Making Cinnamic Acid

[@steavf9455]

Nile's coming through with another top hit "Generic Timelapse Song 1" and it's honestly one of my favs

[@jay8762]

lmfao yeah same

[@tres909]

Definitely a banger!

[@bluelichen9696]

The Bob Ross of chemistry.

[@eclectichoosier5474]

Aaaaaaand we'll just put a happy little moiety right there.

[@elephystry]

Wayne Moore I love you XD

[@Gamma_Radiation]

The only issue is a "happy accident" goes boom

[@DereliqueMahBAWLS]

@@elephystry who is Wayne Moore?

[@elephystry]

@@DereliqueMahBAWLS I’m sure I would remember after three years.

[@NextGenAge]

Beautiful timelapse! Sometimes I forget that this really looks like pure magic, some crystals look like universes floating around :)

[@NileRed]

Crystallizations are always mesmerizing for me. Especially the ones that grow nice and long crystals

[@ParadoxDetected]

@@NileRed you like it nice and long eh 👀

[@bruhmomento8038]

@@ParadoxDetected bruh

[@LulfsBloodbag]

@@NileRed Hey Nile, would you ever think of remaking this video? Cinnamate can be devirved from cinnamon oil apparently, and I think that would be a co twist - turning cinnamon into cinnamic acid or something like that

[@drasiella]

Me: Talk dirty to me babe Nile: _Decarboxilation_

[@balasahebdeore8828]

carboxylation.

[@professionalchemist5599]

Hydrogenation

[@johnapple6646]

Distilled water.

[@starlight4649]

Esterification

[@pan_man69]

I don't know why but this made me laugh so hard that my mom screamed from the other room are you okay

[@pockpock6382]

after watching a whole bunch of NileGreen this is very refreshing and nice to watch and follow. I like this classic chemistry vids from Nileboi

[@ChevisPreston]

Nile, I just wanted to say thanks. I got into your videos a long while ago, and, because of them, I was influenced into choosing biochemistry over a typical bio-premed track. After working with organic chemistry and all that jazz, I've got to say, I love chemistry so much. I would have never known without you bud.

[@alex3mirillas]

Nile! I love when you explain all the reactions!

[@NileRed]

thanks! :)

[@apburner1]

The last time I decarboxylated it was in the oven at 230° F for 45 minutes... umm... nevermind.

[@NileRed]

#reportedtothepolice

[@elephystry]

NileRed #snitch

[@drasiella]

Share some with me!

[@cvspvr]

@@elephystry wait a minute! you changed your name!

[@elephystry]

caspar valentine I did!

[@Antonio-wh8lh]

10:28 NileRed: uses thermometer to stir mixture Every chemistry teacher: You weren’t supposed to do that.

[@chemistryofquestionablequa6252]

We ALL do it

[@GrassPossum]

Those who can, do. Those who cannot, teach.

[@christopherwellman2364]

@@GrassPossum Those who cannot teach... teach gym.

[@kevinbyrne4538]

Your videos just keep getting better and better. I was impressed by the presentation of the reaction's mechanism (4:48). Very professionally done.

[@mannys9130]

Those crystals are really beautiful Nile. Nice "generic time lapse music." :)

[@aptom203]

Verley-Doebner modification of the Knoevenagel Condensation sounds like something they'd make up to sound scientific on Doctor Who or Star Trek.

[@SunlightAldo]

0:22 "were gonna be using the very dope modification of the nova bagle condensation"

[@eclectichoosier5474]

After you've made styrene, maybe you could make one about how to convert it back to benzene or other useful things? It would be a great way to recycle all of the styrofoam packaging from the glassware!

[@elephystry]

Wayne Moore Extractions&Ire did a few lovely videos on converting soda bottles to benzene.

[@AquibMohammedAyman]

Did he made the styrene yet? Really want to see

[@ralbiruni]

This synthesis is elegant because it avoids the passage through the ester!

[@BlizzardofDiamonds]

Started watching NileRed years ago but I just passed my organic chemistry lab and exam at uni last week and the knoevenagel condensation was one of my faves to learn actually :D

[@Mic_Glow]

Knoevenagel Condensator sounds like a magic device from Witcher.

[@zillertalernazihass]

He pronouced it completly wrong. Its spelled Knöwenagal (The letter ö doesnt exist in English)

[@aqdrobert]

Doctor Who: It DINGS when there's STUFF!

[@skipfred]

@@zillertalernazihass en.wikipedia.org/wiki/Emil_Knoevenagel

[@efenedick1305]

The fact that there's both a trans- and cis- version of the acid makes for some great pun potential!!

