Making anisole

[@Drjusmar]

Nile, the fact that you'll reupload just for a error you could cover with an annotation is admirable. Keep it up dude.

[@NileRed]

Thanks for the support :)

[@johnb820]

I can imagine, back to camera and mic, then the editing program, then export, then upload! What a job! love this guy.

[@KnakuanaRka]

Especially since KZbin dumped all its annotations as of recently. Yeah, people were spamming them, and getting them to work on mobile was problematic, but look at all the cool things people did with them; don’t throw the baby out with the bathwater!

[@ATLTraveler]

They got rid of annotations in like 2016 buddy...

[@comando1911]

Hell. major news sources dont even do that!

[@exys2086]

I would like KZbin devs to add a feature to see how much time you've spent watching a single channel. Knowing nothing about chemistry, I still watch a lot of those :\

[@clintonbehrends4659]

knowing KZbin they'll somehow do the complete opposite

[@drasiella]

I need that for Nile Red and SEA

[@toxiccan175]

@@clintonbehrends4659 Knowing KZbin, they already know

[@druidofthefang]

isn't that a thing already?

[@nekrugderzweite8298]

Same

[@fefemess]

I remember watching this in high school and thinking it was really cool. Now I'm actually studying these reactions in college and they're beautiful

[@AmidaNyorai48]

😀

[@smerdyakov_11]

Indeed man, organic chemistry is the best

[@xXHatsuneMikuFanXx]

i feel like the person that named anethole just said anisole, but with a lisp

[@butterflygroundhog]

It's probably a chemical isolated from aneth and anise seeds, both are from the apiacea/carrot family, so that would make sense

[@turgidbanana]

No

[@jastintheceooffinanasapost6204]

@@turgidbanana why?

[@dampandrew]

anis hole

[@dougsteel7414]

@@dampandrew don't like those words near the word 'moist'

[@twizz420]

My parents made an anisole... I call him "brother"

[@heathc148]

I dont get it

[@bcl56]

@@heathc148 Anisole sounds like a**hole

[@conservat1vepatr1ot]

My brain read the title of this video the very same way lol.

[@cDoogle]

i thought this was wholesome and you were calling him sweet. :(

[@violetvargas9387]

@@cDoogle same

[@zhiang0113]

The anisole undergoes 4-substitution (via aromatic electrophilic substitution) with propanal to form 4-(1-hydroxypropyl)anisole, which is protonated by the acid. Water leaves as it is a good leaving group, producing a benzyl carbocation which is stabilised by the benzene ring, and Cl- attacks it to produce 4-(1-chloropropyl)anisole. Pyridine acts as a base to eliminate HCl from that to form the C=C double bond, thus producing anethole! :)

[@PatrickStarthnxroxrock]

I like your funny words magic man.

[@ChemEDan]

@@PatrickStarthnxroxrock anethole is what bugs bunny calls wabbit hunters.

[@frosthoe]

Thanks again NileRed. Sharing Knowledge is awesome, and I feel fortunate that you take the time to explain things to us less Chemistry savvy folk.

[@thatilluminati_3421]

Good on you for actually correcting your mistake. You'd be surprised how many youtubers are afraid of doing that.

[@JohnLeePettimoreIII]

" ... I'll get on that. Eventually." You sound like me on one of my good days. 😃

[@grazen321]

Too much commitment for me..

[@SuperSpaceMonkey]

I’ve always liked chemistry but watching him really inspires me

[@CookingWithCows]

Not to be confused with Anusol

[@origamigek]

anus oil ?

[@CookingWithCows]

It's a brand name for a hemorrhoid ointment :P

[@origamigek]

ah

[@professorprotonfan7287]

I read anisole as anus hole.

[@Chrissy4605]

Now that IS funny!!!

[@FurryAzzre]

Sometimes I love watching people create interesting chemicels from scratch. Amazing video.

