In 40 yrs of synthetic chemistry I have never used oxymercuration

@lefthandedspanner

Жыл бұрын

I've used it exactly once, in the second year of undergraduate labs, along with hydroboration/oxidation - they were two parts of the same experiment, to demonstrate how regioselectivity can be controlled

@peters1711

Жыл бұрын

@@lefthandedspanner during my second year in undergraduate labs in organic chemistry we had never used the oxymercuration reaction. Hydroboration/oxidation yes.

@lefthandedspanner

Жыл бұрын

@@peters1711 it was nearly 20 years ago, I don't know if they'd still do it these days

@singularityJoe

Жыл бұрын

One of the only ways for shape selective alkene differentiation. We considered using it to functionalize a 1,1 disub alkene in the presence of a 1,2 disub olefin

@thisiswhereidied3054

Жыл бұрын

I never in my 80 years of life used this reaction. I might be a machine engineer but still, never used it!

Carrot-mediated reduction is S-tier. At least.

@That_Chemist

Жыл бұрын

C-tier for carrot

@aqdrobert

Жыл бұрын

When Judy Hopps, Lola Bunny, and Thumper took chemistry.

@limmuquan4796

Жыл бұрын

It takes very long though

@thecarrotindustry7521

Жыл бұрын

@@That_Chemist Carrots improve eyesight, S-Tier for sight. Stay rooted, my friends!

“Oxymercuration” has to be one of the most cursed names for a chemical reaction

@cyan_oxy6734

Жыл бұрын

Because English has shitty pronunciations.

@NewWesternFront

Жыл бұрын

why

I was nodding my head multiple times throughout this video. It's funny how religiously I studied some of these mechanisms only to never use them in the lab. Reductive amination is also an easy S-tier for me, although I learned about it quite late in my studies.

As a Chem. Engr I have to pick this group of rxns as the most useful: hydrogenation / dehydrogenation / isomerization and polymerization. It's not uncommon to see these all at one plant or within a organic product ecosystem. I know these are mundane to the modern chemist, but these rnxs pay the bills I say, typing on a keyboard made of polystyrene.

@sharpfang

Жыл бұрын

Not a bad take, but hey, nobody rates bread and water as top gourmet dish, even though they've been staple of nutrition for past couple millennia.

@HiwasseeRiver

Жыл бұрын

@@sharpfang The title said "Useful" even that's subjective depending on ones needs. I'm very oriented to C4 molecules. Just realized I left out cracking dammit.

@barnicskobalazs

Жыл бұрын

As a (hopefully soon to be) organic chemist, I loved learning about cracking. So many cool ideas like size exclusion and catalysts (?) if I recall.

@Stripping_Bolts

Жыл бұрын

What about saponification?

@joshp6061

Жыл бұрын

@@Stripping_Bolts I learned that in gen chem lol

Funny story about ozonolysis. One of the PI's at my school had to do an ozonolysis when in grad school, but in the second step, conversion to of the ozonide was too slow, so he had a lot of ozonide build up in his flask. Eventually the flask exploded and shot glass shards into his hands and he was out of lab for 6 weeks. When he came back, the first reaction he had to run was the same ozonolysis reaction.

@joshp6061

Жыл бұрын

“Oh my god are you ok?! Welcome back I hope you’re feeling better after that horrible reaction, we never should have asked you to do it. Ok let’s start you off this time around with another ozonalysos for S&G”

As someone studying solid-state Diels-Alder reactions in my PhD program, I'm a little hurt that Diels-Alder was put into B tier, put I'll get over it.

@Sac_the_king

Жыл бұрын

Solid-state Diels-Alder, you say? Count this idiot intrigued

Dear diary, today someone more experienced than I discredited all my knowledge in OChem. It's the second time it happens.

My college teacher gave us this A3 sheet that has all of the reactions on it, like how to get from an aldehyde to an ester, an alkene to a haloalkane, and along each reaction there's the conditions and reagents needed, as well as the name of the mechanism. Really helpful

@That_Chemist

Жыл бұрын

Yeah having a flow chart like that is super useful; if I ever take a month off of KZread, I would like to spend some time making resources like that

@rspeks9461

Жыл бұрын

@@That_Chemist That would really be cool

@_callmechase

Жыл бұрын

Duuuuude my tutor suggested we draw one from scratch to study for our exam and it was the most helpful thing ever, especially since drawing it really cements it into ur memory

@rspeks9461

Жыл бұрын

@@_callmechase ooh gonna have to give that a go

@TheTKPizza

Жыл бұрын

That is just a great idea, gonna do that right now, got my OC exam next week.

