Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

Axial vs Equatorial

Organic Chemistry

4. Alkanes and Cycloalkanes

Axial vs Equatorial

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6:17 minutes

Problem 3eBruice - 8th Edition

Textbook Question

For each of the following disubstituted cyclohexanes, indicate whether the substituents in the two chair conformers are both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers: a. cis-1,2- b. trans-1,2-

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Identify the structure of the cyclohexane ring and the positions of the substituents for each compound. For cis-1,2-disubstituted cyclohexane, both substituents are on the same side of the ring. For trans-1,2-disubstituted cyclohexane, the substituents are on opposite sides.

Draw the two possible chair conformations for each compound. Remember that in a chair conformation, each carbon atom has one axial and one equatorial position.

For cis-1,2-disubstituted cyclohexane, place both substituents on the same side (either both up or both down) in each chair conformation. Analyze whether both substituents are equatorial in one conformation and both axial in the other, or if one is equatorial and one is axial in each conformation.

For trans-1,2-disubstituted cyclohexane, place one substituent up and the other down in each chair conformation. Determine if both substituents are equatorial in one conformation and both axial in the other, or if one is equatorial and one is axial in each conformation.

Compare the stability of the chair conformations for each compound. Generally, the conformation with the most substituents in the equatorial position is more stable due to reduced steric strain.

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Key Concepts

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

Chair Conformation

Chair conformation is the most stable form of cyclohexane, allowing for minimized steric strain. In this conformation, carbon atoms alternate between axial (pointing up or down) and equatorial (pointing outward) positions. Understanding chair conformations is crucial for analyzing the spatial arrangement of substituents on cyclohexane rings.

Axial and Equatorial Positions

In cyclohexane, substituents can occupy axial or equatorial positions. Axial substituents are aligned parallel to the axis of the ring, while equatorial substituents extend outward, reducing steric hindrance. The preference for substituents to occupy equatorial positions is key to determining the stability of different conformers.

Cis and Trans Isomerism

Cis and trans isomerism refers to the relative positioning of substituents on a cyclohexane ring. In cis isomers, substituents are on the same side, while in trans isomers, they are on opposite sides. This distinction affects the conformational analysis, as it influences whether substituents can both be equatorial or axial in the chair conformations.