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Homework Help: OCHEM SN1 and SN2 Major Products

  1. Apr 19, 2014 #1
    1. The problem statement, all variables and given/known data

    Determination of Major Products in SN2 reactions?
    What would be the major product of 2,3-dichloro-3ethyhexane reacted with:
    1. one equvalent of NaI in acetone?
    2. one equavelent of AgNO3 in methanol
    and explain your reasoning.

    2. Relevant equations


    3. The attempt at a solution

    I understand the first one. Iodide would be your nucleophile (Nu) here. The Cl on the C3 will not undergo Sn2 b/c the C3 is tertiary. But the Cl on C2 will in fact work for Sn2 b/c it is secondary. So the product would be 3-chloro-3-ethyl-2-iodohexane.
    For the second once, with the AgNO3 in methanol, I am confused.
    Would this reaction even occur? If so, could someone explain to me why?
  2. jcsd
  3. Apr 20, 2014 #2
    The second one proceeds by SN1 mechanism with Ag+ snatching out a Cl- from the tertiary carbon. Do you see why the Cl- from tertiary carbon is removed?
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