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

Cis vs Trans Conformations

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans Conformations

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1:40 minutes

Problem 40c

Textbook Question

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.
(c)

Verified step by step guidance

Identify the chair conformation structure provided in the image. Note the positions of substituents (hydrogen atoms and alkyl groups) on the cyclohexane ring.

Determine the axial and equatorial positions of the substituents. Axial substituents are perpendicular to the plane of the ring, while equatorial substituents are roughly parallel to the plane of the ring.

Convert the chair conformation into a planar (flat) representation. In a planar form, the cyclohexane ring is drawn as a hexagon, and substituents are placed above or below the plane based on their axial or equatorial positions.

Place the substituents in their respective positions in the planar form. For example, substituents in axial positions will be drawn above or below the hexagon, while equatorial substituents will be drawn extending outward from the sides of the hexagon.

Ensure that the stereochemistry (up or down orientation) of each substituent is preserved in the planar form. Double-check the positions to confirm accuracy.

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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 a three-dimensional representation of cyclohexane and its derivatives, which minimizes steric strain and torsional strain. In this conformation, carbon atoms are arranged in a staggered manner, allowing for more stable interactions between substituents. Understanding chair conformations is crucial for visualizing the spatial arrangement of atoms in cyclic compounds.

Cis and Trans Isomerism

Cis and trans isomerism refers to the different spatial arrangements of substituents around a double bond or a ring structure. In cis isomers, substituents are on the same side, while in trans isomers, they are on opposite sides. This concept is essential for predicting the physical and chemical properties of organic molecules, as the arrangement can significantly influence reactivity and stability.

Planar Representation

Planar representation involves drawing a molecule in two dimensions, typically to simplify the visualization of its structure. For chair conformations, this means translating the three-dimensional arrangement into a flat diagram, which can help in understanding the relative positions of substituents. This representation is particularly useful for comparing cis and trans configurations in cyclic compounds.

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Related Practice

Textbook Question

Is each of the following a cis isomer or a trans isomer?

Multiple Choice

Which structure is cis-1,3-dimethylcyclopentane?

Textbook Question

Name the following compounds. Remember that two up bonds are cis; two down bonds are cis; one up bond and one down bond are trans.

(c)

(d)

Textbook Question

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.

(d)

Textbook Question

Is each of the following a cis isomer or a trans isomer?

Textbook Question

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.

(b)

Textbook Question

Name the following compounds. Remember that two up bonds are cis; two down bonds are cis; one up bond and one down bond are trans.

(e)

(f)

Textbook Question

Use your results from Problem 3-27 to complete the following table. Each entry shows the positions of two groups arranged as shown. For example, two groups that are trans on adjacent carbons (trans-1,2) must be both equatorial (e,e) or both axial (a,a).

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Given the following chair conformations, draw each in its planar form as if you were viewing it from above. (c)

Key Concepts

Chair Conformation

Cis and Trans Isomerism

Planar Representation

Watch next

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.
(c)