Axial - Equatorial (larger view)

Axial - Equatorial (larger view)

 

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cis-1,4-Dimethylcyclohexane 
What is the difference in energy between the two chair conformations of cis-1,4-dimethylcyclohexane? Cis-1,4-substitution in a chair cyclohexane means that one group (methyl) must be equatorial and the other axial [Review]. The left hand structure has an axial blue methyl group and the an equatorial red methyl group. A chair-chair interconversion merely switches the position of the two groups: equatorial ---> axial; axial ---> equatorial. The right hand structure has a red axial methyl group and a blue equatorial methyl group. Therefore, ΔGo = 0 kcal/mol and Keq = 1 for the two chair conformations. The total energy for each chair conformation is 1.8 kcal/mol.