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

1. A Review of General Chemistry

Constitutional Isomers

Organic Chemistry

1. A Review of General Chemistry

Constitutional Isomers

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Problem 48e

Textbook Question

For each molecular formula, represent all constitutional isomers using line-angle drawings.
(e) C₆H₁₄

Verified step by step guidance

Understand the problem: The molecular formula C₆H₁₄ represents an alkane (a saturated hydrocarbon with only single bonds). Constitutional isomers are compounds with the same molecular formula but different connectivity of atoms. We need to draw all possible unique structures for C₆H₁₄ using line-angle drawings.

Step 1: Start with the straight-chain alkane (n-hexane). This is the simplest structure where all six carbon atoms are connected in a single continuous chain. Draw this structure using a line-angle representation.

Step 2: Create branched isomers by shortening the main chain and adding methyl (CH₃) or ethyl (C₂H₅) groups as substituents. For example, create a 5-carbon chain (pentane) and attach a methyl group to one of the carbons. Ensure that each structure is unique and follows the rules of valency (each carbon should have four bonds).

Step 3: Continue creating additional branched isomers by further shortening the main chain to 4 carbons (butane) and adding substituents in different positions. For example, attach two methyl groups to different carbons or the same carbon in the chain. Again, ensure that each structure is unique.

Step 4: Verify that all possible isomers have been drawn. Check for duplicates (structures that are identical when rotated or flipped) and confirm that each structure adheres to the molecular formula C₆H₁₄. You should end up with a total of 5 constitutional isomers for C₆H₁₄.

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Key Concepts

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

Constitutional Isomers

Constitutional isomers are compounds that have the same molecular formula but differ in the connectivity of their atoms. This means that the arrangement of atoms in the molecule varies, leading to different structural forms. Understanding constitutional isomers is crucial for recognizing how variations in structure can affect the properties and reactivity of organic compounds.

Line-Angle Drawings

Line-angle drawings, also known as skeletal structures, are a shorthand way of representing organic molecules. In these drawings, carbon atoms are represented by the ends and intersections of lines, while hydrogen atoms are often omitted for simplicity. This method allows chemists to visualize complex structures quickly and is essential for illustrating the various constitutional isomers of a given molecular formula.

Molecular Formula

A molecular formula indicates the number and types of atoms in a molecule, represented by chemical symbols and subscripts. For example, C₆H₁₄ indicates a molecule with six carbon atoms and fourteen hydrogen atoms. Understanding molecular formulas is fundamental in organic chemistry, as they provide the basis for identifying possible isomers and their structural variations.

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For each molecular formula, represent all constitutional isomers using line-angle drawings.(e) C6H14

Key Concepts

Constitutional Isomers

Line-Angle Drawings

Molecular Formula

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For each molecular formula, represent all constitutional isomers using line-angle drawings.
(e) C₆H₁₄