Which of the following is the lowest energy chair conformation of with a group at carbon and a group at carbon ?
A
The conformation where the group is equatorial and the group is axial
B
The conformation where both the and groups are axial
C
The conformation where both the and groups are equatorial
D
The conformation where the group is axial and the group is equatorial
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1
Identify the substituents on the cyclohexane ring and their positions: a tert-butyl group at carbon 1 and a methyl group at carbon 2.
Recall that in cyclohexane chair conformations, bulky groups prefer the equatorial position to minimize 1,3-diaxial interactions, which are steric hindrances with axial hydrogens on carbons 3 and 5.
Determine the preferred position of the tert-butyl group, which is very bulky, so it strongly favors the equatorial position to reduce steric strain.
Analyze the position of the methyl group at carbon 2: after placing the tert-butyl group equatorial at carbon 1, the chair flip will place the methyl group in the axial position at carbon 2, or vice versa.
Compare the steric interactions in both possible chair conformations and conclude that the lowest energy conformation is the one where the tert-butyl group is equatorial and the methyl group is axial, because the bulky tert-butyl group’s preference dominates the stability.