Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

4. Alkanes and Cycloalkanes

Equatorial Preference

Organic Chemistry

4. Alkanes and Cycloalkanes

Equatorial Preference

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4:24 minutes

Problem 60e

Textbook Question

For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.]
(e)

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Identify the substituents on the cyclohexane ring and their positions (e.g., axial or equatorial) based on the given structure. Remember that wedged substituents are 'up' and dashed substituents are 'down' in the chair conformation.

Draw the first chair conformation of cyclohexane. Place the substituents in their respective axial or equatorial positions, ensuring that 'up' substituents are correctly oriented as either axial up or equatorial up.

Perform a chair flip to draw the second chair conformation. In the flipped chair, axial substituents become equatorial, and equatorial substituents become axial, while maintaining their 'up' or 'down' orientation.

Analyze the stability of each chair conformation. Stability is influenced by steric hindrance: bulky groups prefer the equatorial position to minimize 1,3-diaxial interactions.

Compare the two chair conformations and determine which is more stable based on the placement of substituents (e.g., fewer steric interactions in the equatorial position).

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Chair Conformation

The chair conformation is a three-dimensional representation of cyclohexane that minimizes steric strain and torsional strain. In this conformation, carbon atoms are arranged in a staggered manner, allowing for more stable interactions between substituents. Understanding chair conformations is crucial for analyzing the stability of cyclohexane derivatives, as substituents can occupy equatorial or axial positions, influencing overall stability.

Equatorial vs. Axial Positions

In the chair conformation of cyclohexane, substituents can occupy two types of positions: equatorial and axial. Equatorial substituents extend outward from the ring, minimizing steric hindrance with other groups, while axial substituents point vertically, which can lead to 1,3-diaxial interactions that increase steric strain. The stability of a molecule often depends on the preference for substituents to be in equatorial positions.

Flipping the Chair Conformation

Flipping the chair conformation involves rotating the cyclohexane ring to convert axial substituents to equatorial and vice versa. This process is essential for comparing the stability of different conformations of the same molecule. By analyzing both chair forms, one can determine which conformation is more stable based on the positioning of substituents and the resulting steric interactions.

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Related Practice

Textbook Question

Draw two chair conformations of the molecules below. Indicate which is most stable.

(a)

Textbook Question

For each pair of conformations you drew in Assessment 3.41, indicate which is most stable.

Textbook Question

For each pair of conformations shown, choose which is most stable. If both are equally stable, then write 'no difference.' [If both conformations have the same number of axial substituents, choose the one with the smallest axial substituents.]

(e)

Textbook Question

(g)

Textbook Question

For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.]

(g)

Textbook Question

Draw the two chair conformers for each of the following and indicate which conformer is more stable:

b. trans-1-ethyl-2-methylcyclohexane

Textbook Question

Draw the two chair conformers for each of the following and indicate which conformer is more stable:

d. cis-1,2-diethylcyclohexane

Textbook Question

Draw the more stable chair conformer of cis-1-ethyl-2-methylcyclohexane.

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For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.](e)

Key Concepts

Chair Conformation

Equatorial vs. Axial Positions

Flipping the Chair Conformation

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For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.]
(e)