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August 26, 2021

As we construct more complex organic molecules, it can start to feel like decrypting a complex code. Organic synthesis takes simple starting materials, and turns them into complex structures, and reverse engineering can help figure out the steps in between. In this episode of Crash Course Organic Chemistry, we’ll practice multistep synthesis problems, learn about how we can use retro synthesis to make more complex molecules, and use liquid-liquid extraction to separate solvents. As always, we’ll work through examples and connect everything back to the Mold Medicine Map!

Music:
Plucky Daisy by Kevin MacLeod
Link: incompetech.filmmusic.io/song/4226-plucky-daisy
License: filmmusic.io/standard-license

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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