Carboxylic Acid Derivatives & Hydrolysis Reactions: Crash Course Organic Chemistry #31

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
Link: incompetech.fi...
License: filmmusic.io/s...
Episode Sources:
Kennedy, J: Common names of carboxylic acids jameskennedymo...
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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[@crashcourse]

This is a reupload to correct a copy/paste error in the mold medicine map. Thanks for your support!

[@rsaunders57]

But it's not the right thumbnail photo. That looks like it's a history course.

[@3DIYshow]

@@rsaunders57 nope that's the right thumbnail. It's a scene from this episode and everything.

[@mominansare948]

AMAZING! These videos are so good at being thorough but consice with the details. I also love how the electron transfers are shown so clearly. Losing track of them one of the easiest ways to get confused by a mechanism, but this clear depiction helps a lot. Animation is so useful in helping people get a better spacial idea of what's going on, and I love seeing that with electrons so much.

[@scofah]

Amazing. P.s. Thank you for not having a continuous background soundtrack of “music” - The minimal sound effects are appreciated.

[@heronimousbrapson863]

Captain Cook reputedly prevented scurvy amongst his crew by initially feeding them sauerkraut. I suppose they switched to citrus because, even though they were no longer dying of scurvy, they were being overcome by strong, objectionable odors....

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And that’s why British sailers are referred to as limies!

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Finally! Crash course finally updated organic chem!

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🙏🏻Excellent explanation, Perfect understanding...👌🏻

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hi CrashCourse, hi everyone " that was very complicated, but I think I learned something", :)

[@hsd-learnbiology2355]

Thanks a lot to giving us a important information..

[@henryelicker2403]

My previous comment was: "When life gives you lemons, make carboxylic acid".

[@midwestchem368]

This is a great series!

[@AdriceMC]

Very good video! 👍

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I love this video can you do more of this video

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Thanks for this video ❤

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Too underrated. We need 2k comments!

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Fun Fact: Letters J and Q don’t appear anywhere on the periodic table. Go ahead and double check.

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[@biggeibuwa941]

Please, which of these is not a carboxylic acid derivative; A. CH3CO2CH3 B. CH3CONHCH3 C. CH3(CH2)2 COCL D. C6H5OCH3 Many thanks

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Very nice vedio

[@Lawsome1997]

Two videos of the same course at the same time? Did someone mess up?

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Read the first comment. Correct a copy paste error

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First