Making a carbon snake with P-Nitroaniline

[@Blackdragon5284]

I like how the videos are structured like a lab report

[@nitroanilinmusic]

I feel represented.

[@amploquimica4832]

a p is needed

[@ezzedinezeid6049]

You're feeling re_resented, for there is P missing. Or you simply had to drink more, that you will have P on your own

[@prapanthebachelorette6803]

Love how punny you guys are

[@raymondsalazar4562]

This is what Demo/tutorial/informative content should truly be. Your knowledge in this field is outstanding. Your explanations so thorough and editing, spot on. It will be interesting to see how the world benefits from you and your skills, in the future. Keep it up and dont forget about us supporters/patreons when you make it big.

[@chromiumdog6453]

This was one of two interesting reactions my 7th grade "science" teacher showed me (I'm an Aussie, so this is the first year of high school for us, when the cool stuff starts to get taught) before we found out that the fume hoods in the labs we used vented into the upstairs library airconditioning ducts. It's one of the images that has stuck with me.

[@zambo6453]

14:35 "A snake was produced, but not as big as the ones I had seen on the internet" *deep inhale* THAT'S WHAT SHE SAID

[@gorillaau]

"Is that a test tube in your pocket, or just happy to see me?"

[@JonathanBartlesSWBGaming]

That wasn't what he said so your quote is not a quote

[@JonathanBartlesSWBGaming]

@Jackie Strider I'm not wrong

[@JonathanBartlesSWBGaming]

@Silicon Nomad need some cheese for that whine?

[@JonathanBartlesSWBGaming]

@Jackie Strider no, people need corrected when they're wrong

[@Noah-hz5ll]

I laughed out loud on the last reaction. Poor little carbon snake got blowed to bits hahaha

[@Renville80]

Noah Alonge Boy howdy, but it done blowed up good!

[@aarchMoth]

@@Renville80 He's just Noah

[@Daedalussy]

*BLOWN

[@Noah-hz5ll]

@@Daedalussy 1) this comment is 5 years old. I've literally graduated, gotten married, and bought a puppy since I made this. 2) you done did missed the original (5 year old) tong'n'cheek syntax joke, pardner! 🤠

[@Daedalussy]

@@Noah-hz5ll you actually took the time out of your day to write this I'm surprised

[@DoRC]

I havent the slightest clue about chemistry but i still very much enjoy these videos!

[@clintflippo917]

"I did my recrystallization in ANYHYDROUS ethanol..." Such an elitist.

[@alexcaffri9091]

But 95% is okay... if you're a plebian.

[@stephenjacks8196]

Denatured or undenatured. 95% Ethanol is Everclear (190 proof).

[@andie_pants]

I hydrate my ethanol with ice and Coke.

[@ultrametric9317]

Dude! Your demos are outstanding! And thanks for not dumbing it down!

[@Jeffrey_Wong]

I just had an exam on this stuff and this video makes so much more sense than it did when I first watched it.

[@sethmitchell2176]

It would be so totally meta if you made a video on the synthesis and properties of Nile Red, Nile Red :P

[@NileRed]

+Seth Mitchell I plan to eventually !

[@Xtr3m3ickers]

+Seth Mitchell what is nile red?

[@rich1051414]

+11Chemistry *N* ile *R* ed *N* erd *R* age This is nerd rage without the voice distortion. Oh... half-life 3 confirmed.

[@patricksweetman3285]

+Output Nile red (also known as Nile blue oxazone) is a lipophilic stain. It is produced by boiling a solution of Nile blue with sulfuric acid. Can you see where this is going?

[@maxbuskirk5302]

It'd be so meta if the acylamino group was a meta director :D

[@StopChangingUsernamesYouTube]

Downside to growing up: I still think for a split second, "I have money now! That looks like an amazing hobby!" Then I immediately slap myself and think, "I'd burn my foot off and laboratory glassware is expensive." Thanks for uploading all this, so I can at least learn more about chemistry and see the reactions from the safety of my monitor.

[@Akbarwayse]

Awesome! I really enjoy the explanation! Most videos don't go as in depth, keep this up! Hopefully most of the nurdrage subscribers can find a home here.

[@NileRed]

Thanks!

[@rushikeshbhor6069]

Hey Nilered, I have been watching your videos for quite a while! Today it helped me in a national level test where they asked us about the major product in a reaction between acetanilide and Conc. HNO3. All my friends marked the ortho isomer because they thought h bonding might affect the major product. However i rememberd your video and it bought me 2 marks!(+0.5 if you count my friends’ negative marks!)

