It's so much more fun to watch this when you're not expected to memorize it for an exam with 200 other reactions.

@roshnigupta9914

2 жыл бұрын

Ugh tell me about it I gave up halfway through the semester and just cheated on the exam

@eulalawrence4389

2 жыл бұрын

Yep

@0rzhy

2 жыл бұрын

Lul

@nishagupta4899

2 жыл бұрын

Definitely it's jee

@saadusmani78

2 жыл бұрын

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. :)

@Metalhammer1993

6 жыл бұрын

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.

@AlldaylongRock

5 жыл бұрын

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...

@Metalhammer1993

5 жыл бұрын

@@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

@drsciencebj996

5 жыл бұрын

obpinkslip when he says “damp” it sounds like “dam” so it sounds like “the dam crystals”

@PunitaBhardwaj

5 жыл бұрын

@@drsciencebj996 OMG SAME AND I WAS SO AMUSED

The crystallization timelapses are always awesome.

@xpndblhero5170

4 жыл бұрын

I love them too¡! 😊

@TheEmanu3lson

3 жыл бұрын

U right

@HashiNuke

3 жыл бұрын

with some nice crystals

@janbaxa3282

3 жыл бұрын

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?

@blood-redeemeddragon

2 жыл бұрын

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 =)

@bulgna

2 жыл бұрын

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

@Drunken.J0hn

2 жыл бұрын

@@bulgna same

@suniltembhare6800

2 жыл бұрын

Same here...

@abbiereynolds8016

2 жыл бұрын

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.

@ST3VI3RICHI3

5 жыл бұрын

Gustavo Marzullo rip

@spiderdude2099

5 жыл бұрын

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

@esquizofreniasobrenatural

5 жыл бұрын

@@spiderdude2099 but with smaller and multiple separations will improve the yield.

@christopherweaver9524

5 жыл бұрын

that was my first thought to. to much washing. could carbonate work? to wash. thT mite be a stupid question lol

@ADebbil

5 жыл бұрын

@@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.

@linxuser897

2 жыл бұрын

Telugu person spotted.

@majimadavis3602

2 жыл бұрын

im doing now hehe

@vanjinathan5877

2 жыл бұрын

@@linxuser897 every book has it 💀

@linxuser897

2 жыл бұрын

@@vanjinathan5877 He said "plus two". I think that terminology is only used in Telugu states.

@linxuser897

2 жыл бұрын

@@goos6005 o i c

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

@aajjeee

7 жыл бұрын

also i saw a mechanism that included a dimer intermediate, not requireing the Hydride to be kicked

@aajjeee

7 жыл бұрын

so yea some of it might go toward benzoine

@mmmhorsesteaks

7 жыл бұрын

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

@aajjeee

7 жыл бұрын

we actually did both to compare the yield, but yeah, scary stuff

@mmmhorsesteaks

7 жыл бұрын

Barnesrino Kripperino oh snap! so which was better?

The automatic subtitles said "candid sorrow reaction" and tbh, I really felt that...

@Wishingweezy

4 жыл бұрын

AKZ can u sub to me??

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

7 жыл бұрын

All good suggestions!

@cezarcatalin1406

7 жыл бұрын

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.

@jacogomez1093

6 жыл бұрын

ᏰĪᏝᏝ ՇÎρɧᏋƦ a little over kill i think...

@esquizofreniasobrenatural

5 жыл бұрын

This

@jacoba756

3 жыл бұрын

@@jacogomez1093 this made me laugh out loud

"candid sorrow reaction". Gotta love those automatic subtitles.

@dougsteel7414

2 жыл бұрын

That's quite a nice phrase as it goes

@user-pr6ed3ri2k

3 ай бұрын

I thought this said aromatic subtitles

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.

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

@tornadotaylor8956

2 жыл бұрын

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

Your videos are super interesting. I love binge watching them.

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.

Awesome vid as always. I can't wait for the molecule keychains I saw on your site.

@NileRed

7 жыл бұрын

I am trying to get them made as soon as possible!

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!!!!!!

When you have no idea what's going on but enjoy the videos: Yea, science!

@Cisconnotthesinger

6 ай бұрын

You hear that Mr white?! Yeah since!

very nice video , studied chemical engineering and i'm still learning when i'm watching your videos.

Thanks for helping me study for my OChem 2 test. You're the man

This has to be one of the most beautiful recrystalizations I have ever seen.

Such an amazing video, thank you so much!!

