E/Z Alkenes, Electrophilic Addition, & Carbocations: Crash Course Organic Chemistry #14

Alkenes are an important type of molecule in organic chemistry that we’re going to see a lot more of in this series. But before we can really get into the many cool reactions alkenes do, we need to go over some of the basics. In this episode of Crash Course Organic Chemistry, we’ll review and build on our knowledge of alkene nomenclature, revisit our friend the carbocation, and learn Markovnikov’s Rule: an important tool that will help us predict the products of addition reactions involving alkenes.
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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[@lessgogeezers]

KZbin recommended me this 1 day before chemistry exam. Damn, even KZbin cares more about me than I do.

[@zachheilman784]

I've been following several chemistry channels (NurdRage, NileRed, Explosions&Fire) and this series has really started to connect some of the dots when they talk about the reactions they're doing - thanks so much for these videos!

[@zayrael]

Absolutely amazing video, the animations help SOOO much and the concepts were explained so well! Made for a great review. Thank you CC for once again carrying my OChem grade.

[@bleuemoone8710]

Could have used this series back when I took ochem but now I'm in biochem so is probably useful still!

[@diegoroman7092]

This video was pretty good. Understood some bits and pieces of my lecture today, but this video connected all the dots. Thank you!

[@anjulovesdoracakes22]

First comment!!! I'm currently studying chemistry and didn't understand organic chemistry so well, but after this series, I understood it nicely!

[@dianavanwinkle2299]

Honestly the part when she says, "okay, deep breath" is so real.

[@vaughnjohnson8767]

“We can use the Ez method.” Me: are you sure about that?

[@Thanos-hp1mw]

This is definitely one of my favorites of crash course.

[@samudrajs5409]

This series is really really helpful! Seeing Organic Chemistry in a whole different view!

[@maglo8]

So I’m actually a PhD chemist who mainly does organic chemistry. I watched this in the hope to see if E and Z isomers have different reactivity to HBr. That topic was unfortunately not mentioned…. But when I listen to this, I’m no longer surprised that so many students tell me that organic chemistry is confusing. If this video here is a good representation on how it’s taught then I would probably also get confused. There is no need to introduce a major principle on addition reactions but then spending more time on special cases than on the most common one. And the foundation needs more detail. 1. It’s always like a magnet: negative charge goes towards positive charge to form an intermediate and the reaction takes place if that can easily stabilize into something more favorable. When I start explaining reactions in org chem then I first talk about electronegativity. 2. You need to first explain at length why certain carbocations are more stable than others, practice that a little bit and then apply this to addition reactions. Markovnikov derives from there automatically. Proton shifts can happen occasionally, while methyl shifts are much more rare. If you talk about that then you also need to explain why a methyl group can actually move while most other groups don’t. Better would be not to teach that at all though.

[@ShirinRose]

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Hey, CrashCourse, love the videos. I'm not sure if it's been discussed already, but are there any plans for a mathematics playlist? I'd like to see that.

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Just a day after I took an exam on this...

[@jneal1347]

Same XD

[@nathatleue]

IB HL Chem here! My exam is in 2 weeks lol

[@magnesiumswift]

9:45 I love this part lol, it's so cool, I'm actually shocked, never been taught in high school

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Kudus!! Great video I really wanted the same video while I was taking my University organic chem exam.

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woooohoooo......that episode was just more than a series fo me........that was amaazzzzziiiinnnnnnn........😍😍😍😍😍😍😍😍

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Time to learn

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Don't even study chemistry I just want to be more aware and knowledgeable

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Same here :)

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@@dredgen__ren6889 amazing 👌

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Good will hunting energy right there

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Nice video I love it

[@mr.scientifictemper3056]

great crash course of organic chemistry i thank the creators.

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This was amazing!

[@edward_myc]

Not "on ze zame zide" 😆 I will remember that for the rest of my life!

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Excellent!

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If you are on a unicycle, your best bet is to practice from a wall. When you fall, the unicycle likes to shoot outward, which could hurt one of your friends.

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thanks crash course team fo helping us in here....🙋🙏😇

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Very good

[@lewissiekaiqiang7665]

because your explaination is very awesome

[@vishen7464]

thank you!!!!