I totally agree with you about the Birch reduction ! This reaction was a key step in my bachelor thesis for the Synthesis of a highly oxidized ring system, at least that was the plan, but in the end everything was just garbage. Working with liquid ammonia is definitely no fun and to this day one of the worst smells I know. We stored the condensed ammonia in a Schlenk flask in a refrigerator (where it remains to this day, one power outage away from disaster) and each addition of ammonia had to be carefully planned each time (transport from refrigerator to fume hood, bring to Schlenk line and quickly add to already chilled down solution, then quickly back to refrigerator). In addition, we didn't have a glovebox, so had to use sodium instead of lithium, and in the end none of this worked and my products even rearomatized 😐

@DipanGhosh

Жыл бұрын

That reaction sure is a b**ch.

@jeremymcadams7743

Жыл бұрын

@@DipanGhosh birch*

@barnicskobalazs

Жыл бұрын

Oh the good ol' rearomatising birtch (sic!).

@NoLongerBreathedIn

Жыл бұрын

At least it's beautifully colored.

Putting Birch reduction into E-tier is probably accurate, but it does sting a bit. Was always my favorite reaction, because what's more metal (heh) than doing a reduction with solvated electrons? "You want electrons? Oh I'll give you some fucking electrons, allright!" It's the most sledgehammer approach imaginable, but somehow it works.

@That_Chemist

Жыл бұрын

Solvated electrons are pretty rad , ngl

@barnicskobalazs

Жыл бұрын

And it's blue 😯

@minklmank

Жыл бұрын

It looks gorgeous - I really gotta admit that

@davidli6931

Жыл бұрын

Using sodium to do reduction is far more useful for inorganic chemistry to achieve zerovalent or even lower oxidation state, like forcing chromium/molybdenum/tungsten to go to a -II (d8) or even -IV (d10) oxidation state. Organic substrates usually don't require such harsh reduction conditions.

@minklmank

Жыл бұрын

@@davidli6931 highly depends on the element in my opinion. I am sure it works great for the elements you mentioned - I really love chromium, tungsten, manganese, molybdenum, you name it chemistry but for example the group 13 elements like aluminum are insanely convenient to just prepare as metal organic Al(III) Complexes with a single hydrogen attached an then just force a reductive elimination to Al(I) , vacuum pump the side product off, or wash it off and be done. My personal favorite though is to use vacuum evaporation and recondensation with a suitable solvent at low temperature to get M(0) Complexes without the need to do any in situ reduction. Can be done with basically the entire d block and if you're just going for the "low melting ones" up until iron, nickel or vanadium you can use a dirt cheap resistively heated crucible setup. Gotta love the 60s

Fischer S-tierification. Come on, it was right there! lol

@That_Chemist

Жыл бұрын

Hahaha

@limmuquan4796

Жыл бұрын

good one

Nice to know my favorite reaction (🅱ignards) (which is unequivocally the best reaction because it’s easy and the one I actually remember) is easy S-Tier. I may suggest next time putting Grignard in G(od) tier?

I think I'm the undergrad Ochem student you speak of since I just finished off ochem 2 this summer. I love this list, it's giving me a lot of context for the reactions I learned and it's funny seeing which ones aren't as used

@That_Chemist

Жыл бұрын

Glad to hear it :)

This will be interesting since not every undergrad learns the same reaction when taking organic chemistry as class! Will be curious to see how this goes!

Excellent video!! I wish I had seen this when I started my PhD! I learnt the harsh as I’m sure happened to most people. It’s just so funny when junior people join the lab and feel confident they remember all the reactions learned in class, only to find out that lab routine is a different planet 😂😂

"I expect this episode to be really polarizing" wise thing to say after ranking haloform F tier to start the video. Sadly, I agree, and haloform is still in my top 5 favorite :( even though it's not useful, it's wonderful. I'll probably drop more comments thruout the video but I couldn't help but comment this lol.

@That_Chemist

Жыл бұрын

:)

@barnicskobalazs

Жыл бұрын

I mean, yeah, haloform is pretty cool, but is it 'C-H activation by Pd(II)' level of cool? But then again, I'm a sucker for those 'unexpectedly' sick 6 membered transition states.

