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Chapter 13: Problem 33

Which of the following in each pair is likely to be more soluble in hexane, \(\mathrm{C}_{6} \mathrm{H}_{14}:\) (a) \(\mathrm{CCl}_{4}\) or \(\mathrm{CaCl}_{2}\), (b) benzene \(\left(\mathrm{C}_{6} \mathrm{H}_{6}\right)\) or glycerol, $\mathrm{CH}_{2}(\mathrm{OH}) \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OH},\( (c) octanoic acid, \)\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH},$ or acetic acid, \(\mathrm{CH}_{3} \mathrm{COOH}\) ? Explain your answer in each case.

Short Answer

Expert verified
The compounds more soluble in hexane are: (a) \(\mathrm{CCl}_4\), (b) benzene, and (c) octanoic acid. This is because hexane is a nonpolar solvent, and these compounds are overall less polar than their counterparts in each pair, following the principle "like dissolves like".

Step by step solution

01

Pair (a): \(\mathrm{CCl}_4\) or \(\mathrm{CaCl}_2\)

In this pair, we have \(\mathrm{CCl}_4\) (carbon tetrachloride), which is a nonpolar molecule, and \(\mathrm{CaCl}_2\) (calcium chloride), which is an ionic compound and thus highly polar. Based on the principle "like dissolves like", the more soluble compound in hexane is the nonpolar \(\mathrm{CCl}_4\).
02

Pair (b): Benzene or Glycerol

In this pair, we have benzene (\(\mathrm{C}_6\mathrm{H}_6\)), which is a nonpolar aromatic compound, and glycerol (\(\mathrm{CH}_2(\mathrm{OH}) \mathrm{CH}(\mathrm{OH})\mathrm{CH}_2 \mathrm{OH}\)), which is a polar molecule due to the presence of multiple hydroxyl groups. Based on the principle "like dissolves like", the more soluble compound in hexane is the nonpolar benzene.
03

Pair (c): Octanoic Acid or Acetic Acid

In this pair, we have octanoic acid (\(\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{COOH}\)), a linear nonpolar hydrocarbon chain with a polar carboxylic acid group at the end, and acetic acid (\(\mathrm{CH}_3\mathrm{COOH}\)), a smaller molecule that also has a polar carboxylic acid group. Although both molecules have polar carboxylic acid groups, the longer nonpolar hydrocarbon chain in octanoic acid makes it overall less polar than acetic acid. Therefore, octanoic acid is more likely to dissolve in hexane than acetic acid, based on the principle "like dissolves like".

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Most popular questions from this chapter

A solution contains \(0.50 \mathrm{~mol} \mathrm{H}_{2} \mathrm{O}\) and an unknown number of moles of sodium chloride. The vapor pressure of the solution at \(29^{\circ} \mathrm{C}\) is \(3.85 \mathrm{kPa}\). The vapor pressure of pure water at this temperature is \(4.05 \mathrm{kPa}\). Calculate the number of grams of sodium chloride in the solution. (Hint: Remember that sodium chloride is a strong electrolyte.)

You take a sample of water that is at room temperature and in contact with air and put it under a vacuum. Right away, you see bubbles leave the water, but after a little while, the bubbles stop. As you keep applying the vacuum, more bubbles appear. A friend tells you that the first bubbles were water vapor, and the low pressure had reduced the boiling point of water, causing the water to boil. Another friend tells you that the first bubbles were gas molecules from the air (oxygen, nitrogen, and so forth) that were dissolved in the water. Which friend is mostly likely to be correct? What, then, is responsible for the second batch of bubbles? [Section 13.4]

Indicate whether each statement is true or false: (a) If you compare the solubility of a gas in water at two different temperatures, you find the gas is more soluble at the lower temperature. (b) The solubility of most ionic solids in water decreases as the temperature of the solution increases. (c) The solubility of most gases in water decreases as the temperature increases because water is breaking its hydrogen bonding to the gas molecules as the temperature is raised. (d) Some ionic solids become less soluble in water as the temperature is raised.

Consider two ionic solids, both composed of singly charged ions, that have different lattice energies. (a) Will the solids have the same solubility in water? (b) If not, which solid will be more soluble in water, the one with the larger lattice energy or the one with the smaller lattice energy? Assume that solute-solvent interactions are the same for both solids. [Section 13.1]

Benzene \(\left(\mathrm{C}_{6} \mathrm{H}_{6}\right)\) boils at $80.1^{\circ} \mathrm{C}\( and has a density of \)0.876 \mathrm{~g} / \mathrm{mL} .$ (a) When \(0.100 \mathrm{~mol}\) of a nondissociating solute is dissolved in $500 \mathrm{~mL}\( of \)\mathrm{C}_{6} \mathrm{H}_{6}$, the solution boils at \(79.52^{\circ} \mathrm{C}\). What is the molal boiling-point-elevation constant for \(\mathrm{C}_{6} \mathrm{H}_{6} ?\) (b) When \(10.0 \mathrm{~g}\) of a nondissociating unknown is dissolved in \(500 \mathrm{~mL}\) of $\mathrm{C}_{6} \mathrm{H}_{6}\(, the solution boils at \)79.23^{\circ} \mathrm{C}$. What is the molar mass of the unknown?
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