Make p-Toluenesulfonic Acid

[@blackmagicprod7039]

Loved the last 5 minutes explaining the mechanism for para- favoritism. We really appreciate that you don't dumb it down unnecessarily for the camera. Keep it up!

[@frollard]

I did like it and how the analogy ended up. "normally electrons would push it that way...but in this case, sulfonate is fat and has masculinity problems"

[@DrewskisBrews]

@@frollard ...and the "urinal analogy"

[@killersmaideniron]

It was great. I watch these videos because I'm semi into chemistry, I don't really practice it, but I like to learn about it, so this helped me understand the reactions much better. Sometimes chemistry can feel a bit like a black box (much like artificial intelligence), so explaining why it happens is so interesting to me. Cheers from Denmark!

[@danielgrantcoleman]

That poor poor toluene molecule. Shaped more like a toilet than a urinal though. Lol

[@blackbloodsunit3233]

Very good idea fo the last part of the video, it's the most interesting thing to learn the mechanisms

[@charlesthomas7970]

That's the best analogy of steric effect ever. Thanks Nurd!

[@spiderdude2099]

Same analogy can be used for huckels rule explaining how electron orbitals fill up. Even though each orbital can hold 2 electrons the electrons will try to find an empty orbital first before doubling up.

[@spiderdude2099]

Al2Me6 I know, I'm just saying a very similar analogy works for describing orbital filling.

[@edgeeffect]

"Two guys is a washroom with a row of urinals".... throw in a bit of quantum mechanics and it all makes sense. Excellent explanation Dr. Lithium.

[@justADeni]

So does that mean that sulfuric acid in meta position is gay? :D

[@Ryan6.022]

@@justADeni no...yes? Maybe idk

[@Qalnut]

The bit at the end was gold! Very clear exposition with nice figures to show what's happening visually. Thanks for including it.

[@glorylord6]

Looks like I’m staying up another 15-20 min, thanks NR

[@corybackus3449]

I have been watching this channel for years. I don't understand most of what is explained and demonstrated, but I find it very enjoyable to watch.

[@Mageling55]

THat last 5 minutes was an entire lecture in my O-chem class... And you explained it better

[@garethdean6382]

I would argue that the resonance forms are just a way of rationalizing things too. There's no 'switching' going on in benzene or any other aromatic compound, those bond lengths ARE identical and not just because the atoms are jumping around faster than we can see. The multiple possible, equal-energy states are merged into one hybrid state and that's the be-all and end-all of it.

[@johnathancorgan3994]

Was going to comment on this until I saw yours. Completely agree; the resonance forms don't actually exist, but visualizing them helps to understand the actual "hybrid" state that really occurs. The diagrams he uses showing electron density are a much more accurate depiction.

[@theyaoster]

I appreciate the effort you put into the lesson at the end; as someone who only "studied" chemistry in high school, I found it insightful.

[@Alan96555]

Nothing better than a little chemistry at 5 in the morning :,)

[@johnathancorgan3994]

Thanks for the reaction mechanism explanation at the end--it really is useful in explaining *why* reactions occur the way they do, and not just *how*.

[@LuckyThat1Guy]

I just finished my ochem classes last semester, but I'm glad I could still follow everything you said, even at the end. Another great video!

[@AcoAegis]

I've been following your channel about 10 years now, and I'm so happy you explained the bits at the end. I really appreciate how clear it was as well. Thanks Nurdrage

[@oak_meadow9533]

Dear Prof. N. Lithium; Just a note to say thank you for sharing the wonderful lab aspirator build you detailed. I viewed it last night and immediately went into Ebay and got a stainless aspirator and a 1/2 hp 160psi pump. I built myself a bunsen a la Doug's Lab, to flare off noxious gases including an input for O2 when I need more complete combustion. As an BSEE I love all things technical or math based. I had 2 years of inorganic chem, but wanted to study organic, you made it possible. Between you and Vogel's 1st & 5th edition, I am learning little by little. Thanx for your kindness Bill from Texas

[@Felixkeeg]

I will use that explanation at the end as teaching material. And I'll use that bathroom-urinal analogy! :D

[@lstein8670]

Really enjoyed the ending where you explained the reaction in more depth. Hope that you can do this a little more often because it nice to review old organic chemistry material.