[@ASandwichNinja]

For the mechanism of the reaction to form anethole, I would assume in step 1 the first thing to happen would be that the oxygen in the propionaldehyde would be protonated to make the carbonyl carbon more electrophilic. It would then undergo a Friedel-Crafts acylation by reacting with the anisole at the para position due to favourable resonance forms of the Wheland intermediate, removing a hydrogen from the benzene ring as a proton and forming a carbon-carbon bond between the ring and the aldehyde (which is now an alcohol). I think that the alcohol group would then be protonated by HCl and via a nucleophilic substitution reaction (like Sn1 due to the possible resonance forms of the carbocation intermediate) water would be lost sand replaced by chloride. In step 2 the pyridine acts as a base and initiates an elimination (possibly E1 for the same reasons as for Sn1, and especially if the pyridine is dilute). The pyridine abstracts a proton the carbon adjacent to the halogenated carbon and the hydrogen's electrons are donated to form a carbon-carbon double bond as the chlorine is kicked off as chloride. I think that's how the reaction would work, just trying to go off of what I've learned so far at uni.

[@bingbong430]

how much words are here?! XD

[@oldpop788]

@@bingbong430 yes

[@revolverguy]

But what happened to the phalanges ?

[@nushurasaher9876]

I think it’s not specifically a freidal crafts acylation since the reagents used are different here. Friedal crafts acylation is done using anhydrous Alcl3 and not H3po4 it is an acylation process but not friedal craft. Its actually an ESR reaction

[@alexnope2223]

Nice use of google. Next time change some words so it isn't verbatim.

[@ExplosiveBrohoof]

You've already extracted limonene from orange peels, right? You should use that limonene to prepare carvone! You'll turn oranges into mint!

[@binaryguru]

Every time I hear you say Anisole it keeps reminding me of Anusol.

[@editname6868]

Ikr

[@Mrshane288]

He's over here... "If you want to know more about SN2...." I'm still stuck on sodium being in mineral oil to preserve it. Yeah I didn't go far in science class in school. This is extraordinarily interesting and I understand most of what you're explaining but man I'm simply amazed at how much we collectively know. Humans truly are amazing.

[@MrRishik123]

Yay more content. Will you ever make something like paracetamol? I think it might be a good video.

[@NileRed]

I plan to go from aspirin to paracetamol! So aspirin --> phenol - > p-nitrophenol --> p-aminophenol --> paracetamol

[@MrRishik123]

Can't wait :D

[@krisztianszirtes5414]

+NileRed Couldn't you go like PET -> terephtalic acid -> benzene -> chlorobenzene -> phenol and from that the same as yours but cheaper and larger quantities? :D

[@horaciorodriguez3280]

Paracetamol in industry is made from phenol-p-nitosophenol-p-aminophenol-and acetilating.....N-acetyl p-aminophenol(paraacetamol), right? is the most easy pain release of make, I think.

[@horaciorodriguez3280]

No, that way is not , the way in industry is,,,,phenol-p-nitrosophenol-p-amino phenol-and acetilating...N-acetyl p-aminophenol-paracetamol.

[@moyrml]

Love your videos. As for making a botch of the mechanism, I propose this: At first, the hydrogen of the HCl (after dissolving in solution) is attacked by the oxygen of the propanal. This makes the aldehyde carbon positive, and free for an attack by the chloride anion. First step creates a 3-carbon chain with a chloride and an alcohol on the first carbon. Next, the H3PO4 creates a substitution reaction on the benzene ring. The carbon of the carbon chain attacks the double bond and attaches in para position. Next, a hydrogen from the para position carbon leaves, restoring aromaticity and transferees to the alcohol group. A water molecule leaves giving the product. It has been some time since finishing my organic chemistry course. Forgive me if i completely distorted the rules of chemistry.

[@NileRed]

Follow me on Twitter: twitter.com/NileRed2

[@chrischristen8904]

NileRed hey. how's it going?

[@hh7h137hhh]

Hmm... the methoxy group of the anisole is ortho/para directing due to its electron donating effects so assume a nucelophillic attack at the activated aldehyde? Then I assume the alcohol group present after the attack will protonate generating a good leaving group and from there a chloride ion can attack at the alpha carbon and displace the water?

[@NileRed]

***** haha thanks

[@NileRed]

Alex Blitz Good and you?

[@NileRed]

David Ashworth Sounds about right :)

[@sara6069]

Nile: suggest a mechanism! Me: *barely passed chem 30*

[@IbnEmadAlmouaibed]

extract nicotine from cigarettes

[@horaciorodriguez3280]

Is like extract cocaíne chlorhydrate from coca plant

[@roro-mm7cc]

extract morphine from papaver somniferum (opium poppy)

[@tlowry6338]

Extract dmt from toads

[@notpulverman9660]

@@tlowry6338 poor toads

[@notpulverman9660]

I think he already showed use of soxhlet extractor to extract piperine or st.... So it would be the same as that, possibly with a different solvent if nicotine isnt soluble in alcohol.

