ฝัง
- เผยแพร่เมื่อ 21 ก.ย. 2016
- Hey guys, today we are going to be making some hexanoic acid, also known as Caproic acid. We will be carrying out a Grignard Reaction between 1-pental and CO2 gas.
1-bromopentane video: • Making a Bromoalkane (...
-------------------------------------------------------------------------------
Merch - nilered.tv/store
-------------------------------------------------------------------------------
■ NileRed is now available on Nebula! go.nebula.tv/nilered
(when signing up with this link, a portion of your membership directly supports the channel)
Join the community:
Patreon - / nilered
Discord - / discord
NileRed Newsletter - nile.red/home#newsletter
You can also find me here:
Facebook - / nilered2
Instagram - / nile.red
Twitter - / nilered2
Nile talks about lab safety: • Chemistry is dangerous. - วิทยาศาสตร์และเทคโนโลยี
the essence of the goat
The purest of nectars.
Satan's perfume
I love this 😅😂
Greatest Of All Time
WAAAAAAAAAAAAAAAAH!
I’m here for the Eau-de-Goat.
Round-bottom flask, you make my rockin’ world go ‘round!! 🎵🎶
I want the whole parody song at some point now.
@@charybdis1618033 same
2:10 "slight orange color"
*flask proceeds to go oranger that mathematically orangeable*
Aman Jaiswar So is yours, and mine
🍶
Hahahaha 🤣
Lou Bernabeu ...what?
Lou Bernabeu you think that's orange, you should see potassium dichromate, it's ridiculously orange almost neon.
our chemistry-prof always said with enough love, we'll eventually start our grignards :D (aka. if nothing happens, heating the flask with our hands etc.)
My suggestion for merch would be to do what Ben on Applied Science did. Rather than sell clothing with his logo, he sells iron-on patches. That way, anyone can have the logo on any item they like, even clothes they already own, and I expect they'd be cheaper to boot.
Pro tip:
Absolutely NEVER add all your alkyl halide if the gringnard rxn hasn’t started yet. Not just because you don’t want a thermal runaway, but because you can get undesired side reactions that destroy your Grignard reagent before it can react. Until you see the initiation of your rxn, only add 10-30% of your alkyl halide solution
8:50 “in the end, i just decided to make hexanoic acid, which i thought could be cool because it’s DANK”
Nah he says stank but still lol
While being a chemistry student years ago, I did numerous Grignard reactions. Mostly to create deuterium labelled alcohols and acid. I needed to heat the flasks beforehand to get out the water, flush with nitrogen and use only super dried solvents. With all these precautions you should be able to get yields of about 80% . When hydrolizing the Grignard reactand with water, an alcohol is formed, in your case it could have been 1-pentanol as the side product... So, with your faster approach the yield is okay, I would think. Big fan of your experiments, BTW. Keep it up!
i think that the low yield you obtained is mainly due to Wurtz coupling side reaction. to avoid it you shoud not pour all the halide even if the Grignard synthesis does not start well, but you should try to start it with max one fith of your halide, and then adding the rest dropwise. also, overheating of the solution also favors thé Wurtz coupling.
still, your are doing an incredible job without a decent fumehood !
Me, browsing NileRed content for stuff I haven't watched yet, spotting this thumbnail:
"That one. That's what I was looking for".
Lol same 😂
How about battery related chemistry? Pretty important these days and there are plenty of weird ones (flow batteries, molten salt, air batteries etc)
I'd love to see chemistry related to batteries.
conduit122 Oops, sorry.
I'd like that too.
There is still a lot to discover with batteries I reckon.
How about A-SALT-N-BATTERY :P
I wanna see someone make a [moderately comparable to modern lithium batteries] battery in the method of these videos, where they compare it to an existing cell and measure the performance of both and then take the existing one apart and measure the dimensions compared to theirs, see how efficient they can get with a shop lab type setup, basically just a step or two above backyard science, and if they compare the costs of the two it would be even cooler
I will buy the hell out of beakers and a lab coat. No, really. You are one of the few content creators who I would gladly support by buying merchandise. (Plus I'd get to show off my awesome beakers and labcoat)
Totally agree with ya. Most TH-cam merch I've seen is really "meh" and overpriced at that. I know Nilered would give us quality equipment that we would be proud of.
Forgot to say to follow my twitter! twitter.com/NileRed2
i would be really amazing if you made some nilered merch, love your videos keep it up
How many goatsworth is that yield though?
Gavin Jenkins about 3 bags full
How many horsepower was that hot plate?
@@tomlobur111 Yes, sir. Yes, sir.
I’ve herd that before.
3 women exchanged to goats in saudi arabia.
