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SN1 reaction question

  1. Oct 13, 2011 #1
    tert-butyl bromide reacts with HOH to give HBr and the corresponding alcohol ,
    C
    C-C-C
    OH

    But tert-butyl alcohol reacts with HCl to give tert-butyl chloride.

    HBr is a "stronger" acid than HCl. Is this part of the explanation of the different reactions?
     
  2. jcsd
  3. Oct 13, 2011 #2
    In order to get tBuX [X=Cl, Br] from the corresponding alcohol, you need to use conc. HX. If the proportion of water is too high (i.e. the concentration of X- is low] you will mostly have the alcohol in the equilibrium mixture. This is why when you treat tBuX [X=Cl, Br] with water you get hydrolysis - water is in vast excess compared to Br- at equilibrium.
     
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