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Homework Help: Synthesis via Sn2/Sn1, E2, E1

  1. Aug 7, 2014 #1
    Hi all,
    I was looking at the answers in my textbook. They seem to make incongruent choices of solvents.

    In e) and j), why choose EtOH and H2O/CH3OH? I would rather choose an aprotic solvent like DMF to better allow Sn2 to occur. Especially with j), there is a lot of competition with E2 because OH- is a strong base and because we are attacking a secondary carbon.

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  2. jcsd
  3. Aug 7, 2014 #2
    I see this again in k). Secondary carbon attacked: why not add DMF to prevent E2 and get best yield?

    Attached Files:

  4. Aug 10, 2014 #3
    Depends on the acidity/basicity of the end product. A reaction proceeds towards the weaker base/acid. If your end products are more acidic or basic than the reactants, it will not occur.
  5. Aug 10, 2014 #4
    Teemo, I don't see how an unreacting reagent can cause a change in acid base interactions.
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