Chemical Reaction Tierlist

In this tierlist, I rank several of the common reactions taught in introductory organic chemistry!

[martinowton]

In 40 yrs of synthetic chemistry I have never used oxymercuration

[Valdagast]

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

[andrewjin]

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.

[HiwasseeRiver]

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.

[Twadeps]

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.

[rspeks]

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

[UpTheIrons]

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.

[sadia]

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

[csebeschen]

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 😐

[janmelantu]

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

[Atmix]

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.

[uiucchemistry]

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!

[sleepysakamoto]

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

[trumanrudloff]

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?

[lexinwonderland]

"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.

[Ensavier]

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

[defenestrated]

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.

[lefthandedspanner]

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

[ae]

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

[colombanoalessandro]

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 😂😂