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Ch.11 - Liquids & Phase Changes
Chapter 11, Problem 13

Arrange the following molecules from lowest to highest boiling point. (LO 8.9) (I) Molecular structures labeled A to D for boiling point comparison in chemistry.
(II)
(III)
(IV)
(a) I 6 II 6 III 6 IV (b) II 6 III 6 I 6 IV (c) IV 6 II 6 III 6 I (d) IV 6 I 6 II 6 III

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Key Concepts

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

Boiling Point and Intermolecular Forces

The boiling point of a substance is influenced by the strength of its intermolecular forces. Stronger forces, such as hydrogen bonding, dipole-dipole interactions, and London dispersion forces, lead to higher boiling points. Molecules with significant hydrogen bonding, like alcohols, typically have higher boiling points compared to non-polar molecules or those with weaker interactions.
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Molecular Structure and Polarity

The molecular structure, including the presence of functional groups and the overall shape, affects polarity. Polar molecules, which have an uneven distribution of charge, tend to have higher boiling points due to stronger dipole-dipole interactions. In contrast, non-polar molecules primarily exhibit London dispersion forces, which are generally weaker.
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Hydrogen Bonding

Hydrogen bonding is a specific type of strong dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen, nitrogen, or fluorine. This interaction significantly increases the boiling point of compounds containing -OH groups, as seen in alcohols, compared to hydrocarbons that lack such polar functional groups.
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Related Practice
Textbook Question
Consider a compound that has a melting point at 65 °C and a boiling point at 175 °C. Which of the following images represents a heating curve for the compound from 40 °C to 200 °C? (LO 11.5)
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Textbook Question
Which molecule has polar bonds but is nonpolar? (LO 8.6) (a) SF6 (b) SF2 (c) F2 (d) NF3
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Textbook Question
What types of intermolecular forces exist in a sample of acetone? (LO 8.8)

(a) Dispersion forces (b) Dispersion forces and dipole–dipole forces (c) Dipole–dipole forces (d) Dispersion forces, dipole–dipole forces, and hydrogen bonding
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Textbook Question
The DNA base thymine dissolves in water due to hydrogen bonding. Which of the following hydrogen bonds drawn between thymine and surrounding water molecules are valid? (LO 8.10) (a) I and II (b) I, II, IV (c) I, II, III (d) III and IV
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Textbook Question

Assume that you have a liquid in a cylinder equipped with a movable piston. There is no air in the cylinder, the volume of space above the liquid is 200 mL, and the equilibrium vapor pressure above the liquid is 28.0 mm Hg. What is the equilibrium pressure above the liquid when the volume of space is decreased from 200 mL to 100 mL at constant temperature?

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Textbook Question
A phase diagram for a substance that exhibits the liquid crystalline state is shown. (b) If the substance is at a temperature and pressure repre- sented by point 1 and the temperature is increased until the phase changes, what is the phase transition? Describe how the ordering of molecules changes, and propose a reason for the change.

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