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Question 4.63: The diaxial conformation of cis-l-chloro-3-methylcyclohexane......

The diaxial conformation of cis-l-chloro-3-methylcyclohexane is 16 kJ mole^{−1} less stable than the diequatorial conformation. Why is this value larger than the sum of the steric strains of a chlorine atom and a methyl group?

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The steric strains all due to repulsion between an axial group and the axial hydrogen atoms at C-3 and C-5. Repulsion between an axial methyl group and a larger atom at C-1, such as chlorine, is substantially larger.

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