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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5:43 minutes

Problem 51e,f

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-

Verified step by step guidance

Step 1: Understand the problem. We are tasked with analyzing the chair conformations of disubstituted cyclohexanes (cis-1,4- and trans-1,4-) to determine the positions of the substituents (axial or equatorial) in each conformer.

Step 2: Recall the key concepts. In a cyclohexane chair conformation, substituents can occupy either axial (perpendicular to the ring plane) or equatorial (roughly parallel to the ring plane) positions. The relative positions of substituents (cis or trans) determine their placement in the chair conformers.

Step 3: Analyze the cis-1,4-disubstituted cyclohexane. In the cis configuration, the two substituents are on the same side of the ring. For the chair conformers, this means that one substituent will be axial and the other equatorial in both conformers. This is because the 1,4-relationship alternates axial and equatorial positions around the ring.

Step 4: Analyze the trans-1,4-disubstituted cyclohexane. In the trans configuration, the two substituents are on opposite sides of the ring. For the chair conformers, this means that both substituents will be equatorial in one conformer and both will be axial in the other conformer. This is due to the alternating axial and equatorial positions in the 1,4-relationship.

Step 5: Summarize the findings. For cis-1,4-, the substituents are one axial and one equatorial in each conformer. For trans-1,4-, the substituents are both equatorial in one conformer and both axial in the other conformer.

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Key Concepts

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

Chair Conformation

The chair conformation is the most stable form of cyclohexane, allowing for minimized steric strain. In this conformation, carbon atoms are arranged in a staggered manner, which provides equatorial and axial positions for substituents. Understanding how substituents occupy these positions is crucial for analyzing the stability of disubstituted cyclohexanes.

Equatorial vs. Axial Positions

In cyclohexane chair conformations, substituents can occupy equatorial or axial positions. Equatorial substituents extend outward from the ring, minimizing steric hindrance, while axial substituents point vertically, which can lead to 1,3-diaxial interactions and increased steric strain. Identifying these positions is essential for 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 of the ring, while in trans isomers, they are on opposite sides. This distinction affects the conformational analysis, as it influences whether substituents can be both equatorial or axial in the chair conformations.

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Related Practice

Textbook Question

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

a. in axial positions.

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:

c. cis-1,3-

d. trans-1,3-

Textbook Question

a. cis-1,2-

b. trans-1,2-

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?