Damn going back to this after a few years you can tell much more energy/excitement he shows in newer videos

@p020z5

2 жыл бұрын

It seems like he was doing that for the university in the first place

@wpc456cpw

2 жыл бұрын

Hes definitely gotten a lot more comfortable with his narrating

That NMR video idea you mentioned in the past sounds very good!

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

man, every time he mentions redox reactions i'm reminded of the hell on earth that was high school ap chemistry

@Wishingweezy

4 жыл бұрын

Sarah cN u sub to me plzz ??

@XevianLight

3 жыл бұрын

@@Wishingweezy no. No one is going to sub to you

@Wishingweezy

3 жыл бұрын

@@XevianLight I know 😢 😖

Benzyl makes everything sound so happy.

@elephystry

5 жыл бұрын

It sounds like Denzel.

@pacificcoastpiper3949

3 жыл бұрын

Benzene is one of the things that make gasoline smell like it does

@guillomeke

2 жыл бұрын

@@pacificcoastpiper3949 in Dutch the common name for gasoline is ‘benzine’

@pacificcoastpiper3949

2 жыл бұрын

@@guillomeke interesting 🤔

@VisTerAl0ne

2 жыл бұрын

@@guillomeke in most languages in Europe people use this word for gasoline including German, Russian, Italian, Czech, Estonian, etc

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.

How about extracting Nicotine from cigarettes?

@TungHoang-xe5eg

7 жыл бұрын

Is that legal?

@NileRed

7 жыл бұрын

I will eventually!

@TungHoang-xe5eg

7 жыл бұрын

Thank you! I'm looking forward to it!

@DustinRodriguez1_0

7 жыл бұрын

It should be legal... I mean, I buy bottles of nicotine mixed into vegetable glycerin all the time for vaping.

@TungHoang-xe5eg

7 жыл бұрын

I agree

Great explanation.

Hey; I love you broski. Thank you for all of your videos. -O

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!

Congrats on 100k

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

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)

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.

Any idea what the orange-brown crap might be? My first thought is alkoxide-promoted polymerization of the benzaldehyde.

@michaeladdis3323

4 жыл бұрын

Was wondering the same thing

@aidancoleman4866

3 жыл бұрын

Hi professor Evans just started watching this after your lecture!

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?

@anchopanchorancho

2 жыл бұрын

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.

@aamborella

2 жыл бұрын

@@anchopanchorancho oh I figured as well, I just didn't know what he was comfortable with!

Hearing Nile say "crap" really just warms my cold dark soul.

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 love you, i was struggling to prepare this reaction as a student and now everything gas illuminated in my brain

Just been recommended this... Don't fully get the chemistry... but I'm loving it!

Looks like a nice cup of tea.

Love your videos Nile! Keep up the good work! 😀 (Noti Squad!)

@NileRed

7 жыл бұрын

Thanks!

Haha, just wrote this reaction in my test and got full marks

Watching crystallization is amazing

its funny that i hear your Voice when i read the Description of your Glassware in your shop :D

@Wishingweezy

4 жыл бұрын

Lol Can u sub to me ??

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.

Nice! I want to see crossed Cannizaro Reaction with formalin or paraformaldehyde, do it please!

This is so awesome,just almost two years late. Should've watched in high school.

@Wishingweezy

4 жыл бұрын

Goblin can u help me with a sub to nne??

You can still get Afghan hash in Canada, apparently any reagent you want imported as well.

And don't forget that benzaldehyde actually oxidises very easily in air, especially at temperature, so that might also explain your yeld

You've just reminded me one of my lab exercises in university. I did exactly the same reaction but I've used chloroform as extragent, then rotovap to exclude CHCl3 and then - vacuum distillation. May be that is a point of improvement. Since Benzyl alcohol has quite high boiling point some of it can decompose, I don't remember exactly what pressure I had... just a few mmHg and in this conditions benzyl alcohol boils around 60C.

very good video, once again :)

@NileRed

7 жыл бұрын

Thanks!

Falling asleep to the soothing science 😴. Guess its the Canadian voice that is relaxing.

You must do more smaller size liquid-liquid separations to reach more efficiency on the benzyl alcohol.

@bloodakoos

4 жыл бұрын

weird pepsi

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

@NileRed

7 жыл бұрын

Yeah it took me a really long time to make. I like to be detailed though!

@Eliewan

7 жыл бұрын

NileRed And we do as well !

@benjaminlarson6168

7 жыл бұрын

Yes, I know I appreciate it.

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 never get anything that is said in any of your vids, but it is really entertaining to watch

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!

