Cyclohexane derivatives exist primarily in the most stable of the available chair conformations.Give the position, axial or equatorial, of each of the three groups shown when the ring is in themost stable chair conformation. If a group divides its time equally between axial and equatorialpositions, indicate this with ax/eq.The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain EnergyIncrements" section of the Reference tool is useful for answering this question.aCO2H"CH3Group a isGroup b isGroup c is

Answered: Cyclohexane derivatives exist primarily…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

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Cyclohexane derivatives exist primarily in the most stable of the available chair conformations.
Give the position, axial or equatorial, of each of the three groups shown when the ring is in the
most stable chair conformation. If a group divides its time equally between axial and equatorial
positions, indicate this with ax/eq.
The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy
Increments" section of the Reference tool is useful for answering this question.
aCO2H
"CH3
Group a is
Group b is
Group c is

Expert Solution

Step 1

Explanation -

A conformation in which both substituents are equatorial will always be more stable than a conformation with both groups axial.

Substituents prefer equatorial rather than axial positions in order to minimize the steric hindrance of 1,3-diaxial interactions.

As can be seen in the structures above, cis-1,3-disubstituted cyclohexane's most stable conformer has both methyl groups and carboxylic group at equatorial, while trans-1,3-disubstituted cyclohexane always has one group is equatorial and one group axial.

This means that the cis isomer 1,3-disubstituted cyclohexane is more stable than the trans isomer. And that is opposite what we found for 1,2-disubstituted cyclohexane.

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