[@lilylavender4709]

Facts lol

[@absolutelyrandom4978]

tempted to use this video to come out someday “i relate a lot to the chemical he makes in this” *attaches video link*

[@Awsome-im5hq]

You're videos never fail to entertain me and help me keep my mind off of anything and everything that could possibly be going wrong. Thank you and keep up the great work!

[@brunodemarzio]

I could swear this was something present in cinnamon 😂🤣

[@evebruun]

cinnamaldehyde is

[@FilbieTron]

I already watch these videos to fall asleep and the pleasant music at 9:37 really amplifies my sleepiness 🥱😴

[@ECM398]

idk about the branded beekers but depending on the price id be down for a labcoat

[@a3xccy379]

Same also spatula or tongs would also be cool

[@eclectichoosier5474]

I got some of the beakers. They're pretty nice.

[@yungcahley9196]

I am an organic chemistry student at the University of Oregon and I recently performed this reaction in lab. In our procedure we placed malonic acid, piperdine, benzaldehyde and ethanol in a reaction tube and heated in a microwave. Afterwards we acidified with HCl and vacuum filtered the product. I thought your procedure was extremely interesting and one I had not considered before. I was curious if there is anything interesting I might be able to make with my remaining cinnamic acid?

[@beanlets]

Esterification?

[@lebakas_peppi]

How did university work out?

[@marialiyubman]

3:20 I giggled when you said Dr. Seuss reaction. 😂😂 I also get a tingle down my spine when you recrystallize stuff. I feel like it’s snowing. 😍

[@ishzarkklyon9590]

Smh e-girl

[@ATLTraveler]

You giggled? Are you 12...

[@cvspvr]

chemistry... asmr?

[@manuelbonet]

You are amazingly good at explaining

[@NileRed]

Thanks!

[@diegociolpan7441]

I love this video. You really saved me in my OC1 Lab with this video.

[@justinhowcroft7441]

you could make a time lapse album and get it published. i suggest giving the songs real names 😀

[@NileRed]

Are you telling me that Generic timelapse song #1 isn't a good and real name? :(

[@johnblacksuperchemist2556]

GREAT VIDEO. Can't wait till i am this far in the lab

[@MegaWizardman1]

I would deadass buy a Nile red lab coat and wear it every single lab I have throughout my undergrad and graduate schooling, as well as if I secure a job teaching college level chemistry!!!

[@mukundsharma1006]

man i miss these longer videos

[@professorprotonfan7287]

Yay! A new NileRed video.

[@dumdumdumbest834]

Professor proton is not real its sheldons hero

[@cannagorilla]

ill take a beaker with your name on it, i would def become a top tier supporter. your the best out here brother

[@NileRed]

Thanks! :)

[@Derpysaur]

this is a cinnamic masterpiece

[@steves6762]

That's an interesting way of using beta-alanine

[@KingNast]

I think it would be cool if you put together some branded chemistry starter kits

[@NileRed]

That would be the ideal in the future

[@Asdayasman]

NileRed Nile my dude if you put together a starter kit and did a bunch of videos of stuff you can do with it, I'm fucking for h*cking sure buying that. If I had kids I'd be buying them each a set, too.

[@thenadonation2664]

I dont know why i enjoy listening to the nerd so much, but i have watched probably all of his videos more than once.

[@ishzarkklyon9590]

The stir bar is crazy

[@rachidabkar9747]

Very professionally done

[@manuelbonet]

I am willing to see the Nylon video

[@gustavopires3400]

This one is really nice! Love to see those mechanisms! 😁

[@SpiGAndromeda]

Whoose heart also stopped for a moment when he dropped the stirr bar right into the flask?

[@gamingmarcus]

Thank god we'll get at least one more video this month =P

[@NileRed]

One last will be posted tomorrow, but i made it in sept

[@buzzlightyear2827]

This dude is on a list

[@tyler6602]

Your mom's contact list

[@Cinnimin]

thank you nile red for finding my origins.

[@obihz2415]

I did it 2 months ago Using the aldolic condesation

[@theginginator1488]

The lab coats should absolutely be make with the dye, Nile Red

[@sammylovescookies7439]

I think the Beaker and Lab Coat ideas are really good ^ - ^

[@lucasimark7992]

could you try making PLA plastic (Polylactic acid)? That would fit in nicely with your polymer experiments!

[@Mike111Hunt]

The discolouring in the Pyridine could be from additives to prevent its usage in drug production of PCP. Oxidising the Pyridine to Piperidine with Raney-Nickel.

