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Homework Help: Substitution reaction and configuration

  1. Mar 5, 2013 #1
    1. The problem statement, all variables and given/known data

    (2S,3S)-2-chloro-3-methylpentane + high concentration of CH3O- ---> ???

    3. The attempt at a solution

    I need to find the product and usually my method is to knock off the -Cl replacing it by
    -OCH3 and when drawing the compound I just make an mirror image. In (2S,3S)-2-chloro-3-methylpentane there are two asymmetric centers and for the product with Cl replaced with OCH3 I assume that it changes configuration so that it becomes 2R instead of 2S. My problem is now, that I cannot draw the product without getting (2R,3R).
    Is this correct? I assume that it should be 2R,3S because I do not knock off any atom or molecule from the second asymmetric center.
  2. jcsd
  3. Mar 6, 2013 #2


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    Science Advisor
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    Gold Member

    It is a secondary halide adjacent a tertiary carbon center. You sure you're gonna get Sn2 product? How about E2?
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