Are the cis and trans isomers of 4 tert-butyl cyclohexanol chiral? If not, what symmetry element do they possess?

The cis and trans isomers of 4 tert-butyl cyclohexanol are not chiral. Chirality arises when a molecule cannot be superimposed on its mirror image, typically due to the presence of a chiral center. In the case of 4 tert-butyl cyclohexanol, both isomers have a plane of symmetry, which allows for superimposition with their mirror images.

Specifically, the cis isomer places the tert-butyl group and the hydroxyl group on the same side of the cyclohexane ring, while the trans isomer places them on opposite sides. In both cases, the arrangement leads to a symmetrical structure:

  • For the cis isomer, you can visualize a vertical plane that divides the molecule such that the tert-butyl and hydroxyl groups reflect upon each other.
  • For the trans isomer, a horizontal plane can be identified that bisects the molecule, also allowing for symmetry.

Therefore, due to the presence of these symmetry elements, both isomers of 4 tert-butyl cyclohexanol do not exhibit chirality.

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