Doug's Lab - 2018-01-29
In this video, I make p-toluenesulfonic acid by sulfonating toluene. Patreon Link: https://www.patreon.com/DougsLab Twitter: @YTDougsLab Google+: https://plus.google.com/u/1/103236004133559189742
0:57 "used in some upcomming reactions" .... they never came....
13:49 Those are some weird tongs.
They're flesh tongs!
hahaha I came to the comments as soon as i saw him do that lol
When is that long lab tour coming?
Nice work. Could you do yield calculation in the future?
you're awesome
you should make videos dedicated to teaching chemistry
Love your videos! I was wondering if you could make a video on how to clean glassware as I think it would be helpful for other amateur chemists
Should fill up the trap with toluene first, that's what we do when we make 4,000 gallons of tsa.
Sweet. A nice relaxing chemistry video before I hit the hay.
Thank you for this video about the too silly acid. :)
Still would live to see a video completely devoted to solvents
Awesome video prax. Wish i knew how to do those reactions.
Hey Doug very nice video, can you also show hydrolysis of sulfonated toulene with NaOH to make para cresol. Also can I reach you on email somewhere ?
Hey Doug, can you tell us where to buy that rubber scraper? Thanks man, love your videos, It's awesome that you are back.
Hey, thanks! I got them a long time ago and I'm not really sure where... but to get you started, go on Amazon and search for "rubber policeman." I'm not joking, that's what they're called.
Love the comment section... Got some true geniuses tapping away.
I need to listen to this in 1 quarter the speeedd y0
Awesome stuff!
Makes a great leaving group for alkyl alcohol elimination by a nucleophile.
I found your channel because of Nilered. Your videos are equally as good. I'm learning a lot. And may one day go to school for chemistry. Very interesting stuff.
Good work ! What's your next experiments ? Do you accept suggestions ? The mine would be synthesis of vanillyl amine.
I am loving your comeback on YouTube! keep up the excellent work!
Professor K still loving it?
Please show all of your glassware and eqiupment in the next video.
How could you convert that to toluenesulfonyl chloride?
Have you planned making tosyl chloride and then tosylate some alcohols?
Astral Chemistry this I would LOVE to see
I'd love to see this as well. Unfortunately probably involves thionyl chloride or some other nasty materials.
You deserve more subscribers!
why haven't I found your videos earlier? your explanations are superb; quick, simple but without too much of dumbing it down. works perfectly for me.
I did thisone, just refluxed (density > 1.6) h2so4 with toluene together with a little s2o7 obtained from electrolysis of diluted h2so4, I got a bunch of crystals.
And what with this ~40ml of trapped Toluene in Dean-Stark apparatus? It just didn't react with H2SO4? Did you count it as a loss?
A large excess of toluene is always needed to drive the water removal mechanism. In this case, sulfuric acid was the limiting reagent by a large margin. However, the toluene in the dean-stark trap is clean and can be dried and reused for other experiments.
I've been wondering how to run a proper sulfonation fro a while now. Do you think this would work with naphthalene to yield naphthalene sulfonic acid?
Not really. If you're looking for 2-naphthalenesulfonic acid, it's pretty simple. The high BP of naphthalene allows you to simply mix naphthalene with sulfuric acid and hold that at a little over 100C to continuously remove water. You literally just heat the two together for like 24h and allow steam to escape, then do an acid/base workup.
Thank you. This makes sense. Great video by the way.
I tried the recipe ... my ketamine never tasted worse
Alkenes. Sulponation process also same procedure??
Really i like this crystal clear explanation and demo
Thank u sir
Hey man! Can you do a refining video on palladium or gold... orrrr silver? Lol please, that's what I focus on, and I'm curious to see other people's experiments and different variables in everyone's steps. I know most are straight forward. However it would still be cool to add that content to your channel :) cheers
Can you buy oleum in your country ?
Hi from Ohio
Hi from Brazil!
Well hello there!
quem se importa?
What about making p-xylenesulfonic acids
How does water cause precipitation? Won't water reverse the reaction back again?
I think it's called a Barrett receiver when it has a stopcock on it.
Fan-freakin-tastic! I was just about to investigate the synthesis of a decent hydroxyl protecting group. It's good for getting certain recalcitrant SN2s to work as well. Thanks, Doug!!! You really brighten up my day! 😀😊
Great, so great to have you back!!
Does this work with styrene as well or will it polymerize in the process? I mean that would be incredible to make some acidic polymer film after polymerizing the p-styrenesulfonic acid.
Thanks for this video anyway, I really enjoy each of them.
Hmmm.. where you buy your rubber scraper?? looks greatt.. please let me know Sir
Google "rubber policeman". That's really what it is called.
I very often thought about whether this is possible, because of benzene being easily sulfonated, too. I might give this a try in the future. Nice video! :)
I wonder if you are in jail and that's why you are not posting :(
Nice synthesis! This method is more secure because it hasn’t use oleum.
Make a video in which you show your new laboratory!
It would be nice if you did a yield on the acid
and what about ortho product? it wasnt made because of steric effects?
since this is an equilibrium reaction, the most stable product (the para isomer) is formed
Good videos
It is, perhaps a silly question, but it has been more than thirty years, and you remind me of why I miss it so. Why is it para? Is it that the meta comes at a higher temperature, or some resonance effect, or are you getting a mixture, and just didn’t mention it?
Not a silly question at all! Para is favored in this case because of the ring activation effect of the methyl group, which is an electron donor and contributes electrons to the resonance via conjugation. This contorts the electron density of the ring to favor ortho- and para- species. Since there are two ortho- sites and one para- site one would expect more ortho- than para-. However, the steric bulk of the methyl group means that for sulfonation in particular, the para isomer is favored over all other outcomes by a huge margin. It is less stable next to the methyl group and will readily rearrange to the para- position at high temperatures. Had I used SO3 in H2SO4 and kept it cold, I could very well have had a significant percentage of the ortho- product.
Doug's Lab Hi,i have a question.
In the last Lab Tour you said you will make a more detailed Lab Tour.Will we see that in one of your next videos?
This is just a suggestion from someone who doesn't know much chemistry, but I find that I have an increasing lexicon of chemicals that I know how to synthesize but not necessarily what I can do with them. If it isnt too difficult, maybe just telling us a few examples of what the particular thing you've synthesized can be used for would be helpful.
Its kind of like programming, the more elements of an API you understand, what you can get done with it increases exponentially.
Jason Patterson - 2019-08-23
Miss you Doug!