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? 

🤓 Based on our data, we think this question is relevant for Professor Mohr's class at UAB.

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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? 

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Carey 8th Edition. You can also practice Organic Chemistry - Carey 8th Edition practice problems.