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

How To Determine Solubility

Organic Chemistry

2. Molecular Representations

How To Determine Solubility

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Problem 42a

Textbook Question

In each pair, (i) choose the compound that is most soluble in water. (ii) Within each pair, which is most soluble in nonpolar solvents?
(a)

Verified step by step guidance

Step 1: Analyze the functional groups in each compound. The first compound contains a hydroxyl group (-OH), which is polar and capable of forming hydrogen bonds with water. The second compound contains a chlorine atom (-Cl), which is less polar and cannot form hydrogen bonds as effectively as the hydroxyl group.

Step 2: Consider the solubility in water. Compounds with polar functional groups and the ability to form hydrogen bonds are generally more soluble in water. Therefore, the compound with the hydroxyl group (-OH) is expected to be more soluble in water.

Step 3: Consider the solubility in nonpolar solvents. Nonpolar solvents dissolve compounds that are less polar or nonpolar due to the principle 'like dissolves like.' The compound with the chlorine atom (-Cl) is less polar than the compound with the hydroxyl group (-OH), making it more soluble in nonpolar solvents.

Step 4: Summarize the reasoning for solubility in water and nonpolar solvents. The hydroxyl group increases water solubility due to hydrogen bonding, while the chlorine atom increases solubility in nonpolar solvents due to its lower polarity.

Step 5: Conclude the comparison. (i) The compound with the hydroxyl group (-OH) is most soluble in water. (ii) The compound with the chlorine atom (-Cl) is most soluble in nonpolar solvents.

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Key Concepts

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

Polarity

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules have a significant difference in electronegativity between their atoms, leading to partial positive and negative charges. This property affects solubility, as polar substances tend to dissolve well in polar solvents like water, while nonpolar substances dissolve better in nonpolar solvents.

Solubility Principles

Solubility is the ability of a substance to dissolve in a solvent, which is influenced by the nature of both the solute and the solvent. The principle 'like dissolves like' indicates that polar solutes are more soluble in polar solvents, while nonpolar solutes are more soluble in nonpolar solvents. Understanding these principles is crucial for predicting the solubility of different compounds.

Hydrogen Bonding

Hydrogen bonding is a strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen, nitrogen, or fluorine. This interaction significantly increases the solubility of compounds in water, as it allows for the formation of strong attractions between the solute and solvent molecules. Compounds capable of hydrogen bonding are typically more soluble in water.

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