NileRed - 2016-10-01
Today we make some Trans-cinnamic acid from benzaldehyde and malonic acid. The reaction is called the Verley-Doebner modification of the Knoevenagel Condensation. The classic Knoevenagel Condensation is similar to the Aldol Condensation Prep that I followed: http://www.chemistry.mcmaster.ca/~chem3d3/expt5-7.pdf.gz Nile talks about lab safety: https://youtu.be/ftACSEJ6DZA ------------------------------------------- • NileRed Store: https://nilered.tv/store • Patreon: https://www.patreon.com/nilered • NileRed Newsletter: https://nile.red/home#newsletter ------------------------------------------- • Discord: https://nilered.tv/discord • Facebook: https://www.facebook.com/NileRed2 • Instagram: https://www.instagram.com/nile.red • Snapchat: https://nilered.tv/snapchat • TikTok: https://www.tiktok.com/@nilered • Twitter: https://twitter.com/NileRed2 -------------------------------------------
Beautiful timelapse! Sometimes I forget that this really looks like pure magic, some crystals look like universes floating around :)
Crystallizations are always mesmerizing for me. Especially the ones that grow nice and long crystals
@NileRed you like it nice and long eh 👀
@ParadoxDetected bruh
@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
The Bob Ross of chemistry.
@Derelique mah bawls I’m sure I would remember after three years.
@Shaina Shortcake hmm 🤔 seems sarcastic to me because I’m sure you wouldn’t
he seems bored to me.
@Olympiakos Piräus Some people just doing like that sometimes.
or the how to basic
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
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.
10:28
NileRed: uses thermometer to stir mixture
Every chemistry teacher: You weren’t supposed to do that.
We ALL do it
Those who can, do. Those who cannot, teach.
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!
Wayne Moore
Extractions&Ire did a few lovely videos on converting soda bottles to benzene.
Did he made the styrene yet? Really want to see
Nile! I love when you explain all the reactions!
thanks! :)
Verley-Doebner modification of the Knoevenagel Condensation sounds like something they'd make up to sound scientific on Doctor Who or Star Trek.
Your videos just keep getting better and better. I was impressed by the presentation of the reaction's mechanism (4:48). Very professionally done.
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?
Esterification?
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!
This synthesis is elegant because it avoids the passage through the ester!
Those crystals are really beautiful Nile. Nice "generic time lapse music." :)
I'd love to buy some lab equipment from you. I love your videos!
could you try making PLA plastic (Polylactic acid)? That would fit in nicely with your polymer experiments!
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.
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.
Me: Talk dirty to me babe
Nile: Decarboxilation
Retro-diels alder condensation
carbocation...
@Stephen Gillie i was gonna say, i know this word from somewhere else lmao
Tar
Dihydrogen Monoxide
The last time I decarboxylated it was in the oven at 230° F for 45 minutes... umm... nevermind.
I do mine on the stove top
I don't get the joke
Never go above 300°F
@Arnav Aditya Singh it's a marijuana joke. In order for edible marijuana to actually be effective, you need to decarboxilate it and turn the THC-a into THC. This is done by cooking it at a lower temperature than its vaporizing point, typically by putting it on a tray in the oven at specific heat ranges for a while.
@rando prior I'd have enough do some deep reading, but I've eaten an 8th of raw nugs once at a concert where cops were searching people and felt some interesting effects for a good while into the next day. I doubt it was from thc but perhaps some of the other chemical constituents.
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?
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!!!
I think the Beaker and Lab Coat ideas are really good ^ - ^
We actually had a lab in Orgo I where we brominated trans-cinnamic acid, interesting to see an unrelated video on it
Is cinnamaldehyde not a possible/more accessible precursor to cinnamic acid? Your cinnamaldehyde clock video was fun to watch, but it killed me to see so much cinnamaldehyde wasted. It took me almost ten hours to synthesize ~15mL.
you could make a time lapse album and get it published. i suggest giving the songs real names 😀
Are you telling me that Generic timelapse song #1 isn't a good and real name? :(
You are amazingly good at explaining
Thanks!
Hi nile, what about the synthesis of trans-3-Methyl-2-hexenoic acid (TMHA) the main contributor to armpit odor?
I guess You could use pentanone and ethyl chloroacetate in Wittig reaction.
NileRed
Yeah Nile, it really seems like your thing. Get it done. ;)
@KK
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.
@Pietro Tettamanti 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.
Crystal meth
I could swear this was something present in cinnamon 😂🤣
cinnamaldehyde is
Do you think that glycine would also do as a catalyst instead of the alanine?
idk about the branded beekers but depending on the price id be down for a labcoat
Same also spatula or tongs would also be cool
I got some of the beakers. They're pretty nice.
You should try synthesizing some fancy organic dye. maybe coloring your labcoat with it or something?
Can you make a video about how molar mass works? I know it's simple but it's something I could never quite get.
I dont know why i enjoy listening to the nerd so much, but i have watched probably all of his videos more than once.
GREAT VIDEO. Can't wait till i am this far in the lab
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.
The trans form may be the most common but it also decomposes the quickest
YES PLEASE!!!!, labcoats and beakers(maybe even more glassware)!!!!
The quality of your videos is outstanding. A video about cleaning and waste disposal would be interesting. Is the waste department asking questions and are you acting as a private individual?
I actually have a bunch of waste sitting around. It all needs to be disposed of eventually. I might have to pay a company
Could you do a video about experimenting with liquid oxygen?
joost00719 he already did
Hi, I'm currently doing this, does it matter what kind of oil you use for the bath? I know it obviously isnt that important but imagine different oils get to different temperatures. What kind of oil do you use? Looks just like vegetable oil, or peanut.
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
I actually got a 65% in my first semester in high school chemistry. In both physics and chem...
Very professionally done
The fact that there's both a trans- and cis- version of the acid makes for some great pun potential!!
Facts lol
tempted to use this video to come out someday
“i relate a lot to the chemical he makes in this” attaches video link
Do you think you can make ethylene oxide? Would be so cool if you succeeded.
Hey man, I have a question:
Have any of these videos yielded you a paper or something like this? Or do you keep it informal?
I haven't worked in the lab for 10 years, but I'll never, ever, forget the smell of pyridine. Yuck. Some describe it as fishy, but I wouldn't use that term. It smells like nothing else. Just - BAD. Nature's way of telling you "stop inhaling me, idiot".
I did this today in lab but i used piperidine instead of beta-alanine.
Knoevenagel is pronounced "ka-noo-fin-aa-ghel", with a hard 'gh' (it's a Dutch name)
Knoevenagel Condensator sounds like a magic device from Witcher.
He pronouced it completly wrong. Its spelled Knöwenagal (The letter ö doesnt exist in English)
Doctor Who: It DINGS when there's STUFF!
@Zillertalerwelthass https://en.wikipedia.org/wiki/Emil_Knoevenagel
steavf - 2019-06-30
Nile's coming through with another top hit "Generic Timelapse Song 1" and it's honestly one of my favs
Jay - 2022-01-21
lmfao yeah same