[@jerem7xd]

Woke up, and saw new NurdRage. It will be a good day :)

[@calyodelphi124]

I definitely loved that explanation at the end of the video. Suitably high-level for those of us who savor it.

[@0Arcoverde]

It's awesome that I understood the explanation today and didn't quite get it 3 yrs ago, I am learning, and quickly

[@synthesizer8026]

I love your use of urinal etiquette to describe para substitution.

[@lokiadhd]

Your explanation after the experiment is great! I wish you could have been my chemistry teacher! Please do more of these in your future videos 😁

[@Shraddha_9923official]

Thank you so much 🤩 sir for well explained

[@willwei98]

Thanks for the insightful explanation at the end! I really appreciate it!

[@atonyb2575]

Thank you very much for your work and especially for the additional information like why e.g. para-product is preferably formed!

[@Nasriya]

As a general chemistry professor, you explained this very well. :)

[@NicholasA231]

My wife overhears "We are not making zwitterionic toluene, and your toluene is not going to spontaneously isomerise into methylidene cyclohexadiene. It's just not going to happen, as awesome as that would be." She laughs and says, "okay, thanks Igon". I almost died. Thanks for the lesson!

[@science_and_anonymous]

JUST IN TIME!!! I needed this for synthesis. Next thing on my list, catechol from phenol

[@Alloran]

Fantastic stuff. As usual I appreciate the detail you put forth as you walk through the methods. The little notes about things that could go better here, maybe a trouble spot there, it's all highly practical and only really something you could find out by experience. Unless you're some kind of mechanisms wizard but that shit is going a little out of my league. (alot. alot out of my league).

[@TheChemicalWorkshop]

Already knew the reason but still watched it I think you should do more of these !

[@Dewey_the_25U]

YES! YOU'RE STILL ALIVE! HUZZAH! I hope you're doing well, be careful and have a great day! You're something that if I could download the videos from KZbin, I'd keep them around simply because of the value you have. Not in the traditional sense, more like the pique ones interest and to arouse curiosity.

[@SoulDelSol]

I can download KZbin videos so I'm sure you can too

[@Dewey_the_25U]

@@SoulDelSol Yeah.

[@CWA1940]

Great explanation of the mechanism of the reaction. I seem to have read somewhere that if you want to understand chemistry, "follow the electrons!" Also, I seem to remember vaguely that alcohols can often be identified as their tosylate derivatives.

[@SomnolentFudge]

I would love to see more videos with detailed reaction explanations like at the end of this one. There arent many good videos blending practical with theoretical chem out there. I like your explanation of steric effects. I've always pictured it as two very overweight people trying to mate, but your version is maybe a bit more youtube friendly.

[@petevenuti7355]

Really!

[@MoleculedMan]

Great video as usual, Nurdrage. You might find it interesting to know (or already know) that in the field of carbohydrate chemistry, p-TsOH can be used as a “dry” substitute for acids when dry acidic conditions are required (installing a propylidene protection group for example). Since carbohydrates are easily oxidized by the usual dry acids like conc. sulfuric acid, p-TsOH and camphorsulfonic acid are good alternatives. At least, that is if you don’t want to turn your precious sugars into a carbon snake! Keep up the great work!

[@orionm4254]

Do you teach chemistry at a school? You should get paid for the lessons. Thumbs up!

[@systemloc]

OMG, best explanation of steric hindrance ever!!1! Also.. I always was very suspicious of those textbook mechanism explanations using deprotinization, as in the methyl group in your example. I totally missed that it was just a mental exercise and not actually happening. I feel much better about the universe now. Thanks for pointing that out!

