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Chapter 26: Problem 47

For each of the following substituted cyclohexanes, draw the two possible chair conformations, label each substituent as axial or equatorial, and identify the more stable conformer. (a) cyclohexanol (b) trans-3-methylcyclohexanol

Short Answer

Expert verified
For cyclohexanol, the more stable chair conformation is the one where the OH group is in an equatorial position, avoiding steric interaction. For trans-3-methylcyclohexanol, the more stable chair conformation is where the methyl group is in an equatorial position, also minimizing steric interaction because it is larger than hydrogen.

Step by step solution

01

Draw Chair Conformations of Cyclohexanol

Draw the two possible chair conformations for cyclohexanol - one where the hydroxyl (OH) group is in an axial orientation and one where it is in an equatorial orientation. Label each OH group as axial or equatorial.
02

Identify the More Stable Conformation of Cyclohexanol

Compare the two chair conformations for cyclohexanol. The conformation with the OH group in an equatorial position will be more stable because equatorial substituents experience fewer steric interactions with other hydrogens on the cyclohexane ring.
03

Draw Chair Conformations of trans-3-Methylcyclohexanol

Now draw the two possible chair conformations for trans-3-methylcyclohexanol - one where the methyl group is in an axial position and one where it is in an equatorial position. Remember the 'trans' designation means the hydroxyl group is on the opposite side of the ring to the methyl group.
04

Identify the More Stable Conformation of trans-3-Methylcyclohexanol

Compare the two chair conformations for trans-3-methylcyclohexanol. The conformation where the larger methyl group is in the equatorial position, thus minimizing steric interaction, will be the more stable chair conformation.

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Most popular questions from this chapter

Among all ethers with the formula \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O},\) draw structures for (a) two ethers with two \(s p^{2}\) and two \(s p^{3}\) carbon atoms (b) an ether with four \(s p^{2}\) carbon atoms (c) an ether with two sp and two \(s p^{3}\) carbon atoms

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