> chemistry > organiques-simples > the-cannizzaro-reaction-nilered

The Cannizzaro reaction

NileRed - 2017-02-02

Today we are going to be exploring the Cannizzaro reaction!


Benzene: https://youtu.be/X10VZeQmFDo
Skatole: https://youtu.be/eZ56LDCABrA
Denatonium Benzoate: https://youtu.be/GOw_I42eUpM
Benzaldehyde from Bitter almond oil: https://youtu.be/a95a0iMOICU

Nile talks about lab safety:  https://youtu.be/ftACSEJ6DZA


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obpinkslip - 2017-02-22

13:49: "a bunch of red orange crap". Scientific and precise to crude in 5 seconds. This is my favorite part. :)

Rémi Héneault - 2020-10-09

My favorite is: "some polimerized junk"

A. Lampman - 2020-10-19

yellow chem bad

orange is just yellow chem with extra steps

orange chem bad

christy mae dal - 2020-11-10


Curtis Miles - 2020-12-01

@christy mae dal you suck

christy mae dal - 2020-12-02

@Curtis Miles no you suck

Gustavo Marzullo - 2017-02-03

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.

Daniel Lelievre - 2020-12-26

95th edition sounded like a meme and I googled it thinking no fucking way a book was at its 95th edition.. and sure enough by the time I looked it was 101st edition... goddamn !!

Jean-Luc McDonald - 2020-12-26

@Daniel Lelievre textbooks are like that

Ricardo Pesenti - 2021-02-07

@Daniel Lelievre Yeah. The handbook of chemistry is amazing and extremely useful. I used the 96 th during my education.

Cynefin Cryptid - 2021-03-08

​@Kasper Abigail r/woooosh

Kasper Abigail - 2021-03-09

​@Cynefin Cryptid r/woooosh yourself. It's obvious but some its not so I clarified. Quit wooshing b4 I call the woosh police. I was gunna be mean about it but I'm not allowed anymore. My boss said its bad for channel growth.

Vokaynroks - 2017-02-02

The crystallization timelapses are always awesome.

XPNDBLhero - 2019-12-01

I love them too¡! 😊

The_Emanu3lson - 2020-11-09

U right

Hashigawa Nuke Plays - 2020-11-16

with some nice crystals

Jan Baxa - 2020-12-28

I am dumb and dont understand anything :D
I am here only for that :D :D :D

Get Crafty Crafty - 2017-02-05

Where did you get the mixer in the beaker?

Shellshocked Bros - 2020-12-28

@I Drink Milk I won't take this blasphemy from a guy who drinks other animals breast milk. "Ever"

Øivin Fjeldstad - 2020-12-28

@I Drink Milk I find it the other way around. So many people are scared of non-stick coatings which is highly unscientific. (Same people who are afraid of vaccines and treat preventable diseases with snake oil etc). Doing the research yourself, however, you can quickly come to the conclusion that PTFE (Trade mark Teflon) is indeed very safe and has been tested as such multiple times.

Now, what is released into the water supply during manufacture is NOT the same as cooking with the final product. I don't know anything about that, but I'm not surprised if a big multinational company has negligent business practices

Lara İpek - 2021-01-17

to my knowledge the dangerous stuff isnt the teflon coating itself, but what gets released once the inert coating is scratched or damaged. people keep using their pans once its damaged and its really dangerous

TrueVikingMorals - 2021-01-24

@I Drink Milk PFOA is the major exotoxic part of teflon synthesis, not PTFE. its use in cookware has been discontinued since 2013, and was phased out of manufacture by US companies in 2015. also you're not gonna get cancer from a stir bar lol. that being said, workplace exposure and environmental contamination through factory waste are both extremely problematic, especially in the global south

I Drink Milk - 2021-01-25

@TrueVikingMorals i wasn't implying you could get cancer from the small amounts in the retail items... i just mean it is overall dangerous and controversial. Which, if you look back at the beginning of this conversation, is the entire point i was trying to make initially.

StonyJoe - 2018-12-02

"Can also ,apparently, be used as a weak local anesthetic."
Did you find that out the hard way?

AKZ Music - 2019-08-31

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

Wishing weezy - 2020-01-31

AKZ can u sub to me??

Tùng Hoàng - 2017-02-03

How about extracting Nicotine from cigarettes?

Christopher Bownes - 2021-01-14

@Maximal Crazy nicotine will give you lung cancer just as easily as caffeine in sugar will give you stomach cancer.

It's what else is in the cigarettes that ends up causing lung cancer. B

Maximal Crazy - 2021-01-14

@Christopher Bownes caffeine in sugar causing stomach cancer...what is this logic...when did sugar start containing tons of caffeine and when in the world did caffeine turn into a carcinogen? Because I can't find shit about Caffeine being a carcinogen. You must be from some alternate dimension with that logic

Christopher Bownes - 2021-01-14

@Maximal Crazy I meant to type soda. My bad. Nicotine won't directly give you lung cancer. It's the tar, and other fucked up shit they throw in cigarettes that gives you lung cancer.

Diony Cepero - 2021-02-24

@Maximal Crazy nicotine isnt the cancer causing stuff in cigarettes. And hes saying youll be just as likely to get stomach cancer from caffeine as satire, because there are no known cases of stomach cancer from just caffeine. I wonder why you got so offended lol

seven ! - 2021-02-27

@NileRed have ya done it i’m not sure if you did sufhelfm

Jayy-B. van Vanite - 2020-12-22

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

Ailerath - 2017-02-07

Benzyl makes everything sound so happy.

Alice Raspii - 2019-03-04

It sounds like Denzel.

Nasheed - 2017-02-02

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 - 2017-02-03

All good suggestions!