[@Thereadingmusiclover]

I read the chem as anus-all so i was expecting the opposite of this "nice- smelling" chem XD

[@austinhall3937]

When someone's mean to Mike Tyson he calls them an "anethole"

[@oldpop788]

BOOOO

[@banjobear3867]

Hahahahaha

[@zigaorazem6516]

HCl is in a water solution in the form of H3O+ and Cl- . The O of the aldehyde attacks the H3O+ and takes a H proton. The pi bond of the O breaks of and the carbon is left with a positive charge. Then the Cl- bond to this positive charge. The phosphoric acid also protonates the water. Another H3O+ (from the phosphoric acid) attacks the -OH group and then this group leaves in the form of water. Again there is a positive charge on the carbon which immediately attacks the para position in the anisole. The H of the anisole is picked up by water and the H3O+ is regained. Then the reaction is completed and we get the product. I hope im correct but if not then np ;). I will at least learn the correct answer in the comments. Btw your videos are the best Nile! :D

[@fabiotonin3938]

You could use an alkaline reaction condition instead of sodium methoxide to have the de-protonation of phenol! Sodium methoxide is necessary for alkilic alcohols but for aromatic alcohols K2CO3 or some drops of NaOH are enough to have the deprotonation... cheers!

[@shubhrajit2117]

I also have the same doubt

[@aech_two_oh]

I had no idea what anisole was when coming into this, but it's a good way to "spend" time

[@markhoutman7721]

Hey NileRed, Would you still like to get the answer to your mechanism question on this video? In that case: The aldehyde is protonated. resonance occurs and causes the carbon from the aldehyde to become a carbocation. Now a "double bond" from the anisole attacks this carbocation. The hydrogen from the aromatic ring is eliminated and the "double bond" in the aromatic ring is restored. Thanks to a strong acid, like the phosphoric acid, the now synthesised wil be protonated. This makes an H2O-group, which is also a good leaving-group. When it leaves, it creates a benzylic carbocation, where the chlorine will attack, creating your desired product. A very interesting way of a nucleophylic aromaric substitution. Looking forward to it.

[@Chrissy4605]

Nile, you are very entertaining and educational. And kudos for doing a follow-up on your error!!!

[@astralchemistry8732]

Great video and good explanation of the polarizable bond! I just want to note that anisole would form an emulsion, and not a suspension with the water (10:00 at the DCM extraction).

[@danielkeith7593]

It was nice of Anna to volunteer her own soul for science.

[@MohammedAdain]

HCl breaks as H+ and Cl-. Cl- attacks the carbon of the aldehyde as that carbon has partial positive charge. The π electrons of C=O shifts towards O giving it a negative charge. H+ from HCl or H3PO4 is attacked by the oxygen bearing -ve charge. Further the oxygen is protonated and there is a loss of water molecule, giving the + -ve charge to the carbon where the Chloride had attacked. Then electrophilic substitution reaction at para position as the Ortho position reaction is difficult due to steric factors.

[@TheWiseSalmon]

Why would H2O be eliminated when the Cl which just added to the carbonyl is a much better leaving group? Any Cl- which attacks the C=O will be immediately kicked back out again, surely? I propose: 1. Electrophilic Aromatic Substitution at para position with the protonated aldehyde acting as the electrophile (para favoured over ortho due to steric reasons) 2. Protonation of the OH followed by loss of H2O leaving group. The lone pair on the MeO group can help kick the H2O out and stabilise the resulting positive charge. 3. Attack by Cl- at the carbon which just lost the H2O prntscr.com/ct3grs

[@LilGugz]

Agree 100% with TheWiseSalmon's synthesis mechanism. Modammed Adain --> the Cl- ion isn't a very good nucleophile, is far too good of a leaving group.

[@MohammedAdain]

SORRY, totally agree to both of you, I discussed the same with my Professor too and he gave another reason which supports you, that in a solvent (protic) in this reaction the anisole acts as a better better nucleophile. Thank you for correcting me or else I would had been under a wrong illusion.