[@akshaykishoredesai2017]

Thanks sir for explaining about how resonating structure work and about mechanics of ortho para 👍🏻👍🏻

[@RaExpIn]

I always wanted to try this, but I don't have a Dean-Stark apparatus and didn't want to separate the water and toluene with a separating funnel or add a large excess of toluene... The addition of the water looks pretty nice! Nice video!

[@andywells8125]

Wow this has so much cool chemistry in it!! Thanks again. Maybe you can show how to convert the p-sulfonyl toluene into tosyl chloride.

[@KainYusanagi]

Great explanation of the steric effect, thanks NurdRage! I remember you going into the steric effect in your sodium synthesis series somewhat, but not in as much detail on it specifically.

[@gamingmarcus]

As someone with a chemistry background I'd say good job on the explanation. I might have put a visualisation of the orbitals in there to show how they are overlapping and therefore influencing each other.

[@laelodhner1361]

All this talk of charge delocalization reminds me that I'd love to see a series on conducting polymers!

[@bromisovalum8417]

I wonder if it can be used to make hydriodic acid solutions from an alkali iodide? Sulfuric acid can't be used as it oxidises most of the formed HI to elemental iodine.

[@TheCuriosium]

Great video! And thanks for the lesson at the end, that was awesome!

[@christopherleubner6633]

Distill the tolulene and then distill the sulfuric acid first. Then you get very nice clean acid.❤

[@danielaustin7643]

convert it to tosyl chloride (the acid chloride) and use that to make tosylate esters which are really useful as the tosylate is a great leaving group. use them in williamson ether synthesis or others.

[@jasonpatterson8091]

After watching your video, Doug's Lab's version of the same reaction was recommended to me, and I watched it (for at least the second time) as well because well... Doug's Lab. He did a pretreatment step to remove 2- and 3-methyl thiophene that are contaminants of commercially available toluene and that will cause discoloration of the product. I realize that you also were using drain cleaner sulfuric acid, which carries its own set of impurities, but this might have been part of the cause of the persistent brownness in your recrystallized product.

[@ThatChemistOld]

I've done a bunch of fischer esterifications with benzoic acids and you don't get any significant sulfonylation whatsoever if you only heat the reaction to 80C. I've done at least 7 of such esterifications with H2SO4 without any issue (8:23)

[@DutchPhlogiston]

Molecules do not quickly change between resonance forms. The bonds in benzene are in fact all exactly the same at any given instant. A molecule _IS_ the 'average' of all resonance forms, even in the briefest of moments. It is actually a weighted average, to which low-energy states resonance forms contribute more than unlikely high-energy forms.

[@darianballard2074]

Good video as usual.

[@preciadoalex123]

Great work again N.R.

[@TheMeilinger]

oh steric hinderance. my go to explenation for basically every single reaction mechanism

[@azafreak]

Noice Free lesson, work can suck it I'm going on 2nd lunch.

[@disasterexperiments493]

Yeah, Fischer indole synthesis time!!! You can use it as catalyst for fischer indole synthesis

[@walterbunn280]

Good stuff. Now that sulfa antibiotic is just one step closer.

[@bormisha]

Thanks a lot! Especially for the explanation, it is really awesome.

[@dreamtheateriano95]

NR is back!!

[@mirkokeca4853]

Your warning started almost like a poem.

[@piratewhoisquiet]

Top notch video as always

[@michaelsambor5286]

@NurdRage, I do not know if you are still active but I would love to see a video on the lab procedure for p-TsCl from p-TsOH and thionyl chloride. Thank you and good work in all your videos

[@disp3rsion]

I like everything you said, except for the explanation of resonance as electron hopping. The problem with this explanation is that it implies that resonance is a physical phenomenon. Actually, resonance is a fictitious concept. It's a deficiency in our ability to accurately represent a molecule using only one lewis structure.

