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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4:05 minutes

Problem 77

Textbook Question

For each of the following compounds, determine whether the cis isomer or the trans isomer is more stable.
a.
b.
c.

Verified step by step guidance

Analyze the structure provided: The compound is a substituted cyclohexane with two bulky groups attached to the ring. These groups are located on adjacent carbons, making it a disubstituted cyclohexane.

Understand the cis and trans isomers: In the cis isomer, both substituents are on the same side of the cyclohexane ring (either both axial or both equatorial). In the trans isomer, one substituent is axial and the other is equatorial, placing them on opposite sides of the ring.

Consider steric hindrance: Bulky groups in the axial position experience 1,3-diaxial interactions with other axial hydrogens on the ring. These interactions increase steric strain, making the axial position less favorable for bulky groups.

Evaluate stability: In the trans isomer, one bulky group can occupy the equatorial position, minimizing steric hindrance. In the cis isomer, both bulky groups may occupy axial positions, leading to increased steric strain. Therefore, the trans isomer is generally more stable due to reduced steric interactions.

Conclude: The stability of the isomers depends on the ability of the bulky groups to avoid steric hindrance. For this compound, the trans isomer is likely more stable because it allows one bulky group to occupy the equatorial position, minimizing steric strain.

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Key Concepts

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

Cis-Trans Isomerism

Cis-trans isomerism, also known as geometric isomerism, occurs in compounds with restricted rotation around a bond, typically in alkenes or cyclic structures. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. This spatial arrangement significantly influences the physical and chemical properties of the compounds, including their stability.

Steric Hindrance

Steric hindrance refers to the repulsion between bulky groups within a molecule that can affect its stability and reactivity. In the context of cis and trans isomers, steric hindrance is often greater in cis isomers due to the proximity of larger substituents, which can lead to increased strain and lower stability compared to trans isomers, where substituents are farther apart.

Ring Strain in Cycloalkanes

Ring strain in cycloalkanes arises from the angle strain and torsional strain present in cyclic structures. Cyclohexane, for example, is the most stable due to its ability to adopt a chair conformation that minimizes strain. In the case of cis and trans isomers of cyclohexane derivatives, the conformation adopted by the substituents can significantly impact the overall stability of the molecule, with trans isomers often being more stable due to reduced steric interactions.

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Related Practice

Textbook Question

For each of the following structures, draw the most stable chair conformer.

Textbook Question

For each pair, indicate which conformer is more stable.

Textbook Question

When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react to form an acetal. This is called the anhydro form of the sugar (it has 'lost water'). The anhydro form of d-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of d-glucose exists in the anhydro form under the same conditions.

Textbook Question

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

e. cis-1-ethyl-3-isopropylcyclohexane

Textbook Question

Predict which side of the equilibrium is favored for each of the chair–chair interconversions (ring flips) shown.

(c)

Textbook Question

Predict which side of the equilibrium is favored for each of the chair–chair interconversions (ring flips) shown.

(a)

Textbook Question

Which of the following conformers has the highest energy (is the least stable)?

Multiple Choice

Draw the MOST STABLE conformation of cis-1-tert-butyl-4-methylcyclohexane.

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For each of the following compounds, determine whether the cis isomer or the trans isomer is more stable.a. b. c.

Key Concepts

Cis-Trans Isomerism

Steric Hindrance

Ring Strain in Cycloalkanes

Watch next

For each of the following compounds, determine whether the cis isomer or the trans isomer is more stable.
a.
b.
c.