[@wvlfpeach]

This channel has superior rewatchability

[@gmjpharmd8823]

I've watched the recently uploaded videos and I'm hooked. Starting from the beginning. Keep up the great work!

[@XtremeBBQ]

You could heat your crude product to ~284°C. At this temperature the impurities will boil away. In the flask only P-Nitroaniline will be remained which boils at about 336°C.

[@prometheustwin1970]

Isn't that also what Viagra does?

[@logankennedy609]

I came here for this joke...and I'm not disappointed...

[@spiderdude2099]

Funnily enough, viagra actually does work by releasing nitrous oxide into your bloodstream, so I mean very topical for a nitration reaction

[@jackblack5082]

ah aromatic chemistry :) always enjoyed this chem start with benzene > nitrate HNO3, H2SO4 > reduce with H2 Pd/c > protect with Ac2O > nitrate again > then deprotect etc .... or you could go the dizoniam salt route which could give you anything you wish

[@jvanvynck]

third year chemistry student here. i've been watching reaction videos like this for years now, since before i started university and i'm just now understanding how these reactions are taking place.

[@JustinKoenigSilica]

John Van Vynck what a load of bullshit, I'm in 3rd semster and you know all of this by the end of it.... What the hell is taking you 6 semesters? ???

[@smarphpharph5021]

@@JustinKoenigSilica some mental electron deficiency.. perhaps bi-polar?

[@youtube.commentator]

"I try to upload at least one video a week" Those were the golden days

[@kerielwatson3197]

Videos are better quality now though. I don't mind

[@galaxyincubus101]

@@kerielwatson3197 in some respects yes

[@jiechang1508]

who's here in 2022? I finally finished all of your video from your channel NileRed!!!!

[@upinapuffofsmoke1653]

So great I wish your newer videos had this much depth. Still love all the stuff you post

[@judobeer]

Great videos with great in depth explanations of all the reactions! Keep up the good work!

[@mariohc100]

Why am I watching this? I was searching on how to make pancakes, when I accidentally wrote "How to make pan" and this came up.

[@realname3538]

You don't need pancakes where we're going.

[@juzeralirangwala3539]

Hi ! Thanks i use to perform this experiment in my PG as lab excercise. Method which was prescribed in our lab manual for hydrolysis of p-nitroacetanilide was bit tedious and yield was also unsatisfactory. Your method is comparatively easier and seems to provide much better results ! However, i would like to point that temperature of Acetanilide- Glacial acetic acid mix. reached upto 20 deg. Centigrade which is responsible for formation of o- nitro acetanilide and o - nitro aniline upto significant. However, if u manage to keep temp. during nitration below 10 deg. C formation of o isomer would be very less becos formation of o-isomer requires compratively high temp. so carrying out nitration below 10 deg. C i m pretty sure it will help u !

[@NileRed]

That could work as far as I know, but it would have to be tested! I don't really have to revisit and test it though, unfortunately.

[@juzeralirangwala3539]

Okay thanks for your reply ! Wish u best of luck for your future attempts !

[@ethanmoore428]

Awesome information you have here. You have earned yourself another subscriber.

[@plasticraincoat1]

Thanks for using my video showing the explosive decomposition

[@NileRed]

Hey, sorry. I totally forgot to credit you!

[@AAmariLive]

these science stuff are always so interesting

[@tainaniat]

watching this feels like watching a cooking show but cooler

[@BenisColada]

can't wait for the nitrous oxide video. keep up the great work

[@NileRed]

I plan to film that soon. I was really hoping to get carbon disulfide to do the "barking dog" experiment. I wasn't able to get it though.

[@Metalhammer1993]

Nile you don´t have a video on Acetanilide haven´t you? don´t know if it´s as easy as i think it is, but would still be interesting. (i think i can neutralize aniline with acetic acid and then gently heat it and maybe at some calcium chloride to catch the water generated in the reaction?

[@ahmadkezzo]

Thank you very much for all of your efforts done in these videos, and if I may suggest, I may suggest and asl to add some explanations in the information section or maybe in the video itself about the uses and applications of each prepared material. Thanks a lot

[@Bigcubefan]

I would've have performed this reaction under basic condiditions, since the N in Acetanilide gets protonated under those extremely acidic conditions and then directs in meta-position.

[@jhyland87]

6:02 whats with the dark stuff at the bottom of the beaker? Whats that?

[@Cmcmillen77]

It’s amazing people know how to do this. I feel so dumb now.

[@dogmeat7486]

15:16 that happened very quickly. i found this humorous.

[@hckr47]

so I agree a reaction that ends like your second snake attempt is always satisfying.