@jeremymcadams7743

Жыл бұрын

@@barnicskobalazs no but hear me out. Simultaneous generation of a disulfide and carboxylate group in 1 pot. Is it totally not worth it for potential side reactions? Almost certainly. But is it nice to see multiple transformations in 1 reaction? For me it is

@barnicskobalazs

Жыл бұрын

For context, this is what I'm talking about (excuse my scuffed drawing). pasteboard.co/6aHpukqjHMe5.jpg pasteboard.co/Ifhwiswkp2no.jpg Hexagons are the bestagons.

@lexinwonderland5741

Жыл бұрын

Can't say I disagree with any of yall folk about your cool reactions. They are, indeed, bitchin'. I just have a special place in my heart for making chloroform out of bleach and acetone as a young undergrad haha I'll never forget the day I did my demo and the professors face sunk as I explained "no, I need ANOTHER halo-org waste container." lol

always a great feeling to to see a new video, keep up the great work!

Awesome video! And some nice reminders of rxns as I go into 2nd yr! Thanks!

As someone who understands nothing of chemistry, YET, the big words made me happy to listen to.

The more I learn about chemistry the more it looks to me like a spicy variant of software development - making physical things do actions exactly as we want, and not in any other perfectly valid and legal ways :D

I think your videos and explosions&fire are the videos I look forward to the most.

Honorable mention for Vilsmeier-Haack reaction. Not super common, but it's often astoundingly selective, readily goes to >98% conversion with high yield, and the activated reagent is a beautiful bright canary yellow (sorry E&W!). I give it A or B tier. Also not really undergrad, but if you were going by medchem reactions, Suzuki coupling is an easy S (for Suzuki). We used that constantly in our lab.

That was super informative, thanks! A few of those reactions were new to me but one of the comments mentioned that different universities have different lists of reactions they teach so it makes sense. We got the Heck reaction and Suzuki reaction emphasized but I think that's because the Prof was a metal catalyst researcher. Follow-up idea for you, rank reactions/mechanisms purely by how cool or cursed the curved arrow diagram looks.

@joshp6061

Жыл бұрын

Those two as well as stille coupling and sonogashira I learned were extremely important. But that wasn’t OChem it was inorganic

perfect timing, just starting with reactions in OChem 1 rest in peace my free time

Thumbnails with dogs are always S-Tier.

@That_Chemist

Жыл бұрын

You can thank Tay in the discord

Williamson ether synthesis. I worked at a company where one of the people in charge of ordering materials was... let's say a little slow at her job. I needed dibenzyl ether, was tired of waiting for it, and had benzyl bromide and benzyl alcohol on hand...

@That_Chemist

Жыл бұрын

Did it work well?

@adrianhenle

Жыл бұрын

@@That_Chemist Yup! IIRC I ran it in refluxing toluene w/ Hünig's base. Workup by aq. bicarb wash & rotovap; purified by vac transfer (>50 °C bp difference between product and anything else). Yield/purity were good, and I had enough DBE to last me until the order from Sigma finally came in.

@adrianhenle

Жыл бұрын

Of course, this might be the most facile example ever for this reaction. Nice reactive halide, no real plausible side reactions, massive boiling point change...

I loved this video. Both entertaining and informative

I know I didn’t bust my butt in ochem for most of these reactions to be rated below B tier im going to flip a lab table Edit: nvm at least the Wittig rxn was s tier i always loved that reaction

@NewWesternFront

Жыл бұрын

lol yep. boring ass hydrogenation in S

In the beginning of my PhD I actually used OsO4-dihydroxylation a decent amount. Reaction works great. I had a bottle of corn oil (unsaturated fatty acids) in my hood to use as a "stain" for active OsO4. It would turn black if active OsO4 was still around. I always got questions on why I had corn oil in my hood lol.

out of all the stem disciplines, you chemists are truly an extradimensional asset in the scientific community.

I wish I saw this video at the start of my undergrad, but to be fair, the depth at which each of them were taught to me highly correlates with their ranking. The main outlier being Fischer esterification, but that's understandable since in undergrad org chem the emphasis was bigger on understanding mechanisms in early years when we learned about Fischer, and the practical side got more attention in the later years when we learned about more recent chemistry like cross couplings.

