Which of the following substituted cyclohexanes has the most negative value of ΔG° for ring flipping from the conformation in which the substituent is axial to the one where it is equatorial?
A) methylcyclohexane
B) chlorocyclohexane
C) isopropylcyclohexane
D) ethynylcyclohexane

Question

Quizplus · Accepted Answer

Isopropylcyclohexane has the most negative ΔG° for ring flipping from axial to equatorial because the isopropyl group is larger and causes more steric hindrance when in the axial position compared to the other substituents listed. This results in a more stable equatorial conformation and a larger energy difference between the two conformations.

Which of the Following Substituted Cyclohexanes Has the Most Negative