Cyclopropanation of Alkenes Carbene via Haloform and Simmons Smith Reactions
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- Опубликовано: 26 окт 2021
- Leah4sci.com/Alkene-Reactions presents: Cyclopropanation of Alkenes: Carbene via Haloform and Simmons-Smith Reaction and Mechanism
Need help with Orgo? Download my free guide ’10 Secrets to Acing Organic Chemistry’ HERE: leah4sci.com/orgo-ebook/
In this video, you’ll learn about the two common cyclopropanation reactions, in which an alkene reacts to form a cyclopropane in place of its pi bond.
In the first reaction, a haloform is used to form an unstable and very reactive carbene intermediate.
In the second reaction, known as the Simmons-Smith reaction, a zinc-copper complex is used to form a more stable carbenoid intermediate.
You’ll learn to draw the concerted reaction mechanism for both reactions and be able to show proper stereochemistry in drawing your product molecule.
Links & Resources Mentioned In This Video:
Formal Charge Formula and Shortcut leah4sci.com/formal-charge-fo...
Hybridization, Geometry and Bond Angles leah4sci.com/hybrid
Alkene Epoxidation leah4sci.com/alkene-epoxidation
E1 and E2 Beta Elimination leah4sci.com/substitution-eli...
In this video:
[0:21] Definition of Cyclopropanation
[1:04] Definition of Carbene
[2:38] Overview of Two Common Cyclopropanation Reactions
[3:40] Using a Haloform to Form a Carbene
[5:57] Mechanism for Reaction of Carbene with Alkene
[7:27] Simmons-Smith Reaction to Form a Carbenoid
[8:21] Mechanism for Simmons-Smith Reaction
Catch the entire Alkene Reactions Video Series along with the Alkene Reactions Practice Quiz and Cheat Sheet on my website at leah4sci.com/Alkene-Reactions
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For more in-depth review including practice problems and explanations, come join my online membership site the organic chemistry study hall: leah4sci.com/join
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Organic chemistry usually melts my brain. You make it so simple
I'm sorry to hear that orgo melts your brain, but happy to potentially provide another solution. Thank you :)
The ability to explain the concepts, theories and techniques the way that students understand easily - that's the definition of an excellent teacher.
Aww thanks so much for your kind words!
Excellent explainations, very well illustrated as well... THANKS
Glad you enjoyed it and you're so welcome!
You have a lovely voice, thank you for your lectures and the time you put into this channel!! 😊
Thank you so much for the kind words and you are very welcome
This was a lifesaver. I had too many doubts in the questions that had reagants of simmons smith reaction as it wasn't taught to us and i couldn't even find the name for it. Thanks a lot😭
You're very welcome
Nice Lecture It helped me a lot
Glad it helped
Love your work♥️
Thank you!
Thank you! Good explanation!
You're so welcome!
I have been out of college for years and have no use for organic chem in my profession. But I still enjoy watching these videos and pretending I know what's going on. Lol
Hahaha nice! glad my videos are helping to hopefully entertain you :)
Your lectures are so attractive and very informative lessons and thank you for a bundle for creating a new video😊🙏✍.
Thank you very much
Dear professor,
I have a question about ether systhesise.
which is the best way to systhesise tert-butyl ethyl ether?
1.treatment of ethyl bromide with sodiun tert-butoxide?
2.heating a mixture of tert butanol and ethanol in sulfuric acid?
Let's keep the comments relevant to this video please. I cover ether synthesis in the Orgo Study Hall: Leah4sci.com/join
this may be a very stupid question but could someone explain more in detail, why the cl ion in 4:18 finally breaks away? and why are the chlorine ions stabilizing the negative carbene ion? is it because they are making it very partially positive, as a contrast to the c atom that doesn't like the negative charge and thus its stabilizing it? thanks
The chlorine atoms are highly electronegative. Since carbon is NOT very electronegative and does NOT like holding a negative charge, the presence of the chlorines nearby stabilizes the negative charge through induction. (i.e. They are pulling that negative charge towards themselves and saying 'hey, it's okay for you to be here.')
One chlorine atom ultimately breaks away pulling that negative charge all the way away from carbon. Again, because chlorine is highly electronegative and likes to hold negative charge so much more than carbon does. Everything is happier when this happens.
Hello! I found this extremely helpful, but my professor wants us to know 3 ways a cyclopropane can be made. The lectures are very confusing and slides oriented in a way I find difficult to understand so I come to youtube with what he asks of us. What is a third way?
I'm sorry, but I don't offer tutoring over social media. For help with questions like this and more, I recommend joining the organic chemistry study hall. Details: leah4sci.com/join or contact me through my website leah4sci.com/contact/
oo this was interesting, kind related it with the carbylamine test (the lab smelled awful ofc)
Haha I haven't smelled those chemicals in a very long time
Ever since graduation I just do 'pen and paper' chemistry as you see here. Glad you found it interesting
it helps a lot! :D
Hi medam vanakam 🙏🙏 and u video very useful tk 🙏🙏🙏
you're very welcome
You and your video both are beautiful love you
Thank you! 🤗
i am going to fail this exam for sure. There are way too many reactions.
Oh no! If it's not too late to save your grade, or if you need to retake, make sure to add active writing to your study blocks to help you not only memorize, but to understand: leah4sci.com/memorize
I feel like a carbene🥲
Hahaha! Better than feeling like a carbocation?