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See linked video.

Nice! 👍

One trick at a time 😂

Thanks! Doing my best to keep up with the timeline and help you folks!

It kinda works with emphasis on "kinda" for these reactions.

You're very welcome! I'm glad you found it useful. I have more resonance videos btw, in case you didn't see them.

You're welcome!

Good luck with your lab component and grad school applications!

I appreciate the comment, but you do see that there's the linked video, right?

I literally go over that at 4:50.

You're very welcome! Glad you find it helpful!

I've seen this explanation too but there's a problem with it: we can only rely on thermodynamic considerations like that if we're dealing with an equilibrium reaction, and this one is not an equilibrium. And the step is exothermic, so if we apply the Hammond postulate here, we're dealing with the early transition states, meaning that we care more about the enolate than the product. The *real* explanation is in the MO of the enolate. The HOMO orbital is a non-bonding orbital with a relatively high contribution from that carbon. Plus, we have lithium coordinating around oxygen, effectively "shielding" it from any electrophiles. There's also the HOMO-LUMO gap between the enolate and electrophile that we need to mind. Changing a leaving group does affect the outcome. This is truly where the C=O > C=C argument breaks apart. For instance, if you take an enolate and react with MeI, you get mostly C-substitution, but if instead you do the reaction with MeTf, you get way more of the O-substitution. Switch base to KH and add crown ethers, and boom, you have predominantly O-substitution!

@VictortheOrganicChemistryTutor thank you for the clarification

That's on my to-do list for this semester.

Thank you so much for your kind words! It means a lot to know my videos made a difference for you. Keep up the great work!

Well, you have 200+ of my tutorials here, so, it's pretty much what you'd see in real life if you were in an audience during any of my lectures.

You’re very welcome! Glad you find it helpful!

Absolutely. Within the scope of the reactions we cover in an intro organic chemistry course, there are not many methods we can use to improve the selectivity here. The bond in the ring is a smidge more stable, so it would still be a major-ish product.

@VictortheOrganicChemistryTutor hi, so why an endocyclic alkene is more stable than the exocyclic?

Glad you find it helpful! Good luck with the exam!

That's why I try to show different methods to help broaden one's synthetic horizons, so to speak.

haha Thanks! I'm glad you find my videos helpful.

I’m gonna keep staring at you till you come to your senses 👀

You’re very welcome! Best of luck on your exam!

@@VictortheOrganicChemistryTutor thanks sir!