Portmess Homework Q&S 82

Portmess Homework Q&S 82 - 76 ALCOHOLS AND ALKYL...

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In the other isomers methyl and hydroxyl will be in a 1,2, 1,3, or 1,4 relationship and can be cis or trans in each. We can write the preferred conformation by recognizing that the methyl group will always be equatorial and the hydroxyl either equatorial or axial. 4.25 The assumption is incorrect for the 3-methylcyclohexanols. cis -3-Methylcyclohexanol is more stable than trans -3-methylcyclohexanol because the methyl group and the hydroxyl group are both equa- torial in the cis isomer, whereas one substituent must be axial in the trans. 4.26 ( a ) The most stable conformation will be the one with all the substituents equatorial. The hydroxyl group is trans to the isopropyl group and cis to the methyl group. ( b ) All three substituents need not always be equatorial; instead, one or two of them may be axial. Since neomenthol is the second most stable stereoisomer, we choose the structure with one axial substituent. Furthermore, we choose the structure with the smallest substituent (the hydroxyl
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