It's weird watching this video, since I only just started my undergrad studies at 26, at my local community college. But this got me really excited to learn as much as I can, and even though I'm only about to start Gen Chem I in less than a week, I'll bookmark this. That way, I can look back a few years from now and understand all of it!

There was a Quantum Leap episode that touched on commercial versus DIY reagants.

Osmium Tetroxide is used for electron microscope contrast agent. Other agents have been tried like ChloroPlatinate or Tungstic acid (but heavier atoms like Lead, Bi not used).

I dunno about B being generous, I remember doing some fairly cool chemistry using diels-alder reactions as an undergrad. This was not just in o-chem lab but also undergrad research, such as using diynes or cyclopentadienone derivatives.

for dihydroxylation, the Prévost-Woodward reaction is a much more practical and less toxic alternative; plus, you can selectively produce the syn or the anti diol by varying the reactants in my third year of undergrad labs I did a Sharpless asymmetric dihydroxylation, using an AD mix and a 1% solution of OsO4, with N-morpholine oxide as the stoichiometric oxidant - that step worked, but I ultimately wound up with the wrong molecule

@That_Chemist

Жыл бұрын

Yeah - it’s common enough, but I don’t know any zealots for it

@barnicskobalazs

Жыл бұрын

Who in their right mind give OsO4 to undergrads? I mean, I know I was among the more lab savvy ones but I wouldn't have trusted myself with it back then, let alone some people I know (and like). But to be fair, the GTAs did a good job of overseeing the riskier experiments (like the n-BuLi reduction).

@lefthandedspanner

Жыл бұрын

@@barnicskobalazs at my university, anyone who survived to the third year had gone through two years of 9-5 Monday-Friday lectures and labs, which weeded out all but the most committed students, and the third year marked the point that the workload became truly insane; in the same year, undergraduates had the option to do a low-temperature Wittig reaction and Ziegler-Natta polymerisation (with trimethyl aluminium as an initiator) in the labs

@barnicskobalazs

Жыл бұрын

@@lefthandedspanner pretty hardcore. here we had some BSc students (mainly from asia and middle east) who were a. sponsored by a company or b. pressured by their parents; to do a degree at a good western university and their competence/determination often reflected that lack of internal drive. a minority to be sure but not negligible. in addition to that, covid restrictions cut our our lab practice in half. for context, we lost 30% of students after the 1st year and 10% after the 2nd. interestingly, i found later years easier but that was due to the fact that i could not take early report writing exercises seriously.

When you said diels-alder, my beginner trauma re-emerged from my soul. That was something I haven’t thought about in FOREVER.

As an inorganic chemist, I find that many of these reactions are the antithesis of useful, turning desired products into tar and easily removed side products into separation challenges. For example, I spent a couple of years in grad school trying to make high valent transition metal complexes of the bulky alkoxide tri(tert-butyl)methoxide, which always barfed up the metalate and the tri(tert-butyl)carbenium, which Wagner-Meerweined to tar. And current work involves acetaldehyde as a byproduct, which would be easy to separate, but it aldol condenses to crotonaldehyde under the reaction conditions, which requires fairly sophisticated distillation to remove from the desired products. I've also been bitten by Friedel-Crafts reactions before, with expensive aromatic ligands turning into triarylcarbeniums when trying to make transition metal complexes in chloroform (did make some amazing deep purple solutions though, so it wasn't a total loss). The haloform reaction is a great way to get rid of bromine. Just rinse out your excess bromine with acetone into an Erlenmeyer, place it in the back of a hood and wait for the Foomp. (The reaction is autocatalytic in HBr, so there is a bit of an induction period before it runs away.) First time was an accident, next couple of times was curiosity. How could you have left out free radical halogenation? From an organic synthesis standpoint it is not used much currently, but it is still the basis for many industrial processes and the early chapters of many an organic chem textbook.

@NewWesternFront

Жыл бұрын

good catch. im still just a student but radically halogenating an alkane is the beginning of many of our synthesis questions. would have been cool to see it ranked (even if low)

Grignard is so important, it is literally the first orgo reaction taught in Polish highschools

@barnicskobalazs

Жыл бұрын

A bit hardcore for high school, but its cannot be overstated nonetheless.

