> chemistry > acides > p-toluenesulfonic-acid > make-p-toluenesulfonic-acid-nurdrage

Make p-Toluenesulfonic Acid

NurdRage - 2019-08-22

In this video we make p-Toluenesulfonic acid from sulfuric acid based drain cleaner and paint thinner containing toluene.

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BlackMagicProd - 2019-08-22

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!

killersmaideniron - 2019-08-22

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!

Daniel Coleman - 2019-08-23

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

BlackBloods Unit - 2019-08-23

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

ShadowDragon8685 - 2019-09-11

Agreed! I love all of NurdRage's videos, but that explanation was just... I don't know hardly jack about chemistry, but I was mostly able to follow the broad gist!

Racker26 - 2019-10-03

10/10 would watch again. Though not with one of my siblings. I feel I might enjoy these videos less when watched with a chemical engineer.

edgeeffect - 2019-08-22

"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.

prostě Deni - 2019-11-07

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

Ryan - 2020-04-06

@prostě Deni no...yes? Maybe idk

Charles Thomas - 2019-08-22

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

spiderdude2099 - 2019-08-22

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.

Al2Me6 - 2019-11-03

@spiderdude2099 That's Hund's rule, not Huckel's rule. (The latter is that aromatic compounds have 2N+2 pi electrons.)

spiderdude2099 - 2019-11-03

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

Qalnut - 2019-08-22

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

Robert Chambers - 2019-08-22

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

Gareth Dean - 2019-08-22

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.

Johnathan Corgan - 2019-08-22

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.

Flux Gxnisxs - 2019-08-22

O-Chem Professor eat your heart out

Alan96 - 2019-08-22

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

Felixkeeg - 2019-08-22

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

LStein - 2019-08-22

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.

Johnathan Corgan - 2019-08-22

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*.

Mirko Keča - 2019-08-22

Your warning started almost like a poem.

theyaoster - 2019-08-22

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.

LuckyThat1Guy - 2019-08-22

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!

Dr Gonzo - 2019-08-22

Just like my Orgo prof said: “it’s always because of sterics!”

Orion M42 - 2019-08-22

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

Calyo Delphi - 2019-08-23

I definitely loved that explanation at the end of the video. Suitably high-level for those of us who savor it. <3

Ask Questions, Try Things - 2019-08-22

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)

Mageling55 - 2019-08-22

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

Lael Odhner - 2019-08-23

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

Stłuczony Ziemniaczek - 2019-08-22

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

Aco - 2019-08-23

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

Lachlan Hamilton - 2019-08-26

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

Zilch ­ - 2019-08-22

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

Kain Yusanagi - 2019-08-22

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.

loki - 2019-08-27

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 😁

Im 33 and it sucks. - 2019-08-23

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

Nightlife_Rolf - 2019-08-22

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

science_and_anonymous - 2019-08-23

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

Geoffrey James - 2019-08-23

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

Andy Wells - 2019-08-24

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.

ToTouchAnEmu - 2019-08-25

I was expecting an insanely complicated explanation at the end and just ended up with ochem flashbacks.

Adam Wiess - 2019-08-22

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.

bormisha - 2019-08-22

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

Akshay Kishore Desai - 2019-10-11

8:36 Gayest person on patreon 😂😂😂

Entenkommando - 2019-08-22

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.

Nicholas Alt - 2019-08-27

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!

seraphpegasus - 2019-08-23

13:19 also sulfonation is reversible.

Jason Patterson - 2019-08-23

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.

Brian Streufert - 2019-08-23

Ok...the last part of the video; where you get really technical. Yeah, more of that shit. Thats the stuff right there, that is it.

ipity dafool - 2019-09-06

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

CWA1940 - 2019-08-23

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.

Nathan Klaft - 2020-01-20

Man, I guessed about the stearic effect only because another one of your videos, I was very happy
I hope you still read these comments youtube chemist like you, nile, cody, and the like have given me a new hobby/passion

Grant Keller - 2019-08-22

Dam, that moment when you realize your worthless education only taught you not to stand next to another dude in the head...Where's my tidepods...(much respect to those who understand this) Please use your knowledge for good... Peace

Orion M42 - 2019-09-21

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

Atony B - 2019-08-25

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

TheCuriosium - 2019-08-23

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

Dawid Bursy - 2019-08-22

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?

Fossil Draws - 2019-08-23

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

Nasriya - 2020-06-09

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