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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4:38 minutes

Problem 37c,d

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

Verified step by step guidance

Understand the problem: You are tasked with drawing and naming two structures for each description. The descriptions involve specific stereochemical configurations (cis and trans) and substituents on cycloalkanes. Let's break this down step by step.

Step for part (c): 'cis-diethylcyclohexane':

1. Recall that 'cis' means both substituents are on the same side of the cyclohexane ring (either both axial or both equatorial).

2. Draw the cyclohexane ring in its chair conformation. Place one ethyl group on a carbon atom in the ring. Then, place the second ethyl group on a different carbon atom such that both groups are on the same side of the ring (either both pointing up or both pointing down).

3. Repeat the process to create a second structure by placing the ethyl groups on different carbons of the ring, ensuring the 'cis' configuration is maintained.

4. Name the structures according to IUPAC nomenclature, ensuring the positions of the ethyl groups are correctly numbered to give the lowest possible locants.

Step for part (d): 'trans-dihalocyclopentane':

1. Recall that 'trans' means the two halogen substituents are on opposite sides of the cyclopentane ring (one pointing up and the other pointing down).

2. Draw the cyclopentane ring. Place one halogen atom (e.g., chlorine or bromine) on a carbon atom in the ring. Then, place the second halogen atom on a different carbon atom such that the two halogens are on opposite sides of the ring.

3. Repeat the process to create a second structure by placing the halogen atoms on different carbons of the ring, ensuring the 'trans' configuration is maintained.

4. Name the structures according to IUPAC nomenclature, specifying the positions of the halogen atoms and their identities (e.g., 1,2-dibromocyclopentane).

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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 bond, typically in cyclic structures or alkenes. In cis isomers, substituents are on the same side of the double bond or ring, while in trans isomers, they are on opposite sides. Understanding this concept is crucial for drawing and naming structures like cis-diethylcyclohexane and trans-dihalocyclopentane.

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. They can exhibit different conformations and isomeric forms based on the arrangement of substituents around the ring. Recognizing the properties and naming conventions of cycloalkanes is essential for accurately representing structures like diethylcyclohexane and dihalocyclopentane.

Substituent Naming and Positioning

In organic chemistry, substituents are groups attached to the main carbon chain or ring. Proper naming involves identifying the type and position of these substituents, which is critical for distinguishing between isomers. For example, in diethylcyclohexane, the positions of the ethyl groups must be specified to differentiate between cis and trans forms, as well as in dihalocyclopentane where the halogen substituents' positions affect the compound's name and properties.

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