@limmuquan4796

Жыл бұрын

high schools? damn

@lefthandedspanner

Жыл бұрын

that's some quality education right there

@1brytol

Жыл бұрын

@@barnicskobalazs wouldn't say so. The mechanism is simple af, it is extrmely useful etc. I would say only reaction easier to learn is SN2 substitution

We need part 2! Please

I don't agree with everything but I do agree with most of S tier. I would put LAH and Fischer Esterification in A tier, as I just don't think they stack up to the other contenders. I think Diels Alder could also go into A tier just for the historical factor and the swag factor. Everyone loves a good Diels Alder.

All these icky messy organic reactions with their weird names is why I became a physical chemist specializing in NMR of complex mixtures. You orgo guys can’t live without my giant magnets to sort your crap out🙃🤪😵‍💫

Yay I got here early!! 🥳🥳 Great tier list as always!!

Happy to see that we agree on the grignard being S tier - i am an inorganic / metal organic Chemist, grignard are our go-to universal transmetalation reagent, you can basically transmetalate onto any transition metal if you just turn the damn thing into a grignard Personal favorite reaction has to be the "nazarov cyclization reaction" though - absolutely Niche, D tier at best but if you are in that niche of cyclopentadiene chemistry it's a divine gift that makes your life so much easier Personal favorite odd reaction: Duff-Reaction - for what it is, for, the amount of side products and the absolutely horrendously bad atom economics of that madness - it just works way too well

You should do a tier list of something like most terrifying chemotherapy drugs.

@That_Chemist

Жыл бұрын

I’m working on a chemo drug on atm - it’s probably a cursed structure one

Reach me out if you’d like to make an industrial pharmaceutical version of this tier list. I’ve several years of plant experience working on CDMO projects. I think it would be cool to compare lab and industry (both western and chinese/indian)!! Hope to hear from you!

In 3d printing, chloroform is very useful to glue pla, but it is difficult to acquire. For me haloform reaction is the most used one (I don't work as a chemist despite having a master degree in chemistry). For clarification: I am an analytical chemist. I work on instruments, from maintenance to ex novo construction.

Glad to see the only ones I actually remembered are S-tier

Forgot the most useful, the Maillard reaction 🤤

Methyl hydrazinocarboxylate in a Wolff Kishner is easily S tier and I'll die on that hill

@That_Chemist

Жыл бұрын

DM me a paper on discord - I’m happy to change my mind

9:50 My professor told me that decades ago they were required to write applications for OsO4 experiments. The chemistry department would then inform all labs on their floor, as well as floors above and below them. If they didn’t infrom, all these labs would know right away because of the stench.

This is a great video! I'm surprised that sodium borohydride reduction of carbonyls wasn't included though.

You should look at Superatoms, like Super Halogens. Also, you should talk about chemicals that can't exist when they theoretically should, such as Ammonium Hypochlorite, and anything that's a Perfluorate salt.

I've been told that Fischer esterification can be improved by refluxing and adding a desiccant in a trap on top of the flask so that the refluxing solvent gets dehydrated and comes back. I do not know the name of the glass equipment for doing that. Someone in my lab raised the yields to 90 percent doing that.

@That_Chemist

Жыл бұрын

A Dean stark trap

@niconeuman

Жыл бұрын

@@That_Chemist This wasn't a Dean Stark, although it can probably be used. It was a an adapter, on top of the rbf, with a big filter paper wrap of sodium sulfate. The solvent (methanol in this case), would reflux into the adapter, get dried by the Na2SO4, and fall back to the rbf. I haven't tested it myself but apparently it increased the yields of ester considerably. Neither the person who suggested this nor me are proper organic chemists, just people who do "some" organic chemistry, as part of our jobs.

You should do this tier list for reactions in general. Or just your top 10 reactions.

@That_Chemist

Жыл бұрын

I will do another one if ppl are interested

Just recently found the channel, and I'm always fascinated by the way synthetic chemists know all these organic reactions. I've been a chemical engineering student for 5 years now, but I always had a hard time understanding and learning organic, so after the exams I basically forgot everyting. No wonder I became an analytical chemist at last, I am more interested in measurement methodology and statistics, as well as the engineering side of things, than actual chemistry. Which is weird, because some part of me always wanted to have at least a decent organic chem knowledge, but unfortunately it's just not for me. Really weird example, but I sometimes think about that should a huge environmental disaster happen and our toolbox reduces to pots and fire, as a chemical engineer I would be expected to mix up some Aspirin, but all I would say is 'where is my HPLC'? :) Interested to hear you guys' thoughts on this, is it okay to forget about organic chemistry as and analytical chemist, or is organic a must for chemical engineers?

