Carboxylic Acid Derivatives - Interconversion & Organometallics: Crash Course Organic Chemistry #32

We get it, learning so many different organic reactions is probably giving you a headache, but hopefully this episode can help! We’re getting even deeper into carboxylic acid derivatives, some of which are used in common headache relieving painkillers. In this episode of Crash Course Organic Chemistry, we’ll learn how to convert more reactive carboxylic acid derivatives into less reactive ones, turn carboxylic acids into acid chlorides, reduce carboxylic acid derivatives using metal hydrides, and more! Plus, we’ll get to add the first stage of synthesizing Penicillin V to our Mold Medicine Map! Episode Sources: https://www.worldofmolecules.com/drugs/tylenol.htm https://cen.acs.org/articles/92/i29/Does-Acetaminophen-Work-Researchers-Still.html https://pa01000125.schoolwires.net/cms/lib/PA01000125/Centricity/Domain/366/Chap14%20Ester%20Amide.pdf Gates, M., & Tschudi, G. (1956). The synthesis of morphine. Journal of the American Chemical Society, 78(7), 1380-1393. Seavill, P. W., & Wilden, J. D. (2020). The preparation and applications of amides using electrosynthesis. Green Chemistry. Introduction to Organic Chemistry, Brown & Poon, 5th edition. 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. *** Watch our videos and review your learning with the Crash Course App! Download here for Apple Devices: https://apple.co/3d4eyZo Download here for Android Devices: https://bit.ly/2SrDulJ Crash Course is on Patreon! You can support us directly by signing up at http://www.patreon.com/crashcourse Thanks to the following patrons for their generous monthly contributions that help keep Crash Course free for everyone forever: Michael M. Varughese, Ben Follows, Kyle & Katherine Callahan, Laurel A Stevens, Chris Routh, Evan Lawrence Henderson, Vincent, Emilee Murphy, Michael Wang, Jordan willis, Krystle Young, Michael Dowling, Alexis B, Rene Duedam, Burt Humburg, Aziz, Nick, DAVID MORTON HUDSON, Perry Joyce, Scott Harrison, Mark & Susan Billian, Junrong Eric Zhu, Alan Bridgeman, Rachel Creager, Jennifer Smith, Matt Curls, Tim Kwist, Jonathan Zbikowski, Jennifer Killen, Sarah & Nathan Catchings, Brandon Westmoreland, team dorsey, Trevin Beattie, Divonne Holmes à Court, Eric Koslow, Indika Siriwardena, Khaled El Shalakany, Jason Rostoker, Shawn Arnold, Siobhán, Ken Penttinen, Nathan Taylor, William McGraw, Andrei Krishkevich, ThatAmericanClare, Rizwan Kassim, Sam Ferguson, Alex Hackman, Eric Prestemon, Jirat, Katie Dean, TheDaemonCatJr, Wai Jack Sin, Ian Dundore, Matthew, Jason A Saslow, Justin, Jessica Wode, Mark, Caleb Weeks __ Want to find Crash Course elsewhere on the internet? Facebook - http://www.facebook.com/YouTubeCrashCourse Twitter - http://www.twitter.com/TheCrashCourse Tumblr - http://thecrashcourse.tumblr.com Support Crash Course on Patreon: http://patreon.com/crashcourse CC Kids: http://www.youtube.com/crashcoursekids