Imma be honest with you Nile, I really dont care about chemistry. At least I never did in school. Even though I still have zero passion for it, your straightforward, can do, everything is possible attitude realliy is reassuring. Especially in times of stress or overwhelm like it has been lately. I just play your videos in the background and your voice gives me hope and comfort. Thank you. Hard to describe how much this means to me right now.
Thanks Nile for all of your great videos. I once didnt like anything about chemistry or biology, I thought it was complicated and weird, but you've shown me that chemistry is a vast land of exciting reactions. They way one can manipulate a substance to get a single other substance is just mind blowing. So keep up the great work. =)
I'm so glad you stuck with it, great video
i love falling asleep to your videos but the background is white and so bright
Here is an easy procedure to pre-activate magnesium turnings for grignard reactions that has always worked very well for me:
- In a Buchner funnel or a fritted glass funnel + vacuum flask, add a excess amount of magnesium turnings.
- in 4 different containers, set aside enough of each liquid to cover up your turnings : 1M HCl, demineralised water, methanol or ethanol, diethyl ether.
- Add the 1M HCl on top of your turnings, a vigourous production of hydrogen gaz will occur.
- After a few seconds, quickly apply vacuum to remove the HCl solution.
- Quickly rince off your turning by adding the demineralised water, then applying vacuum again removing most of the liquid. Proceed the same way again using methanol/ethanol, then the diethyl ether.
The magnesium turnings you get that way shoud be pretty much dry and oxide free at that point. Use them immediately for best result. No further activation using iodine, dibromoethane, or grinding should be required if your conditions are anhydrous enough. This procedure can be used with old tarnished turnings as well.
That is very interesting. Thanks!
also, you should only add more from the addition funnel when you know the reaction started ... i knew many cases in which impatient students killed their grignard by adding to much, when things havent heated up properly :D
I hate cleaning grignard experiments...
Fun fact: The names are descriptive in very different ways. Caproic refers to the smell ("Caper" is Latin for Goat, so it's goat-like), while Hexanoic refers to the 6-carbon structure, and its similarity to hexane (which is sometimes found in gasoline).
10:00 best misuse of a volumetric pipette I've ever seen 😂
You had me at "goat-like."
I seen the thumbnail. I wanna know how to make homemade goat scent.
Now I need a playlist that’s each of your videos and right after each Nile red video, the Nile blue video of the cleanup reactions (they aren’t as good without seeing the initial reaction and knowing the steps of that, it’s less sensical without it, I almost don’t even wanna watch a playlist of just the red videos just to not spoil the blue videos, at least at the rate I’m watching them I can forget them easily enough
I was synthesizing benzoic acid the same way lately and had the same problem: my phenyl bromide wasn't reacting with the magnesium. What worked for me was adding the iodine in a later stage. My labjournal:
...
When a quarter of the phenyl bromide was addes and wasn't reacting with the magnesium, stirring was stopped. An iodine crystal was added and after a couple of minutes the reaction started. Addition and stirring continued.
...
I had to do Grignards for a long time and this was one of my observations. It also looks nice since the magnesium starts jumping a bit in the ether.
Hope this might be useful in the future.
A fellow chemist
Put together a lab glass starter kit
Carter Cole glassware is not cheap
Exactly, which is why one would appreciate getting everything they'd need all at once, instead of trying to build a kit and maybe not doing the best job. This guy knows how to chemistry, he should pick the pieces.
Yeah, for example, what is needed for making methamphetamine... I mean, my science project.
I made caproic acid once using malonic synthesis. Could be interesting to see.
The ether in this video was inhaled directly before Nile came up with the idea to turn gloves into soda.
"Instead of scrapping everything, I just changed what I was making".... that's what I say in my lab everyday
Ethyl hexanoate is one of my favorite chemicals to make; it has a wonderful pineapple smell.
In a research lab environment the reagent synthesis would had been carried out on a Schlenk line with dry nitrogen.
Yessss finally you said "sieves" as expected xD
I think a tee shirt with your channel logo would look pretty cool, and for the beakers and lab coats, I think your channel logo would do fine also
Do you think your reduced yield could be from the reaction of the grignard reagent with oxygen? I didn't notice any steps you may have taken to exclude oxygen from your reaction mixture.
Looks like forbidden tea
If somebody is wondering how to calculate boiling points under different pressures, look into the barometric formulas and the Clausius-Clapeyron-Equation :)
Thank you^^
I recommend using a nomogram as a quick and easy way to do conversion. Sigma Aldrich got an interactive one on their website !
www.sigmaaldrich.com/chemistry/solvents/learning-center/nomograph.html
B. Grab that is brilliant
B. Grab that is brilliant
Love this channel
Glad to have you here!
