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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0:54 minutes

Problem 3

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.

Analyze the structure to determine if the parent chain is the longest continuous carbon chain. If a longer chain exists, identify it as the new parent chain.

Reassign the numbering of the parent chain to ensure that substituents (like the methyl group) receive the lowest possible locants (numbers).

Rename the compound according to IUPAC rules, ensuring the name reflects the correct parent chain and the proper position of the substituent(s).

Double-check the final name to confirm it adheres to IUPAC nomenclature rules, including proper alphabetical order for substituents if applicable.

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Key Concepts

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

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (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.

Alkane Structure

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. The general formula for alkanes is CnH2n+2, where 'n' is the number of carbon atoms. Recognizing the structure of alkanes helps in determining the correct naming and identifying any discrepancies in the provided names.

Substituent Naming

Substituents are groups of atoms that replace hydrogen atoms in a hydrocarbon chain. In IUPAC nomenclature, substituents are named based on their structure and position on the main carbon chain. Correctly identifying and naming substituents is crucial for renaming compounds accurately, especially when correcting errors in the original names.

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Related Practice

Textbook Question

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

(d) 4-butyldecane

Textbook Question

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

(b) 1,5-dimethylcyclohexane

Textbook Question

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.]

(k) rule 6

Textbook Question

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.]

(n) rule 7

Textbook Question

What is each compound's systematic name?

Textbook Question

Draw the structure for each of the following:

c. 4,4-diethyldecane