[@holguacamol8408]

is it just me or does Nile sound like a 15 year old? its not bad or anything, i actually think its pretty cool. like a 15 year old chemist.

[@RonJohn63]

I'd like to see a video comparing the p-nitroaniline plus sulfuric acid reaction with the reaction of sucrose with sulfuric acid.

[@maxbuskirk5302]

1:10 Hey I wish I remembered this on my o chem test!

[@ronaldojonass4885]

Wouldn't igniting a mixture of sugar and saltpeter produce the same 'black snake' with a lot less effort?

[@oldmal60]

Very honest accessmate of results and good advise on improvements.

[@vladimirnachev324]

14:00 what do you mean "to run a column"?

[@chrisshyi8999]

Vladimir Nachev column chromatography (en.wikipedia.org/wiki/Column_chromatography) is one of the most common ways used to purify organic compounds

[@davidoakley5028]

Great videos. Keep up the good work.

[@maryudomah4387]

I saw green smoke in thumbnail. I quickly clicked.

[@JevinJohnson-CloudShift]

7:20 I love the Canadian maple leaf

[@titaniumsandwedge]

The commercial process to produce PNA is to start with nitrobenzene and directly add the amine group into the para position using ammonia. Yields are much higher. But the process require high pressure (30 bar?).

[@hayroshime]

Gotta say, is this organic lab at your university? Just curious. In commercial pharmaceutical chemistry labs, this would be considered cowboy chemistry. All the physical practices described here and the glassware being used is not ideal, and your right a 3 neck rbf with overhead stirring should be used, along with N2 and always a temp probe.

[@unknownboi8683]

0:20 My immune systems effectiveness after I ate 5 Flintstones Gummy Vitamins while dealing with COVID-19

[@196Stefan2]

15:20 Mr. Hankey!

[@TheFlipside]

What's the reason why aniline couldn't be used as the starting material? Couldn't you just nitrate that and skip the hydrolysis step? My best guess is either it'd be too dangerous/messy to work with, or the relatively bulky acetanilide group increases the yield of the para product relative to the ortho

[@apostle333]

also, (sorry this is an after thought) I"m curious if using Nickle as a catalyst in this particular reaction might enhance the yield? Please "check my math", so to speak, but it stands to reason that the hydrolysis should occur, far more efficiently in the pressence on nickle metal...what do you think?

[@pacoyamomoto5427]

Is an aluminum soap and its properties a topic you would be willing to address?

[@patricksweetman3285]

Nile Red, you asked for suggestions. I would suggest working up the spent mother liquor for the side products by column chromatography. Chromatography grade silica gel is kind of unobtanium, so some OTC substute would add to the value. I have crushed & sieved kitty litter that may work, but you may know of something better.

[@davidm2472]

haha was not expecting that last carbon snake explosion!

[@NileRed]

Thanks David M!

[@196Stefan2]

It is remarkable that there is no obvious sign at all (vapours of NO2) for a nitration in progress.

[@pietrotettamanti7239]

196Stefan2 if you see NO2 vapors while nitrating something, then you're doing it wrong😂😂😂. Sorry but to me your comment sounds like a "your cake didn't turn black. You're doing it wrong!" During nitration reactions you must keep the temperature below 15°C, otherwise the unstable NO2+ will become NO2, which is obviously bad for your reaction.

[@196Stefan2]

Hello Pietro, no, I did some nitrations of aromatic hydrocarbons (Nitrobenzene and m-Dinitrobenzene, o- and p-Nitrotoluene) during my vocatinal training many years ago and I always observed the evolution of brown NO2, sometimes more sometimes less. The NO2-formation did even occur inside the reaction vessel where no oxygen should be present to oxydize NO to NO2 (if there was any). The yields were always within the range of expectation. Nitrobenze was later used as starter material for the Dintrobenzene and Aniline.

[@pietrotettamanti7239]

196Stefan2 I'm not saying that NO2 production will stop the reaction, I'm just saying that it should be better to avoid it, and if you have excess nitric acid it won't impact the yield. Of course there are some nitrations (like TNT synth or TNF synth) where you have to heat up the mixture to get the reaction going and in this case NO2 production has to be expected. But for mono notrations the reaction is fast even without heating it, and producing NO2 is always an issue. I am currently doing some aromatic nitrations in my school lab and my teacher always tells me not to let the temperature rise. Maybe when you did your reactions teachers were a little less concerned about safety. By the way I think you're messing up a little bit with some reactions. NO2 production doesn't come from NO oxidation (there isn't NO in your reactants, and oxidizing NO to NO2 is a catalyzed reaction which occours at high temperatures). NO2 comes from the breakdown of nitric anhydride N2O5, which comes from the dehydration of HNO3 (when you have both NO3- ions and NO2+ ions in solutions they can combine to form N2O5, which is highly hygroscopic and normally it rehydrates before it can break down). But if you heat up the mixture you increase the production of N2O5 and allow it to escape, and increase its decomposition rate.