Caproic and Buytric acid are naturally present in dunder, or the probiotic element used in fermenting and distilling Jamaican rum!
Please try it!
I know there are as many opinions on how to start a Grignard out there as there are chemist, but my most sucessful initiations were as follows:
Just overlay the Mg turnings with Et2O. Add a few mL of your electrophile (pure, no solvent) WITHOUT stirring.
Heat the reactions mixture, I prefer a heatgun to the heat it at the spot where the electrophile was added.
As soon as the reaction becomes milky white, dilute the residual electrophile in the addition funnel and off you go.
Maybe this is helpful to some of you :)
And as always great video Nile, reminded me of my undergraduate years as my first grignard also was for the formation of a caboxylic acid....boring benzoic acid though :D
Awesome video , Nile red
Delicious reaction. What about making a pentyl ether an check how it smells?
YOU PRONOUNCE SIEVE RIGHT I'M SO HAPPY
Get every kind of alcohol you can and do a whole bunch of esterifications. Maybe you could even just do a one pot esterification with all the alcohols mixed together and see how it comes out smelling. You could put small amounts of the final product on strips of paper and sell it to your Patreon supporters, like NileRed cologne samples.
It could be nice to convert the hexanoic acid into hexanoyl chloride or bromide. And as an added bonus, when doing an esterification (under dry conditions) you should get a better yield than doing the standard Fisher-esterification with an alcohol and a carboxylic acid.
Oh I'd love nile red branded glassware! But I gave no idea where you'd get custom printed glass that resist lab use.
nice work
"I thought would be cool because it stank" 🤣
Essence of goat you say?
{ALCHEMU INTENSIFE}
GOAT......greatest of all time ...reagent?
Put it on.
Smell like the goat.
Goat-tra-band coming soon to stores near you.
This guy is a guy to have when the world changes.
The major loss is probably not just from water, but also from the atmosphere and most importantly ; from how and in which order you added the reagents. Putting all of the brominated stuff before the first reaction even started, and the only adding the CO2 after all of the possible Grignard reagent was produced : you're gonna end up with a whole lotta side-products.
Would using a bigger condenser help with it not getting overloaded or would it not matter either way. That was crazy how it was just pouring out the condenser like you were adding stuff.
love your videos. would deffenetly buy Nile red glass wear for my experiments. I say go for it. what do you have to lose here? lol
Just wondering, is there a specific way you can insert a gas straight from a tank, instead of having to do the sodium carbonate stuff?
I heard of a series of Ionic Liquids based on choline and carboxylic acids. Perhaps you can try to make cholinium hexanoate.
I would love some nile red branded stuff. College makes it hard to motivate donating money but i could convince my self if there was a cool lab coat in it. I need to retire my blue one soon and p-o-chem is starting soon
As a Physicist I'm a big fan of dry ice. Its like the poor mans liquid nitrogen, less fun, less cold, but still generally similar benefits. They both turn straight to gas rapidly and float on a cushion of air making them pretty fun to play with. They can both freeze objects which are fun to shatter (liquid nitrogen can splash from vigorous boiling and be dangerous though). They can both be held, and doing it wrong can maim you. And they're both great for throwing around the lab because they leave no mess and don't need a clean up. Any excuse to use either should be taken, if only to kick around and play football with (as it glides across the floor almost frictionless).
I would make natrium caprate salt, dry it and set the goat free by mixing with h2so4. without the ether you can make an easier destillation.
Used in perfume industry....having flashbacks to when we made crude perfume in highschool chemistry. None of it smelt pleasant
it looked like your second washing turned out more yellow than the first and third, do you know where that came from? the color seemed to carry through to the final product
Essence of Goat
NileRed: Since, as I understand it, caproic acid is what causes goat milk to taste and/or smell goaty, do you have any ideas on a way to process goat milk that possibly converts the caproic acid into something you can precipitate out without making the milk otherwise curdle?
Nile Red Labcoats? Booh yeah! Make sure you can access them in europe :P
you need to dry diethyl ether over sodium with benzophenone as indicator. There may be plenty of water present in diethyl ether..
Legend has it if you comment early, Nile red replies.
low yield is probably to wurtz reacion combining bromopentane and bromomagnisiumpentane destroying your grignard
Sometimes I perform what's known as the Arnold Palmer reaction and I react lemonadeythl with iced teaoxide, yeah I know I'm a chemist.
One of my teachers used a sonicator to kickstart a Grignard reaction at room temperature. He said it's a good alternative to using iodine if heat is insufficient in initiating the reaction. How much would you corroborate this account?
