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

Chair Flip

Organic Chemistry

4. Alkanes and Cycloalkanes

Chair Flip

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Problem 57e

Textbook Question

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]
(e)

Verified step by step guidance

Step 1: Understand the concept of chair flipping in cyclohexane. When a chair conformation flips, axial substituents become equatorial, and equatorial substituents become axial. However, the substituents remain attached to the same carbon atoms.

Step 2: Identify the substituents and their positions on the original chair conformation. In this case, there is a bromine (Br) substituent at carbon 3 in the axial position and another bromine (Br) substituent at carbon 4 in the equatorial position.

Step 3: Draw the flipped chair conformation. Ensure that the carbon numbering remains consistent (carbon 1 through carbon 6) and the overall structure of the cyclohexane ring is preserved.

Step 4: Place the substituents on the flipped chair conformation. For carbon 3, the bromine substituent that was axial in the original chair conformation will now be equatorial. For carbon 4, the bromine substituent that was equatorial in the original chair conformation will now be axial.

Step 5: Double-check the positions of the substituents to ensure accuracy. Verify that the axial/equatorial designations have been correctly swapped and that the substituents remain attached to their respective carbons.

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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 a three-dimensional representation of cyclohexane that minimizes steric strain. In this conformation, the carbon atoms are arranged in a way that allows for staggered bonds, making it the most stable form of cyclohexane. Understanding chair conformation is essential for visualizing how substituents are positioned in space.

Axial and Equatorial Positions

In chair conformations, substituents can occupy two types of positions: axial and equatorial. Axial substituents are oriented perpendicular to the plane of the ring, while equatorial substituents are oriented parallel to the plane. The designation of these positions changes when the chair conformation is flipped, which is crucial for predicting the stability of different substituent arrangements.

Flipping the Chair

Flipping the chair refers to the process of converting one chair conformation of cyclohexane into another. This involves rotating the ring structure, which causes axial substituents to become equatorial and vice versa. This concept is important for understanding how the spatial arrangement of substituents affects the overall stability and reactivity of cyclohexane derivatives.

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Related Practice

Textbook Question

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]

(f)

Textbook Question

What is the mistake that was made in drawing each of the flipped chairs on the right from the chair on the left? [In these, assume that the angle through which you view the chair conformations doesn't change.]

(a)

Textbook Question

Using the numbers shown in the chair conformation on the left, label the carbons of the flipped chair on the right. [Assume that the angle through which you view the chair conformation doesn't change.]

Textbook Question

(c)

Textbook Question

Which of the following structures represent the same compound? Which ones represent different compounds?

(e)

Textbook Question

Use your models to do a chair–chair interconversion on each ring of the conformation of cis-decalin shown in Figure 3-27. Draw the conformation that results.

Multiple Choice

Determine if the following pairof chairs are identical, conformers or different.

Multiple Choice

Determine if the following pairof chairs are identical, conformers or different.

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For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.](e)

Key Concepts

Chair Conformation

Axial and Equatorial Positions

Flipping the Chair

Watch next

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]
(e)