[@JimmyJamesJ]

I watched this video while enjoying a glass of ice cold ethanol. Much better use of ice cold ethanol, IMHO.

[@schrumli2074]

I don't know what I should use for the recrystalisation... Water or ethanol? NileRed didn't say what he prefers...

[@FranktheDachshund]

Thanks for the post.

[@DiesIstEineURL]

Why do you always use a roundbottom flask? Wouldn't it be more efficient to use an erlenmeyer flask? With that you can use a hotplate and can regulate the heat/speed of a distilation/reaction better.

[@fredjones5698]

Tetahydril he has more surface area with the heating mantle I think instead of just the bottom of a flask

[@rb-uv5bs]

Very interesting,, please tell us the extent of your education

[@uncle_thulhu]

Can you not make the same reaction (though less impressive) with plain sugar and H2SO4?

[@epic5204]

12:24 forbidden corn flakes

[@aajjeee]

Hey, i did this starting with about 34.8g of acetanilide and ended up with 14.9 of p nitroaniline even though I skipped the water recrystallization. The product is very brown but i hear it can be '' yellow or brown''. Since my school went on strike, the nitroacetanilide was left to dry for a month after i filtered it. I will be making the reaction with sulfuric this afternoon.

[@kapamax64]

I got the same problem. I did the synthesis twice, but I got the very brown product twice. The problem might be, that the reaction is not cool enough when it gets nitrated. The first time I tried it my reaction temperature while nitrating was about 20°C and at the second (where the product was not that brown as at the first try) try about 12°C.

[@royalprince8858]

Great video bud, keep up the good work 👍.

[@stephenjacks8196]

Duh. There are twice as many ortho positions as para positions so ortho is statistically favored. Also formed is the nitramide which in acid rearranges ortho. Nitration of Aspirin the initial sulfuric sulfonates the ring stabilizing the phenol to oxidation by nitric a. Both ortho and para are differently acidic with the dinitroacetanilide being even more acidic. A short Alumina column would separate them easily. One trick for whiter crystals is treating solution with activated charcoal before crystalization.

[@EvertvanIngen]

10:39 Looks smokable

[@fano72]

Oh no I wouldnt smoke that 😂

[@Quarks0010lss]

The link is for a reaction with 4-nitroacetanilide if 4-nitroaniline is used instead what are the correct amounts of 4-nitroaniline and nitric acid and what should be the molar concentration of the acid? I can not imagine the amounts and concentrations are the same as the reactivity is different. Thanks

[@pacoyamomoto5427]

very nicely done..

[@homealchemy]

Wow. I got to try this! A great explanation. Keep it up...perhaps you can be the replacement for nurdrage...

[@JohnLeePettimoreIII]

Second reaction is similar to the reaction I have after eating Indian food. (Including the cloud of smoke.)

[@ohcheah317]

what is the approximate molarity of the glacial acetic acid? I would assume its fairly weak because its used to dissolve the acetanilide. any info this would be greatly appreciated. Thanks

[@BeepingSheep]

Glacial AcOH is >98%

[@BlackWolf42-]

You mentioned 'anhydrous acetic acid' rather than glacial acetic acid. I learned that 'anhydrous' acetic acid was acetic anhydride and not glacial acetic acid. Please advise, thank you.

[@NileRed]

Anhydrous acetic acid is the same thing as glacial acetic acid. Acetic anhydride is a totally different chemical and it can somewhat be viewed as the combination of two acetic acid molecules. It is no longer produced using acetic acid though. When acetic anhydride is added to water, the anhydride linkage will be hydrolized and two molecules of acetic acid will be formed. In essence, acetic acid is a carboxylic acid, but acetic anhydride is an anhydride. If you look up these chemicals on Wikipedia, it will likely show you everything you need to know!

[@KB4QAA]

Do they not call round flasks "Florence Flasks" anymore?

[@jameskiller1000]

+Pelican1984 florence flask got a flat bottom, but the flask in the video got a round bottom so I think there's no problem there

[@AidanGieg]

There is a slight difference between Florence flasks and Round Bottom flasks. Florence flasks have flat bottoms.

[@michaelappleby2076]

How about alkaloid extraction ?

[@ghettopeackock]

You should seriously consider a career in social science because you have proven your ability to distract me from doing my lab report.

