Dude this channel is insane. I've been watching RU-vid my whole life, so I remember watching NurdRage and NileRed who got me into chemistry. Idk something about the way he describes everything
Heterocyclic compounds are always cute, and have also cute names due to Hantszch-Widman (or something like that) nomenclature rules. Imagine 1,2 diazete, Thiirane, Oxepine, or even Oxetane. So cute 😂
In the 1970s I made an oxetane intermediate in the synthesis of a pheromone. I started with butyraldehyde and 1-pentene, and reacted them under UV light in acetonitrile solvent. This resulted in the formation of a longer molecule with an oxetane ring in its middle.
Nice video! Wondering why the first step is necessary since in theory you should generate the same alkoxide intermediate from 1-chloropropanol if you treat that with base. Oxetanes are cool molecules, though they can be a pain to work with in pharmaceuticals. They tend to ring open under acidic conditions (ie stomach acid or even silica gel) due to their strain. However, they have interesting properties and can be used as ketone bioisosteres! 😊
I was wondering the same thing, though I don't think cyclization would proceed with just Et3N as a base. Making the acetate and treating it with hydroxide liberates alkoxide readily. You could definitely just use NaH and use the chloroalcohol directly, can also prepare the iodide for even better reactivity via Finkelstein.
Try polymerizing oxetane with Lewis acids - a rather interesting reaction, and if you pass acetylene through a polymerizing mass, you get an even more interesting product.
You sometimes fill your flask and separatory funnel too full. I think it make it hard to shake or mix the mixture effectively or to prevent overflow, when high exotherm reactions take place.
Thank you so much for showing the mechanisms! They make it so much easier to understand. But theres no way that Oxetane is stable right? The first thing I thought when I saw the structure was steric hindrance. I kinda put this in the same catagory as cyclopropane.
Nilered is like "these funny chemicals look similiar, wondering how you can turn each into another" and you are "oh i saw an interesting molecule model/graph in my textbook, wondering how it looks like in practice"
just a suggestion: when showing the structures of the compounds and blurring the background like at 1:35, try darkening the footage so that the white text is easier to make out. it's hard to see the small white lines on a background that is nearly the same color.
Probably because the sp3-carbon bound to the chlorine gets closer to the collapsing ether bond, through the attraction of the chlorine to the carbonylcarbon
@@lukassorowka2672 Is this really a concerted reaction? I would assume it is a two step reaction, forming an alcoholate, which than reacts in an intramolecular SN2 reaction. This would be similar to the formation of oxetane using 3-chloro-propan-1-ol, but the reaction of the hydroxide as nucleophile with the carbonyl center is much more attractive in contrast to do a SN2 or E2 reaction at the C-3/C-2 Carbon directly. Therefore, the formation of undesired sideproducts is lower when using 3-chloropropyl acetate compared to 3-chloro-propan-1-ol.
@@a830485a I never said that its concerted. It is in fact as shown in the last third of the video a two step reaction. The coordination of the chloride to the carbonylcarbon is just my assumption on why the reaction with the 3-Chloroacetate rather takes place in an intramolecular fashion, while the williamson ethersynthesis probably leads to more polymerisation, as somebody already suggested as a reply here, because the sp3-carbon on the hydroxy-group isn't that electrophilic. But nevertheless I agree with you in that sense that the reaction with 3-Chloroacetate yields less side products because of the more electrophilic carbonylcarbon which avoids the E2/Sn2. Btw you can try all day long to yield Oxetane from 1-chloro-propan-1-ol, that won't work 😆. You need 3-Chloro-1-propanol as stated by chemiolis already
My only comment is that the mechanism for the first reaction implies that the 3-chloro-1-propanol is still protonated in the presence of the triethylamine when the acetyl chloride is added. It's probably already a salt with the protonated triethylamine making the mechanism 1 step simpler. Good video!
Just a question, How come you cant just react 3-chloro propanol in basic conditions, causing the negative oxygen to preform a sn2 reaction with the 3 carbon and forming oxetane?
@@spaceavenue_ YEAH I've been obsessed with the Explosions&Fire/Extractions&Ire and now Chemoilis competing to make it! I've been a back-porch chemist since I was about 16 (5yr+) I started dissolving pennies in acid and then once I started getting the glassware to distill I was on fire. I have most everything I need now to do random projects, not quite the collection that these channels have, but I'm self funded for fun so... As for the 90° comment, I was aware of these molecules I've seen them drawn... I just falsely believed that it was just a theoretical chemical a student came up with that couldn't actually form so when the video popped up it was like... wait how tf and then ofc you're just self condensing a propane with 2 leaving groups lol I keep trying to tell people chemistry is cool.
