Amines: Crash Course Organic Chemistry #46

Did you know that the fishier a fish smells, the longer it’s been out of the water? This is due to a chemical called trimethylamine, which is an amine, the class of organic compounds we’re discussing in this episode! Although they tend to be pretty stinky, amines are important in many fields like biochemistry, medicine, and agriculture. In this episode of Crash Course Organic Chemistry, we’ll explore amine formation and basicity, and revisit some old friends, imines and enamines!

Episode Sources:

Series Penicillin References:
Nicolaou, K. C., & Sorensen, E. J. (1996). Classics in total synthesis: targets, strategies, methods. John Wiley & Sons.
Sheehan, J. C. (1982). The enchanted ring: the untold story of penicillin.
Primary literature for Sheehan’s penicillin synthesis: Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1948, 70, 1985; Sheehan, J.C. & Izzo, P.T. J. Am. Chem. Soc. 1949, 71, 4059; Sheehan, J.C. & Bose A.K. J. Am. Chem. Soc. 1950, 72, 5158; Sheehan, J.C., Buhle, E.L, Corey E.J., Laubach, G.D. & Ryan J.J. J. Am. Chem. Soc. 1950, 72, 3828; Sheehan, J.C. & Laubach, G.D. J. Am. Chem. Soc. 1951, 73, 4376; Sheehan, J.C. & Hoff, D.R. J. Am. Chem. Soc. 1957, 79, 237; Sheehan, J.C. & Corey E.J. J. Am. Chem. Soc. 1951, 73, 4756

Series Sources:
Brown, W. H., Iverson, B. L., Ansyln, E. V., Foote, C., Organic Chemistry; 8th ed.; Cengage Learning, Boston, 2018.
Bruice, P. Y., Organic Chemistry, 7th ed.; Pearson Education, Inc., United States, 2014.
Clayden, J., Greeves, N., Warren., S., Organic Chemistry, 2nd ed.; Oxford University Press, New York, 2012.
Jones Jr., M.; Fleming, S. A., Organic Chemistry, 5th ed.; W. W. Norton & Company, New York, 2014.
Klein., D., Organic Chemistry; 1st ed.; John Wiley & Sons, United States, 2012.
Louden M., Organic Chemistry; 5th ed.; Roberts and Company Publishers, Colorado, 2009.
McMurry, J., Organic Chemistry, 9th ed.; Cengage Learning, Boston, 2016.
Smith, J. G., Organic chemistry; 6th ed.; McGraw-Hill Education, New York, 2020.
Wade., L. G., Organic Chemistry; 8th ed.; Pearson Education, Inc., United States, 2013.

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[tekohaatawhai]

My favourite amine is full metal alchemist, their bond is something special.

[justinanderson]

Was confused what ANIME had to do with CHEMISTRY, but then I remembered I’m dyslexic lol

[andi_]

this is such a blessing... every time we begin a new organic Chem chapter, y'all drop the exact same topic's video! Thank

[AVRGWIBWTHACN]

Not gon lie the title baited me because I thought it said Animes instead of Amines

[midwestchem]

Pyridine is one of the most disgusting smells ive personally come across. After carefully wafting it towards my nose out of curiousity I had a gagging fit. Surprised I didnt vomit but the smell stuck with me for a short time but it is super gross. I love this particular crash course(astronomy is my second fav) the visuals really help a lot.

[RisingRay]

Thanks for these videos, they really help me with my school work :D

[suvigyabasnotra]

Who read the title as 'Anime' first...?

[neeharkale]

These are really helpful! I was wondering if (a) you could create a series pertaining to math such as geometry, etc. (b) could you guys update the website to reflect all the new series and episodes thereof?

[darwinsaquilayan]

A little disappointed that this wasn’t an episode about a rapper from Oregon, but good video all in all

[josiahkruse]

Not even gonna lie. I read Anime, and thought Crashcourse ran out of things to talk about. 😂

[hazimeart]

a lot of information in a few minutes 😆

[bluegod]

who else got concerned thinking it said anime

[henryelicker]

I know a guy named Amine. He never smelled bad though, thankfully.

[Polf]

Please do a crash course on music theory

[teentraveler]

I remember meeting someone with trimethylamine. It was very uncomfortable. But I somehow understood they must have had a good reason why they smelled bad. So I wasn't rude.
And know I learned why. :D

[COLORMIND.mp]

not to be nit picky but….this isnt anime at all

[tanzim_sadab]

Jesse! They're giving our secrets in a youtube video!

[hoangtrunganh]

Glad that I am not the only one misread it to "anime"

[felixtheduke]

This reminds me of the science experiment where these scientists spilled this chemical that had such a strong putrid smell that it made a whole city sick. By any chance, is this how that chemical was created?

[jesscorbin]

I doubt car manufactures have found good enough substitutes for sodium azide.