sometimes a better way to do something.
Coming from an Astronomy and Astrophysics grad student this stuff is way beyond my chem 2 and thermodynamics knowledge but some of things I can put together and it’s really cool to see all the different ways there is to do certain reactions. We in my major tend to forget how dynamic and fun chemistry can be in this aspect
Thanks for helping me study for my OChem 2 test. You're the man
Can you extract iron from blood?
Ew, why would you do that?
Brutal
Yes, it can be done. The pigment "Prussian blue" ( iron(III) ferrocyanide ) was first made from animal blood.
Yes!!!! Is it worth doing? NO!!!!
Magneto can.
Be me, be italian, be like he actually said cannizzaro right, be proud off you
R0T0M0L0T0V or a Born of Osiris fan. Their singer is Ronnie Cannizzaro
6:30 Me eating cheetos nodding along while pretending to understand what this is.
Haha, just wrote this reaction in my test and got full marks
Pro tip: After the water washings, wash with a solution of saturated sodium chloride. This pulls out a lot of water. Then you'll need less drying salt (magnesium or sodium sulfate). Because a lot of solvent will stay in the sulfate, which you'll need to wash out will more solvent while filtering.
Came out of chemistry class sick of making crystals, to watch you make crystals. Story of my life.
Crystals are life
Inorganic synthesis is much more colorful
Man I'd love to go back to my highschool chem class, that shit was so fun.. best teacher I've ever had too. NileRed gets me that chem fix lmao
And don't forget that benzaldehyde actually oxidises very easily in air, especially at temperature, so that might also explain your yeld
For anyone who is confused, an anhydride is a compound that absorbs lots of water since it does not contain any sort of water molecules. In the process, it also absorbs impurities almost like a solute would.
I'm not sure but maybe the benzyl alcohol formed some azeotropes with water or with some side products so you lost some of it. Also if you want to maximize yield when extracting with dcm you can make more washings (for example you get 85% with 3 washings but you could get 95% with 5)
Yes, benzyl alcohol forms a low boiling azeotrope with water that boils at 99.9˚C. To prevent this, you could use a solvent other than DCM that is less soluble in water such as chloroform.
+Philip Polkovnikov im pretty sure he has adequat ventilation, though
baguvix aezakmi thats what i thought lol
Congrats on 100k
very nice video , studied chemical engineering and i'm still learning when i'm watching your videos.
distill into a cold bath, the colder the better.
Watching crystallization is amazing
Ah yes, The Cannizzaro Reaction. It's that hidden camera, magic, TV show.
You must do more smaller size liquid-liquid separations to reach more efficiency on the benzyl alcohol.
weird pepsi
I love you, i was struggling to prepare this reaction as a student and now everything gas illuminated in my brain
Nile red helping me get through high school chem.
Every time I try this experiment somebody always takes a shit in the separatory funnel.
Hey; I love you broski. Thank you for all of your videos.
-O
I'm not a scientist or a chemist or anything I just like watching these
I love how in your older videos, you explain stuff like recrystallization, but in newer videos, we all just know what you’re doing, so you don’t
I recently did this experiment in my ochem 1 lab. We used methylene chloride instead of DCM as our organic solvent. After extraction, we performed a sodium bicarbonate washing in the organic layer. The aqueous washings were discarded and the organic layer was dried using anhydrous sodium sulfate. Instead of distillation, the organic solvent was evaporated off (bp. 39.6C) and the crude benzyl alcohol solid was recrystallized using xylene. Our yield was still fairly low, but this is just another method.
Such an amazing video, thank you so much!!
Where the fuck I was 3 years ago. Damn there's so much chemistry in your videos than what I was taught in my whole college degree.
Here in Germany I would have trouble getting CH2Cl2.... ;-) Its use is restricted to labs and industry and not for private use! ;-) Nicely demonstrated! Check the water solubility of your alcohol! And during the destillation you should have added a solvent that has a higher boiling point than your desired alcohol!
Your videos are super interesting. I love binge watching them.
This is so awesome,just almost two years late. Should've watched in high school.
Goblin can u help me with a sub to nne??
I wonder why it is a controlled substance in the US.
That's a good question with a lot of things lol
Because some losers want to make some shit to get high, and we have to protect our worthless losers from themeselves.
It's a precursor for the manufacturing of methamphetamine.
