Radical Reactions & Hammond's Postulate: Crash Course Organic Chemistry #19

Throughout this series we’ve mostly talked about pairs of electrons, but electrons don’t always have a buddy. An atom or group of atoms with a single unpaired electron is called a radical. In this episode of Crash Course Organic Chemistry, we’ll learn all about radicals including the three key steps in a radical reaction and Hammond’s Postulate, an important tool to help us understand these reactions. We’ll also see ways radicals can react with alkanes, alkenes, and alkynes.

Episode Sources:
Davies, K. J., & Doroshow, J. H. (1986). Redox cycling of anthracyclines by cardiac mitochondria. I. Anthracycline radical formation by NADH dehydrogenase. Journal of Biological Chemistry, 261(7), 3060-3067.
Ball, P. (Interview with Nick Lane) Yes, life in the fast lane kills you. May 5, 2016.
Nimse, S. B., & Pal, D. (2015). Free radicals, natural antioxidants, and their reaction mechanisms. Rsc Advances, 5(35), 27986-28006.
Santos-Sánchez, N. F., Salas-Coronado, R., Villanueva-Cañongo, C., & Hernández-Carlos, B. (2019). Antioxidant compounds and their antioxidant mechanism. In Antioxidants. IntechOpen.
Review of Vitamin C

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]

We made a couple of simplifications for this episode. The first is the structure of dioxygen (0:31), which is shown with a valid Lewis structure—but oxygen actually has diradical character itself! Read more at the link below. At 10:09 we show a mechanism with orbitals. The “p-orbital” we refer to is technically an antibonding π* molecular orbital, which is an advanced topic that we haven’t covered in this series. Thanks for watching!

[thelonespeaker]

Oh, I was thinking about other types of radical reactions - you got the timing just right

[TheTexas]

After all the stuff that has happened today, it took me a minute to realize radical reactions was referring to organic chemistry

[TJF]

"Radical Reactions", what a time for this title to hit the upload queue.

[SentEmFlying]

I love how I learn more here than history class

[bobbiemarkwick]

Radical reactions was definitely the right topic for today

[vicenteardissone]

"Radical reactions"
Hehe political timing.

[koningA]

1. You forgot "Crash Course Organic Chemistry #19" in the title
2. Be less shy and include your names in the doobly doo (dooblidoo?)
I had to turn on captions to finally put the presenters name with correct spelling into my brain :)
I am thoroughly loving the content, hope you're as proud of it as you should be!

[Leah_Luxxe]

Thank you for being such good friend for us 🇺🇸

[joannavillegas]

Thankyou crash course for making an app!!!!

[almasing]

Why don't the solvated electrons continue filling the other empty p orbitals and turn the alkene into an alkane?

[rebeccawike]

Me and my husband were discussing how capsaicin reacts in our esophagus and were wondering how it can cause a tear in the tissues

[spherizir]

Is anybody else confused by the explanation for why the difference between Bromine and Chlorine results in different proportions of final radical products? I still can't wrap my head around that part...

[lionkingfan]

.the free radicals topic is new to me but I know a little about alkanes and the different types

[mosquitobight]

the thumbnail made me think of the song "Renegades" by the Ambassadors

[richardcollier]

Great to hear some science about anti-oxidants, but why did Deboki have to end the party?

[jasons]

I thought the title involved Richard Hammond, boy was I wrong.

[iwontliveinfear]

I keep hearing R o U S and thinking "I don't think they exist."

[tednoob]

Hammond's Postulate in a channel called Crash Course makes me think of a hamster.

[thb]

Oi Hammie, this exhoost fume tastes kinda funny.