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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5:25 minutes

Problem 19e

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)

Verified step by step guidance

Understand the structure of norbornane, which is bicyclo[2.2.1]heptane. It consists of a bicyclic system with seven carbon atoms.

Identify the types of carbon atoms present in norbornane. In this structure, there are bridgehead carbons and other carbons forming the rings.

Classify the hydrogen atoms based on the carbon atoms they are attached to. A primary hydrogen is attached to a primary carbon (a carbon bonded to only one other carbon).

Identify secondary hydrogens, which are attached to secondary carbons (carbons bonded to two other carbons).

Determine if there are any tertiary hydrogens, which would be attached to tertiary carbons (carbons bonded to three other carbons). In norbornane, check the connectivity of each carbon to classify the hydrogens correctly.

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Key Concepts

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

Hydrogen Atom Classification

In organic chemistry, hydrogen atoms are classified based on the carbon atom they are attached to. A primary (1°) hydrogen is attached to a carbon bonded to only one other carbon, a secondary (2°) hydrogen is attached to a carbon bonded to two other carbons, and a tertiary (3°) hydrogen is attached to a carbon bonded to three other carbons.

Norbornane Structure

Norbornane, also known as bicyclo[2.2.1]heptane, is a bicyclic compound consisting of a seven-membered ring with two bridgehead carbons. Understanding its structure is crucial for identifying the types of hydrogen atoms present, as the unique arrangement affects the connectivity of carbon atoms.

Bicyclic Compounds

Bicyclic compounds contain two interconnected rings, which can influence the classification of hydrogen atoms due to the specific arrangement of carbon atoms. In norbornane, the bicyclic nature results in bridgehead carbons and affects the degree of substitution of hydrogen atoms, making structural analysis essential.

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Related Practice

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(e) rule 3

Textbook Question

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(g) rule 4

Textbook Question

Give IUPAC names for the following compounds.

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

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

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

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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