Course content

0h03m

Crash Course Organic Chemistry Preview

Welcome to Crash Course Organic Chemistry hosted by Deboki Chakravarti! Starting next week, we'll be tackling the notoriously complicated subject of organic chemistry, and hopefully having some fun along the way!

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

0h10m

What Is Organic Chemistry?: Crash Course Organic Chemistry #1

Organic chemistry is pretty much everywhere! In this episode of Crash Course Organic Chemistry, we’re talking about the amazing diversity among organic molecules. We’ll learn about the origins of organic chemistry, how to write Lewis structures, condensed structures, and skeletal formulas, and what gross organic compound the Romans used to dye their fabrics pretty colors.

Episode Sources:
Dean, J., Casselman, K. D., Wild Color, 1st ed.; Potter Craft, New York, 2010.
Formula for indigo dyeing with urine. http://www.wildcolours.co.uk/html/urine_indigo_vat.html
From Gunpowder to Teeth Whitener: The Science Behind Historic Uses of Urine https://www.smithsonianmag.com/science-nature/from-gunpowder-to-teeth-whitener-the-science-behind-historic-uses-of-urine-442390/
Tie-Dye Instructions. https://www.dharmatrading.com/techniques/tiedye/tie-dye-instructions.html, last accessed 12/12/2019.
(Retinal) Clayden, J., Greeves, N., Warren, S., & Wothers, P. Organic Chemistry. New York 2001. Oxford U

0h12m

The Basics of Organic Nomenclature: Crash Course Organic Chemistry #2

Language is complicated, especially in organic chemistry. This episode of Crash Course Organic Chemistry is all about nomenclature. We'll dive into IUPAC systematic naming of organic molecules, and get to practice with the help of three trusty steps!

Episode Sources:
IUPAC Organic Chemistry Nomenclature for organic compounds, https://www.acdlabs.com/iupac/nomenclature/

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 Chemistr

0h12m

More Organic Nomenclature: Heteroatom Functional Groups: Crash Course Organic Chemistry #3

Oxygen is pretty dang amazing! Some of the most intensely studied functional groups in organic chemistry have oxygen atoms. In this episode of Crash Course Organic Chemistry, we're building on the last episode's discussion of nomenclature by learning about IUPAC's naming rules for even more functional groups.

RE-UPLOAD: There was an error in the graphic at 10:03 and in order to make sure students were not memorizing these structures incorrectly, we've chosen to re-upload the episode.

Episode Sources:
Lambert, J. B., Traces of the Past. . Unraveling the Secrets of Archeology through Chemistry, page 134-137: Perseus Publishing, Massachusetts, 1997.

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.

0h14m

3D Structure and Bonding: Crash Course Organic Chemistry #4

The organic molecules that make up life on Earth are more than just the 2-D structures we’ve been drawing so far. Molecules have 3-D shapes that help us understand what they can do. In this episode of Crash Course Organic Chemistry, we’ll learn how orbital hybridization and valence bond theory can help us explain 3D molecular structures and about constitutional and geometric isomers.

Episode Sources:
Discovery of DNA Double Helix: Watson and Crick | Learn Science at Scitable
Citation: Pray, L. (2008) Discovery of DNA structure and function: Watson and Crick. Nature Education 1(1):100
https://www.nature.com/scitable/topicpage/discovery-of-dna-structure-and-function-watson-397/
Nature 1953.
Watson J.D., Crick F.H. A structure for deoxyribose nucleic acid. Nature 1953;171:737–738.
Harding, S. E., Channell, G., & Phillips-Jones, M. K. (2018). The discovery of hydrogen bonds in DNA and a re-evaluation of the 1948 Creeth two-chain model for its structure. Biochemical Society transactions,

0h13m

IR Spectroscopy and Mass Spectrometry: Crash Course Organic Chemistry #5

It’s time for molecular analysis! On this episode of Crash Course Organic Chemistry, we’re learning about mass spectrometry and infrared spectroscopy through the lens of a forensic investigation. Put on your lab coats, and let’s solve this mystery!

