Chemoselectivity and Protecting Groups: Crash Course Organic Chemistry #33

Things have been getting more and more complicated here in Crash Course Organic Chemistry, and as we deal with more complex molecules, parts of molecules we don’t want to react will start reacting along with the parts that we do. Luckily, we have protecting groups, which act like a chemical disguise and help us control how molecules react. In this episode, we’ll look at what makes a good protecting group, as well as identify some good protecting groups for different functional groups. We’ll also see what role protecting groups play in the synthesis of penicillin! 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: Toni Miles, Oscar Pinto-Reyes, Erin Nicole, Steve Segreto, Michael M. Varughese, Kyle & Katherine Callahan, Laurel A Stevens, Evan Lawrence Henderson, Vincent, Michael Wang, Krystle Young, Michael Dowling, Alexis B, Rene Duedam, Burt Humburg, Aziz, DAVID MORTON HUDSON, Perry Joyce, Scott Harrison, Mark & Susan Billian, JJurong, 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, Jennifer Dineen, 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, 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


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