[@helved807]

great cooking instructions! smells great in my taco mix

[@hughiemac]

how do you dispose of compounds that are dangerous for aquatic animals or humans?

[@NileRed]

Hugh Macdonald In the lab, we have hazardous waste management. At home, I put it in a container and then I call a local company to deal with it. Nothing remotely dangerous ever goes down the drain.

[@warywolfen]

Nile Red In the chem lab classes I took, ALL the nasty stuff went down the drain! :) In fact, the pipes were made of glass, so they could resist those acids. Of course, PVC pipes would have been unsuitable, since all kinds of organic solvents went down the drain, too! That was in the 1970s. I guess things have changed a bit since then. And here's a little story.... My chem-eng advisor used to work for a chemical plant in Texas. They dumped their waste into a nearby river. He said that one day, the river caught fire. Ah, the good old days!

[@hughiemac]

***** Idiots have to fulfill their roles it seems. Either that or become politicians. My local city tells people to be concerned about toxics and yet provides no way to dispose of them.

[@Quintinohthree]

+Steve Johnson Should have left it at diluted drain cleaner.

[@Quintinohthree]

***** Your admission. It's all you'd ever really done anyway.

[@joeestes8114]

Awesome video!, thanks for sharing!

[@antigen4]

i remember these from childhood along with the other fireworks

[@plasticraincoat1]

However crediting my Chanel plasticraincoat1 would always be appreciated . Thank you !:)

[@NileRed]

yeah sorry, I totally forgot! I added the credit in now and Ill add an annotation :)

[@plasticraincoat1]

@@NileRed HI thanks for your comment - Please do check out my new exciting chemistry demos in my new lab with live commentary ! Enjoy! :)

[@ClownWhisper]

I would like to see how to make Red lead. or Red Lead oxide. I am not a chemist but I need some and can not seem to find instruction.

[@NileRed]

Why do you want to make it?

[@ClownWhisper]

ne Idea for lead acid. I need it for one of the electrodes

[@NileRed]

Sorry, i really dont know much about lead :P

[@ClownWhisper]

Nile Red DAMN I had two windows opened, did not pay attention and posted this to the wrong channel !!! sorry lol

[@MrItsthething]

6:27 Mmmmm! Ice cream!

[@TheSnakeboy11]

@@trollsus_ r/whooosh

[@mephistosprincipium]

0:20 me when my girlfriend text me that she is home alone

[@viktorkarel9714]

Hey anyone can explain or direct me to site that explains mechanism of the hydrolysis step ?

[@paulscottpadgett1996]

Much Respect......

[@redsquirrel9961]

Proper protection must be used.

[@Christopher.Marshall]

Where did you buy a heating nest like you are using in the video?

[@NileRed]

***** The heating mantle? I used that lab one, but you can buy one from Ebay if you would like one.

[@vincevic1062]

Looks fun!

[@TheModernHermeticist]

looks tasty

[@d3athreaper100]

God I hate it when people pour their powders on the walls of their beaker. just pour the powder slowly!

[@eritra4303]

You should really have used vinyl gloves when working with nitric acid as you do in current videos.

[@petebuxton3341]

This was far superior to the usual boring "snakes"....very funny, but violent reaction.

[@vladimirnachev324]

isn't it better with acetone instead of ethanol?

[@nicktohzyu]

does the carbon snake work with o-nitroaniline?

[@denispetal952]

Why cannot be anilline used for the nitration?

[@JuanCarlosFernandez-re7nk]

If u try to nitrate aniline u obtain m-nitroaniline due to acid conditions. U can nitrate it but i dont know if the product you want is that. Well, being correct, you obtain ammonium salt. Sorry for my english haha

[@Bouzsi]

I want to become a chemist just so I can work with p-nitroacetanilide, because I can’t think of a scenario where I’d be able to bring that word up in conversation without being a chemist...

[@BunsenBurns]

Hi! We are going to publish a video on this same reaction Friday and would like to show a small clip of your reaction if you would allow it. Thanks!

[@NileRed]

+Bunsen Burns Sure no problem!

[@BunsenBurns]

+Nile Red So speaking of weird dehydrations that don't work as nicely as other videos... ours caught fire! Reproducible as well not sure what was going on with that. Video is up by the way - thanks!

[@NileRed]

Yeah, i found that with a lot of reactions, you need to run them several times to get the pretty stuff you see online. Ill check your video out

[@NileRed]

Bunsen Burns I just watched it. I like your style. Also, maybe it lit on fire because there was residual solvent?

[@tillyqtillyq3750]

Oohh what if you made the snake in your triple necked round bottom flask

[@Insanityhead]

What is the yellow smoke made of?