Episode Sources:
Silverstein, R. M., Webster, F. X., Kiemle, D. J., & Bryce, D. L (2007). Spectrometric identification of organic compounds, 8th ed., Hoboken, NJ: John Wiley & Sons, Inc.
Spectra for pseudoephedrine: BioRad/Sadtler Data Collection, Bio-Rad Laboratories, Philadelphia, PA (US), Spectra ID: BR125952
Spectra for methamphetamine: Kunalan, V., Daeid, N. N, Kerr, W. J., Buchanan, H. A. S., McPherson, A. R., “Characterization of Route Specific Impurities Found in Methamphetamine Synthesized by the Leuckart and Reductive Amination Methods,” Anal Chem, 2009, 81, 7342-7348.

Other spectra reproduced with permission from: SDBSWeb : https://sdbs.db.aist.go.jp/ (National Institute of Advanced Industrial Science and Technology, 6/9/202

0h11m

Alkanes: Crash Course Organic Chemistry #6

Alkanes are kind of the wallflowers of organic chemistry, but they still have important functions in the world around us. In this episode of Crash Course Organic Chemistry we’re building our knowledge of organic molecules by learning all about these so called couch potatoes from how they are separated from crude oil to how to use Newman projections to predict torsional strain and steric hinderance. We’ll also learn the names of some common conformers and get an introduction to cycloalkanes.

Episode Sources:
M. Faraday and W. Crooks, The Chemical History of a Candle, a Course of Lectures Delivered Before a Juvenile Audience at the Royal Institution, 1908. https://archive.org/details/chemicalhistoryo00faraiala/page/158

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 C

0h14m

Cyclohexanes: Crash Course Organic Chemistry #7

Hexagons appear all over the natural world from honeycomb to bubbles, and they even appear in organic chemistry! In this episode of Crash Course Organic Chemistry, we're learning all about cyclohexanes, including how rings pucker to relieve strain, the boat and chair conformations, and how ring flips can switch substituents from axial to equatorial. We'll practice a lot of chair flips, but don't flip an actual chair just yet! Lots of practice is key to understanding organic chemistry's favorite manifestation of the hexagon.

Episode Sources:
Philip Ball, Why Nature Prefers Hexagons: The geometric rules behind fly eyes, honeycombs and soap bubbles. Nautilus, 2016., Last accessed 1/26/2020. nautil.us/issue/35/boundaries/why-nature-prefers-hexagons
References within: Kashyap Vyas, Why is the hexagon everywhere? All about this seemingly common shape. https://interestingengineering.com/why-is-the-hexagon-everywhere-all-about-this-seemingly-common-shape. Last access 1/26/2020.
https

0h14m

Stereochemistry: Crash Course Organic Chemistry #8

The shape of molecules is super important to life as we know it. In this episode of Crash Course Organic Chemistry we’re learning about stereochemistry and how to identify molecules as chiral or achiral. And as always, we’ll be doing a lot of practice!

Episode Sources:
“THINK BIG! Must the molecules of life always be Left-Handed or Right-Handed?” Smithsonian Magazine.
Spinoff 2004 - “A NATURAL WAY TO STAY SWEET”, NASA.

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 Pu

0h12m

More Stereochemical Relationships: Crash Course Organic Chemistry #9

Enantiomers have almost all the same chemical and physical properties, so it can be tough to separate them. But it’s still super important that we know how to tell them apart! In this episode of Crash Course Organic Chemistry, we’ll recap all the types of isomers we’ve learned about so far, and also learn about polarimetry as a way to separate enantiomers and how to predict the number of stereoisomers a molecule will have.

Episode Sources:
“THINK BIG! Must the molecules of life always be Left-Handed or Right-Handed?” Smithsonian Magazine.
Spinoff 2004 - “A NATURAL WAY TO STAY SWEET”, NASA.

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. Nor