[@disp3rsion]

@Hurricane's channel Resonance is extremely useful. It explains 95% of reactivity in organic chemistry. Still it should not be confused as a physical phenomenon.

[@jonprider3041]

The saving grace.

[@16SKB]

Could you make an ionic liquid with this? I found them facinating, but you can't find that good videos of them. Maybe you could use an ionic liquid to upgrade the aspirator pump?

[@dawidbursy3825]

I really liked your performance of that reaction. My first reaction in organic chemistry was to obtain sodium p-toluene sulfonate. I'm sentimental about this reaction. From what I can remember, the reaction leads to this product at temperatures above 100 degrees Celsius. To obtain the ortho product you need to perform it in lower temperatures less than 20 degrees Celsius. Can you check if I'm right?

[@5speedfatty]

Hey Nurd, a nile red video on plasma showed a significant amount of sodium in the glass he used. I know this isnt a sodium viideo but im thinking maybe that was part of the reason that experement was killing flasks. it was pulling the sodium from the glass. i am no chemist but it seemd interesting when i saw it.

[@mgritsch]

The poor yield is mainly due to the workup... I recommend: - not to use the lowest possible quality of sulfuric acid - not to unnecessarily throw back in the toluene, rather distill off some excess - pour the reaction mixture into some beaker for forming the hydrate - this really pays off because it solidifies badly... - recrystallise from conc. HCl (uncomfortable but easy to remove in a desiccator over KOH) or 70% sulfuric acid (comfortable to handle but some will remain in the product) - it is extremely hygroscopic, so don’t play too long in the open air or you will be left with a slush or complete melt...

[@billsmathers7787]

Excellent advice-- in my hands this preparation yielded 80% yield even with some sloppiness.

[@muffinman8744]

KZbin finally gets around to to telling me u have a new video.

[@jonnymakeschemicals2714]

A bit of a late comment but you should make sulfanilamide from the sulfonic acid, all you need to do is replace the ch3 groups with nh2 groups.

[@eulemitbeule5426]

You forgot to mention the main reason why toluenesulfonic acid is used in labs: It is a solid acid, that means you can measure the amount of acid you use much more precisely (by weighing it) than with normal liquid acids like HCl/H2SO4 that have a concentration that may or may not be accurate (especially with HCl as it is just a gas in solution).

[@borttorbbq2556]

Mind trying to make conductive glass bonus points if you can make it able to catch very fine particles of activated charcoal and get it to stick like when you take & coated it in soot

[@BothHands1]

Lol @ the urinal analogy 😂 Same thing happens in the woman's room, pick a stall with one empty space b/t yourself and others if it can be helped lol

[@thecrazychemist]

Most of the water-insoluble material in the crude is di-(p-tolyl)sulfone.

[@2.7petabytes]

I noticed your stir bar is a bit grimy when you started. Could any impuritys come from the stir bar? Honest question as I’m NOT a chemist.

[@yesrayell8118]

Great job ! Thank you.

[@mareksvrcina5279]

Yes, I will

[@gamingmarcus]

You could convert it to the chloride form in case you ever need to do a fancy substitution reaction.

[@lachlan1971]

The smell of toluene always reminds me of the chemistry labs at uni.

[@kakitasekita33]

Hola soy un joven drogadicto y con este video logre drogarme con tolueno prácticamente gratis. Like y a fav

[@victordonchenko4837]

I don't think you even need to use toluene or select for the para form if you're making it yourself, can just use benzene. The reason para-toluene sulfonic acid is used over other solid sulfonic acids is it's a byproduct in the production of the artificial sweetener saccharin, and thus is very cheap. If you're making the acid yourself that is no longer a concern.

[@kibnob]

Can someone explain why the product doesn't hydrolyze while boiling down the aqueous solution

[@chemicalaffair.]

