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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5:36 minutes

Problem 33

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.

Verified step by step guidance

Begin by understanding the concept of isomers. Isomers are compounds with the same molecular formula but different structural arrangements. Diethyl ether and butan-1-ol both have the molecular formula C4H10O, but their structures differ significantly.

Examine the solubility properties of both compounds. Solubility in water is influenced by the ability of a compound to form hydrogen bonds with water molecules. Both diethyl ether and butan-1-ol can form hydrogen bonds due to the presence of an oxygen atom, which explains their similar solubility.

Consider the structural differences between diethyl ether and butan-1-ol. Diethyl ether is an ether, with an oxygen atom bonded to two alkyl groups, while butan-1-ol is an alcohol, with an oxygen atom bonded to a hydrogen atom and an alkyl group. This structural difference impacts their boiling points.

Analyze the boiling point differences. The boiling point of a compound is influenced by intermolecular forces. Butan-1-ol can form strong hydrogen bonds due to the presence of the hydroxyl group (-OH), leading to a higher boiling point. Diethyl ether, lacking a hydroxyl group, primarily exhibits weaker van der Waals forces, resulting in a lower boiling point.

Conclude by summarizing that the similar solubility is due to the ability of both compounds to interact with water through hydrogen bonding, while the difference in boiling points is due to the presence of stronger hydrogen bonding in butan-1-ol compared to the weaker van der Waals forces in diethyl ether.

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Key Concepts

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

Isomerism

Isomers are compounds with the same molecular formula but different structural arrangements. Diethyl ether and butan-1-ol are isomers, meaning they have the same number of carbon, hydrogen, and oxygen atoms but differ in how these atoms are connected. This structural difference leads to variations in physical properties such as boiling points and solubility.

Hydrogen Bonding

Hydrogen bonding is a strong type of dipole-dipole interaction that occurs when hydrogen is bonded to electronegative atoms like oxygen. Butan-1-ol can form hydrogen bonds due to its hydroxyl group, which significantly increases its boiling point compared to diethyl ether, which lacks this capability. This difference in hydrogen bonding capacity explains the disparity in boiling points between the two compounds.

Solubility in Water

Solubility in water is influenced by the ability of a compound to interact with water molecules. Both diethyl ether and butan-1-ol have similar solubility because they can form interactions with water, albeit through different mechanisms. Diethyl ether can engage in dipole-dipole interactions, while butan-1-ol can form hydrogen bonds, allowing both to dissolve in water to a comparable extent.

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Related Practice

Textbook Question

Draw the hydrogen bonding that takes place between

a. two molecules of ethanol.

b. two molecules of propylamine.

Textbook Question

For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning.

a. (CH3)3C—C(CH₃)₃ or (CH₃)₂CH—CH₂CH₂—CH(CH₃)₂

b. CH₃(CH₂)₆CH₃ or CH₃(CH₂)₅CH₂OH

c. CH₃CH₂OCH₂CH₃ or CH₃CH₂CH₂CH₂OH

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

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

List each set of compounds in order of increasing boiling point.

a. hexane, octane, and decane

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.

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