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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Problem 71e

Textbook Question

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]
(e) 2,6-diethyl-1-methylcycloheptane

Verified step by step guidance

Draw the structure of the compound based on the given incorrect name, 2,6-diethyl-1-methylcycloheptane. Start with a cycloheptane ring (a seven-membered ring) as the parent structure. Add a methyl group at carbon 1 and ethyl groups at carbons 2 and 6.

Check the numbering of the substituents to ensure it follows the IUPAC rule of assigning the lowest possible locants to the substituents. In this case, the numbering may not be optimal, so re-evaluate the numbering.

Reassign the numbering of the cycloheptane ring to minimize the locants for the substituents. Start numbering from the carbon that gives the substituents the lowest possible set of numbers.

Rename the compound based on the corrected numbering. List the substituents in alphabetical order, and include their positions on the ring. Ensure the name follows the IUPAC format: [position]-[substituent][parent chain].

Verify the final name by cross-checking it with IUPAC rules, ensuring that the name is unambiguous and correctly represents the structure of the compound.

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Key Concepts

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

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds. It provides rules for naming based on the structure of the molecule, including the longest carbon chain, functional groups, and substituents. Understanding these rules is essential for correcting incorrect names and ensuring clarity in communication within the field of chemistry.

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. The naming of cycloalkanes involves identifying the ring size and the position of substituents. In the context of the question, recognizing the structure of cycloheptane and how substituents like ethyl and methyl groups are positioned is crucial for accurate nomenclature.

Substituent Positioning

Substituent positioning refers to the correct identification and numbering of substituents on a carbon chain or ring. In IUPAC nomenclature, substituents must be numbered to give the lowest possible numbers to the substituents. This concept is vital for renaming compounds accurately, as it affects the overall name and clarity of the compound's structure.

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Related Practice

Textbook Question

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

c. 2-methylbutane

d. cyclohexane

Textbook Question

Classify each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

e. norbornane (bicyclo[2.2.1]heptane)

Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

(d)

Textbook Question

Label each hydrogen atom in the following compounds as primary (1°), secondary (2°), or tertiary (3°).

(e)

(f)

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.

e. a (2,3-dimethylpentyl)cycloalkane

Textbook Question

(•••) Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.](e) 2,6-diethyl-1-methylcycloheptane

Textbook Question

Draw the structure and give the molecular formula for each of the following compounds.

a. 1-ethyl-3-methylcycloheptane

b. isobutylcyclohexane

Textbook Question

Draw the structure and give the molecular formula for each of the following compounds.

e. 3-ethyl-2,4-dimethylhexane

f. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane

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