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

IUPAC Naming

Organic Chemistry

4. Alkanes and Cycloalkanes

IUPAC Naming

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Problem 71

Textbook Question

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]
(a) 4-methylhexane

Verified step by step guidance

Draw the structure of the compound based on the incorrect name '4-methylhexane'. Start with a six-carbon chain (hexane) as the parent chain, and place a methyl group (-CH₃) on the fourth carbon.

Check the numbering of the parent chain to ensure it follows the IUPAC rule of assigning the lowest possible locants to substituents. In this case, the chain should be renumbered if necessary.

Identify the longest continuous carbon chain that includes the substituent. If the numbering can be adjusted to give a lower number to the substituent, do so.

Rename the compound based on the corrected numbering and structure. Ensure the substituent's position and name are correctly included in the IUPAC name.

Verify the final name by cross-checking it with IUPAC rules, ensuring that the name is unambiguous and follows the standard conventions.

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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 accurately identifying and renaming compounds, ensuring clear communication in the scientific community.

Structural Representation

Structural representation involves depicting the arrangement of atoms within a molecule, which is crucial for understanding its properties and reactivity. Drawing the compound corresponding to a name allows one to visualize the molecular structure, identify any discrepancies in the name, and apply IUPAC rules to correct it. This skill is fundamental in organic chemistry for both learning and practical applications.

Substituents and Parent Chains

In organic chemistry, substituents are groups of atoms that replace hydrogen atoms in a hydrocarbon chain, while the parent chain is the longest continuous chain of carbon atoms. Correctly identifying the parent chain and its substituents is vital for proper nomenclature. For example, in the name '4-methylhexane', recognizing the hexane as the parent chain and the methyl group as a substituent is key to renaming the compound accurately.