Two different molecules from SN1?

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In summary, there are two results for the molecule (1s,4s)-4-(tert-butyl)-1-methylcyclohexan-1-ol and (1r,4r)-4-(tert-butyl)-1-methylcyclohexan-1-ol, which have a trigonal planar structure. Both molecules are achiral due to a plane of symmetry along carbon 1 and 4. The "r" and "s" are not capitalized because the tert-butyl group can freely rotate, making the compound the same regardless of the position of the hydroxy or methyl group on the wedge/dashes. This can be tested by drawing a Newman projection and rotating the front and
  • #1
alingy1
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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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  • #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.
 

Related to Two different molecules from SN1?

1. What is SN1?

SN1 refers to a type of nucleophilic substitution reaction in organic chemistry. It involves the formation of a carbocation intermediate before the nucleophile attacks the molecule.

2. What are the two different molecules involved in an SN1 reaction?

The two molecules involved in an SN1 reaction are the substrate and the nucleophile. The substrate is the molecule that undergoes the substitution reaction, while the nucleophile is the molecule that attacks and replaces a leaving group on the substrate.

3. How does the structure of the substrate affect the SN1 reaction?

The structure of the substrate plays a crucial role in determining the rate of an SN1 reaction. Substrates with more stable carbocation intermediates, such as tertiary substrates, undergo SN1 reactions faster than primary substrates with less stable carbocation intermediates.

4. What are the characteristics of SN1 reactions?

SN1 reactions typically occur in polar protic solvents, involve a unimolecular rate-determining step, and result in racemic mixtures of products. They also tend to occur more readily with secondary and tertiary substrates.

5. What are some common examples of SN1 reactions?

Some common examples of SN1 reactions include the hydrolysis of tert-butyl chloride to form tert-butyl alcohol, the synthesis of tertiary alcohols from tertiary halides, and the formation of esters from alcohols and acid halides.

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