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Exam 4: Organic Compounds: Cycloalkanes and Their Stereochemistry

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Question 1

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Which of the following statements is not true regarding the conformation of substituted cyclohexanes?

A) ring flip of substituted cyclohexanes flips the axial and equatorial positions of substituents
B) substituted cyclohexanes are destabilized by 1,3-diaxial interactions
C) the twist-boat conformation of cyclohexane is more stable than the chair conformation
D) the relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy

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Question 2

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Refer to the structure below to answer the following question(s). -Refer to instructions. Which of the labeled groups is trans to b?

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Question 3

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Refer to the structure below to answer the following question(s). -Refer to instructions. Which of the labeled groups in the structure are equatorial?

Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane?

For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. -Draw and label:

In cycloheptane, which of the following factors contributes the least to the stability of the ring conformation?

The following is an incorrect name according to IUPAC nomenclature rules. Correct it such that it is a proper IUPAC name. 3-methylhexylcyclopentane

Which of the following structures represents trans-1,2-dimethylcyclohexane?

Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane?

If cyclohexane were planar, how much torsional strain would be present in the planar molecule? Assume that the energy cost for each H↔H eclipsing interaction is 4.0 kcal/mol.

Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?

Label each pair of compounds below as: -Label: and

Which one of the following structures represents a different compound from the other three?

In which of the following compounds would the carbon−carbon bond angle diverge the greatest from 109°?

Which one of the following structures represents a different compound from the other three?

If the 1,3-diaxial strain for an ethyl group is 4.0 kJ/mol, what is the energy difference between the axial and equatorial conformations of ethylcyclohexane?

Provide the proper IUPAC name for the compound below.

Which of the following cycloalkanes has the most ring strain?

D-Pinitol is an interesting hexahydroxycyclohexane, whose structure is shown below. On the templates provided, draw the two chair conformations that are in equilibrium for D-pinitol. Circle the most stable conformation.

Which of the following structures represents trans-1,3-dimethylcyclohexane?