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Halohydrin Formation

October 20, 2012 By Leah4sci 18 Comments

Halohydrin formation alkene reaction mechanism tutorial videoAlkene Reactions Series: Video 4
This tutorial takes you through the halohydrin formation mechanism, a type of electrophilic addition which adds both a halogen and alcohol to an alkene by using water instead of an inert solvent like CH2Cl2 or CCL4 to yield a halohydrin which features both a halogen and alcohol on the carbon chain

This video provides with a step by step breakdown of the mechanism and helps you understand WHY this reaction undergoes anti addition and still follows Markovnikov’s rule.


(Watch on YouTube: Halohydrin. Click cc on the bottom right for video transcription.)

<– Watch Previous Video: Halogenation of Alkenes Reaction Mechanism
–> Watch Next Video: Acid Catalyzed Hydration of Alkenes

This is Video 4 in the Alkene Reaction Mechanisms Video Series. Click HERE for the entire series.

Ready to test your skills? Try the Alkene Reactions Practice Quiz after watching the series!

Filed Under: Organic Chemistry Tutorial Videos Tagged With: alkene reaction mechanism, electrophilic addition, halohydrin, halohydrin formation

Comments

  1. blahblah1233445 says

    June 5, 2019 at 2:17 pm

    Hi, I was wondering if you could explain the stereochemistry in the resulting products. More specifically, why OH and Br are in the same plane. Thank you

    Reply
  2. Sabecca says

    November 26, 2018 at 8:35 pm

    For the second halohydrin reaction with Cl 2 you added the OH in the secondary carbon instead of the halide. Should we always do that for any halohydrin reaction?

    Reply
  3. Shreyas says

    October 3, 2017 at 4:17 am

    Does the same reaction occur with ethene?
    i.e. Ethene + Bromine (water) ——-> ethylene bromohydrin

    Reply
  4. joanna says

    April 22, 2017 at 8:34 pm

    these videos are very helpful. Just wondering if you could explain when to use stereochemistry

    Reply
  5. Celia Jackson says

    December 14, 2016 at 4:50 pm

    So helpful! This type of step-by-step explanation is much appreciated.

    Reply
    • Leah4sci says

      December 29, 2016 at 4:08 pm

      You’re welcome, Celia!

      Reply
  6. Ben says

    October 20, 2016 at 1:00 am

    how does the slight polarization of bromine happen?
    on 1:56 minute of video

    Reply
  7. Mobeena khan says

    October 7, 2016 at 2:00 pm

    you r truly awesome

    Reply
    • Leah4sci says

      October 19, 2016 at 12:44 pm

      Thanks, Mobeena!

      Reply
  8. Cashman says

    May 29, 2016 at 4:27 pm

    You make Organic chemistry so simple, thank you so much.

    Reply
    • Leah4sci says

      June 10, 2016 at 3:09 pm

      Thanks Cashman. Glad to help

      Reply
  9. haityler says

    April 1, 2016 at 3:01 pm

    If the reagents were 2 Iodines and Ethanol, would there be an extra Ethanol molecule that would come and take the Hydrogen away from the ethanol ion after it attaches to the secondary Carbon? Or would the extra Iodine be able to attach since there is only an alcohol and not water.

    Reply
  10. Mary says

    November 27, 2014 at 5:38 pm

    so would this be considered anti addition since they add on opposite sides of the double bond and steriochemistry antimarkovnikov since the cl ended up on the less substituted carbon?

    Reply
    • Leah4sci says

      November 28, 2014 at 12:39 pm

      Careful there Mary. It’s anti-addition as you said, but follows Markovnikov’s rule since the OH adds to the more substituted carbon atom. Markovnikov’s rule is about the carbocation intermediate stability, and this molecule puts more partial positive on the more substituted carbon

      Reply
  11. Shama says

    November 7, 2014 at 4:39 pm

    Can you have a step by step reaction for ozonlysis, and demercuration

    Reply
    • Leah4sci says

      November 9, 2014 at 1:36 pm

      Shama, did you check my complete alkene reaction series?

      Reply
  12. Aicha says

    October 21, 2012 at 12:56 pm

    You are truly awesome!

    Reply

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