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

Naming Cycloalkanes

Organic Chemistry

4. Alkanes and Cycloalkanes

Naming Cycloalkanes

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6:51 minutes

Problem 35a

Textbook Question

Draw and name the five cycloalkane structures of formula C₅H₁₀. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.

Verified step by step guidance

Step 1: Understand the molecular formula C5H10. This formula corresponds to a cycloalkane because it follows the general formula for cycloalkanes, CnH2n, where n = 5. Cycloalkanes are saturated hydrocarbons with a ring structure.

Step 2: Draw the five possible cycloalkane structures with the formula C5H10. These include cyclopentane (a single five-membered ring) and four isomers with smaller rings and one or more substituents (e.g., methylcyclobutane, ethylcyclopropane, etc.).

Step 3: Analyze each structure to determine if it can exhibit geometric (cis-trans) isomerism. Geometric isomerism occurs when there are two substituents on a ring that can be positioned either on the same side (cis) or opposite sides (trans) of the ring plane. For example, methylcyclobutane can exhibit cis-trans isomerism if two substituents are present on different carbons of the ring.

Step 4: Draw the cis and trans stereoisomers for the structures that can exhibit geometric isomerism. Use wedge-and-dash notation to indicate the spatial arrangement of substituents. For example, in cis-methylcyclobutane, both substituents are on the same side of the ring, while in trans-methylcyclobutane, they are on opposite sides.

Step 5: Name each structure and its stereoisomers using IUPAC nomenclature. Ensure that the names reflect the correct positions and configurations of the substituents. For example, name the cis and trans isomers as 'cis-1,2-dimethylcyclobutane' and 'trans-1,2-dimethylcyclobutane,' respectively.

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Key Concepts

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

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. The general formula for cycloalkanes is CnH2n, where n is the number of carbon atoms. For C5H10, there are several possible cycloalkane structures, including cyclopentane and various substituted forms. Understanding the structure of cycloalkanes is essential for identifying their properties and potential isomerism.

Geometric Isomerism

Geometric isomerism, also known as cis-trans isomerism, occurs in compounds with restricted rotation around a bond, typically a double bond or a ring structure. In cycloalkanes, this isomerism arises when two substituents are attached to the same carbon atoms, leading to different spatial arrangements. The 'cis' isomer has substituents on the same side of the ring, while the 'trans' isomer has them on opposite sides, affecting the compound's physical and chemical properties.

Stereoisomers

Stereoisomers are compounds that have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of their atoms. This category includes geometric isomers as well as other types of isomers, such as enantiomers. In the context of cycloalkanes, recognizing the potential for stereoisomerism is crucial for understanding their reactivity and interactions, particularly in biological systems and synthetic applications.

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Related Practice

Textbook Question

What is each compound's systematic name?

Textbook Question

Draw all the isomers with molecular formula C₆H₁₂ that contain a cyclobutane ring.

Textbook Question

Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.

c. a cis-diethylcyclohexane

d. a trans-dihalocyclopentane

Textbook Question

Draw and name the six isomeric cyclopentanes of molecular formula C₇H₁₄. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.

Textbook Question

trans-1,2-Dimethylcyclobutane is more stable than cis-1,2-dimethylcyclobutane, but cis-1,3-dimethylcyclobutane is more stable than trans-1,3-dimethylcyclobutane. Use drawings to explain these observations.

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(a) rule 1

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(e) rule 3

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Draw and name the five cycloalkane structures of formula C5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.

Key Concepts

Cycloalkanes

Geometric Isomerism

Stereoisomers

Watch next

Draw and name the five cycloalkane structures of formula C₅H₁₀. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.