@Virtuous_Rogue

Жыл бұрын

I did chemical engineering too. I enjoyed O-Chem but hated bench work so the more computational side of things is better for me. I don't have much industry experience but it seems to me like the chemical mechanism stuff gets covered by a PhD chemist and the engineer's job is to scale it with max yield.

@joshp6061

Жыл бұрын

@@Virtuous_Rogue oh yeah of course, it’s (chemical) Engineering. Chemistry is a after thought you’re really just an engineer with a background in chemistry sufficient enough to understand and apply classical engineering to scale fundamental chemistry into industrial

@cyan_oxy6734

Жыл бұрын

Man I'm 100% the reverse. Loved chemistry but doing maths feels like a chore. Just thinking about physical chemistry makes me want to get drunk. This made me quit my studies as I was basically studying physics with some chemistry fun facts attached.

there are also less hazardous ways to reduce carboxylic acids than LAH - borane, or Red-Al if you've got C=C double bonds in the molecule plus, many acids can be converted to acid chlorides using cyanuric chloride, which is a much less offensive reagent than thionyl chloride or oxalyl chloride

@That_Chemist

Жыл бұрын

Red-Al is totally under-taught; vitride is an amazing reducing agent

right off the bat with the haloform reaction, we were told it was an extremely useful reaction as my professor said any reaction where we can add or remove carbon-carbon bonds is useful for synthesis, I feel lied to

Haloform! Not useful? 😭

I fucking love these videos

Re Hydroboration there’s a big difference between BH3 etherate and 9-BBN.

Maillard reaction for sure

I've run a lot of catalytic hydrogenations on the hundred gram to kilogram scale. Definitely based chemistry. Also, imagine that drake meme but with the Swern oxidation being bad and the Parikh-Doering oxidation being good. One final point, I performed a Friedel-Crafts acylation of benzene on a decent scale in industry. The reaction worked fairly well but I was left with a brown sludge containing my product. Dealing with all the aluminium chloride was awful. Useful chemistry, but absolutely not a fan of doing it in practice.

I would miss some important c-c bojne coupling reactions like Heck/Suzuki-coupling reactions. Or some more example of Methathese reactions beside Wittig. Maybe do another Video for such reactions.

Now I'm kind of curious about a typical undergrad experiments tier list

ozonolysis is used to make azelaic acid (an anti-acne treatment), by cleaving the double bond in oleic acid, which comes from vegetable oil

@That_Chemist

Жыл бұрын

That name sounds way cooler than it’s structure is

@lefthandedspanner

Жыл бұрын

​@@That_Chemist and no bugger I know can pronounce it properly; it's "azeh-lay-ick acid" not "azee-lick acid"

@monarchatto6095

Жыл бұрын

@@That_Chemist a lot of dicarboxylic acids are tbh

It seems that there is no intro has Suzuki coupling covered🙃

I bet the Birch reduction is probably one of the most popular reductions in "backyard chemistry", though almost entirely in the modified form where it eliminates a benzylic alcohol.

@That_Chemist

Жыл бұрын

👀👀👀

Based on what I know now, I should have majored in chemistry in college - I was math-impaired enough not to be able to succeed as a physics major. I probably might have succeeded as a pyrotechnic chemist, or a food chemist (I cook a whole lot).

Hmm even though i have limited experience in org synth, i would disagree with diels-alder position in the tier list. I thought i have really prominent use in synthetic organic chemistry, especially in building really wacky scaffolds of phytochem/marine chem. Yes the endo/exo mixture could be a problem but picking the right condition and/or right building blocks will generate better access to some really complex multicyclic molecules

My University has an Ozonation System, and my Org. Chem. Professor once told us the Story, that someone hat this thing running all over the weekend, and than it blew up. Turns out they used air instead of pure O2 for the Ozone generator, which generated NOx, and they used Toluene as a solvent, which was turned into TNT. Also my country had a famous company which used Ozonation on an industrial scale, one day it blew up, they rebuild it, it blew up again immediately afterwards, than it shut down.

I would put DA reactions straight up in S Tier since it is so ubiquitous in total synthesis

@That_Chemist

Жыл бұрын

But how many of those total syntheses are used for producing chemicals on a large scale? It may be significant, and I may just be ignorant.

