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

Axial vs Equatorial

Organic Chemistry

4. Alkanes and Cycloalkanes

Axial vs Equatorial

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2:42 minutes

Problem 22b

Textbook Question

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups
b. in equatorial positions.

Verified step by step guidance

Start by drawing the basic structure of cyclohexane in its chair conformation. This is the most stable conformation of cyclohexane, where alternating carbon atoms are positioned above and below the plane of the ring.

Label the six carbon atoms in the cyclohexane ring (C1 through C6) to keep track of the positions where the substituents (methyl groups) will be added.

Recall that in the chair conformation, each carbon atom has two substituent positions: one axial (pointing straight up or down) and one equatorial (pointing outward and slightly angled). For this problem, all methyl groups need to be placed in equatorial positions.

Add a methyl group (-CH₃) to each carbon atom (C1 through C6) in the equatorial position. Ensure that the equatorial positions alternate directions around the ring to maintain the correct geometry of the chair conformation.

Double-check your drawing to confirm that all six methyl groups are in equatorial positions and that the chair conformation is correctly represented. This ensures the structure is accurate and adheres to the problem's requirements.

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Key Concepts

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

Cyclohexane Conformation

Cyclohexane can adopt different conformations, primarily chair and boat forms. The chair conformation is the most stable due to minimized steric strain and torsional strain. Understanding these conformations is crucial for visualizing how substituents, like methyl groups, are positioned on the ring.

Equatorial vs. Axial Positions

In the chair conformation of cyclohexane, substituents can occupy either equatorial or axial positions. Equatorial positions extend outward from the ring, reducing steric hindrance, while axial positions point up or down, potentially causing 1,3-diaxial interactions. For stability, bulky groups prefer equatorial positions.

Substituent Effects on Stability

The placement of substituents on cyclohexane affects the overall stability of the molecule. In the case of 1,2,3,4,5,6-hexamethylcyclohexane, having all six methyl groups in equatorial positions minimizes steric interactions, leading to a more stable structure compared to having any in axial positions.

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Related Practice

Textbook Question

a. Draw Newman projections of the two conformers of trans-1,3-dimethylcyclohexane.

b. Which of the conformers predominates at equilibrium?

Textbook Question

This is a Newman projection of a substituted cyclohexane.

c. Give the IUPAC name.

Textbook Question

Draw the two chair conformers for each of the stereoisomers of trans-1-tert-butyl-3-methylcyclohexane.

Textbook Question

Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groups

a. in axial positions.

Textbook Question

This is a Newman projection of a substituted cyclohexane.

b. Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.

Textbook Question

This is a Newman projection of a substituted cyclohexane. a. Draw the equivalent chair form.

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:

e. cis-1,4-

f. trans-1,4-

Textbook Question

c. cis-1,3-

d. trans-1,3-

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