Cezar Catalin - 2017-09-07

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.

jaco gomez - 2017-09-23

ᏰĪᏝᏝ ՇÎρɧᏋƦ a little over kill i think...

Pax Liberum - 2018-11-11


Jacob Andrew - 2020-10-16

@jaco gomez this made me laugh out loud

Barnesrino Kripperino - 2017-02-03

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

mmmhorsesteaks - 2017-02-03

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

Barnesrino Kripperino - 2017-02-06

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

mmmhorsesteaks - 2017-02-06

Barnesrino Kripperino oh snap! so which was better?

Barnesrino Kripperino - 2017-02-06

cyanide by far, ther was about 30% yield with thiamine and nearly quantitative with cyanide

Mathew Alani - 2019-07-19

@Barnesrino Kripperino i learnt what thiamine does followed by later catalysts which give much better results just a few months ago

TheRokkis - 2020-10-15

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 =)

Sarah Mechem - 2019-12-24

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

Wishing weezy - 2020-01-31

Sarah cN u sub to me plzz ??

GigglySam Entz - 2017-02-04

17:13 The crystals ! They're beautifuuuul !

daniel gorzel - 2017-02-03

Too much knowledge for me,can't watch it or my brain will evaporate.

daniel gorzel - 2017-02-11

@Hacker doge samurai dinossauro megazord felps good idea,i'll do that in a sec.brb

Mystic Virgo - 2017-05-15

an ethanol wash of contaminated brain matter is highly effective :)

Dual Perception - 2017-08-16


Noodle Kaboodle - 2018-02-01

twoja stara no your brain would sublimate, because an evaporation is a conversion of a liquid to a gas whereas sublimation is a conversion from a solid to a gas. So unless your brain is a liquid it’s not going to evaporate

Ectomorpheus - 2018-10-25

or "Nilate" ;)

Michael Evans - 2017-02-04

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

Michael Addis - 2020-03-30

Was wondering the same thing

Aidan Coleman - 2020-10-16

Hi professor Evans just started watching this after your lecture!

Saishab Lohani - 2019-07-19

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

Tom's Lab - 2017-02-03

I'm supposed to be doing homework but NileRed is more important!

NileRed - 2017-02-03

Dont fail because of me!

Rosi Mortu - 2018-11-01

NileRed is my homework, I love my teacher

Alguien De Internet - 2020-01-10

@Rosi Mortu yo is that true

taktoa - 2017-02-02

I liked the video. Your explanation of recrystallization was pretty surprising, given the billions of other videos you've uploaded in which you recrystallize a reaction product without explaining the concept.

NileRed - 2017-02-02

Yeah that is true. I just felt like adding a little bit of extra info here.

Benjamin Larson - 2017-02-03

taktoa yeah that surprised me as well

Terrence Zimmermann - 2017-02-03

Yeah, but he did a whole video on the topic once. He recrystallized urea as an example.

Benzene ring - 2017-02-04

What program do you use to draw the reaction mechanisms ? Chem sketch ? Or something else ?

Michael Howlett - 2017-02-07

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.

Maddie - 2017-02-11

Yay, now to can cure your athlete's foot and ringworm.... if you have them that is...

hungrypikachu135 - 2018-11-18

"red-orange crap"

Tommy - 2020-09-28

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

Nate M - 2020-08-05

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

TheKnaeckebrot - 2017-02-04

I think you lost some of your benzoyl alcohol in the destillation because of the water present, it'll form an azeotrop of 9% benzoylalcohol and a BP of 99,9°C ...

we need to get you a rotavap! :D

Faris Omar - 2020-12-20

Why i didnt discover this content during my bachelor in Chemistry!? i failed my oc paper many times 😰

7ele5crivente - 2020-12-27

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

IED - 2018-10-12

14:42 spicy ginger ale

Mason Gatz - 2017-02-03

What's your favorite type of reaction to perform?

NileRed - 2017-02-03

Hmm, i am honestly not sure. I like the ones with nice crystals

Owen Jackson - 2017-05-08

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


Lokendra Pavan Kumar Pappala - 2019-06-03

19%, you drank it Nile.

Manoj Kumar - 2019-10-05

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

R0T0M0L0T0V - 2018-09-15

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

Creme Jockey - 2020-02-03

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

Cat Mat - 2021-02-18

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

TASEEN - 2020-11-20

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.

johnnybro13 - 2017-02-03

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

magic wizard man - 2017-02-03

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.

Ineedmoney - 2019-06-21

I wonder why it is a controlled substance in the US.

Pendragon - 2019-06-22

That's a good question with a lot of things lol

sammorgan31 - 2020-02-23

Because some losers want to make some shit to get high, and we have to protect our worthless losers from themeselves.

CyberCyborg 20XX - 2020-04-22

It's a precursor for the manufacturing of methamphetamine.

Garik14 - 2017-04-21

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

John Yeager - 2019-03-26

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

Ben van Delft - 2020-12-28

Using a second and third distilation to improve yeild.

José Luis Rivero Aragón - 2018-05-30

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

Thomas Burkhart - 2020-06-29

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

Silent Gamer - 2018-10-20


Jose Alberto Aldana Osma - 2017-02-02

NileRed I love your web page, I hope you make this new tool something equally wonderful as this channel. I fully share your opinion of the website about what is the chemistry and the proposal of your work, I try to do the same every day In a country where there is no interest or respect for this act of faith so wonderful that it is to be chemist full time. Congratulations, a hug.

NileRed - 2017-02-03


Z Zacque - 2020-01-28

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

Yelz G - 2017-02-06

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

LimitlessDeadline - 2017-02-02

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

NileRed - 2017-02-02


Shreyan Mhatre - 2020-12-16

we have similar reactions in India 12 th organic chemistry so it was to see in practical