@Virtuous_Rogue

Жыл бұрын

Wikipedia gives 2 industrial applications: production of cyclopentadiene and production of vitamin B6. My suspicion (based on my undergrad in chemical engineering that I barely use) is that industrial production avoids DA where possible because of the side products. You're looking at a separation of 2+ chemical species likely with similar properties which could require a lot of effort and equipment to separate at scale.

Ah yes the diels-alder, when I started my career in industry we were making Michael acceptors as covalently bonding anti-cancer drugs. Acryl-Cl was working fine but by suggestion of Phil Baran, we installed cyclpentadiene as a protecting group on acrylamides. Sadly the retro-DA conditions were suboptimal. Being that cyclopentadiene was "expensive" my cheap ass boss made us recover the stuff after multiple steps which was put right back into the sigma bottle it came in then put in the fridge where it was lost among the other relics of failed synthesis.

@That_Chemist

Жыл бұрын

Furan is a little bit easier to take off than cyclopentadiene

@That_Chemist

Жыл бұрын

Lmao saving it

@craigjohnson775

Жыл бұрын

@@That_Chemist As far as I can remember those suboptimal conditions were: take it and cook it

Anything that makes cool crystals, turns pretty colors, melts through the table, generates fire balls, emits radiation, explodes when hit by a laser, or creates toxic fumes resulting in undergrads to evacuate lab, waiting for HAZMAT. Doctor Evil snaps at Austin Powers, "They laughed at me. I will make them PAY, Baby!"

Currently trying to employ the wittig reaction to synthesize the substrate for an intramolecular macrocyclization. It is NOT working, lmao what tf is it forming?? I’m using a funky phosphonium with little research done with it, and by NMR it looks like the resulting phopho oxide is getting a phenyl ring kicked off?? Really not sure 😂

LiAlH reduction caught me by surprise. Also, where does organolithium stand vs grignard?

Being an organotin chemist, I was greatly relieved to see that Grignard made it to S tier…..

The only reaction I've used in my job that I can name is the Sandmeyer reaction, and it isn't even on here

You forgot to mention Suzuki Miyaura coupling and Gilman reaction. Both are practically useful

11:06 Is this how 2-methyl,2-butanol (t-Amylol, Amylene Hydrate) is prepared on an industrial scale?

Re: Oxy-Mercuration; Cuprous Acetate adds across EWG-Enes, Copper replaced by H+. CuH adds to 1,3 Cyclohex-4-eneDione (H- Cu+).

@stephenjacks8196

Жыл бұрын

I.E. Copper powder and Sodium Hydroxide reduce Resorcinol.

I approve of this ranking

@That_Chemist

Жыл бұрын

🌶

Out of curiosity, because there are so many ways to reduce nitro groups, which method do you think tops the list? I'm also kind of surprised that the Suzuki wasn't listed here.

@That_Chemist

Жыл бұрын

Probably Pd/C and H2 but a lot of ppl use HCl and Fe

@pietrotettamanti7239

Жыл бұрын

Suzuki usually isn't taught in the first year, it's quite common to have an organometallics course separated from the rest in later years. It makes more sense since organometallic reactions tend to have completely different mechanisms from first year reactions.

Finkelstein reaction? If you just take it as the classic NaI in acetone then not too useful. But if you include the more general application of catalytic iodide salts to bromide/chloride reagents it's very common. Also Williamson ether synthesis. Easy S-tier. Everyone makes phenol ethers.

Coupling reaction is the most useful reaction nowadays, where is it?

A question about the osmium tetroxide dihydroxylation of alkenes which has always puzzled me: I know the purpose of the NMO is to re-oxidise the osmium, so that you only need a catalytic quantity of the osmium tetroxide, which makes this less expensive and a little less dangerous. However, finely divided osmium metal and its lower oxides can be oxidised by atmospheric oxygen, which is of course the main danger of working with osmium metal - if exposed to air, there will always be some of the horrifyingly toxic tetroxide present. So if you were doing the dihydroxylation reaction with osmium tetroxide, would it not be possible to bubble oxygen (or just plain old air) through the reaction in order to re-oxidise the osmium? That way you wouldn't need the NMO in there, and the workup and purification would be simpler, would it not?

@That_Chemist

Жыл бұрын

I guess you would need to pump lots of oxygen through the reaction mixture, and maybe other ligands in the system (solvent, etc) would slow the re-oxidation process. I haven’t ever used OsO4 tho, so I can’t comment much more than that

Fun-fact: the Friedel-Crafts reaction is commonly used in the illicit production of stimulants This is the only reaction I know anything about here.