The Cannizzarro is one of the lesser favourable name reactions. It's a disproportionation reaction converts a valuable compound (aldehyde) into a mixture of two less valuable (alcohol and carboxylic acid). It's like the acidic ether synthesis which is only favourable if you want to create symmetric ethers. For asymmetric, the Williamsen synthesis with the alcoholate of the on chain and the alkyl halide of the other chain is more favourable because it is a specific reaction. Likewise, you create esters by using an alcoholate and an acyl halide.
is it possible to extract taurin from energy drinks?
Oh u mean Bull pee
@@Shazzkid I suggest Red Bull.
@@hotaru8309 boy do i have news for you :D
Concerning your Question: I'm pretty sure that some of the produced Benzylalcohol reacted with oxygen to fomr benzoic acid.
NileRed you should do a tour of your lab with all your crazy glassware, like is your house a lab? Im just super curious to see all your equipment and where you film and stuff
Just been recommended this... Don't fully get the chemistry... but I'm loving it!
Hi NileRed, another solid video, thanks! Did you use a procedure you found or did you put it together yourself? I'm trying to plan an experiment for some visiting students to try but I haven't found a straightforward prep so far.
Love your videos Nile! Keep up the good work! 😀 (Noti Squad!)
Thanks!
You can still get Afghan hash in Canada, apparently any reagent you want imported as well.
2:05 Bitter almond oil is available on Etsy and Benzaldehyde on Ebay. Pretty sure it isn't a controlled substance.
Etsy is full of Essential Oils
Plot twist: he’s teaching us all the chemicals you need to manufacture crystal meth in all his video. Each video is a different ingredient.
So what?
What program do you use to draw the reaction mechanisms ? Chem sketch ? Or something else ?
One factor that may have led to the loss of the benzylalcohol is that you used DCM to extract it. DCM has a high tendency of forming an emulsion with water, which is the cloudiness you spoke about. Since you had quite a bit of DCM still in the water after the separation some of the benzylalcohol may have been dissolved in the aqueous part. If you had used another solvent for the extraction, like chloroform that doesn't form emulsion with water as much as DCM, your yield would have been higher.
I went to the Cannizzaro High school, yeah
I don't know why but I felt this video was a lot of work (maybe a bit more than usual?) with the ton of details that you provide :D
Looking forward for the next videos then :P
Yeah it took me a really long time to make. I like to be detailed though!
NileRed And we do as well !
Yes, I know I appreciate it.
he said the reaction does not work if the aldehyde Does Not have an acidic alpha hydrogen. This means it should work with Formaldehyde. 𝙄𝙣𝙩𝙚𝙧𝙚𝙨𝙩𝙞𝙣𝙜.
I dont understand any thing but it is fun to watch the video
That NMR video idea you mentioned in the past sounds very good!
Why is benzaldehyde illegal in the US? Is it just because its really poisonous?
Purin1023 it's a precursor to amphetamine and methamphetamine.
It's not illegal. Rather, it is on the DEA list of watched chemicals, which means manufacturers and sellers must file reports with the DEA for tracking purposes. Benzaldehyde is a common precursor for many drugs, both legal and illegal.
www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm
Ah right. Drugs was going to be my second guess. Why do people gotta ruin everything?
Thanks guys
Purin1023 For money. That's all.
That makes more sense. I went and looked at the Wikipedia page, curious why it was controlled, and it said the FDA lists it as Generally Regarded as Safe and even the EU approves it as a flavor additive (and they tend to quite aggressively ban anything with a hint of risk about it). It did mention that it was used as a precursor in some pharmaceutical production, though, so I guessed maybe it was something like that. The list you linked to has a bunch of things I am not surprised are watched (like pepiridine and several ephedrine-related things) but also some innocuous things like iodine. The 'List II' contains lots of stuff that I'm pretty sure aren't watched though, like sulfuric and hydrochloric acid. I bought concentrated hydrochloric acid off of Amazon no problem a couple years ago (best tub cleaner for hard water deposits around) and I'd be surprised if that was reported anywhere.
oh yes! the Cannizzaro effect! it is my favorite show
its funny that i hear your Voice when i read the Description of your Glassware in your shop :D
Lol
Can u sub to me ??
You could, using a rotary evaporator, evaporate the DCM which at lower pressure boils at about 30 to 45°C while the benzoyl alcohol boils at room temp at ~200°C so you are kind of fine.
very good video, once again :)
Thanks!
If you want the crystallizing solution to cool down slowly, wouldn't it make more sense to just leave it on the hotplate after turning it off?
I think the alcohol had such a lower yield because of your method of distillation, or rather, your equipment. I believe the best course of action would have been to have used a more complex heater, one that is capable oh holding a temperature automatically. That way you are not hoping that all the alcohol is evaporated by the time the temperature reaches and surpasses its maximum. I believe that the lost alcohol was unable to evaporate before the temperature reached too high and the distillation was stopped.
