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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2:33 minutes

Problem 35b

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

Verified step by step guidance

Step 1: Analyze the functional groups present in each compound. Chlorocyclohexane contains a chlorine atom, cyclohexanol contains one hydroxyl (-OH) group, and cyclohexane-1,2-diol contains two hydroxyl (-OH) groups.

Step 2: Understand the solubility trends in water. Water is a polar solvent, and compounds with polar functional groups (such as hydroxyl groups) are more likely to form hydrogen bonds with water, increasing their solubility.

Step 3: Compare the polarity of the functional groups. The hydroxyl group (-OH) is highly polar and can form hydrogen bonds with water, whereas the chlorine atom in chlorocyclohexane is less polar and cannot form hydrogen bonds as effectively.

Step 4: Consider the number of hydroxyl groups. Cyclohexane-1,2-diol has two hydroxyl groups, which can form more hydrogen bonds with water compared to cyclohexanol, which has only one hydroxyl group.

Step 5: Predict the solubility order based on the ability to form hydrogen bonds. Cyclohexane-1,2-diol is expected to be the most soluble in water due to its two hydroxyl groups, followed by cyclohexanol with one hydroxyl group, and finally chlorocyclohexane, which has the least polar functional group.

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Key Concepts

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

Polarity and Solubility

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Polar molecules, which have a significant difference in electronegativity between atoms, tend to dissolve well in polar solvents like water. Understanding the polarity of the compounds in question is crucial for predicting their solubility in water.

Hydrogen Bonding

Hydrogen bonding occurs when a hydrogen atom covalently bonded to a highly electronegative atom (like oxygen) interacts with another electronegative atom. Compounds capable of forming hydrogen bonds with water, such as alcohols, are generally more soluble in water. Recognizing which compounds can form these bonds is essential for solubility predictions.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In this case, the presence of hydroxyl (-OH) groups in cyclohexanol and cyclohexane-1,2-diol enhances their solubility in water compared to chlorocyclohexane, which lacks such groups. Identifying these functional groups helps in understanding the solubility behavior of the compounds.

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Related Practice

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

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

Textbook Question

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

(a) H₃C ― OH

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

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)

Textbook Question

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(a)

Textbook Question

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(d)

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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

Key Concepts

Polarity and Solubility

Hydrogen Bonding

Functional Groups

Watch next

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