Why Are There Two Different Molecules from SN1?

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SUMMARY

The discussion centers on the formation of two distinct molecules from the SN1 reaction of iodocyclohexane in water, specifically (1s,4s)-4-(tert-butyl)-1-methylcyclohexan-1-ol and (1r,4r)-4-(tert-butyl)-1-methylcyclohexan-1-ol. Both products appear achiral due to the presence of a plane of symmetry between carbons 1 and 4, which leads to confusion regarding the notation of "r" and "s". The lack of chiral centers is attributed to the free rotation of the tert-butyl group and the equivalence of the hydroxy and methyl groups in their spatial arrangement. Visualization techniques such as Newman projections are recommended to clarify the structural differences.

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(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?
 
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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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