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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2:54 minutes

Problem 66

Textbook Question

Draw a picture of the hydrogen bonding in methanol.

Verified step by step guidance

Understand the concept of hydrogen bonding: Hydrogen bonding occurs when a hydrogen atom covalently bonded to an electronegative atom (like oxygen or nitrogen) interacts with another electronegative atom. In methanol (CH₃OH), the oxygen atom is highly electronegative and can form hydrogen bonds with other molecules.

Identify the functional groups in methanol: Methanol consists of a hydroxyl group (-OH) attached to a methyl group (CH₃). The oxygen in the hydroxyl group has lone pairs of electrons, making it capable of forming hydrogen bonds.

Visualize the hydrogen bond donor and acceptor: The hydrogen atom in the hydroxyl group of methanol acts as the hydrogen bond donor, while the oxygen atom with its lone pairs acts as the hydrogen bond acceptor.

Draw the interaction between two methanol molecules: Represent one methanol molecule with its hydroxyl group (-OH) and show the hydrogen atom forming a hydrogen bond with the oxygen atom of another methanol molecule. Use dashed lines to indicate the hydrogen bond.

Ensure proper orientation: In the drawing, make sure the hydrogen bond is depicted between the hydrogen atom of one molecule and the lone pair of electrons on the oxygen atom of the other molecule. Label the partial charges (δ⁺ on hydrogen and δ⁻ on oxygen) to emphasize the polarity of the bond.

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Key Concepts

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

Hydrogen Bonding

Hydrogen bonding is a type of attractive interaction that occurs between a hydrogen atom covalently bonded to a highly electronegative atom (like oxygen or nitrogen) and another electronegative atom. In methanol (CH3OH), the hydrogen atom attached to the oxygen can form hydrogen bonds with the oxygen atoms of neighboring methanol molecules, leading to unique physical properties such as higher boiling points.

Molecular Structure of Methanol

Methanol is a simple alcohol with the chemical formula CH3OH. Its structure consists of a hydroxyl group (-OH) attached to a methyl group (CH3). The presence of the hydroxyl group is crucial for hydrogen bonding, as it provides a site for the hydrogen atom to interact with other electronegative atoms in nearby molecules.

Intermolecular Forces

Intermolecular forces are the forces of attraction or repulsion between neighboring particles (atoms, molecules, or ions). In the case of methanol, hydrogen bonds are a significant type of intermolecular force that affects its physical properties, such as solubility and boiling point. Understanding these forces is essential for predicting how methanol behaves in different environments.

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Textbook Question

Choose the molecule in each pair you'd expect to have the higher boiling point. Explain your reasoning.

(b)

Textbook Question

Ionic compounds like sodium acetate have a high melting point. Despite this, they are highly soluble in water. Why?

Textbook Question

Despite methylcyclohexane (98.2 amu) having a higher molecular weight than toluene (92.1 amu), toluene melts at a higher temperature. Why? [Think about how the molecules can interact with each other based on their shape.]

Textbook Question

Choose the molecule in each pair you'd expect to have the higher boiling point. Explain your reasoning.

(a) eicosane ( C₂₀H₄₂) vs pentadecane

Textbook Question

Which has

g. the higher boiling point: 1-bromopentane or 1-chloropentane?

Textbook Question

Which has

h. the higher boiling point: diethyl ether or butyl alcohol?

Textbook Question

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

c. 1-bromobutane and 1-chlorobutane

Textbook Question

For each pair of compounds, predict which compound has the higher boiling point. Check [TABLE 6-2] to see if your prediction was right; then explain why that compound has the higher boiling point.

b. isopropyl chloride and tert-butyl bromide

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