[@NileRed]

Hey, can you message me on my FB or here on KZbin? I want to send the beaker that I promised

[@MohammedAdain]

Ya Nile red I'm here

[@danielhagen3739]

That neutralisation of the waste liquid looked really cool :)

[@fieromike1]

😂 I read the title of this out loud, “Making an a$$ hole” and my wife responded immediately “your parents already did that and I’d rather not watch the video “. Always quick with a good burn. 😂

[@hamp9061]

Hey Nile. I got some options of other chemists for the synthesis of antethole from anisole. We figued that a possible mechinism would have the propionaldehyde converted to its enol form in a Keno-Enol Tautomerism. The Enol form has a good OH leaving group that would be attacked by the HCl. This produces the 1-Chloropropene that has a slight positive on the 2nd carbon. This is where we got lost. It seems like the HCl unless entirely depleted would attack the 1-chloropropene again but instead we need the activated ring to attack the 1-chloropropene double bond converting it into 1-chloropropane bonded para on the ring. I dont know if this will be helpful at all but I've been trying to work it out all day. Can't wait to see it!

[@nushurasaher9876]

The reaction mechanism is Electrophilic substitution reaction. Since anisole is methoxy benzene and all benzene compounds undergo ESR pretty easily.

[@ethangormong7506]

This is just an alkylation reaction. Phenol already has a very acidic OH, which attacks the electrophilic MeI to make the aryl methyl ether.

[@nushurasaher9876]

Isn't alkylation a ESR

[@ethangormong7506]

@@nushurasaher9876 I think you’re thinking of Electrophilic Aromatic Substitution. But we are creating the phenoxide anion, which attacks the methyl iodide in an SN2 reaction. You are correct, however, that the product, Anisole, would undergo an EAS reaction rapidly due to high electron density in the arene ring.

[@sad6452]

good job with these videos they are fun to watch and help me at school with chemestry

[@deyvismejia7529]

It would be awesome if you could cover general orgo 1 and 2 reactions like this Williamson ether synthesis, or a playlist of relevant videos.

[@tobiasfraser6061]

I read the title 'anusole' and so I thought you were making hemorrhoid cream and just accepted it as a video concept 🤣

[@LiborTinka]

The amount of sodium fits perfectly my imagination of "reasonably sized" :)

[@rexmonarch2]

Brings back memories of the ol' basement laboratory days back in the mid-70's.

[@imogenruthburnett3867]

I don't know a thing about chemistry but I'm pretty sure that self stirring glass bulb was magic.

[@mindbound]

Imogen Ruth Burnett It uses a magnetic stirrer.

[@magey3794]

The glass bulb is not actually glass. It is a magnet and on the stirring thing there is another magnet that spins and because they are attracted the one in the container spins too. Hope I helped.

[@pvcov3250]

man i know nothing about chemistry i wont even have chemistry in upcoming years in school because im in art but these videos are literally just . the one thing i can watch and work to, sleep to- i watched these in elementary when i did chemistry, not for class, for fun- i still had low grades in chemistry but you know not like i needed it anyway ^^

[@deplorableamerican9451]

that Dollar tree glass jar though

[@laurv8370]

Thumbed up 4 times (from alt accounts too) for accepting criticism! Kinda rare on YT jungle nowadays...

[@Mattes_______]

Nile what do you think about making some lidocaine?? The synthesis would fit perfectly to your channel^^ and maybe you could even try your own product on your skin

[@NileRed]

I am actually not able to get the precursors for lidocaine unfortunately

[@sleepful1917]

well he seemed to have figured it out hahahaha

[@editname6868]

A n a l L u b e

[@johnthebarbarian]

Coke

[@fauxpassant]

Under acidic conditions caused by HCl and H3PO4, the aldehdyde is protonated, forming an oxonium ion. The benzene ring attacks the oxonium ion at the para position (it can also attack at ortho) because the resultant cation is more resonance stabilised than at meta. The cation is deprotonated by a base in the environment to restore aromaticity in the ring. Next, the -OH group (coming from the oxonium ion) is protonated, forming -(+)OH2. Water is a good leaving group under such acidic conditions, and so it leaves, leaving behind a secondary carbocation which is actually resonance stabilised by both the benzene ring and also the electron donating -OCH3 group. Cl- acting as a nucleophile, now attacks the carbocation, forming the anisole-p-(1-chloropropane).

