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Oxymercuration-Demercuration Alkene Reaction Mechanism

October 28, 2014 By Leah4sci 21 Comments

Oxymercuration-Demercuration, also referred to as oxymercuration-reduction is slightly more confusing than that average alkene reaction. I think it's a combination of the extra steps, involvement of mercury, and the mysterious reduction by sodium borohydride. But don't let this confuse you.

The video below takes you through the entire reaction mechanism with step by step explanations of every moving arrow, regioselectivity, and reason for lack of carbocation rearrangement.

Watch this video on YouTube or read the transcript (coming soon)

Watch the previous Video: Ring Expansion via Methyl and Hydride Shift

Watch Next video: Alkoxymercuration-demercuration

Return to: Alkene Reaction Mechanism home page;

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

Filed Under: Alkene Reactions Tagged With: alkene reaction, alkene reaction mechanism, oxymercuration

Comments

  1. A says

    December 4, 2018 at 11:35 pm

    What is the mechanism for Demercuration? I mean how Hg(OAC) gets replaced by hydrogen.

    Reply
  2. won says

    May 21, 2018 at 7:30 pm

    will this be anti addition?

    Reply
  3. Karla says

    March 12, 2018 at 8:39 pm

    These videos are very helpful! It would be helpful if you showed which steps are reversible vs. non reversible.

    Reply
  4. Hritik says

    January 18, 2018 at 1:49 pm

    Nice explanation but shouldn’t H2O attack the carbon with more partial positive charge (better electropile/electron deficient region) i.e. 1 degree terminal C ?

    Reply
  5. a-a-ron says

    November 24, 2017 at 1:24 pm

    why wouldn’t the h2o form a bond with the mercury instead of attacking a carbon that’s only partially positive? hg has a positive charge so to me it makes more sense that the h2o would attack the hg than the carbon.

    Reply
  6. Amira says

    January 13, 2017 at 10:26 am

    You helped me get an A in orgo 1 first time taking it! I think I watched every single one of your videos, thank you so much Leah!

    Reply
  7. Valeria says

    November 2, 2016 at 9:17 am

    The reaction is always a “Syn-Addition”?

    Reply
  8. Julie says

    March 5, 2016 at 2:00 pm

    At the end of step 2 do you still have acetic acid as a product? Or is that somehow used up during the reduction mechanism?

    Reply
    • Leah4sci says

      April 4, 2016 at 5:36 pm

      Acetate/acedic acid is a side product

      Reply
  9. nick says

    January 29, 2015 at 6:20 pm

    how can mercury have a pair of electrons? i thought its electron configuration was [xe]4f14 5d10 6s2

    Reply
    • Leah4sci says

      January 29, 2015 at 8:45 pm

      This is a tricky concept Nick and I think the reason most professors skip it. Don’t forget that d-shell electrons are high in energy and may be called upon to react at any point in the mechanism.

      Reply
  10. latha says

    December 24, 2014 at 7:28 pm

    How can one compound be attached to two carbon atoms at same time ? Here HgOAc is attached to both primary and secondary?

    Reply
    • Leah4sci says

      January 4, 2015 at 3:22 pm

      One bond is not dependent on the second. Hg has the ability to form multiple bonds

      Reply
      • latha says

        January 6, 2015 at 6:36 pm

        Oh k thank you….. I love the way u teach

        Reply
        • Leah4sci says

          January 7, 2015 at 9:07 am

          Thank you Latha

          Reply
  11. Jess says

    November 17, 2014 at 10:57 pm

    THANK YOU! I am in OChem 1 and have been struggling through the alkene reactions. You explain this so simply and give fantastic explanations for WHY the intermediates like HgOAc form the two bonds in the molecule. Thank you again!!

    Reply
    • Leah4sci says

      May 7, 2015 at 7:06 pm

      Thanks Jess

      Reply
  12. dsrlington says

    November 6, 2014 at 3:13 am

    I cant play the video kindly send m link to the video

    Reply
    • Leah4sci says

      November 6, 2014 at 11:14 am

      This is a YouTube video, if it doesn’t work for you check your browser settings or try another browser

      Reply
  13. david says

    November 2, 2014 at 10:53 pm

    You are my new favorite teacher! videos are clear and informative.

    Reply
    • Leah4sci says

      November 3, 2014 at 10:54 pm

      Thank you David. Are you in Orgo 1 or Orgo 2?

      Reply

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