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Williamsons ether synthesis (rate)

  1. Jan 15, 2016 #1

    Suraj M

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    1. The problem statement, all variables and given/known data
    Which will undergo faster Williamson ether syntehsis
    It was either faster or better, I'm not sure

    A)3-Chlorobutan-1-ene
    B)1-Bromobutane

    2. Relevant equations


    3. The attempt at a solution
    I thought option A because of its alylic position it will form a stable carbocation (and through SN1)
    Is it correct? Or is it B because bromine is more weakly bound to the primary carbon

    Thank you :-)
     
  2. jcsd
  3. Jan 16, 2016 #2

    Ygggdrasil

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    What mechanism is involved in Williamson ether synthesis, SN1 or SN2? What factors are most important for reactions of that type?
     
  4. Jan 16, 2016 #3

    Suraj M

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    The mechanism depends on the reactants right?
    What factors? I'd say driving force of the stabilized carbocation if it's SN1 else steric factor and strength of the CX bond for SN2?
    Is that right?
     
  5. Jan 16, 2016 #4

    Ygggdrasil

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    You should double check what your text says about the mechanism of Williamson ether synthesis.
     
    Last edited: Jan 16, 2016
  6. Jan 16, 2016 #5

    Suraj M

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    Oh always SN2?
    Then in that case it's option B right?
     
  7. Jan 16, 2016 #6

    Ygggdrasil

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    Yes. If you were to try to form an ether via an SN1 reaction, you would probably have too much competition from the E1 product.
     
  8. Jan 17, 2016 #7

    Suraj M

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    Ah okay
    Thanks Ygggrasil ! :-)
     
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