ฝัง
- เผยแพร่เมื่อ 26 ก.ย. 2024
- Today we are going to be exploring the Cannizzaro reaction!
Videos:
• Benzene: • How to make benzene
• Skatole: • Making skatole - The e...
• Denatonium Benzoate: • Making denatonium benz...
• Benzaldehyde from Bitter almond oil: • Making Benzaldehyde fr...
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Nile talks about lab safety: • Chemistry is dangerous.
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
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.
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
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
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?
"candid sorrow reaction". Gotta love those automatic subtitles.
That's quite a nice phrase as it goes
I thought this said aromatic subtitles
17:13 The crystals ! They're beautifuuuul !
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
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.
The automatic subtitles said "candid sorrow reaction" and tbh, I really felt that...
AKZ can u sub to me??
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
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!
When you have no idea what's going on but enjoy the videos: Yea, science!
You hear that Mr white?! Yeah since!
Where did you get the mixer in the beaker?
@@unizero_ ahhh Teflon. That good old not at all controversial substance.
@@idrinkmilk282 what's the controversy? Considering it's literally designed to be inert in doesn't at all react with the human body... Though I think I read a guy passing out from fumes after dry frying the pan for hours. No long term effects on him either though
@@oivinf 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.
@@idrinkmilk282 OK I see, so it's specifically the brand Teflon and the company producing it - not the chemical itself or its properties
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
the fact that i watched this video for the first time like 3 ish years ago, had no clue what it was, just thought it was rlly cool and now i was searching for the mechanism of cannizzaro for my exams and found it here is just weirdly wholesome to me.
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!
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 😢 😖
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
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!!!!!!
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
This has to be one of the most beautiful recrystalizations I have ever seen.
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!
Hearing Nile say "crap" really just warms my cold dark soul.
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
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
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.
Haha, just wrote this reaction in my test and got full marks
Thanks for helping me study for my OChem 2 test. You're the man
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
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.
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.
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.
Watching crystallization is amazing
Nile red helping me get through high school chem.
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
You must do more smaller size liquid-liquid separations to reach more efficiency on the benzyl alcohol.
weird pepsi
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.
The way you fluffed the benzoic acid seemed a little disappointed or partially satisfied........... LoL
Ur a hero can u sub to me??
And don't forget that benzaldehyde actually oxidises very easily in air, especially at temperature, so that might also explain your yeld
Ah yes, The Cannizzaro Reaction. It's that hidden camera, magic, TV show.
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?
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.
Congrats on 100k
distill into a cold bath, the colder the better.
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??
very nice video , studied chemical engineering and i'm still learning when i'm watching your videos.
Your videos are super interesting. I love binge watching them.
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.
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.
Hey; I love you broski. Thank you for all of your videos.
-O
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.
Why i didnt discover this content during my bachelor in Chemistry!? i failed my oc paper many times 😰
CHARIZARD REACTION... Believe me that's how I read it...
Every time I try this experiment somebody always takes a shit in the separatory funnel.
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
You can still get Afghan hash in Canada, apparently any reagent you want imported as well.
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 wasn't sure if you were in Europe or Canada cause of bilingual labels but now I know. ☺
very good video, once again :)
Thanks!
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.
now I was reading chapter - aldehyde and ketone and notification came
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!
I love you, i was struggling to prepare this reaction as a student and now everything gas illuminated in my brain
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 ??
Love your videos Nile! Keep up the good work! 😀 (Noti Squad!)
Thanks!
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.
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).
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
Concerning your Question: I'm pretty sure that some of the produced Benzylalcohol reacted with oxygen to fomr benzoic acid.
Such an amazing video, thank you so much!!
Just been recommended this... Don't fully get the chemistry... but I'm loving 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
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.
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?
What program do you use to draw the reaction mechanisms ? Chem sketch ? Or something else ?
I'm not a scientist or a chemist or anything I just like watching these
How about the other way round. e.g. ethanol + acetic acid to produce ethanal? Maybe presence of bisulphite could force the reaction towards ethanal?
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 went to the Cannizzaro High school, yeah
If people in the US are curious about the legality of making Benzaldehyde for private/internal/legal use it is probably ok, see below:
PART 1309 - REGISTRATION OF MANUFACTURERS, DISTRIBUTORS, IMPORTERS AND EXPORTERS OF LIST I CHEMICALS
REQUIREMENTS FOR REGISTRATION
§1309.24 Waiver of registration requirement for certain activities.
(h) The requirement of registration is waived for any manufacturer of a List I chemical, if that chemical is produced solely for internal consumption by the manufacturer and there is no subsequent distribution or exportation of the List I chemical.
(k) Any person exempted from the registration requirement under this section must comply with the security requirements set forth in §§1309.71 through 1309.73 and the recordkeeping and reporting requirements set forth under Parts 1310, 1313, 1314, and 1315 of this chapter.
PART 1309 - REGISTRATION OF MANUFACTURERS, DISTRIBUTORS, IMPORTERS AND EXPORTERS OF LIST I CHEMICALS
SECURITY REQUIREMENTS
§1309.71 General security requirements.
(a) All applicants and registrants must provide effective controls and procedures to guard against theft and diversion of List I chemicals. Chemicals must be stored in containers sealed in such a manner as to indicate any attempts at tampering with the container. Where chemicals cannot be stored in sealed containers, access to the chemicals should be controlled through physical means or through human or electronic monitoring.
PART 1310 - RECORDS AND REPORTS OF LISTED CHEMICALS AND CERTAIN MACHINES
§1310.05 Reports.
(d)...manufacturers that produce a listed chemical solely for internal consumption shall not be required to report for that listed chemical. For purposes of these reporting requirements, internal consumption shall consist of any quantity of a listed chemical otherwise not available for further resale or distribution...
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.
fun fact: switch carts are coated in denatonium benzoate to prevent swallowing
To increase the yield do what all year 2 chemistry students do. Start with 200 % raw materials.
19%, you drank it Nile.
Benzoic acid is a major component of lingon berries and makes adding preservatives to those berry products unnessecary.
oh yes! the Cannizzaro effect! it is my favorite show
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)
You propably didnt lose so much benzylalcohol. benzaldehyde got oxidized before it could get used up in the carnizarro reaction. benzaldehyd is a pain in the ass.
That NMR video idea you mentioned in the past sounds very good!
nice pronuciation of Cannizzaro(kahn-its-aa-ro)
Lol
Blabhllaa can u sub to me plzz
Great explanation.
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)
If you ever feel bad for not understanding this stuff (like me) remember this guy has a BSC in chemistry with a minor in pharmacology, and was also a lab tech and has worked in an organic chem environment
That 19% gap because of you equipment. You a real lab.
Regarding benzyl alcohol work up. After the bisulfite step, you washed with distilled water then went and dried with magnesium sulfate. I usually do one brine wash at the end to remove some water, then I dry with magnesium sulfate. I found this way I use way less magnesium sulfate.
omg i was just watching this in class so I had cc on and cannizzaro was changed to "can it sorrow"