Organic Chemistry Practice Problems and Problem Sets
Cycloalkanes and Cyclohexane Chair Forms
Two stereoisomers of trimethylcyclohexane are shown below (compounds A and B). Compare cyclohexane chair forms to determine which isomer has a lower heat of combustion. Explain your reasoning.
A has a chair form that avoids having any substituents in the axial position.
B's most stable chair form has one axial substituent.
So A is more stable than B. Therefore, B is higher eneregy and has a higher heat of combustion than A.
MendelSet practice problem # 318 submitted by Matt on June 7, 2011.