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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5:12 minutes

Problem 31a-d

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?
a. (CH₃CH₂)₂NH
b. (CH₃CH₂)₃N
c. CH₃CH₂CH₂OH
d. (CH₃CH₂CH₂)₂OH

Verified step by step guidance

Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds occur when hydrogen is covalently bonded to a highly electronegative atom like nitrogen, oxygen, or fluorine, allowing for interaction with lone pairs on these atoms in other molecules.

Step 2: Analyze each compound to determine if it can form hydrogen bonds. Look for the presence of N-H or O-H bonds, as these are indicative of hydrogen bonding capability.

Step 3: For compound (a) \((CH_3CH_2)_2NH\), identify the N-H bond. This bond allows the compound to form hydrogen bonds both internally and with water, due to the lone pairs on nitrogen.

Step 4: For compound (b) \((CH_3CH_2)_3N\), note the absence of N-H bonds. This compound cannot form hydrogen bonds internally but can interact with water through lone pairs on nitrogen, though less effectively.

Step 5: For compounds (c) \(CH_3CH_2CH_2OH\) and (d) \((CH_3CH_2CH_2)_2OH\), identify the O-H bonds. These compounds can form hydrogen bonds both internally and with water, enhancing their solubility in water due to the polar nature of the O-H group.

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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 occurs when a hydrogen atom is covalently bonded to a highly electronegative atom, such as nitrogen, oxygen, or fluorine, allowing it to interact with lone pairs on other electronegative atoms. This interaction is crucial for determining the solubility and boiling points of compounds.

Solubility in Water

Solubility in water is influenced by a compound's ability to form hydrogen bonds with water molecules. Polar compounds with functional groups like -OH or -NH are more likely to dissolve in water due to their ability to interact with water's polar nature, enhancing solubility.

Functional Groups

Functional groups such as alcohols (-OH) and amines (-NH) are key in determining a compound's chemical behavior, including hydrogen bonding and solubility. Alcohols can form hydrogen bonds due to the presence of an -OH group, while amines can do so with an -NH group, affecting their interaction with water.

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Related Practice

Textbook Question

Which has

a. the higher boiling point: 1-bromopentane or 1-bromohexane?

b. the higher boiling point: pentyl chloride or isopentyl chloride?

Textbook Question

In Table 7.2, what is the smallest alkane, the smallest terminal alkene, and the smallest terminal alkyne that are liquids at room temperature, which is generally taken to be 20 °C to 25 °C?

Textbook Question

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

c. N,N-Dimethylformamide has a boiling point of 150 °C, and N-methylacetamide has a boiling point of 206 °C, for a difference of 56 °C. Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

Textbook Question

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

(d) HOCH₂—(CH₂)₄—CH₂OH or (CH₃)₃CCH(OH)CH₃

(e) (CH₃CH₂CH₂)₂NH or (CH₃CH₂)₃N

(f)

Textbook Question

Contrary to expectation, the addition of more fluorines to ethane lowers the boiling point. Explain this phenomenon.

Textbook Question

In each pair, choose the compound you would expect to have the highest boiling/melting point.

(b)

Multiple Choice

Which of these phenomena result from hydrogen bonding?

Multiple Choice

What type of intermolecular force is likely to occur between two water molecules or strands of DNA?

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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?a. (CH3CH2)2NHb. (CH3CH2)3Nc. CH3CH2CH2OHd. (CH3CH2CH2)2OH

Key Concepts

Hydrogen Bonding

Solubility in Water

Functional Groups

Watch next

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?
a. (CH₃CH₂)₂NH
b. (CH₃CH₂)₃N
c. CH₃CH₂CH₂OH
d. (CH₃CH₂CH₂)₂OH