What do the smells of feet, armpits, vomit, and goats all have in common? (Besides being super gross…) Carboxylic acids! Despite being responsible for some of our least favorite odors, carboxylic acids are also super useful in organic chemistry. In this episode of Crash Course Organic Chemistry, we’ll review carboxylic acid synthesis and nomenclature, react carboxylic acids to form salts, esters, and acid chlorides, and start our journey towards synthesizing one of the most important organic chemicals in medicine, penicillin! Episode Sources: Kennedy, J: Common names of carboxylic acids https://jameskennedymonash.wordpress.com/2014/11/26/common-names-of-carboxylic-acids/ Thomas, J: Mouldy Mary and the cantaloupe https://mcdreeamiemusings.com/blog/2019/8/11/1013vvme5498w77bglwoh5ck4exowx C H Arnaud, C&EN: Penicillin https://cen.acs.org/articles/83/i25/Penicillin.html 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: 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, Shawn Arnold, Siobhán, Ken Penttinen, Nathan Taylor, William McGraw, Andrei Krishkevich, Sam Ferguson, Eric Prestemon, Jirat, TheDaemonCatJr, Wai Jack Sin, Ian Dundore, 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: null