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. 

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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. 

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Based on our data, we think this problem is relevant for Professor Pradhan's class at UCONN.

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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.