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

Organic Chemistry

4. Alkanes and Cycloalkanes

Cis vs Trans

Previous problemNext problem

4:38 minutes

Problem 2a

Textbook Question

Draw the cis and trans isomers for the following:
a. 1-bromo-4-chlorocyclohexane

Verified step by step guidance

Understand the structure of cyclohexane: Cyclohexane is a six-membered ring that can adopt a chair conformation. Substituents on the ring can occupy either axial (perpendicular to the ring plane) or equatorial (parallel to the ring plane) positions.

Identify the substituents: The molecule has a bromine atom at position 1 and a chlorine atom at position 4. These substituents can be arranged in either a cis (same side of the ring) or trans (opposite sides of the ring) configuration.

Draw the cis isomer: In the cis isomer, both substituents (bromine and chlorine) are on the same side of the cyclohexane ring. For example, both can be in axial positions or both in equatorial positions. Ensure the relative stereochemistry is consistent with the cis configuration.

Draw the trans isomer: In the trans isomer, the substituents are on opposite sides of the cyclohexane ring. For example, one substituent can be in an axial position while the other is in an equatorial position. Ensure the relative stereochemistry is consistent with the trans configuration.

Verify the stereochemistry: Double-check that the drawings correctly represent the cis and trans isomers by confirming the relative positions of the substituents on the ring. Use wedge and dash bonds to indicate the 3D orientation of the substituents if needed.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Cis-Trans Isomerism

Cis-trans isomerism, also known as geometric isomerism, occurs in compounds with restricted rotation around a double bond or a ring structure. In this type of isomerism, the spatial arrangement of substituents differs, leading to distinct isomers. 'Cis' refers to substituents on the same side, while 'trans' indicates they are on opposite sides, affecting the compound's physical and chemical properties.

Cyclohexane Structure

Cyclohexane is a six-membered carbon ring that can adopt various conformations, primarily the chair and boat forms. The chair conformation is the most stable due to minimized steric strain and torsional strain. Understanding the cyclohexane structure is crucial for visualizing how substituents can be positioned in either a cis or trans arrangement relative to each other.

Substituent Positioning

In the context of cyclohexane derivatives, the positioning of substituents (like bromine and chlorine in 1-bromo-4-chlorocyclohexane) is essential for determining the isomer type. When substituents are on the same side of the ring, the compound is a cis isomer; when they are on opposite sides, it is a trans isomer. This positioning influences the molecule's reactivity and interactions with other substances.

Watch next

Master How to name different types of double bonds or rings with a bite sized video explanation from Johnny

Start learning