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Ch.13 - Properties of Solutions
Brown - Chemistry: The Central Science 14th Edition
Brown14th EditionChemistry: The Central ScienceISBN: 9780134414232Not the one you use?Change textbook
All textbooksBrown 14th EditionCh.13 - Properties of SolutionsProblem 33
Chapter 13, Problem 33

Which of the following in each pair is likely to be more soluble in hexane, C6H14: (a) CCl4 or CaCl2, (b) benzene (C6H6) or glycerol, CH2(OH)CH(OH)CH2OH, (c) octanoic acid, CH3CH2CH2CH2CH2CH2CH2COOH, or acetic acid, CH3COOH? Explain your answer in each case.

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Identify the nature of hexane (C_6H_14) as a solvent. Hexane is a nonpolar solvent.
Consider the structure of benzene (C_6H_6). Benzene is a nonpolar molecule due to its symmetrical ring structure.
Consider the structure of glycerol (CH_2(OH)CH(OH)CH_2OH). Glycerol is a polar molecule because it contains multiple hydroxyl (OH) groups, which can form hydrogen bonds.
Apply the principle 'like dissolves like', which suggests that nonpolar solutes are more soluble in nonpolar solvents, and polar solutes are more soluble in polar solvents.
Compare the solubility of benzene and glycerol in hexane. Since hexane is nonpolar, benzene, being nonpolar, is likely to be more soluble in hexane than glycerol, which is polar.

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Key Concepts

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

Solubility and Like Dissolves Like

The principle of 'like dissolves like' states that polar solvents tend to dissolve polar solutes, while nonpolar solvents dissolve nonpolar solutes. Hexane (C6H14) is a nonpolar solvent, so it is more likely to dissolve substances that are also nonpolar, such as benzene (C6H6), rather than polar substances like glycerol, which contains multiple hydroxyl (OH) groups.
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Polarity of Molecules

Polarity refers to the distribution of electrical charge over the atoms in a molecule. Molecules with significant differences in electronegativity between atoms, such as those containing O-H bonds, are polar. Glycerol is polar due to its hydroxyl groups, while benzene is nonpolar due to its symmetrical structure and lack of electronegative atoms, affecting their solubility in hexane.
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Hydrogen Bonding

Hydrogen bonding is a strong type of dipole-dipole interaction that occurs between molecules containing hydrogen atoms bonded to highly electronegative atoms like oxygen or nitrogen. Glycerol can form hydrogen bonds due to its hydroxyl groups, making it less soluble in nonpolar solvents like hexane, while benzene, lacking such interactions, is more compatible with hexane.
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Related Practice
Textbook Question

Which of the following in each pair is likely to be more soluble in water: (a) cyclohexane (C6H12) or glucose (C6H12O6),

Textbook Question

Which of the following in each pair is likely to be more soluble in water: (c) HCl or ethyl chloride (CH3CH2Cl)? Explain in each case.

Textbook Question

Which of the following in each pair is likely to be more soluble in water: (b) propionic acid (CH3CH2COOH) or sodium propionate (CH3CH2COONa)

Textbook Question

Oil and water are immiscible. Which is the most likely reason? (a) Oil molecules are denser than water. (b) Oil molecules are composed mostly of carbon and hydrogen. (c) Oil molecules have higher molar masses than water. (d) Oil molecules have higher vapor pressures than water. (e) Oil molecules have higher boiling points than water.