Perfectionists take note: even titans of catalysis make embarrassing mistakes with their chemistry. Just look at this little oopsie that was caught by an astute reader in the Midwest.
It seems like there might be a bit of confusion hanging over the chemists developing methods for anti-Markovnikov hydroamination of alkenes at the Center for Enabling New Technologies Through Catalysis (CENTC):
Ummm….yeah….that’s not the difference between Markovnikov and anti-Markovnikov addition.
Those of you who’ve taken sophomore organic chemistry will remember that Markovnikov’s rule states that protic functional groups (e.g., H-NR’R') will typically add to double bonds such that the hydrogen adds to the less substituted carbon (and the other group, e.g., -NR’R', adds to the more substituted carbon.) What Hartwig and coworkers have drawn as the Markovnikov product is still anti-Markovnikov. The products they’ve drawn might charitably be called conformational isomers, but they’ve failed to note any 3-D structure.
Of course, the true Markovnikov product would place the amine on the same carbon as the R group.
Those are some very colorful Group I halide salts you’ve got there, kiddos. Also, the word is “dissociates” …there’s no need to stick an “ass” in there, no matter how fun it is.
Hey, look what the American Chemical Society produced for St. Paddy’s Day: it’s a tutorial on the chemistry of alcohol, including its effects on your body and how your body attempts to rid itself of the poison.
Uh oh, but there’s a WWWTP? in there. If you pause at the 2:45 mark, you can see that they flubbed the structure of “amyl alcohol”:
While there are several isomers of amyl alcohol, instead of drawing one of those, the ACS has shown the structure for isoamyl acetate (commonly known as banana oil). When banana oil is dilute, it kind of smells like Juicy Fruit bubble gum. In concentrated form, it smells really gross. I know, because I made it in 6th period orgo lab in high school and the people around me in 7th period religion paid the price.
But good effort, ACS! This is exactly the sort of info we (as chemists) should be communicating to the People. It’s news they can use. Of course, in the future, try to get the structures right! (And for the record, you also misspelled “judgment” at 0:49. Boo.)
Sometime last year, my girlfriend DVR’d a copy of this commercial for Garnier Fructis shampoo because she saw it had chemistry in it and because she is awesome:
If you pause the video at 0:13, you will notice quite a few chemical atrocities:
Basically, nothing is right. Note the surfeit of Texas carbons. I also love the asymmetry of their elemental fluorine, though maybe those things labeled “F” are atoms of fruit? And what is up with that ideal gas law? You’d think they’d be able to get a structure for biotin in there, considering how big they wrote the word on the chalkboard. Argh…
Anyway, great catch by the ol’ g/f…whom I am now happy and proud to call my fiancée.