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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1:18 minutes

Problem 71b

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

Verified step by step guidance

Step 1: Begin by drawing the structure of the compound based on the incorrect name '1,5-dimethylcyclohexane'. Cyclohexane is a six-membered ring, and the name suggests two methyl groups attached at positions 1 and 5.

Step 2: Analyze the structure you have drawn. In cyclohexane, positions 1 and 5 are not adjacent but opposite to each other on the ring. Verify if the numbering follows the lowest locant rule for substituents.

Step 3: Apply the IUPAC nomenclature rules. Check if the numbering of the substituents can be adjusted to provide the lowest possible locants. For example, if the methyl groups are opposite each other, the numbering should start at one substituent and proceed around the ring to minimize the locant numbers.

Step 4: Rename the compound based on the corrected numbering. If the methyl groups are opposite each other, the correct name would likely be '1,4-dimethylcyclohexane' because positions 1 and 4 provide the lowest locants for the substituents.

Step 5: Confirm the corrected name by ensuring it adheres to all IUPAC rules, including the lowest locant rule and proper identification of the parent chain or ring structure.

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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.

Cycloalkanes

Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. The naming of cycloalkanes involves identifying the number of carbon atoms in the ring and any substituents attached to it. Recognizing the structure of cycloalkanes is crucial for correcting names and ensuring proper representation of the compound.

Substituent Positioning

In organic chemistry, substituents are atoms or groups of atoms that replace hydrogen atoms in a hydrocarbon. The position of these substituents on the main carbon chain or ring is indicated by numbers in the compound's name. Correctly identifying and numbering the positions of substituents is vital for accurate nomenclature and for avoiding ambiguity in compound names.

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Textbook Question

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed.

k. 2-methyl-2-isopropylheptane

Textbook Question

Draw a condensed structure and a skeletal structure for each of the following:

g. 4-(1,1-dimethylethyl)heptane

Textbook Question

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

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

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

(•••) 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

Textbook Question

What is each compound's systematic name?

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