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)

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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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