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Ch.11 - Liquids and Intermolecular Forces
Chapter 11, Problem 28d

Based on the type or types of intermolecular forces, predict the substance in each pair that has the higher boiling point: (d) phosgene (Cl2CO) or formaldehyde (H2CO)

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Identify the types of intermolecular forces present in each molecule. Phosgene (Cl<sub>2</sub>CO) and formaldehyde (H<sub>2</sub>CO) both exhibit dipole-dipole interactions due to their polar nature.
Consider the possibility of hydrogen bonding in each molecule. Formaldehyde (H<sub>2</sub>CO) has hydrogen atoms bonded to oxygen, which can participate in hydrogen bonding.
Assess the molecular weights and size of the molecules. Phosgene (Cl<sub>2</sub>CO) is heavier and larger compared to formaldehyde (H<sub>2</sub>CO), which can influence the strength of the dipole-dipole interactions.
Compare the overall strength of the intermolecular forces in each molecule. The presence of hydrogen bonding in formaldehyde (H<sub>2</sub>CO) generally leads to stronger intermolecular forces compared to just dipole-dipole interactions in phosgene (Cl<sub>2</sub>CO).
Predict the substance with the higher boiling point based on the stronger intermolecular forces. In this case, formaldehyde (H<sub>2</sub>CO) is likely to have a higher boiling point due to the presence of hydrogen bonding.

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Key Concepts

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

Intermolecular Forces

Intermolecular forces are the attractive forces between molecules that influence physical properties such as boiling and melting points. The main types include hydrogen bonding, dipole-dipole interactions, and London dispersion forces. Understanding these forces helps predict how substances behave under different conditions, particularly in terms of phase changes.
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Boiling Point

The boiling point of a substance is the temperature at which its vapor pressure equals the external pressure, allowing it to transition from liquid to gas. Substances with stronger intermolecular forces typically have higher boiling points because more energy is required to overcome these attractions. Thus, comparing boiling points can provide insights into the nature of the intermolecular forces present.
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Polarity and Molecular Structure

Polarity refers to the distribution of electrical charge over the atoms in a molecule, which affects its intermolecular interactions. Molecules like formaldehyde (H2CO) are polar due to the presence of a carbonyl group, leading to dipole-dipole interactions. In contrast, phosgene (Cl2CO) has a more complex structure that can influence its overall polarity and the types of intermolecular forces it exhibits.
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Related Practice
Textbook Question

(b) Which of the following molecules can form hydrogen bonds with other molecules of the same kind: CH3F, CH3NH2, CH3OH, CH3Br?

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Open Question
Rationalize the difference in boiling points in each pair: (a) HF (20 °C) and HCl (-85 °C) (b) CHCl3 (61 °C) and CHBr3 (150 °C) (c) Br2 (59 °C) and ICl (97 °C)
Textbook Question

Ethylene glycol (HOCH2CH2OH), the major substance in antifreeze, has a normal boiling point of 198 °C. By comparison, ethyl alcohol (CH3CH2OH) boils at 78 °C at atmospheric pressure. Ethylene glycol dimethyl ether (CH3OCH2CH2OCH3) has a normal boiling point of 83 °C, and ethyl methyl ether (CH3CH2OCH3) has a nomral boiling point of 11 °C. (a) Explain why replacement of a hydrogen on the oxygen by a CH3 group generally results in a lower boiling point.

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Open Question
Look up and compare the normal boiling points and normal melting points of H2O and H2S. Based on these physical properties, which substance has stronger intermolecular forces? What kinds of intermolecular forces exist for each molecule?
Textbook Question

A number of salts containing the tetrahedral polyatomic anion, BF4-, are ionic liquids, whereas salts containing the somewhat larger tetrahedral ion SO42- do not form ionic liquids. Explain this observation.

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Textbook Question

The generic structural formula for a 1-alkyl-3-methylimid- azolium cation is where R is a -CH2(CH2)nCH3 alkyl group. The melting points of the salts that form between 1-alkyl-3-methylimidazolium cation and the PF6- anion are as follows: R = CH2CH3 (m.p. = 60 °C), R = CH2CH2CH3 (m.p. = 40 °C), r = CH2CH2CH2CH3 (m.p. = 10 °C), and R = CH2CH2CH2CH2CH2CH3 (m.p. = -61 °C). Why does the melting point decrease as the length of alkyl group increases?

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