Alkene Addition Reactions: Crash Course Organic Chemistry #16

Like a trendy dance, a fighting combo, or a secret handshake, organic reactions can be broken down into simpler steps. In this episode of Crash Course Organic Chemistry, we’ll specifically be looking at alkene addition reactions, and with each new reaction ask ourselves three questions to help us puzzle through the mechanism and understand what’s going on.
Episode Sources:
Le Couteur, P, Burreson, J. Napoleon’s Buttons: 17 molecules that changed history., Penguin, New York, 2004, Chapter 1.
Whipps, H., “How the Spice Trade Changed the World,” www.livescience.com/7495-spic... Last accessed, 3/28/2020.
Henriques, Martha, “How spices changed the ancient world,” www.bbc.com/future/bespoke/mad... Last accessed, 3/28/2020.
Hashimoto, K., Yaoi, T., Koshiba, H., Yoshida, T., Maoka, T., Fujiwara, Y., Yaamoto, Y, Mori, K., “Photochemical Isomerization of Piperine, a Pungent Constituent of Pepper”, Food Sci. Technol., Int. 1996, 2 (1), 24-29.
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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I've been in organic chemistry education for years, and this is beautifully presented

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[@clssgn]

I think I might have to check back my notes about oxymercuration. It is actually passed my learning time but seeing that reaction makes me really curious. I think you could add some additional notes about the reaction if it is not in the video, it could really help a lot. But overall, really glad seeing more people gain an interest in one of the hardest chemistry fields in my opinion. Cheers!

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we are doing addition rxns rn in chem!! timing perfection

[@gaurisreenidhi]

How old are you?? We did all this in like grade 10! We also did reaction mechanisms in detail! What do you have??

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@@gaurisreenidhi and they go over it again in undergrad and even more detail in Graduate level in the states.

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[@benscrafield9575]

Hydroboration does not mean “adding water using boron”; it refers, unsurprisingly, to adding a hydrogen and a boron. We use the term for additions of HBR2 even when not following up with oxidation, e.g. when preparing boron species for cross-coupling.

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its 37 min past the hour and youtube seems to finally be working in Houston, Tx. just an FYI. try a refresh and see if that helps.

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[@teyrasiridae4704]

Isn't the regioselectivity of hydroboration driven by the electropositive nature of boron versus hydrogen (causing the delta minus hydrogen to end up on the more electrophilic site), rather than the difference in size?

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Whilst trying to break down organic reactions for us, it seems as CrashCourse may have broken KZbin in the process.

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[@whengale]

I've also been trying to practice naming some of the compounds in these videos & I'm uncertain about the name of the pre-reaction alkene at 7:45. Is it (Z)-1-cyclohexyl-2-methylbut-2-ene? I keep google image searching that and (Z)-1-(2-methylbut-2-enyl)cyclohexane and I'm getting some molecules that are very very similar, but no exact matches.

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Green chemistry practices discourage the use of mercury. We even stopped using mercury thermometers in the laboratory. Is oxymercuration still used today?

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[@whengale]

at 7:45, even without the oxymercuration, would a 1,2-alkyl or 1,2-hydride shift even happen in this reaction? the initial carbocation that forms is *already* a tertiary carbocation. Shifts only occur if they generate a *more stable* carbocation, right? The biggest candidate for a shift seems to be the hydride on the cyclohexane's carbon--but that wouldn't form a more stable carbocation. So it wouldn't even occur in the first place, right? is oxymercuration actually necessary in this particular reaction or am I missing something? I'm really confused because I can't tell if I'm missing something or not.

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[@cliff8459]

For benzene halogenation shouldn't we add a catalyst like "Fe"

[@PavanKumar-xv1hg]

Benzene shows substitution not addition as benzene would like to keep it's aromaticity very much. If we react it normally with Br in a solvent(like CCl4 or peroxide) it isn't electrophilic enough to get attacked by the benzene C-H bonds so we use a Lewis acid like *FeBr3* which reacts with the bromine and forms a Lewis acid-base complex. Br-Br + FeBr3 = Br-Br(+)-Fe(-)Br3 [Charges on Br and Fe] This Lewis acid base complex is sufficiently electrophilic to form a halogenated benzene. (feel free to correct me !)

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