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

Cis vs Trans Conformations

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans Conformations

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1:48 minutes

Problem 3.21Wade - 9th Edition

Textbook Question

The cyclohexane chair shown in [FIGURE 3-22] <IMAGE> has the headrest to the right and the footrest to the left.

Draw a cyclohexane chair with its axial and equatorial bonds, showing the headrest to the left and the footrest to the right.

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Identify the current orientation of the cyclohexane chair with the headrest to the right and the footrest to the left.

Visualize the cyclohexane chair structure, noting that it consists of alternating axial and equatorial bonds.

To reverse the orientation, imagine flipping the chair horizontally so that the headrest is now on the left and the footrest is on the right.

Redraw the cyclohexane chair with the new orientation, ensuring that the axial and equatorial bonds are correctly positioned relative to the new headrest and footrest positions.

Check that the axial bonds are perpendicular to the ring plane and the equatorial bonds are roughly parallel to the ring plane, maintaining the correct 3D geometry.

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Key Concepts

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

Cyclohexane Chair Conformation

The cyclohexane chair conformation is a three-dimensional arrangement of cyclohexane that minimizes steric strain and torsional strain. In this conformation, the carbon atoms are arranged in a staggered manner, allowing for more stable interactions between hydrogen atoms. The chair form can flip, interchanging axial and equatorial positions of substituents, which is crucial for understanding the stability of different isomers.

Axial and Equatorial Bonds

In the chair conformation of cyclohexane, substituents can occupy two types of positions: axial and equatorial. Axial bonds are oriented perpendicular to the plane of the ring, while equatorial bonds extend outward from the ring's plane. The positioning of substituents affects steric interactions and overall stability, with equatorial positions generally being more favorable for larger groups due to reduced steric hindrance.

Chair Flip Mechanism

The chair flip mechanism refers to the process by which cyclohexane interconverts between two chair conformations. During this flip, all axial bonds become equatorial and vice versa, allowing for the redistribution of substituents. This concept is essential for understanding the dynamic nature of cyclohexane and how substituent positions can influence the molecule's reactivity and stability.