Came out of chemistry class sick of making crystals, to watch you make crystals. Story of my life.

@NileRed

7 жыл бұрын

Crystals are life

@cibusvinum16

6 жыл бұрын

Inorganic synthesis is much more colorful

@hungrypikachu135

5 жыл бұрын

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

Be me, be italian, be like he actually said cannizzaro right, be proud off you

@cremejockey8636

4 жыл бұрын

R0T0M0L0T0V or a Born of Osiris fan. Their singer is Ronnie Cannizzaro

Nile red helping me get through high school chem.

Ah yes, The Cannizzaro Reaction. It's that hidden camera, magic, TV show.

oh yes! the Cannizzaro effect! it is my favorite show

How about the other way round. e.g. ethanol + acetic acid to produce ethanal? Maybe presence of bisulphite could force the reaction towards ethanal?

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.

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.

distill into a cold bath, the colder the better.

Feel like you need a longer cooling tube during distillation. Possibly losing the alcohol to vapor escaping from the water chilled column. Or run colder water through it.

I just picked up a set of beakers. I figured as a Chemistry major I should have some of my own ;)

Concerning your Question: I'm pretty sure that some of the produced Benzylalcohol reacted with oxygen to fomr benzoic acid.

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)

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

now I was reading chapter - aldehyde and ketone and notification came

what book could i use for learn more about synthesis in laboratory? ... i love you channel!

I don't know why but I watch Nile's videos to sleep.

Outstanding

I think so using diethyl ether would be much better as you won't risk forming an emulsion while mixing the two solutions....DCM may form a emulsion so it needs to be shaken less vigorously, but that's not the case with Diethyl Ether.... But It was too good to see something else than acetaminophen and all.... Excited for your next one......

Where did you get the mixer in the beaker?

@idrinkmilk282

3 жыл бұрын

@@unizero_ ahhh Teflon. That good old not at all controversial substance.

@oivinf

3 жыл бұрын

@@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

@idrinkmilk282

3 жыл бұрын

@@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//.

@shellshockedbros4458

3 жыл бұрын

@@idrinkmilk282 I still don't see the problem after reading and watching the movie. Do elaborate more please.

@oivinf

3 жыл бұрын

​@@idrinkmilk282 OK I see, so it's specifically the brand Teflon and the company producing it - not the chemical itself or its properties

Thanks dude. I always wanted to learn how to turn an aldehyde into carboxylic acid and alcohol. Those are all definitely things I know. Yup.

I would love to see a process for dealing with the green liquid that is generated from dissolving the metals that back gold (like in jewelry and computer parts). Can any of the dissolved metals be extracted?

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.

You should have made some furfural from corn cobb and perform the Canizzaro reaction on it ;)

omg i was just watching this in class so I had cc on and cannizzaro was changed to "can it sorrow"

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.

Using a second and third distilation to improve yeild.

I love this video make more videos on famous named reactions like this! All the best!

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)

@collinbardini

7 жыл бұрын

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.

@user-yb5cn3np5q

7 жыл бұрын

Correct, but chloroform should be used in a lab, not in a garage. NileRed explained why he uses DCM once.

@vx-iidu

7 жыл бұрын

+Philip Polkovnikov im pretty sure he has adequat ventilation, though

@michael101117

7 жыл бұрын

baguvix aezakmi thats what i thought lol

@user-yb5cn3np5q

7 жыл бұрын

It's like cooking cyanides in your kitchenware. It doesn't matter how good are you at washing. If you do it in kitchenware, you're going to die. No sane person is going to work with chloroform without a ventilated box. NileRed doesn't have one, he does his scariest syntheses outdoors.

Hi, may I know if there's any way to make the redox reaction to favor the production of only one product?

Maybe instead of using DCM using an aprotic solvent that can participate in hydrogen bonding, such as ethyl acetate and with benzyl alcohol, I would have done 5-6 washings, it still has some water solubility.

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

So cool!

I just checked out your online store and im not sure if this is the right place to be asking but i was wondering if you were able to ship outside of the US and Canada like to say New Zealand, the xanthine key chain looks way too epic.

Thanks

CHARIZARD REACTION... Believe me that's how I read it...

Distillation is a very poor way to extract a substance. It is just one of the more cost effective by volume. For smaller volumes either freezing, or centrifuge has a higher yield. When freezing it may take several runs to get the purity you are looking for.

18:40 "Yes, yes, makes sense" he nods while having no clue what the magic words man is telling him