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Two different molecules from SN1?

  1. Jul 23, 2014 #1
    (1s,4s)-4-(tert-butyl)-1-methylcyclohexan-1-ol
    (1r,4r)-4-(tert-butyl)-1-methylcyclohexan-1-ol
    These are the two results given by the solution's manual textbook to this question:
    Keeping in mind that carbocations have a trigonal planar structure, (a) write a structure for the carbocation intermediate and (b) write structures for the alcohol (or alcohols) that you would expect from reaction of iodocyclohexane in water.


    Now, I want to understand why there are two molecules that are different. Both of them seem to be achiral because of the plane of symettry along carbon 1 and 4. Why are the "r" and "s" not capitalized?
     
  2. jcsd
  3. Jul 26, 2014 #2
    Yeah I looked over this yesterday, I was just too befuddled to reply. There are no chiral centers because the tert-butyl group experiences free rotation and because the compound is the same, whether the hydroxy or the methyl group lies on a wedge/dashes. If it is difficult to visualize in your head, you can always test this by drawing a Newman projection and rotating the front and back to see if there are indeed different compounds if you switch the position of the wedge/dashes.
     
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