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

2. Molecular Representations

Intermolecular Forces

Organic Chemistry

2. Molecular Representations

Intermolecular Forces

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2:30 minutes

Problem 10a

Textbook Question

List each set of compounds in order of increasing boiling point.
a. hexane, octane, and decane

Verified step by step guidance

Understand that boiling point is influenced by molecular weight and intermolecular forces. In alkanes, as the molecular weight increases, the boiling point generally increases due to stronger van der Waals forces.

Identify the molecular formula for each compound: hexane (C₆H₁₄), octane (C₈H₁₈), and decane (C₁₀H₂₂).

Recognize that these compounds are all alkanes, which are nonpolar and primarily exhibit van der Waals forces. The longer the carbon chain, the greater the surface area for these forces, leading to a higher boiling point.

Compare the molecular weights: hexane has the lowest molecular weight, followed by octane, and then decane, which has the highest molecular weight.

Arrange the compounds in order of increasing boiling point based on their molecular weights: hexane < octane < decane.

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Key Concepts

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

Boiling Point

Boiling point is the temperature at which a substance transitions from a liquid to a gas. It is influenced by molecular weight, intermolecular forces, and molecular structure. In organic compounds, longer carbon chains typically result in higher boiling points due to increased van der Waals forces.

Intermolecular Forces

Intermolecular forces are the forces that hold molecules together, affecting properties like boiling point. In hydrocarbons, van der Waals forces (dispersion forces) are predominant. These forces increase with molecular size, leading to higher boiling points for larger molecules.

Molecular Size and Structure

Molecular size and structure significantly impact boiling points. In alkanes, as the number of carbon atoms increases, the molecular size grows, enhancing van der Waals forces. Thus, among hexane, octane, and decane, decane has the highest boiling point due to its larger size.

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Related Practice

Textbook Question

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(e)

(f)

Textbook Question

Draw the hydrogen bonding that takes place between

c. a molecule of dimethyl ether and two molecules of water.

d. two molecules of trimethylamine and a molecule of water.

Textbook Question

Diethyl ether and butan-1-ol are isomers, and they have similar solubilities in water. Their boiling points are very different, however. Explain why these two compounds have similar solubility properties but dramatically different boiling points.

Textbook Question

N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C.

b. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanol has a boiling point of 141 °C. These two isomers have a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boiling point difference than the two amine isomers.

Textbook Question

Rank the following compounds from highest boiling to lowest boiling:

Textbook Question

Explain the following:

a. 1-Hexanol has a higher boiling point than 3-hexanol.

Textbook Question

Explain why

c. H₂O (100 °C) has a higher boiling point than HF 120 °C2.

d. HF 120 °C2 has a higher boiling point than NH₃ (-33 °C).

Textbook Question

Which of the following compounds forms hydrogen bonds between its molecules?

1. CH₃CH₂OCH₂CH₂OH