Hydride shifts and methyl shifts can occur in organic chemistry reactions if there is a carbocation intermediate. While Markovnikov's rule placed the carbocation on the more substituted of the 2 former sp2 (double bound) carbon atoms, if there is an EVEN MORE substituted carbon nearby you'll get a carbocation rearrangement.
This video helps you understand the logic behind the carbocation rearrangement, along with specific patterns to look for when deciding between a hydride shift or methyl shift.
(watch this video or YouTube or view the transcript – coming soon)
Click for previous video – Acid Catalyzed Hydration
Next video: – ring expansion
This is video 6 in the Alkene Reaction Mechanism series. Click to see the entire series
Is it true that the alkyl/hydride shift is only limited upto a certain range(certain no. of carbon atoms in the molecule.)?
if one can do a hydride shift or a methyl shift, both equal in carbocation stability, which one is preferred?
thanks Leah You the Best your videos are very helpful…
I’m wondering how you would go about changing the cis/trans stereochemistry of an alkene. Specifically, my instructor is asking us to synthesize cis-2-hexene from either 1-hexene or trans-2-hexene and I’m stumped. I had thought about an alkyl shift, but that doesn’t seem right. Could you guide me to the right video?
Great video! thanks
You’re welcome, Emily!
Hey Leah, wow. thank you! Is there anyway to see the steriochemistry for all of these reactions? If that’s part of the subscription how can I sign up? I don’t have use for the one on one tutoring because I kind of need the videos on demand. Much appreciated. I don’t understand why this isn’t the format professors use in class, it all makes sense now. Also, your voice is very soothing, panic has subsided :).
I don’t have a specific video on that, however I do cover stereochemistry of reactions in some of the study hall videos
very veyr interested video it gave me more stretegy to know how can i solve some howework
excellent! glad to help