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Carboxylic Acid Derivatives & Hydrolysis Reactions: Crash Course Organic Chemistry #31
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Esters have a wide range of uses, from giving perfumes and colognes their fragrances, to preventing diseases like scurvy. Vitamin C, that scurvy preventing antioxidant, is derived from carboxylic acids, a class of organic compounds we’ve already learned a lot about! In this episode of Crash Course Organic Chemistry, we’ll look at four different carboxylic acid derivatives and their reactivities, react them with nucleophiles, and learn some hydrolysis reaction mechanisms that we can use in our synthesis of penicillin!
Music:
Vegas Glitz by Kevin MacLeod
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.
***
Watch our videos and review your learning with the Crash Course App!
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?
Music:
Vegas Glitz by Kevin MacLeod
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.
***
Watch our videos and review your learning with the Crash Course App!
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?
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