@@williamackerson_chemist Ah gotcha, and also I'm sure those bonds are slightly off from 90° because of the oxygen being a different size, whereas for instance I think cyclobutane has exact 90° bonds due to its symmetry. In addition, I'm guessing these bonds might be slightly bent due to the strain and if you look at electron density, they should bow out slightly, less so than with cyclopropane. Around 109° should be the least strained bond angle for an sp3 hybridized carbon, but 90° is possible. The bond angles involving the hydrogens in these molecules, however, will be greater than 109° as they have extra room.
@@MrBradshawbenjamin YES THAT is what I remember. My AP Chem/ Physics 1 & 2 teacher had just dropped that 1 off about the sp3 hybridized impossibility of that kind of electron density at 90°. I need to read up more on my foundations. I have trouble with my memory mainly recall after 2yr of pretty hard drug use hope I get at least another decade before I get dementia. Or hey maybe once my brain has more than 3mo off, maybe it will come back a bit. I'm trying to go back to school and become either a chemistry teacher or research in novel drug development.
I was wondering if the final mechanism might be sn2 displacement of the chloride for hydroxide which is then deprotonated under the basic conditions. This O- then kicks off the acetate in another SN2 reaction?
the best, most clickbating title would be "The guy who made smell of dirt makes the smallest square ever". Oh boy this video would get so many views and interactions
hey why do you separate the organic layer and aqueous layer both through the bottom of the separatory funnel? the organic layer is gonna be contaminated from that and reduce yield.
Thank you sir for your educational illustration. There is a question in my mind regarding the synthesis Dose the oxatane molecule synthesize by [2.2] cycloaddation using Paterno-Buchi reaction Could the started materials be formaldehyde with Ethene ? Thank you sir
Why doesnt adding 3-bromopropanol to some strong base such as sodium t butoxide work? 3 bromo propanolate should always be in low concentration and depending on the amount of solvent t butoxide could also be?
I wanted to make nepalm and I wanted to know the formula for it. I know you can make it if you combine polystyrene and gasoline. But I want to know some of these things(at least one of these): 1. What is the formula?? 2. How mutch polystyrene and gasoline do I need for 50 grams of nepalm 3. Is there a better way u could make It??
Good video! As always, thanks for the mechanism. I was wondering, why do you convert the alcohol to the acetate initially, if you are putting it in such highly basic conditions afterwards anyway? Couldn't you just put the alcohol into the potassium hydroxide directly?
Difference in boiling point of Oxetane and vynilalcohol is great, but... many-many-many liquids are forming azeotropes. And this makes really hard or impossible task to separate liquid substances by fractional distillation. :(
@@dimaminiailo3723 The keyword is "Probably". Till you have specific research reports you can't state. I checked references about different azeotropes: binary, ternary, quaternary and many substances form azeotropes when no one could ever expect it. So.. better to do some research. I synthesized oxetane derivatives from oxiranes, but they where crystalline substances and were easy purifiable.
The hydroxide was added as a nucleophile for the hydrolysis of the ester, to form the oxetane in a consecutively intramolecular SN2-Reaktion. The oxetane has already been distilled during the reaction. KOH had no purpose for the distillation itself and the excess of it remained as leftover.
@@a830485a Thanks for taking the time to reply, my confusion was that at 7.30 he adds additional hydroxide to his crude product even though none of the starting material should be in this flask as far as I can tell? does this react with the unwanted allyly alcohol/ other side products or something ? sorry if I've misunderstood!
@@harryparr4879 Ah okey, now I understand your question. The crude distillation product contained still starting material, therefore the KOH is added. The boiling point for the product is around 50 °C, the starting material is around 70 °C and the allyl alcohol is around 100 °C, while the reaction takes place at 140-150 °C. In the first distillation you only get rid of the high boiling fractions. In the second distillation the product gets properly separated via the vigreux column.
as the other commentor said, clayden warren is pretty much the org chem bible :) I saw another one called Reaction Mechanisms in Organic Chemistry by Metin Balci, seems to be a good one
