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Hydride Shift and Methyl Shift Mechanism

November 10, 2012 By Leah4sci 10 Comments

hydride shift methyl shift tutorial videoHydride 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

Ready to test your skills? Click HERE for my FREE Alkene Reactions Practice Quiz

Filed Under: Organic Chemistry Tutorial Videos Tagged With: alkyl shift, hydride, hydride shift, hydride shift mechanism, methyl shift, shift

Comments

  1. Riya says

    January 16, 2019 at 3:15 pm

    Ma’am,
    Is it true that the alkyl/hydride shift is only limited upto a certain range(certain no. of carbon atoms in the molecule.)?
    Thank you.

    Reply
  2. kay says

    December 2, 2018 at 11:09 pm

    if one can do a hydride shift or a methyl shift, both equal in carbocation stability, which one is preferred?

    Reply
  3. gmail.com says

    March 8, 2018 at 7:21 pm

    thanks Leah You the Best your videos are very helpful…

    Reply
  4. sandra26 says

    January 5, 2018 at 10:01 pm

    Hi Leah,

    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?

    Reply
  5. Emily says

    April 17, 2016 at 10:12 pm

    Great video! thanks

    Reply
    • Leah4sci says

      August 22, 2016 at 2:58 pm

      You’re welcome, Emily!

      Reply
  6. Entirephile says

    November 23, 2015 at 2:11 am

    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 :).
    Joy

    Reply
    • Leah4sci says

      November 23, 2015 at 2:35 pm

      I don’t have a specific video on that, however I do cover stereochemistry of reactions in some of the study hall videos

      Reply
  7. elmin_moussa says

    August 6, 2015 at 8:50 pm

    very veyr interested video it gave me more stretegy to know how can i solve some howework

    Reply
    • Leah4sci says

      August 7, 2015 at 4:19 pm

      excellent! glad to help

      Reply

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