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Reaction of alkyl halides with strong unhindered bases

  1. Aug 13, 2014 #1
    Please look at the image. For (b) and (c), what the solution manual says makes no sense to me.
    You're reacting a primary alkyl halide with an unhindered base EtONa. They say that the only product is the alkene. Why do they not consider the SN2 reaction that WILL take place in larger quantity?
    I'm uploading the question too.
     

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  3. Aug 13, 2014 #2
    There is no other SN2 reaction. There aren't any other leaving groups.
     
  4. Aug 16, 2014 #3
    I am actually not too sure, but I think it is due to the steric hinderance. The hinderance does not always have to be on the beta carbon, if you compare the structure to a neopentylic structure, which can never participate in an Sn2, there are similarities, except that there are only two metyl substituents, instead of three.

    In all honesty, if I would not have known the answer i would have gone for Sn2 as well so I would also love to see a good explanation.
     
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