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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6:17 minutes

Problem 5c,d

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.

Verified step by step guidance

Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds are a type of dipole-dipole interaction that occurs between a hydrogen atom bonded to a highly electronegative atom (such as oxygen, nitrogen, or fluorine) and another electronegative atom with a lone pair of electrons.

Step 2: For part c, identify the functional groups involved. Dimethyl ether has an oxygen atom with lone pairs, and water molecules have oxygen atoms with lone pairs and hydrogen atoms that can participate in hydrogen bonding.

Step 3: Draw the structure of dimethyl ether, which is \( \text{CH}_3\text{OCH}_3 \), and two water molecules \( \text{H}_2\text{O} \). Show the lone pairs on the oxygen atoms in both dimethyl ether and water molecules.

Step 4: Illustrate the hydrogen bonds. The oxygen atom in dimethyl ether can form hydrogen bonds with the hydrogen atoms of the water molecules. Draw dashed lines to represent these hydrogen bonds between the oxygen of dimethyl ether and the hydrogen atoms of water.

Step 5: For part d, identify the functional groups involved. Trimethylamine has a nitrogen atom with a lone pair, and water has oxygen atoms with lone pairs and hydrogen atoms. Draw the structure of trimethylamine \( \text{(CH}_3\text{)}_3\text{N} \) and a water molecule \( \text{H}_2\text{O} \). Show the hydrogen bonds between the nitrogen atom of trimethylamine and the hydrogen atoms of the water molecule.

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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 dipole-dipole interaction that occurs when a hydrogen atom, covalently bonded to a highly electronegative atom like oxygen or nitrogen, interacts with another electronegative atom. This bond is weaker than covalent bonds but stronger than van der Waals forces, playing a crucial role in determining the structure and properties of compounds.

Electronegativity

Electronegativity refers to the ability of an atom to attract shared electrons in a chemical bond. In the context of hydrogen bonding, atoms like oxygen and nitrogen have high electronegativity, which allows them to attract hydrogen atoms from nearby molecules, facilitating the formation of hydrogen bonds. Understanding electronegativity is essential for predicting molecular interactions.

Molecular Structure and Polarity

The molecular structure and polarity of a compound determine its ability to form hydrogen bonds. Dimethyl ether has a polar C-O bond, allowing it to interact with water molecules, while trimethylamine has a lone pair on nitrogen, enabling hydrogen bonding with water. Recognizing these structural features helps in visualizing and drawing hydrogen bonding interactions.

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Textbook Question

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

e. CH₃(CH₂)₃CH₃

f. CH₂=CH—CH₂CH₃

g. CH₃COCH₃

h. CH₃CH₂COOH

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

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

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:

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