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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3:22 minutes

Problem 31

Textbook Question

Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Verified step by step guidance

Identify the structural features of each isomer that influence boiling point, such as molecular weight, branching, and functional groups.

Consider the impact of molecular weight: Generally, higher molecular weight leads to higher boiling points due to increased van der Waals forces.

Evaluate the degree of branching: More branching typically results in lower boiling points because it reduces the surface area available for intermolecular interactions.

Assess the presence and type of functional groups: Polar functional groups or those capable of hydrogen bonding can significantly increase boiling points.

Rank the isomers based on the analysis of these factors, starting with the isomer with the lowest boiling point and ending with the one with the highest boiling point.

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Key Concepts

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

Intermolecular Forces

Intermolecular forces, such as hydrogen bonding, dipole-dipole interactions, and London dispersion forces, play a crucial role in determining the boiling points of molecules. Stronger intermolecular forces result in higher boiling points because more energy is required to separate the molecules during the phase transition from liquid to gas.

Molecular Structure and Shape

The structure and shape of a molecule influence its boiling point by affecting how closely molecules can pack together. Linear or elongated molecules typically have higher boiling points than branched ones due to increased surface area, which enhances London dispersion forces. Understanding the geometry of isomers helps predict their boiling behavior.

Isomerism

Isomers are compounds with the same molecular formula but different structural arrangements. This structural variation can lead to differences in physical properties, such as boiling points. For example, cis-trans isomers may exhibit different boiling points due to variations in polarity and intermolecular interactions, making isomerism a key factor in ranking boiling points.

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For each pair of compounds, predict the one with a higher boiling point. Which compounds have zero dipole moments?

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Textbook Question

Rank the boiling points of the following molecules. Explain your ranking ( 1 = highest bp; 3 = lowest bp ).

Textbook Question

a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?

b. Which would you expect to have a higher boiling point?

Textbook Question

Imidazole boils at 257 °C, whereas N-methylimidazole boils at 199 °C. Explain the difference in boiling points.

Textbook Question

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(a)

Textbook Question

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(d)

Textbook Question

In each pair, which would you expect to have the higher melting point?

(b)

Textbook Question

Identify the hydrogen bond donors and hydrogen bond acceptors in the following molecules.

(b)

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