[@margaretgodfrey9946]

This helped me sooo much

[@robintoonen8515]

Love that I am dutch and that there are easier way to memorize german. Entgegen --> tegen(over) ; zuzamen --> samen. Respectively against and together

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Es ist "Zusammen" verdammt noch mal ! Of is 't Nochmal aanmekaar geschreeft?

[@vrutipatel9539]

Thanks ma'am 😇😇😇😇🌸🌸🌸🌸

[@rambles2727]

For those confused by later episodes come back to this one and pay attention to markovnikovs rule

[@ahmedsalafap5898]

Interesting and useful . Great job on animations of hyperconjugation 👍

[@SuperAndrewlove]

Thank you so much! I really racked my brain trying to make the hyperconjugation animation as clear as possible as I thought a lot of the existing references on the concept were kinda hard to understand! I'm glad to hear you found it helpful! :D

[@Arthur-ks4ho]

@@SuperAndrewlove I love your animations. May I ask what program do you use to make them?

[@SuperAndrewlove]

@@Arthur-ks4ho thanks so much! we use Adobe After Effects for all our Crash Course animations! If you want to see exactly how we do it, there are actually tutorials on the Thought Cafe KZbin channel!

[@Arthur-ks4ho]

@@SuperAndrewlove thanks bro! ❤️ i would love to animate some reaction mechanics but i tried in adobe animate , what do you think? should i stay in adobe animate or should i switch to after effects?

[@veronikaz2509]

how do you know the 1,2-shift will happen or happens?

[@abhi-wi2mj]

Wohoo thanks for this

[@hibiscus1105]

I’m early!!! Yayy😍

[@lewissiekaiqiang7665]

I hope you can update the next episode quickly

[@user-ut9vt8gq9s]

Excelent!

[@JoelJimenezMerejo]

It’s the way my teacher was JUST teaching this topic today....

[@abdulwaseh8043]

❤️

[@maxleibrecht7484]

Where is the difference to the Wagner Meerwein Shift ?

[@kindlez98]

Haha, I knew about (Z) for zussamen but for (E) I thought it was Eigen as in unique because they were in a unique place

[@selmangokdemir7181]

In 4:01, why din't you name it as an alkene?

[@ZucchiZ]

At this point, it feels like I am watching a sci-fi movie with many futuristic terms

[@nihilrocks]

Markovnikov’s rule states that the electrophile attaches to the most stable part of the carbocation which consists the “least hydrogen”. Can someone back me up…

[@hetaeramancer]

When a protic acid (HX) is added to an asymmetric alkene, the acidic hydrogen attaches itself to the carbon having a greater number of hydrogen substituents whereas the halide group attaches itself to the carbon atom which has a greater number of alkyl substituents.

[@zachariahayers6273]

Simple mechanics and complex Mechanics Theory

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Yay I missed u ❤️

[@adriansyahariakusumah7825]

3:59 is it supposed to be (Z)-4-bromo-3-ethylpent-3-en-1-yne?

[@ghaithballich5952]

there are a triple bond so using the longest chain, which is hexane. However, I'm confused as why is bromo 5 not 6?

[@adriansyahariakusumah7825]

@@ghaithballich5952 oh i got it, thx. the chain starts from the "yellow no 1" to the "white no 2" (from upper right to the lower left). Bromo located on Carbon no 5 that double bound with Carbon no 4. In this case, Carbon no 4 attached with ethyl group. So that it is 5-Bromo.

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7:13 that Pizzamas shirt of John lol

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Where are the dashes and wedges :’))

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Interesting.

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Isoprene rocks.

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With English subtitle please🙏

[@maxmusterman3371]

Is this CC nomenclature grammar rules?

[@andreameigs1261]

I read that you have to have IDENTICAL groups on each side of the double bond for it to be cis or trans, but that's not what you are showing here.

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WE NEED MATERIALS SCIENCE COURSE

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Could you do videos on animal science???

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heck yes! :D

[@fchurca]

First?

[@hetaeramancer]

no

[@vivi.arreola]

You lost me with the shift stuff ! I hate chemistry