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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2:35 minutes

Problem 22a

Textbook Question

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

Verified step by step guidance

Step 1: Begin by drawing the basic structure of cyclohexane, which is a six-membered ring. Cyclohexane typically adopts a chair conformation to minimize steric strain.

Step 2: Label the carbon atoms in the ring from 1 to 6 to keep track of the positions where the methyl groups will be added.

Step 3: 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 will be placed in axial positions.

Step 4: Add a methyl group (CH₃) to the axial position of each carbon atom in the ring. Use dashed or solid wedges to indicate whether the axial position is pointing up or down, depending on the orientation of the chair conformation.

Step 5: Double-check your drawing to ensure that all six methyl groups are correctly placed in axial positions and that the chair conformation is accurately represented. Verify that the structure adheres to the rules of stereochemistry and avoids any errors in bond placement.

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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. In this conformation, substituents can occupy either axial (pointing up or down) or equatorial (pointing outward) positions, affecting the overall stability of the molecule.

Axial vs. Equatorial Positions

In cyclohexane derivatives, substituents can be positioned axially or equatorially. Axial substituents are aligned parallel to the axis of the ring, while equatorial substituents extend outward from the ring. Axial positions can lead to 1,3-diaxial interactions, increasing steric strain and making the molecule less stable compared to when substituents are in equatorial positions.

Steric Hindrance

Steric hindrance refers to the repulsion between atoms that occurs when they are brought close together, often due to the size of the substituents. In the case of 1,2,3,4,5,6-hexamethylcyclohexane, placing all methyl groups in axial positions increases steric hindrance, leading to greater strain and a less stable conformation compared to a configuration with equatorial methyl groups.

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Related Practice

Textbook Question

Draw 1,2,3,4,5,6-hexachlorocyclohexane with

a. all the chloro groups in axial positions.

b. all the chloro groups in equatorial positions.

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

b. in equatorial 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-

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Draw 1,2,3,4,5,6-hexamethylcyclohexane with all the methyl groupsa. in axial positions.

Key Concepts

Cyclohexane Conformation

Axial vs. Equatorial Positions

Steric Hindrance

Watch next

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