In a cyclohexane derivative featuring both a chlorine atom and a methyl group, which substituent position (axial or equatorial) would likely lead to a more stable chair conformation?

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Seekh · Accepted Answer

In a cyclohexane chair, bulky groups want to be equatorial because that position keeps them away from the other axial hydrogens, reducing 1,3‑diaxial clashes. Chlorine is larger than a hydrogen but smaller than a methyl group, so it still prefers the equatorial side to avoid steric crowding. The methyl group is even bulkier, so it also strongly favors the equatorial position. If the chlorine were axial and the methyl equatorial, the chair would experience significant strain from both groups; flipping the chair so both are equatorial gives the lowest energy. Thus, the more stable conformation has both substituents in the equatorial positions.

In a cyclohexane derivative featuring both a chlorine atom and a methyl group, which substituent position (axial or equatorial) would likely lead to a more stable chair conformation?

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Deep Dive: Cyclohexane Chair Conformations

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