Organic Chemistry Practice Problems Equatorial Preference Practice Problems Solution: A hydroxyl group is a somewhat “smaller” substitue...

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Solution: A hydroxyl group is a somewhat “smaller” substituent on a six-membered ring than is a methyl group. That is, the preference of a hydroxyl group for the equatorial orientation is less pronounced than that of a methyl group. Given this information, write structural formulas for all the isomeric methylcyclohexanols, showing each one in its most stable conformation. Give the substitutive IUPAC name for each isomer. 

Problem

A hydroxyl group is a somewhat “smaller” substituent on a six-membered ring than is a methyl group. That is, the preference of a hydroxyl group for the equatorial orientation is less pronounced than that of a methyl group. Given this information, write structural formulas for all the isomeric methylcyclohexanols, showing each one in its most stable conformation. Give the substitutive IUPAC name for each isomer.