Making Hexanoic Acid

[@marialiyubman]

I’m here for the Eau-de-Goat. Round-bottom flask, you make my rockin’ world go ‘round!! 🎵🎶

[@charybdis1618033]

I want the whole parody song at some point now.

[@Neuvimain24]

@@charybdis1618033 same

[@robmckennie4203]

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.

[@kaischapen3552]

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!

[@MrZyphose]

It really smells like the Panda enclosure at the San Diego zoo.. Pretty foul.

[@Rubikorigami]

2:10 "slight orange color" *flask proceeds to go oranger that mathematically orangeable*

[@sugarbooty]

Aman Jaiswar So is yours, and mine

[@beanlets]

🍶

[@sendark001]

Hahahaha 🤣

[@ARSZLB]

Lou Bernabeu ...what?

[@spiderdude2099]

Lou Bernabeu you think that's orange, you should see potassium dichromate, it's ridiculously orange almost neon.

[@marksmod]

the essence of the goat

[@106640guy]

The purest of nectars.

[@SunsetEnvy]

Satan's perfume

[@JGscienceGaming]

I love this 😅😂

[@definitelynotyuribezmenov7611]

Greatest Of All Time

[@aetheralmeowstic2392]

WAAAAAAAAAAAAAAAAH!

[@TheKnaeckebrot]

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.)

[@nat7278]

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.

[@spiderdude2099]

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

[@kafou7505]

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 !

[@nemeanlyan7918]

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)

[@Boogie_the_cat]

Totally agree with ya. Most KZbin 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.

[@ARSZLB]

8:50 “in the end, i just decided to make hexanoic acid, which i thought could be cool because it’s DANK”

[@potatopotato9131]

Nah he says stank but still lol

[@warrentb1]

How about battery related chemistry? Pretty important these days and there are plenty of weird ones (flow batteries, molten salt, air batteries etc)

[@Agustx0]

I'd love to see chemistry related to batteries.

[@Agustx0]

conduit122 Oops, sorry.

[@zenoist2399]

I'd like that too. There is still a lot to discover with batteries I reckon.

[@BRUTALLEGENDD]

How about A-SALT-N-BATTERY :P

[@aterack833]

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

[@sixstringedthing]

Me, browsing NileRed content for stuff I haven't watched yet, spotting this thumbnail: "That one. That's what I was looking for".

[@rochellekesselring4865]

Lol same 😂

[@NileRed]

Forgot to say to follow my twitter! twitter.com/NileRed2

[@tesseract342]

i would be really amazing if you made some nilered merch, love your videos keep it up

[@sunglow9835]

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. =)

[@elijahmoore9886]

i love falling asleep to your videos but the background is white and so bright

[@gavinjenkins899]

How many goatsworth is that yield though?

[@tomlobur111]

Gavin Jenkins about 3 bags full

[@elephystry]

How many horsepower was that hot plate?

[@tonyellen_]

@@tomlobur111 Yes, sir. Yes, sir.

[@marialiyubman]

I’ve herd that before.

[@GodlikeIridium]

3 women exchanged to goats in saudi arabia.

[@StephenGillie]

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).

[@supersmashsam]

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.

[@NileRed]

That is very interesting. Thanks!

[@TheKnaeckebrot]

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

[@RemoveChink]

I hate cleaning grignard experiments...

[@jacks6860]

The ether in this video was inhaled directly before Nile came up with the idea to turn gloves into soda.

[@markhoutman7721]

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

[@GodlikeIridium]

10:00 best misuse of a volumetric pipette I've ever seen 😂

[@comando1911]

"Instead of scrapping everything, I just changed what I was making".... that's what I say in my lab everyday

[@bradtarratt6931]

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?

[@CarterColeisInfamous]

Put together a lab glass starter kit

[@fredwells7403]

Carter Cole glassware is not cheap

[@CriticalTechReviews]

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.

[@jojolafrite90]

Yeah, for example, what is needed for making methamphetamine... I mean, my science project.

[@noname-80lbs]

GOAT......greatest of all time ...reagent?

[@Matt.m6]

Looks like forbidden tea

[@slin1990]

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

[@aterack833]

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

[@MrZyphose]

Patches would be pretty bad ass but I enjoy the reaction socks. Different clothes that had a working light show displaying multiple reactions.

[@olivialambert4124]

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).

[@qazsertyer]

I made caproic acid once using malonic synthesis. Could be interesting to see.

[@ARVash]

I'm so glad you stuck with it, great video

[@martinmiglio]

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

[@SeabornNomad]

"I thought would be cool because it stank" 🤣

[@BGrab]

If somebody is wondering how to calculate boiling points under different pressures, look into the barometric formulas and the Clausius-Clapeyron-Equation :)

[@theSILKROAD210]

Thank you^^

[@supersmashsam]

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

[@elephystry]

B. Grab that is brilliant

[@elephystry]

B. Grab that is brilliant

[@decepticonne]

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.

