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T-butyl vs. isopropyl subsitutions

  1. Oct 31, 2010 #1
    1. The problem statement, all variables and given/known data
    T-butyl chloride can undergo substitution reaction to create C4H9OH, but isopropyl chloride cannot. Why is this?

    2. Relevant equations

    3. The attempt at a solution
    I'm guessing it has to do with the extra carbon. Maybe since it is a secondary halide, the substitution takes the H off instead of the Cl?
  2. jcsd
  3. Nov 1, 2010 #2
    Well, you can form 2-methylpropanol from IPA via things like metallation and addition of formaldehyde, but this is addition, not substitution. So the only thing that's relevant here is the number of carbons, in my opinion.
  4. Nov 2, 2010 #3


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    That's a trick question.
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