[@ahmetselcuk1400]

Anisol fiedel caraft reaction . Please??? Anisol +cloroaceton reaction p2p ????????????????? 1 saniye önce

[@chrisgg1968]

@NileRed: Thank you very much for the sheer amount of high quality chemistry videos. I enjoy every of youre videos I watch. :) Feel free to correct me, I still learn a lot about organic chemistry. My guess for the first mechanism: First you add the propionaldehyde to youre anisole in the para-position using the electrophilic aromatic substitution (SeAr), which adds a proton to the oxygen of the new group. Then this new OH-group gets protonized (using H3PO4 as a catalyst) and leaves the molecule creating a positive charged carbon atom, to which hydrochloride can create a bond, which sets free the 'used' proton and adds chlorine to the molecule (Sn1). My guess for the second step: You use the E2 elimination to get rid of a hydrogen atom of the second carbon atom of the propylgroup using pyridine, which simultaneously eliminates the clorine and creates a double bond.

[@terezi4real]

so true

[@Iridiumalchemist]

Really nice video. I appreciate the effort that went into reuploading it to correct a mistake!

[@thecarrasius]

Really enjoy your videos, quality stuff :)

[@NileRed]

Thanks!

[@illya.ruslanovichshevchenk4106]

Mechanism: The C atom in C2H5-CH=O is electrophilic, it reacts with anisole and H from anisole moves to O from the aldehyde, forming hydroxyl group: H3C-O-C6H5 + O=CH-C2H5 -> H3C-O-C6H4-CH(OH)-C2H5. Then H3PO4 protonates OH-group and makes the C atom more electrophilic. It then reacts with Cl-, that is a nucleophile, replacing OH with Cl, and H+ is regenerated.

[@catonchronic5354]

Do more videos on synthesis of other phenylpropenes. Like elemicin, croweacin, exalatacin etc.

[@KOTOKOARTS]

For the first mechanism you have to add a mixture of 324 g (3 mols) of anisole and 4 g of concentrated H3 PO4 heated to 150° C. in a 500 ml capacity reaction vessel equipped with a thermometer, stirrer and dropping funnel. After the above-mentioned temperature has been reached, 64 g (0.432 mol) of o-anethole (2-methoxy-propen-1-yl benzene) should be introduced into the thoroughly stirred anisole/phosphoric acid mixture over a period of 1 hour, followed by stirring for 1 hour at the same temperature.

[@NileRed]

Where did you get this? Also, that isn't a mechanism, but a procedure. Still useful information though!

[@KOTOKOARTS]

NileRed I apologize for that, I forgot to add the mechanism, but this came from a patent. The link to the process is here, I cant quite remember what mechanism I had found so Ill try to find it and send it again. www.google.com/patents/US4026951

[@phonotical]

You never made the Anethole video! I was pretty interested until I realised there wasn't a video 😔

[@slaveluna]

I went looking for it as well. Maybe he'll get to it eventually.

[@phonotical]

@@slaveluna three years!

[@Thecatssosweetright]

i thought this vid was releaded 4 days back lmao its 4 years back still enjoyed it

[@AMDB1973]

I liked your video very much! And also most of the other videos. And specially I like videos about chemicals in spices and foods. And as the name "anisole" gives away, it's in anise Pimpinella anisum, and others. For me looks a little like a terpene, but anisol doesn't have enough C-atoms, to be a monoterpene (10 C-atoms). Have you thought about to try to make f.ex. menthol? ;) Anyway I think your channel is very entertaining, and it has become one of my favorites. Keep it up Nile! ;)

[@jugernoty9]

I only took basic science in high school so when you start talking about chemistry its a foreign language to me but i do enjoy watching your videos

[@DagothXil]

having intrusive thoughts watching the beginning like "oh my sodium metal is dirty, better take it over to the sink to wash it off"

[@weekendguy100]

You can do this reaction quite easily with any somewhat basic base. Such as potassium carbonate, sodium hydroxide, etc. without having to use something as reactive as sodium, it’s also much easier

[@toothless7849]

This stuff gave me blood-farts.

[@drasiella]

Try Anisol 2

[@ATLTraveler]

You should see a doctor man.

[@siberianstuntman3344]

I had the same problem with pure sodium hydroxide snacks

[@twizz420]

Anisole... Not Anusol.

[@ballisticbananadadude]

Let it absorb, let it evaporate, start back at square 1.