I would say haloform is E tier since you can also use it to make carboxylates from methyl ketones

I've had the honor of performing an oxymercuration/demercuration reaction in grad school. What pisses me off about this reaction is how good and reliable it is. You can use super exotic alcohols and mercury doesn't cause the olefin to migrate. There's also huge drawbacks to the safer acid-catalyzed addition of an alcohol across an olefin. The alcohols are almost always primary and they're typically the solvent, since secondary alcohols love to eliminate. Also the acid can cause your olefin to migrate all over the place. Do you know what palladium, platinum, ruthenium, and iridium have in common? They can't lace mercury's boots when it comes to adding an alcohol across a double bond.

@That_Chemist

Жыл бұрын

True - this is such a based take

So if I was learning basic o-chem to help my daughter with science homework, would it be better just to focus on the S and A tier?

@Dovorans

Жыл бұрын

Nah, even if they obsolescent in a modern lab a bunch of these reactions are very useful for introducing concepts of regioselectivity and HOMO LUMO theory to students.

Hm, I didn't really have any strong disagreements. I mostly agreed with everything give or take a tier. Maybe FC Alkylation deserves to be in at least C tier because it's a C-C bond forming reaction and more importantly FC has a C in it.

suzuki coupling would have been s tier if it were on the list

Seems to me ozonalysis uses Zn or dimethylsulfide DMS rather than DMSO

@That_Chemist

Жыл бұрын

You are correct - it should be DMS

Great list, I have few opinions hope you dont mind: Haloform is probably more usefull as a tool to convert methylketone to carboxylic acid. Still not good enough to get if from the F-tier :D Diels alder is probably bit too low, it can generate multiple chiral centers in one step, its often the key step of total synthesis and the chirality can be controlled (somehow). its not ideal but close to S-tier. Especially when Fisher is S-tier but only works well on simple alcohols. Or if Ketalization is A-tier (I hardly ever saw it as something else than protecting the carbonyl) and in some ponts /OsO4 dihydroxylation/ I dont understand your ranking, I dont think its fair to rank the reactions by their original conditions when significant improvements (as you mentioned osmate salts, asymmetric variants...) were developed and probably none sane would use stochiometric OsO4 today

The video was a nice idea and obviously just a bit of fun. Be careful if you are teaching students and saying the reactions are not useful in real life. This could send the wrong message about the importance of learning these basic reactions . Keep up the good work.

@That_Chemist

Жыл бұрын

I am happy to stand corrected, and I am always interested in making videos on the application side of chemistry (I’m hoping to be able to do more of that once enough KZread revenue comes in to finance travel expenses)

id love to hear if anyone has used any pericyclic reactions in a synthetic context ever

@That_Chemist

Жыл бұрын

💯

What about the useless Wurtz reaction (alkyl halide + alkali metal to get coupling products)?

@That_Chemist

Жыл бұрын

Nobody ever uses it F- tier

@martinofgliwice1486

Жыл бұрын

@@That_Chemist right. For a person without much knowledge this reaction is worse than useless - it creates a false impression of what Organic Chem is like. Maybe it is not a problem at Introductory level, but it is commonly mentioned in Highschool books here where I live (along with very few other reactions). Another dumb reaction found mostly in highschool text books here is oxidation of alcohols with copper oxide. It is easy to balance but does not really happen except at high temperatures/pressure.

@LunaLucia

Жыл бұрын

​@@That_Chemist The Wurtz reaction is far from useless, it's just typically taught in a way that makes it look useless (like showing you can make octane from bromobutane). But the Wurtz reaction is an incredibly powerful tool to make highly strained cyclopropanes and cyclobutanes, which are difficult to make in other ways. Modifications of the Wurtz reaction are even more important in for example the production of triphenyl phosphine. (You did put the Wittig reaction into S-tier...)

Chromium salts are nasty. I had some get with dil sulfuric acid land on a ripped glove not a pleasant experience. 2 Weeks for that burn to heal.

@That_Chemist

Жыл бұрын

:(

Suggestion to do a video on biologically relevant chemical reaction tierlist. Could be interesting.

@That_Chemist

Жыл бұрын

I see you also posted this in the discord lol

@DipanGhosh

Жыл бұрын

@@That_Chemist yup.