[@douro20]

In a research lab environment the reagent synthesis would had been carried out on a Schlenk line with dry nitrogen.

[@alexanderofrhodes9622]

Essence of goat you say? {ALCHEMU INTENSIFE}

[@bcubed72]

You had me at "goat-like."

[@lecringeyay3125]

I seen the thumbnail. I wanna know how to make homemade goat scent.

[@admiralpercy]

YOU PRONOUNCE SIEVE RIGHT I'M SO HAPPY

[@rajshreeK1]

Legend has it if you comment early, Nile red replies.

[@cobaltmn5716]

As a guy who's favorite mammal is the goat I had to watch this.

[@MegaMike327]

This guy is a guy to have when the world changes.

[@helldad4689]

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.

[@TheHikeChoseMe]

ahh nucleophile and electrophile the love story of the ages

[@ashe1.070]

Ethyl hexanoate is one of my favorite chemicals to make; it has a wonderful pineapple smell.

[@MPIronmanJC]

Caproic and Buytric acid are naturally present in dunder, or the probiotic element used in fermenting and distilling Jamaican rum! Please try it!

[@excuseyou7198]

This method is too complicated. I would’ve just squeezed some goats and collect the acid.

[@lecringeyay3125]

Yeah same when he made cadaverine Just juice some corpses

[@Dahb1GOAT]

Put it on. Smell like the goat. Goat-tra-band coming soon to stores near you.

[@knightmarex13]

Used in perfume industry....having flashbacks to when we made crude perfume in highschool chemistry. None of it smelt pleasant

[@markhoutman7721]

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.

[@float_rock]

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.

[@DanDart]

Yessss finally you said "sieves" as expected xD

[@emilyvanmoslfak2295]

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.

[@starlight4649]

Goat juice by Calvin klein.

[@nerfinator6]

Essence of Goat

[@jamieklinder520]

8:56 because it STANK

[@montsaintleondr7491]

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!

[@NileRed]

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

[@fano72]

Delicious reaction. What about making a pentyl ether an check how it smells?

[@codeartha]

Oh I'd love nile red branded glassware! But I gave no idea where you'd get custom printed glass that resist lab use.

[@elmaleante420]

Your videos are awesome but it would be nice if you added an indicator of exactly how much you fast forward something when you actually do 😬

[@NileRed]

I usually do it when it is important. If i am just pouring stuff, I tend not to. For actual reactions or crystalizations, I keep it in real time

[@aterack833]

@@NileRed we all love that you keep it real

[@1HeartCell]

Nile Red Labcoats? Booh yeah! Make sure you can access them in europe :P

[@casualmtg6675]

nile ur videos are great keep them up , I just have one suggestion. ....dont have urself on cameras.......uve seen the comments in the list I imagine

[@NileRed]

What do you mean?

[@casualmtg6675]

a few people on it say things inappropriate bc they think ur cute lmao

[@NileRed]

haha, I took that person's comment down. It was a little bit excessive to say the least :p

[@casualmtg6675]

no kidding it was awful

[@mannys9130]

I suggest the opposite. I liked the Bromine face reveal. Besides, you can't get any better than cute science nerds. Top shelf kinda guys.

[@codexnecro3917]

Aww man I hate the smell of pure butyric acid.

[@crtfit9792]

Love this channel

[@NileRed]

Glad to have you here!

[@ATLTraveler]

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.

[@fano72]

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.

[@THErcbomber]

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

[@johnhavel7685]

Nice we did a grignard reaction back when I took organic chem lab in college though I can’t remember what we made. That was a fun class though organic chemistry lecture was the hardest class I think I took back then and the professor really kinda sucked at teaching. I think the average on the first exam was like 30% so yeah it was pretty bad lol

[@leonidalekseyev3809]

You might add sulphur to grignard next time to make an even stinkier compound lol

[@mikodrzewo6142]

Awesome video , Nile red

[@Boogie_the_cat]

I liked this video but was disappointed that you didn't include any footage of you smelling the final result.

[@rinconcurioso]

I heard of a series of Ionic Liquids based on choline and carboxylic acids. Perhaps you can try to make cholinium hexanoate.

[@mattibboss]

nile red beakers!?!!?!?!?! i hope you ship to Germany :) and customers don't ripp me off....

Get me some of those goat-odor perfuemes.

[@aterack833]

Is that cute fluffer a fox or wolf?

@@aterack833 fox

[@1337fraggzb00N]

Finally I know how to make goatwater.

[@Zuhaibashraf]

Why i am attracted to this channel i hate chemistry in high school still dont like chemistry (i find piece of satisfaction and peace)

[@NileRed]

I don't know! It's a mystery

[@Zuhaibashraf]

thanks for replying huge fan of your videos even tho i dont understand so many of your experiments but i love watching em . Still Why ?