[@theexplodedguys264]

FINALLY! A NILE RED VIDEO! Not a Nile Green video...

[@lemmerelassal610]

Nice video. Couldn't this be done using NaOH and Aliquat?

[@_puffy]

Interesting to watch you procure anisole - I was born with one!

[@nattsurfaren]

I once used sodium instead of cheese on my sandwich. It tasted shit and I burped for hours.

[@nattsurfaren]

Don't do it. It is deadly. I was joking.

[@Swollencod]

nattsurfaren already did it

[@nattsurfaren]

My bad bro. ;)

[@Bender1]

Talk about explosive diarrhea.

[@nattsurfaren]

Roliath, Malebranche Of The Abyss Or explosive stomach. The thing will burn through your intestines. Stomach acid would become highly alkaline. If you survive they have to remove the stomach and connect it with the other end. I know there is one that drunk something corrosive and wanted to kill himself over a stupid girl. He survived and they did exactly what I describe.

[@masterlabLAB]

Anisole can be used also to make TA trinitroanisole which is widely used in melt casting explosive composition for multiple military application, and as high performance rocket propellant.

[@Bender1]

Why do I watch these videos? I don't actually make any these... good video anyways

[@xPROxSNIPExMW2xPOWER]

its interesting

[@1HeartCell]

Thats exactly why you're watching them. You can't make it yourself. It would be somewhat hard to get all these chemicals e.g. in germany.

[@AureaPersona]

You could make this from household items and a little patience. Or from trees, rocks and sea water and A LOT of patience.

[@elephystry]

Dark Magician, Level 7, 2500 ATK 2100 DEF Perhaps on the off chance that you will.

[@Epck]

@@1HeartCell it shouldn't be too hard...chemistry is important more people should learn it

[@0SailorStar0]

anisol synthesis was what i fucked up in my last exam on organic chemistry... should've watched this video! :)

[@DaftknightLP]

"today we're making an ass hole"

[@jamesmcdermott8947]

These videos make me wish I pursued my childhood dream of becoming a chemist. 😔

[@Rhodanide]

I feel like I have seen this before. nah.

[@Rhodanide]

AHAH, WHAT? I see someone doesn't have the ability to sense sarcasmmmm! :) You're quite the frisky one.

[@googleeatsdicks]

+Binky Sop Dude, chill! You are more reactive than fluorine.

[@philidor9657]

I feel like I've definitely seen this before. Eh I'll watch it anyway.

[@NitroTheCat]

This has been recommended to me over 300x

[@kennethkeys2248]

I've never smelt anisole, but wouldn't one expect it to smell not unlike skatole?

[@Nathanmoney10]

no the anisole has a very different shape than an indole so it wouldn't nessicarily smell bad

[@kennethkeys2248]

It was a pun on the phonetic similarity of 'anisole' and 'anus hole'.

[@kennethkeys2248]

MrBabyBitch666 ...

[@kennethkeys2248]

It was a joke.

[@kennethkeys2248]

+MrBabyBitch666 Thanks.

[@tenkkutn]

This brought me back to organic chemistry and o. chem. lab

[@DhanusMLal]

why don't you mix phenol and Na directly to get Na phenoxide

[@kayrakaya4719]

Methanol is important... For health

[@bigbingus4542]

Watching these are so relaxing

[@dipeshsomvanshi4383]

Your content is awesome. One of the best on youtube! I am quite addicted to it. Many youtubers upload shit everyday and they have so many suscribers and views. +NileRed you are doing a great job! Keep it up.

[@seventhkeven5505]

You should make a series of how you can use lettuce to make synthetic opium concentrate as a natural medication for opioid addicts who are trying to quit using illegally

[@Anderson_808]

LOL is that a thing? but this guy turned a rubber glove into grape soda so it wouldn't surprise me.

[@seventhkeven5505]

@@Anderson_808 yeah ive made it before, you can smoke it too

[@SycosTV]

I have no idea why I am watching haha, BUT its really interesting. I don't plan on using this information at all but I really enjoy watching your videos!