[@tommypampalone9850]

We actually had a lab in Orgo I where we brominated trans-cinnamic acid, interesting to see an unrelated video on it

[@krisztianszirtes5414]

10:08 Okay, that's an award winning song name.

[@pinksapphire2898]

now can you vanillic acid. then make both vanillans and cinnamons alcohols?

[@jasperday9020]

Acid... Trippy, man.

[@Mega98RP]

Hi nile, what about the synthesis of trans-3-Methyl-2-hexenoic acid (TMHA) the main contributor to armpit odor?

[@NileRed]

Ill look into it. Might be a little tough to make (depending on what the starting materials are)

[@ATFieldZenkaii]

I guess You could use pentanone and ethyl chloroacetate in Wittig reaction.

[@elephystry]

NileRed Yeah Nile, it really seems like your thing. Get it done. ;)

[@pietrotettamanti7239]

@@ATFieldZenkaii Why complicate your life with ethyl chloroacetate and a wittig reaction when you can just use practically the same reaction as this video? Malonic acid+pentanone and you're done.

[@ATFieldZenkaii]

@@pietrotettamanti7239 I don't think that pentanone is electrophillic enough to react with malonic acid. This modification of Knoevenagel reaction works only with aldehydes, which are far more reactive than ketones. Classic Knoevenagel reaction might work, but it will probably lead into mixture of trans and cis isomers. In this case, Wittig reaction is slightly more selective. If you don't want to use quite nasty ethyl chloroacetate, then corresponding ylide is commercially available.

[@TheGamersRace]

I read the title as: "Cinematic Acid" and just thought "Damn okay this weekend gonna be good."

[@vapenation7061]

I'd love to buy some lab equipment from you. I love your videos!

[@FutureAIDev2015]

Does trans-cinnamic acid have anything to do with cinnamon?

[@joost00719]

Could you do a video about experimenting with liquid oxygen?

[@theginginator1488]

joost00719 he already did

[@aterack833]

Did you ever get around to making that styrene?

[@RutgerHaan]

YES PLEASE!!!!, labcoats and beakers(maybe even more glassware)!!!!

[@ThePaintballgun]

YeSSSS Nile red beaker, I want one

[@マカシオショーン]

you're so good at recording and doing your experiment. I bet you got A's in your chem high school because I failed chem

[@NileRed]

I actually got a 65% in my first semester in high school chemistry. In both physics and chem...

[@ChannelAbundantLife]

What do you do for work? Surely you can get about any chem job you want with this channel as a reference!

[@johnblacksuperchemist2556]

GREAT VIDEO.........(I can not believe it only took pyridine to make the enolate. .I need to make some of that malonic acid and ester and some ethyl acetoacetate

[@ECM398]

You should try synthesizing some fancy organic dye. maybe coloring your labcoat with it or something?

[@TheManThatCan1002]

Can you make a video about how molar mass works? I know it's simple but it's something I could never quite get.

[@Sepp180]

I did this today in lab but i used piperidine instead of beta-alanine.

[@kayn9651]

You heard of the cinnamon challenge. Now is the time of the cinnamic acid challenge.

[@LilyMendoza19]

i loved it!

[@fineline8159]

Can i use muriatic acid from cleaning agents instead of pure hydrochloric acid?

[@Beniguitar94]

As I understand, I guess the reaction mechanism goes like: VD-Modification Malonic acid is decarboxylated generating a carbanion which is stabilized by resonance. The carbanion attacks benzaldehyde's carbonyl an generates an alcohol that is dehydrated into an alkene. Classic knoevenagel Diethyl Malonate alpha-carbon is deprotonated by a base (carbanion stabilized by resonance). Carbanion attacks the aldehyde group, forms an alcohol. Then, it is dehydrated generating the alkene-product. How is this different from an ordinary aldol-condensation? With respect to the V-D modification, one can say decarboxylation is different than the alpha-carbon base-catalized deprotonation. But for classic knoevenagel, it is the same but with a more extensive carbanion resonant structure (more delocalized electrons). Is it called differently just because of that? As a young chemist trying to learn organic chemistry, I find so many reactions names for similar concepts a bit annoying and superfluous. Can anyone throw some light into my issues? Thanks in advance for your support!

[@Beniguitar94]

Although the classic dehydratation of an aldol products goes like an E1cB, it makes no sense if the precursor is not an aldol (in this case, a beta-hydroxy carboxylate) so I guess the following is more probable for this case: Starting from the formed beta hydroxy carboxylic acid, the alpha-carbon is slightly acidic because of the carboxyl group. The base extracts one of the alpha carbon proton. the electron of the C-H bond goes to the C-C bond forming a double bond, the electron of the C-O bond goes to the OH generating a OH- leaving group (although it is a poor leaving group It can't be H3O+ because we are under basic conditions). Maybe, like you suggest, the difference relies on the dehydration step and the beta-hydroxy carboxylate precursor. Thanks for your help!

