2021-06-23

[public] 23.9K views, 2.17K likes, 7.00 dislikes audio only

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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.

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