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Homework Help: Oxymercuration demercuration reaction help.

  1. Oct 1, 2011 #1
    1. The problem statement, all variables and given/known data

    See attachment there is reaction.why --OH attach to 2nd carbon. why not it attach first carbon(from left).

    2. Relevant equations

    steric hindrance

    3. The attempt at a solution

    there seems greater steric hindrance in right carbon(2nd from left) than left one.

    Attached Files:

  2. jcsd
  3. Oct 3, 2011 #2
    Sterics is not really a factor with this type of a reaction, it is electrophillic addtion, which takes place around the planar sp2 alkene. If a carbocation were formed, a methyl shift would most likely result in the OH moving to the 3 degree carbon, however, the mercuration reaction proceeds via a ring transition state, no carbocation is formed.
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