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

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5:56 minutes

Problem 34c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the structures provided in the image. Each structure represents a cyclopentane ring with substituents attached. Pay attention to the positions of the substituents (CH₃ and H) and their stereochemistry (wedge and dash bonds indicating 3D orientation).

Step 2: Compare the substituent positions and stereochemistry of each structure. Two compounds are identical if their substituents are in the same positions and have the same stereochemical configuration. If the substituents differ in position or stereochemistry, they represent different compounds.

Step 3: For the first structure, note the positions of the two CH₃ groups and their stereochemistry (one is on a wedge bond and the other on a dash bond). Compare this with the second structure to determine if they are identical or different.

Step 4: Examine the third structure. It has two CH₃ groups attached to the cyclopentane ring, but their positions and stereochemistry differ from the first two structures. Determine if this structure is identical to any of the others or represents a different compound.

Step 5: Analyze the fourth and fifth structures. Compare their substituent positions and stereochemistry with the previous structures. Determine which ones are identical and which ones are different compounds based on the analysis.

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Key Concepts

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

Isomerism

Isomerism refers to the phenomenon where two or more compounds have the same molecular formula but different structural arrangements or spatial orientations. This can lead to different physical and chemical properties. In organic chemistry, isomers can be classified into structural isomers, which differ in the connectivity of atoms, and stereoisomers, which differ in the spatial arrangement of atoms.

Cis-Trans Isomerism

Cis-trans isomerism is a type of stereoisomerism that occurs in compounds with restricted rotation around a double bond or within a ring structure. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. This difference in arrangement can significantly affect the physical properties and reactivity of the compounds.

Cycloalkanes

Cycloalkanes are a class of hydrocarbons that contain carbon atoms arranged in a ring structure. They can exhibit isomerism due to the different ways in which substituents can be arranged around the ring. Understanding the structure of cycloalkanes is crucial for identifying whether different representations correspond to the same compound or different ones, particularly in the context of cis-trans isomerism.

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