# Problem: By assuming that the heat of combustion of the cis isomer was larger than the trans, structural assignments were made many years ago for the stereoisomeric 2-, 3-, and 4-methylcyclohexanols. This assumption is valid for two of the stereoisomeric pairs but is incorrect for the other. For which pair of stereoisomers is the assumption incorrect? Why?

84% (75 ratings)
###### Problem Details

By assuming that the heat of combustion of the cis isomer was larger than the trans, structural assignments were made many years ago for the stereoisomeric 2-, 3-, and 4-methylcyclohexanols. This assumption is valid for two of the stereoisomeric pairs but is incorrect for the other. For which pair of stereoisomers is the assumption incorrect? Why?