Please show us how to build thermometer you use. do you use a quickfit adapter? greetings from germany!

[@edoardofasolo6032]

Can you use it to make soap? By oxidizing it to benzyl sulphonic acid with potassium permanganate than esterified it with long chain aliphatic alcohols?

[@alfredmolison7134]

Hi. I'm looking for an acid or combination of acids that can dissolve: Granite, granodiorite, quartz diorite, diorite, and pyroxenite (from plutonic intrusives); andesite and dolerite porphyries as well as other porphyritic rocks (from volcanic dikes and lava flows); and basalt. These were the potentially hardest building stones or stones used as tools or abrasives in ancient Egypt. The Egyptians probably had access to sulphuric acid and nitric acid. They had access to other acids, too. These individual acids or acid combinations may have been used to make it easier to cut stone using steel tools or arsenical bronze tools. I'd appreciate your help.

[@TheWanderingChemist]

Maybe the white insoluble goop in water is ditoluylsulfone?

[@ללאכותרת-ט8ל]

What is next? Ohhh wait! Are you going to make Tosyl chloride and then Diazald, and finally Diazomethane?

[@zachheilman784]

Dumb question from someone who isn’t a chemistry major - is there a pathway from p-toluenesufonic acid to the p-chlorotoluene that would allow you to increase the yield of the para product?

[@edweenier]

Have a question I was hoping someone might be able to shed some light on . I make specialty nut butters . When ever the flavoring is added during the mixing process the mixture becomes very thick and it gets very hot . The main carrier ingredient in the flavoring is propylene glycol. Does anyone know what reaction could be taking place here ? The only other ingredients are either peanut or almonds, salt and sugar .

[@somerandomguy2205]

Do you have a cheap method of buying functional hotplate stirrers? They are incredibly hard to afford for the amateur and yet almost irredeemable for decent lab work. I can get really cheap ones that will probably blow up or don't have enough stirring power. Used ones off ebay are still not cheap and mostly pretty much completely corroded

[@ipitydafool3309]

Any chance of replacing the OH with a halogen in some future lecture?

[@reconnaissance7372]

Could you do a video on Extracting Potassium Metal from Bananas xP Would be pretty cool to see what you could yield.

[@Josezwitterion]

Good good good video

[@padpadangz9774]

Nurdrage: I've got a question about getting Sulfuric acid: would getting Sulfuric acid from lead acid batteries be more pure then drain cleaner or would it be a waste of money?

[@Mageling55]

Drain cleaner + distill is probably cheaper (and definitely safer) than buying batteries. Also Pb++ is probably more annoying to remove

[@user21XXL]

does it form an ester with ethanol in recrystalisation?

[@MrRadioGypsy]

What is TSA used for?

[@askquestionstrythings]

Did you see the recent study on dirty stir bars catalyzing reactions and interfere with reactions? It seemed like an interesting source of potential failures and unexpected results in some processes and problems in amateur chemistry. (maybe worth discussing in a video) cen.acs.org/synthesis/catalysis/Stir-bar-contamination-inadvertently-catalyze/97/i13

[@microscopethuglife2396]

do more tutorial to synthetise antibiotic..

[@blahsomethingclever]

That was cool! Btw what'll be your ne next project?

[@orionm4254]

Nurd Rage, you must have inhaled 1 million litres of SF6 by now! Lol

[@kenkowalski1314]

Please please please NurdRage can u teach us step by step how to turn gold into monotomic gold via 35% peroxide and hydocloric acid and ph swings cheers!! Then lye boil There's nothing on it and u could be the first!! It has phisical properties that's defies logic 👍

[@Treemaster16]

Ken Kowalski one, you just detailed the whole process? Second sounds like bullshit mate.

[@DaNiKzz]

This is good.

[@xjunkxyrdxdog89]

I love this channel but after years of watching I've noticed a distinct lack of rage. Our mystery chemist seems pretty laid back.