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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6:04 minutes

Problem 16e,f

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

Verified step by step guidance

Step 1: Begin with the compound 3-ethyl-2,4-dimethylhexane. Identify the parent chain, which is hexane, indicating a six-carbon chain. Number the chain from one end to the other to ensure the substituents get the lowest possible numbers.

Step 2: Add the substituents to the hexane chain. At carbon 3, attach an ethyl group (C₂H₅). At carbons 2 and 4, attach methyl groups (CH₃). Ensure the structure reflects the correct positions of these groups.

Step 3: Count all the carbon and hydrogen atoms in the structure to determine the molecular formula for 3-ethyl-2,4-dimethylhexane. Combine the number of carbons and hydrogens from the parent chain and substituents.

Step 4: For 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane, start with the cyclohexane ring, which consists of six carbon atoms arranged in a ring. Number the ring to give the substituents the lowest possible numbers.

Step 5: Attach the substituents to the cyclohexane ring. At carbon 1, add two ethyl groups (C₂H₅). At carbon 4, attach a 3,3-dimethylbutyl group, which is a butyl chain with two methyl groups at the third carbon. Count all the carbon and hydrogen atoms to determine the molecular formula.

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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 of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry. It provides a standardized way to name compounds based on their structure, ensuring clarity and consistency. Understanding IUPAC rules is essential for interpreting and constructing chemical names, such as identifying the longest carbon chain and the position of substituents.

Structural Isomers

Structural isomers are compounds with the same molecular formula but different structural arrangements of atoms. This concept is crucial for drawing the correct structure of a compound, as different arrangements can lead to different chemical properties. Recognizing structural isomers involves understanding how atoms can be connected differently while maintaining the same overall formula.

Cycloalkanes

Cycloalkanes are a type of hydrocarbon with carbon atoms arranged in a ring structure. They differ from alkanes, which have linear or branched chains. Understanding cycloalkanes involves recognizing the ring structure and how substituents are attached to the ring, which affects the compound's chemical behavior and naming. Cyclohexane, for example, is a common cycloalkane with six carbon atoms forming a ring.

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Related Practice

Textbook Question

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

(e)

(f)

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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

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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

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Textbook Question

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

a. 1-ethyl-3-methylcycloheptane

b. isobutylcyclohexane