How about making 3-methylindole? Or just something mercaptane-like? ;) btw if you added some sulphur, you could obtain something even more smelly! Personally, I would add selenium!
I made 3-methylindole before. It wasn't able to really purify it, but it worked. Made my work area smell like a dirty barn for a while
As a guy who's favorite mammal is the goat I had to watch this.
Have a thing like a old school chemistry set with basic chemicals or what to stock from basic household stuff
I am not sure what you are asking
Oh I was responding to your question about ideas for stuff to sell
ahh nucleophile and electrophile the love story of the ages
Is that the stuff in Passiflora foetida plants?
Could you do a video on microencapsulation, specifically of paraffin wax? Also, I'm curious about hexavalent chrome. Thanks!!
check out doug's lab he makes a few things that contains hex Chrome. might help you
krap101 Hexavalent chromium is something that you generally want to stay as far away from as possible. Think of it as Magic Colorful Cancer Powder.
@@littlegrabbiZZ9PZA colourful you say?
i subscribed and liked!!!!!!!!!!!!!!
can you explain why Acrolein polymerizes?
I’d love to see a whole mini series on that and trying to do something with it afterwards
Have you ever made SO3 or is it just too dangerous or too much of a pain. I saw a video with someone using it and have been trying to figure out why it smokes as soon as it hits air. It looked more like liquid nitrogen than SO3.
I like how it's cool because it has some stank
I remember we did a Grignard reaction in one of lab classes in second year at uni and it just never worked for me....
You might add sulphur to grignard next time to make an even stinkier compound lol
Goattt@@
Okay, what about valeric acid? What does that smell like?
I have a question please, I'm preparing sodium alginate solution 2% put I
need to add hydrogen peroxide to the solution without affecting or
decomposing the alginate polymer,any idea how can I retain the stability
of this solution sod.alg+h2o2 for a period?..tha very much
nile red beakers!?!!?!?!?!
i hope you ship to Germany :) and customers don't ripp me off....
I made the unsaturated dicarboxylic version of hexanoic acid in uni with the HGs2 catalyst: hex-2ene dioic acid, it came out as a white powder
wouldn't it be awesome if you got your hands on some olefin metathesis catalyst?
What is olefin metathesis catalyst? I've honestly never heard of it before
R1=R2 + R3=R4
->R1=R3 + R2=R4
where R Is a C chain and "=" a dubble bond
metathesis is when you switch "partners"
AgNO3+NaCl->AgCl+NaNO3
is also a metathesis reaction
but a olefin one has dubble bonds instead
so we used acrylic acid and penteneoic acid to make hex-2-ene dioic acid +ethylene
HOOCCH=CH2 + CH2=CHCH2CH2COOH
-> HOOCCH=CHCH2CH2COOH+ H4C2
Get me some of those goat-odor perfuemes.
Is that cute fluffer a fox or wolf?
@@aterack833 fox
Do video how to do hexen ii please :D
Beakers and lab coats! Take my money! ( as in other comments, hope you can ship to Europe)
Goat juice by Calvin klein.
Could one react ketones or aldehydes with grignard reagents e.g. Acetone + methylmagnesium bromide -> tert-butanol
I definitely think that’s possible
In the booklet of Slipknot's 3rd album Iowa is a page that's just black with a silver dot and it's said that it smells like goat.
8:05 1-octen-3-ol, isn’t that the stinky mushroom oil? I’ve heard it’s chemically similar to 1-octen-3-one, the major chemical responsible for the smell of metal.
Yep. He make such a nice video about this
It also attracts mosquitoes like a freakin magnet.
I always wondered why the ether had to be dry. So, does that mean if you added water to 1-pentylmagnesium bromide would you make pentane and MgBr(OH)? Since the carbon would act as a nucleophile and attack the delta positive hydrogen on the water molecule to form pentane and the OH- group will be stabilised by association with the MgBr+ group?
Yes, 1-pentylmagnesium bromide reacts with water to make pentane. It is used to remove the halogen atom.
illya.ruslanovich Shevchenko i figured as much, I’m a chemist thanks for answering tho :)
This method is too complicated. I would’ve just squeezed some goats and collect the acid.
Yeah same when he made cadaverine
Just juice some corpses
Why not use a higher concentration of HCl to reduce the water content?
Somethings good get to learn
Can you do a reaction involving Gilman's Reagent?
Where did your bromide went?
Your final magnesium reaction is wrong
Mg++ Br- + 1HCl = MgBrCl
me: Frequent venting
Sad that you idn't have Kipp's Apparatus. That's a very cool and totally unused now piece of lab equipment