I suspect that the biggest issue was in the distillation process of the benzyl alcohol. When you cannot accurately control the temperature of the solution a great deal of the alcohol will be lost before and after the transfer of temperature from 200 to 206.
Hey Nile, love your videos! This is a very interesting process as usual, but I don't think I speak alone when I say I never quite fully understand your videos, even with the side explanations and sources. I'd love to get a better understanding of your videos by doing a crash course of sorts in Organic Chem, as that branch of chemistry seems to make up the larger portion of your videos. I assume you have a degree in Chemistry and likely learned most of what you know from getting it, but are there any particular helpful (and preferably free) sources of basic Organic Chem instruction that you've used in the past? If so it would be awesome if you could point me to them. And, if I could make a suggestion, I'd love to see a cholesterol extraction (or maybe even synthesis) in the future, with it being such an important chemical and all.
Once again, love your videos and hope you continue to make them in the future!
Hey, I appreciate your input. I do want to do some intro videos. What topics would you like me to cover in particular?
NileRed Wow! Thanks for the prompt reply! I suppose the easiest to explain and most helpful generally would be a deeper understanding of organic structures and their models, which once that is understood should help make comprehending a process much smoother. I find this along with terminology for certain reactive processes (e.g. reduction, oxidation, and so on) to be a big blocker when trying to figure out what's going on at a deeper level. Explaining common processes/terminologies could be done by introducing and fleshing out a term or concept and then using an example reaction (perhaps an excerpt from a previous video) to supplement it. These videos could be short and palatable, possibly part of a series, and relatively easy to make (in comparison to your other videos) and help the viewer digest your content easier without taking too much attention away from your bigger projects.
TL;DR - Short, sweet videos covering important processes, model comprehension, and terminology would be nice.
+NileRed For instance when you talked about acidic alpha hydrogens, I can see why non-chemists get lost. When such notions are encountered, maybe you can do an addendum where you explain the theory a bit more, like why a particular hydrogen atom in an organic compound is considered acidic and how to identify the most acidic hydrogen in a compound (you would need to explain resonance and inductive effect I suppose).
Using a second and third distilation to improve yeild.
Looks like a nice cup of tea.
CHARIZARD REACTION... Believe me that's how I read it...
Why i didnt discover this content during my bachelor in Chemistry!? i failed my oc paper many times 😰
Great explanation.
what book could i use for learn more about synthesis in laboratory? ... i love you channel!
Bro chemistry is nuts
Man I studied this do frequently till now but watching it being demonstrated is amazing... Good job (I guess you could try the Aldol condensation too)
Other UA-camrs: Can't handle the slightest amount of constructive criticism.
NileRed: "Feel free to criticise ANYTHING involving my technique, or the method that I used." - What a madlad. ^^
But in all honesty: I'm not a chemist, nor do I have any hobbies involving more than knowing the most basic reactions. But once in a while, I really enjoy watching this guy's content. He explains everything really good. (except for the times he just gives you a chemical structure instead of an explanation, but I'm sure this is explained in other/earlier videos of his making. xD) It's fascinating almost every time, and you still take some knowledge with you, every time you watch. Even if you don't remember every detail.
The internet (and the youth of today, who tend to have access to it waaaaay earlier than my generation) need more people like him. ESPECIALLY with all that TikTok sh** going on.
Very nice demonstration. A problem with using DCM for workups from alkaline aquaeous solutions is that it forms an annoying emulsion. Either diethyl ether or a hexane/ethyl acetate mixture will give you a quicker, cleaner workup.
Thanks for the tip
NileRed You're welcome! I've always wondered why you don't monitor your reactions with TLC. Any particular reason?
A wee tip that i use to dry DCM and Chloroform is to put the wet DCM in the sep. funnel along with some saturated NaCl (brine) solution. it pulls out some water from the DCM into the aqueous and will mean you need to use less magnesium or sodium sulfate :) (also makes filtering off the solids easier)
fun fact: switch carts are coated in denatonium benzoate to prevent swallowing
At 7:45, why not separate the two initially with filtration? The two could then be separated further as you specified; but it seems like less would be removed as waste from the process.
now I was reading chapter - aldehyde and ketone and notification came
The way you fluffed the benzoic acid seemed a little disappointed or partially satisfied........... LoL
Ur a hero can u sub to me??
The problem with Cannizarro reactions is a narrow scope, harsh reaction conditions and low yield, as it's both the reagent and the substrate.