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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6:20 minutes

Problem 37

Textbook Question

In which solvent would cyclohexane have the lowest solubility: 1-pentanol, diethyl ether, ethanol, or hexane?

Verified step by step guidance

Identify the polarity of cyclohexane. Cyclohexane is a nonpolar molecule because it consists only of carbon and hydrogen atoms arranged in a symmetrical ring structure, resulting in no significant dipole moment.

Recall the principle of 'like dissolves like,' which states that polar solvents dissolve polar solutes, and nonpolar solvents dissolve nonpolar solutes. This principle will guide us in determining solubility.

Analyze the polarity of each solvent: (1) 1-pentanol is a polar molecule due to its hydroxyl (-OH) group, (2) diethyl ether is slightly polar because of the oxygen atom, (3) ethanol is polar due to its hydroxyl (-OH) group, and (4) hexane is nonpolar because it is a hydrocarbon similar to cyclohexane.

Compare the polarity of cyclohexane with each solvent. Cyclohexane will have the lowest solubility in the most polar solvent because it is nonpolar and does not interact well with polar solvents.

Determine which solvent is the most polar among the options. Ethanol, with its small size and hydroxyl group, is the most polar solvent listed. Therefore, cyclohexane will have the lowest solubility in ethanol.

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Key Concepts

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

Polarity of Solvents

Solvents can be classified as polar or nonpolar based on their molecular structure and the distribution of electrical charge. Polar solvents, like ethanol, have significant dipole moments due to their electronegative atoms, while nonpolar solvents, such as cyclohexane and hexane, have even charge distribution. The principle 'like dissolves like' suggests that nonpolar solutes are more soluble in nonpolar solvents.

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. In the context of solubility, solvents capable of hydrogen bonding, such as 1-pentanol and ethanol, can interact more favorably with polar solutes, while nonpolar solutes like cyclohexane do not engage in hydrogen bonding, affecting their solubility.

Solubility Principles

Solubility is influenced by the nature of the solute and solvent, temperature, and pressure. For nonpolar solutes like cyclohexane, solubility is generally higher in nonpolar solvents. Therefore, when comparing the solubility of cyclohexane in the given solvents, it is expected to be least soluble in the most polar solvent, which in this case is ethanol.

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Related Practice

Textbook Question

Circle the member of each pair that is more soluble in water.

a. CH₃CH₂OCH₂CH₃ or CH₃CH₂CH₂CH₂CH₃

b. CH₃CH₂OCH₂CH₃ or CH₃CH₂CH₂OH

c. CH₃CH₂NHCH₃ or CH₃CH₂CH₂CH₃

d. CH₃CH₂OH or CH₃CH₂CH₂CH₂OH

Textbook Question

Predict which member of each pair is more soluble in water. Explain your prediction.

(e)

(f)

Textbook Question

Predict which member of each pair is more soluble in water. Explain your prediction.

(c)

(d)

Textbook Question

Methoxychlor is an insecticide that was intended to take DDT’s place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned—in 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?

Textbook Question

Rank the following molecules from least water soluble to most water soluble. Explain your reasoning.

(a) H₃C ― OH

Textbook Question

Predict which member of each group is most soluble in water, and explain the reasons for your predictions.

b. chlorocyclohexane, cyclohexanol, or cyclohexane-1,2-diol

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?

(b)

Textbook Question