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

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Carboxylic Acid Derivatives

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6:00 minutes

Problem 42c

Textbook Question

Peroxyacetic acid (bp = 105 °C) has a lower boiling point than acetic acid (bp = 118 °C), even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

Verified step by step guidance

Understand the concept of boiling point: The boiling point of a substance is the temperature at which its vapor pressure equals the atmospheric pressure, allowing it to transition from liquid to gas.

Consider the molecular structure: Acetic acid (CH₃COOH) and peroxyacetic acid (CH₃COOOH) have similar structures, but peroxyacetic acid contains an additional oxygen atom, forming a peroxide linkage.

Analyze intermolecular forces: Acetic acid can form strong hydrogen bonds due to the presence of the hydroxyl group (OH) and the carbonyl group (C=O), which contribute to its higher boiling point.

Evaluate the effect of the peroxide linkage: The peroxide linkage in peroxyacetic acid (O-O bond) is less effective at hydrogen bonding compared to the carbonyl group in acetic acid, resulting in weaker intermolecular forces.

Conclude the volatility: Due to weaker hydrogen bonding in peroxyacetic acid, it has a lower boiling point and is more volatile than acetic acid, despite having a higher molecular weight.

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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 strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen or nitrogen. Acetic acid can form more extensive hydrogen bonds due to its carboxylic acid group, which increases its boiling point compared to peroxyacetic acid, which has a less effective hydrogen bonding capability due to the presence of the peroxide group.

Molecular Structure

The molecular structure of a compound affects its physical properties, including boiling point. Peroxyacetic acid contains a peroxide linkage, which alters its ability to form hydrogen bonds compared to acetic acid. This structural difference results in weaker intermolecular forces in peroxyacetic acid, making it more volatile despite its higher molecular weight.

Intermolecular Forces

Intermolecular forces, such as hydrogen bonding, dipole-dipole interactions, and van der Waals forces, determine the boiling point of a substance. Acetic acid's stronger hydrogen bonding leads to higher boiling points, while peroxyacetic acid's weaker intermolecular forces due to its peroxide group result in increased volatility and a lower boiling point.

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