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 Bicyclic Compounds

Organic Chemistry

4. Alkanes and Cycloalkanes

Naming Bicyclic Compounds

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5:12 minutes

Problem 37f

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.
f. a bicyclononane

Verified step by step guidance

Step 1: Understand the term 'bicyclononane'. A bicyclononane is a bicyclic alkane with a total of nine carbon atoms. The prefix 'bicyclo-' indicates that the molecule contains two rings, and 'nonane' specifies that there are nine carbons in total.

Step 2: Recall the general formula for bicyclic alkanes: CnH2n-2. For bicyclononane, n = 9, so the molecular formula is C9H16. This accounts for the two rings and the absence of double bonds.

Step 3: Consider the possible ring structures. Bicyclononane can have different arrangements of the two rings, such as fused rings (sharing two or more carbons) or bridged rings (connected by a bridge of carbons). Ensure the total number of carbons in the structure equals nine.

Step 4: Draw two distinct structures that satisfy the description. For example, one structure could have a 6-membered ring fused with a 3-membered ring, while another could have a 5-membered ring bridged by a 4-membered ring. Label the carbons clearly to verify the total count.

Step 5: Name the two structures using IUPAC nomenclature rules for bicyclic alkanes. The name should include the prefix 'bicyclo-', followed by the number of carbons in each ring (excluding the bridgehead carbons), and the total number of carbons in the molecule. For example, 'bicyclo[4.3.0]nonane' or 'bicyclo[3.3.1]nonane'.

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Key Concepts

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

Alkane Structure

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, connected by single bonds. Their general formula is CnH2n+2, where 'n' is the number of carbon atoms. Understanding the basic structure of alkanes is crucial for identifying and drawing their various isomers, including cyclic and branched forms.

Bicyclic Compounds

Bicyclic compounds contain two interconnected rings in their structure. In the case of bicyclononane, it consists of nine carbon atoms arranged in two fused rings. Recognizing the characteristics of bicyclic structures is essential for drawing and naming compounds that fit specific descriptions, such as those involving multiple rings.

Isomerism

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements. In alkanes, isomers can vary in branching, ring formation, and connectivity. Understanding isomerism is vital for generating the correct structures that match the given description of bicyclononane, as multiple isomers can exist for a single molecular formula.

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