[@phillipmitchell2254]

Round bottom flasks make the chemistry world go roouuuund

[@starlight4649]

All I've retained from your teachings is how to get anesthetic from anal lube, sodium hydroxide makes water hot, and how to make soap.

[@Romuls753]

The trans form may be the most common but it also decomposes the quickest

[@souravzzz]

Do you say you are Nile Red on your resume?

[@elephystry]

U Wot M8 "I have a very popular chemistry program on the web"

[@Stettafire]

@@J.G.H. It depends on the job. Some forms of work having large internet following can be seen as problematic

[@mmmhorsesteaks]

i suspect you have water in there; explaining the lower melting point. maybe keep it in a desiccator with p2o5 and a slight vacuum for a week or so; pretty sure you will get a higher melting sample (or don't if dryness isn't super important ;-) )

[@BreadBanana]

Love that 4k vids

[@sorensen011]

I found a variant using ethanol instead of pyridin. Do you think that could work while using more Alinin?

[@GrassPossum]

HI @NileRed. May I ask if there's any reason you'd not use a heating mantle? All descriptions of the Knoevenagel I've come across describe use of a hotplate, or shallow oil bath. Is there a reason for this? I prefer a mantle for heating but find the reaction is slower than descriptions, although raising temperature has improved it. I wondered if the greater heat transfer from a mantle, to the distillation product, in my case toluene/water, (which doesn't make sense to me) is a problem. Doesn't make sense. The heat is intended to push the reaction, but can it be too much? Can it take too long? Is there any degradation of the product or reaction if greater time is taken to complete? ie; 24 hours instead of 5?

[@MohammedAdain]

Would you please do the Victor Meyer Test for alcohols

[@taliagoodwomanmann]

Can you make phenolic acid with the addition of benzoic acid?

[@Grove332]

Shouldn't you be wearing a labcoat while doing reactions?

[@NileRed]

I should be!

[@honheilee1284]

Did you do H-NMR to see whether it's pure? You should filter the hot solution by doing a hot filtration then reduce the volume of the solution a bit when you are doing recrystallisation.

[@samarthhawaldar9931]

I think that doing the Perkin reaction will be better.

[@samlabo1688]

Next let's go through barbituric acid. And some of them interesting things we can create

[@burno55_]

you forgot to put the video on pyridine in the description

[@scienceavocado5571]

Make mustard gas

[@aryansharanreddy3695]

What about Perkin's Condensation Nile?

[@samcat4005]

where do you get the benzylaldehyde from

[@martinofgliwice1486]

Do you think you can make ethylene oxide? Would be so cool if you succeeded.

[@Fayfamilyadventures]

How did you get the malonic acid? I live in the in the US and there is a restriction unless you are a company through Fischer, sigma and spectrum to name a few.

[@LiEnby]

OMG the acid is trans!!

[@beneric73]

superbe idea for the lab coat and stuff, try to make them look like Old school labware with some nerdy patchwork onto. or just a realy simple Nile Red rite on it with image of the most use glassware in a cool graphic design ! and for the glassware... i have no idea :p

[@fauxpassant]

How do you prevent cis-cinnamic acid from forming?

[@DominicNJ73]

You take away its cis privilege and make it attend organic chemistry sensitivity training. LOL

[@geetikawadhwa8418]

you should try to make instant snow...

[@GreenFanBoy]

kzbin.info/www/bejne/ipzYo2augZWDnrM is him technically making instant snow

[@gauravbhushankumar3208]

Can't use parkin reaction?

[@danielkuehn3801]

Could you get aluminum from antiperspirants/deodorants?

[@nabijaczleweli]

Sounds like much more of a Cody'sLab's thing but yes please!

[@nightshadelenar]

Probably way to little aluminium to get from those, though it might be possible it you get a lot of them, and find a relatively high yield (>80%) way of extraction.

[@RockOnDoooooooooood]

Anyone else thought it said cinnamon acid?

[@elephystry]

5k It's close enough. Cinnamaldehyde is an actual ingredient in cinnamon, which is what you get by reducing cinnamic acid.

[@houston7112]

Do dimethyl mercury

[@arteompisarchuk8236]

Hey NileRed I would like to get into some home chemistry as a hobby but I don't know what starters supplies I should get. Could you tell me what starter supplies I should get?