[@tycool086]

I feel like this guy would enjoy the Antibiotic making process in Dr.Stone

[@wedgeantilles1498]

That round bottom flask would make an absolutely skitz bong m8

[@merlix6304]

You should remove the Plug on the separatory funnel for faster phase separation. ;)

[@jaromschafer913]

my guess to the procedure of converting the anisole to anithole is this: the anisole reacts with the propionaldehyde to produce a side product. then the oxygen left over and also the hydrochloric acid reacts to form some water, and then the chlorine attaches itself to the propyl group, which i think also produces hydrogen chloride gas too. i think that the phosphoric acid is just there to catalize the reaction. the second step is the pyridine removes a hydrogen from the second carbon on the propyl group and the only chloride ion on the molecule, which also produces some hydrogen chloride gas. after that the first and second carbon on the propyl group form the dubble bond, giving you your final product of anithole.

[@timg3584]

I have no idea what anisole but I'm ready to learn from red nile

[@HomoMisanthropos]

1) 1st step similar to aldol addition like in phenol-formaldehyde tar synthesis directed in p position due to the steric hindrance, followed by mainly SN1 substitution of benzylic OH by Cl (Secondary benzylic OH should favor SN1, if solvent is water-that's the case) Formally first step may be considered as electrophilic aromatic substitution-it's very similar to chloromethylation reaction, aldehyde is protonated on carbonyl =O, HOMO of anisole is degenerate Ψ2 and Ψ3, LUMO of aldehyde π*. Aromaticity is disrupted, untill positively charged intermediate (stabilized by methoxide sp2 oxonium) looses proton to any base (water for instance). Then benzylic OH is protonated, it leaves as H2O, leaving behind flat benzylic carbocation stabilized by P-sigma hyperconjugaation and resonance with P-methoxyphenyl and coordinated by H2O (oxygens lonely pairs). Carbocation is than attacked by Cl- and we get the product of first step. Major side products of first reaction will be 1,1-di(p-methoxuphenyl)propane, 1-(p-methoxyphenyl-propan-1-ole and 1,1'-dichloropropyl ether 2) E2 Elimination-base is Py

[@DaysofKnight]

When you watch so much of one person back-to-back you start to notice things in their speech. Nile doesn't say "someTHing" he says "some'ing"

[@MillisecondFourthClockhand]

*I don't get all this, but it sure is satisfying to watch.*

[@divyanshrodney8322]

Here's an interesting use for anisole- Anisole was identified as a pheromone for white grub beetles and is being used to attract males of the insect to a tree which is sprayed with insecticide.

[@daliilars3350]

He sounds so normal here.

[@zachw3347]

Dylan Leary is like that kid who points out the teachers mistake on the test for extra credit

[@johnpapa8554]

You are the best!! please make Propylene glycol dinitrate one day if you are in the mood!

[@tykjpelk]

Anisole is used as a solvent for PMMA used as a resist for electron beam lithography. The manufacturer says it's a safer and less viscous alternative to chlorobenzene, but I don't know what other reasons there are.

[@ScoutSniper3124]

Somebody got an A++ in Chemistry.

[@theoriginaldonutdude4950]

This guy must make great homemade bongs

[@aronlongvamk4515]

Me: I have watched every Nile videos Video I have never watched Me: ooo new video! Video: published 5yrs ago

[@dylanjaramillo6958]

i had to reread the title for a second

[@satchelfrost6531]

Not sure if anyone has given the correct answer on the mechanism, but I'll give it a go. The oxygen on anisole is electron donating making it an ortho/para director. The lone pair from the oxygen can resonate to the para position and this in turn will attack the aldehyde in an electrophilic aromatic substitution. Then a tetrahedral intermediate will be formed which is easily protonated by HCl or phosphoric acid. The phosphoric acid protonates the resulting alcohol a second time and now you have a good leaving group. Since this is a benzylic position the reaction should then proceed SN1 and water will leave resulting in a secondary carbocation. Chloride being a good nucleophile can then attack this position forming the first product.

[@ahmetselcuk1400]

anisole formed p2p with chloropropane????

[@itskaiks3469]

The fact that I read this as making AN-ASS-OLE is just…. So perfect for me….

[@ars2995]

Coolest bong rig ever bro!

[@persophone4554]

You add, sodium hydroxide primarily to remove traces of unreacted phenol (soluble in DCM and anisole). Phenoxide ion being charged (thus solvated with water) is soluble in water .

[@onlockmobileskateshop113]

You say words that I understand in sentences that I don't.

[@extv1p3r65]

I have no clue what any of this means but I’m intrigued!