[@tsingtak642]

you need to dry diethyl ether over sodium with benzophenone as indicator. There may be plenty of water present in diethyl ether..

[@Anonymous_404_Not_Found]

You should try synthesizing a halohydrin and use it to make an epoxide, there are a lot of theoretical videos on youtube about it, but none that I know of where the reaction is actually performed. Would be very interesting to see in my opinion, especially since most amateur chemists can't synthesize epoxides the traditional route as they don't have access to peroxy acids.

[@Anonymous_404_Not_Found]

john black​ You cant just drop benzoic acid into 2% hydrogen peroxide and expect good yields, on top of the fact that your product would be contaminated with benzoic acid that was left unreacted. And the average amateur chemist doesnt own a vacuum pump capable of distilling hydrogen peroxide to a high concentration, nor should they as it is explosive at high concentrations. I guess they could concentrate it to about 30% on a hot plate and that may work though. That all aside Ill be watching for your halohydration video.

[@Anonymous_404_Not_Found]

+john black I live in US.. was not aware you could get 30% hydrogen peroxide at lowes. What product is it in? The best ive heard about is 10% in hair bleach.

[@Anonymous_404_Not_Found]

+john black Thats awesome! I appreciate it, I never had bothered with concentrating the 3% because like you said 300ml has only 30ml of 30% and it takes hours to do if you want to ensure the decomposition rate is low.

[@jmac8092]

4 Quarts TNL Certified 35% Food Grade Hydrogen Peroxide + Free Real Blue Cobalt Dropper Bottle. Shipped Fast. Sold by: Pure Health Discounts

[@jmac8092]

4 Quarts TNL Certified 35% Food Grade Hydrogen Peroxide + Free Real Blue Cobalt Dropper Bottle. Shipped Fast. Sold by: Pure Health Discounts

[@ianlee5812]

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?

[@witiwap86]

I like how it's cool because it has some stank

[@CarterColeisInfamous]

Have a thing like a old school chemistry set with basic chemicals or what to stock from basic household stuff

[@NileRed]

I am not sure what you are asking

[@CarterColeisInfamous]

Oh I was responding to your question about ideas for stuff to sell

[@dreadnought9523]

can you explain why Acrolein polymerizes?

[@aterack833]

I’d love to see a whole mini series on that and trying to do something with it afterwards

[@tasoscrazymad3152]

low yield is probably to wurtz reacion combining bromopentane and bromomagnisiumpentane destroying your grignard

[@brettreiff]

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

[@joshuajames1822]

Lab coats sound cool

[@rassnic]

Where did your bromide went? Your final magnesium reaction is wrong Mg++ Br- + 1HCl = MgBrCl

[@subzeroelectronics3022]

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.

[@fabri___1883]

Yep. He make such a nice video about this

[@theLuigiFan0007Productions]

It also attracts mosquitoes like a freakin magnet.

[@WalterFabian]

Beakers and lab coats! Take my money! ( as in other comments, hope you can ship to Europe)

[@ColinRies]

Why not extract the acid with ether, wash it with water, convert to sodium salt, wash with ether and then convert back to acid, extract with ether and dry? I think this might have saved you the distillation.

[@kiganbriody6314]

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?

[@denelson83]

Okay, what about valeric acid? What does that smell like?

[@ineedmoneysp]

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.

[@xenomancer1]

A lab coat and a beaker would be nice.

[@Elwynful]

Today we obtained PhMgCl from 12 kg of magnesium for the first time.

[@Kony420]

me: Frequent venting

[@reubenmckay]

I remember we did a Grignard reaction in one of lab classes in second year at uni and it just never worked for me....

[@ChromeBirb]

*G O A T O I L*

[@fft2020]

Capri is latin for goat, hence the caproic acid

[@ralmin]

Capricorn is goat horn

[@Schwarzvogel1]

Capri is not the exact Latin word for "goat." _Caper_ is Latin for goat (a she-goat would be _capra_). Capricorn ==> cornus (horn) caprinus (goaty, from/of goats) so capricon = "horn of goat(s)" Latin lessons aside, I think we can all agree that goats are awesome. If you don't like goats, then I don't know what to say. They taste good, produce good milk/cheese, and are a lot smarter and more environmentally friendly than cattle which are among the most unintelligent of mammals extant on this planet. The domesticated ones we commonly call "cows" are even worse, given that they no longer would have the survival instincts of their wild cousins. Still, since they also taste good and produce good milk/cheese, they are very useful creatures, at least until someone figures out a way to genetically engineer more compact cattle that can digest plastic with no ill effects and produce meat with a uniform quality of the finest wagyu beef. If you manage to figure that out young lads, you'll be on your way to becoming a trillionaire.