BCH 1100 1.

Answers for Tutorial (MCWC)

Dichlorobenzene, C6H4Cl2 exists in 3 forms (isomers) called ortho, meta and para:
Cl Cl Cl Cl Which of these isomers would have a non-zero dipole moment ?
ortho meta para

Cl

Cl

Ans. Ortho- and meta-dichlorobenzenes have non-opposing CCl bonds and therefore nonzero dipole moments.

2.

n-Propyl alcohol (CH3CH2CH2OH) and isopropyl alcohol [(CH3)2CHOH] are isomers. Identify the types of intermolecular forces present in these alcohols, and predict which isomer has the higher boiling point.

Ans. (DRAW THE MOLECULES IN PAIRS!) Both molecules experience hydrogen bonding through their OH groups and dispersion forces between hydrocarbon chains. The most important difference is that the OH group in isopropyl alcohol is more crowded and its position makes it slightly more difficult for other molecules to approach (due to repulsion), which decreases the extent of hydrogen bonding. Also, isopropyl alcohol is less rod like (therefore less surface area and less contact between molecules) than n-propyl alcohol, so dispersion force are weaker. So the boiling point is lower for isopropyl (82 C) compared with n-propyl (97 C) alcohol because it has weaker hydrogen bonding and dispersion forces.

3.

Identify the types of intermolecular forces present in each of the following substances, and predict the compound in each pair that has the higher boiling point. Explain your answers.

Ans. (a) C6H14: dispersion. C8H18: dispersion. C8H18 has higher boiling point due to greater molar mass leading to slightly stronger dispersion forces. Ans. (b) C3H8: dispersion. CH3OCH3: dipole-dipole and dispersion. Although molar masses are similar, CH3OCH3 has higher boiling point due to stronger intermolecular forces. Ans. (c) HOOH: hydrogen bonding, dipole-dipole and dispersion. HSSH: dipole-dipole and dispersion. HOOH has higher boiling point due to the effects of hydrogen bonding. Ans. (d) CH3CH3: dispersion. NH2NH2: hydrogen bonding, dipole-dipole and dispersion. NH2NH2 has higher boiling point due much stronger intermolecular forces. 1

4.

Predict the trends in the following table of solubilities of a homologous series of linear alcohols in water and hexane. What types of intermolecular forces should be considered for this series of compounds and how do their relative importance change as the number of carbon atoms increase ?

Ans. Due to the presence of the OH group and alkyl chain in these alcohols, hydrogen bonding and (London) dispersion forces should be considered. For short-chain alcohols, the dominant interaction is hydrogen bonding. As the length of alkyl chain increases, dispersion forces between carbon chains become more important and eventually dominate. Therefore, as the number of carbon atoms increase, solubility in water decreases and solubility in hexane increases. 5. Two isomers of the planar compound 1,2-dichloroethene are shown below, along with their melting and boiling points:

H C Cl
Melting point (C) Boiling point (C) 80.5 60.3

H C Cl

H C Cl
49.8 47.5

Cl C H

cis isomer

trans isomer

(a) Predict which isomer has a higher boiling point. Ans. The cis isomer has a molecular dipole and will undergo dipole-dipole forces, while the trans isomer does not and is basically non-polar. So the boiling point of the cis isomer is higher. (b) Try to explain the difference in melting points. Ans. While boiling points are primarily a measure of the strength of intermolecular forces, they may not be the dominant factor for melting points, which are also influenced strongly by solid-state properties and crystal packing efficiency. Since the non-polar trans isomer, with weaker intermolecular forces, has the higher melting point, it must pack more efficiently so that more energy is required to melt the substance.