Sample Exercise 11.

1 Identifying Substances That Can Form Hydrogen Bonds Solution Analyze

We are given the chemical formulas of four compounds and asked to predict whether they can
participate in hydrogen bonding. All the compounds contain H, but hydrogen bonding usually
occurs only when the hydrogen is covalently bonded to N, O, or F. Plan We analyze each formula
to see if it contains N, O, or F directly bonded to H. There also needs to be a nonbonding pair of
electrons on an electronegative atom (usually N, O, or F) in a nearby molecule, which can be
revealed by drawing the Lewis structure for the molecule. Solve The foregoing criteria eliminate
CH4 and H2S, which do not contain H bonded to N, O, or F. They also eliminate CH3F, whose
Lewis structure shows a central C atom surrounded by three H atoms and an F atom. (Carbon
always forms four bonds, whereas hydrogen and fluorine form one each.) Because the molecule
contains a C  F bond and not a H  F bond, it does not form hydrogen bonds. In H2NNH2 ,
however, we find N  H bonds, and the Lewis structure shows a nonbonding pair of electrons on
each N atom, telling us hydrogen bonds can exist between the molecules:

How do I rank the following compounds from lowest to highest boiling point: calcium carbonate,
methane, methanol (CH₄O), dimethyl ether (CH₃OCH₃)?
Chemistry Intermolecular Bonding Properties of Intermolecular Bonds
1 Answer

Ernest Z.
May 17, 2014
The order of boiling points is: CH4<CH3OCH3<CH4O<CaCO3
Explanation:
The order of strengths of intermolecular forces is: ion-ion > H-bonding > dipole-dipole > London
dispersion.
Compounds with stronger intermolecular forces have higher boiling points.
The strongest intermolecular force in each of the compounds is:
CaCO3 — ion-ion attractions.
CH4 — London dispersion forces
CH3OH — hydrogen bonding
CH3OCH3 — dipole-dipole attractions
CaCO3 is an ionic compound. It has the highest boiling points
Next comes methanol, CH4O or CH3OH.
Methanol has strong hydrogen bonds. It will have the next highest boiling point.
 employees.csbsju.edu
Dimethyl ether, CH3OCH3, is a polar molecule.
The C-O bond dipoles reinforce each other, so the molecule has a dipole moment.
Dipole-dipole forces are not as strong as hydrogen bonds, so dimethyl ether has a lower boiling point than
methanol does.
Finally, the C-H bonds in methane are nonpolar, so the molecule is also nonpolar.
It has only weak London dispersion forces,

abetterchemtext.com
CH4, has the lowest boiling point.
The order of boiling points is:
CH4<CH3OCH3<CH4O<CaCO3
Here's a good video on ordering compounds according to their intermolecular forces and boiling points.

ANSWER KEYS FOR PRACTICE WORKSHEETS

Intermolecular Forces Practice #1
1. Why are the intermolecular attractions in H2O (g) much weaker than the attractions in
H2O (l) or H2O (s)?

The particles in a gas are further apart, so there would not be as much attraction
between the particles

2. Consider the following: Br2, Ne, HCl, and N2.

a. Which of the above would have the largest dispersion forces? Why?
 Br2, because it has the largest mass.

b. Which of the above would have the largest dipole-dipole attractions? Why?

HCl, because it is the only molecule that is polar.

3. Which of the following molecules would exhibit hydrogen bonding: methane

(CH4), hydrazine (H2NNH2), methyl fluoride (CH3F), or hydrogen sulfide (H2S)?

Hydrazine would form hydrogen bonds.

Methyl fluoride does NOT form hydrogen bonds, because the H and F are not
bonded together when you draw the lewis structure.

4. List the type(s) of intermolecular forces that are present in each of the following
examples:

a. HBr dipole / LDF i. ClF3 dipole / dispersion

b. I2 LDF (dispersion) j. CH3COOH hydrogen

bonding / dipole / dispersion
c. CS2 LDF
d. H2Ohydrogen bonding /
dipole / LDF
e. CH2Cl2 dipole / LDF

f. C2H6 dispersion

g. NH3 hydrogen bonding /

dipole / dispersion
h. H2S dipole / dispersion
Intermolecular Forces Practice #2

1. Use your understanding of intermolecular forces to explain why:

a. ICl boils at 97 °C, while Br2 boils at 59 °C.

Br2 and ICl have similar masses (giving them similar dispersion forces). ICl
is more polar than Br2, resulting in dipole-dipole attractions. This gives ICl
stronger IMF and a higher boiling point than Br2.

b. CHCl3 boils at 61°C while CHBr3 boils at 150 °C.

CHBr3 has stronger IMF because it has greater dispersion forces than CHCl3
(higher mass = more dispersion)

2. For each of the following, select the molecule that you would expect to have
the higher boiling point and explain your reasoning:

a. HF or HCl

HF would have the higher boiling point because it forms hydrogen

bonds.

b. CH4 or C3H8

C3H8 would have the higher boiling point because it has a greater
mass / more dispersion.

3. List the substances BaCl2, H2, CO, HF, and Ne in order of increasing boiling
points and explain how you arrived at your answer.

BaCl2 > HF > CO > Ne > H2

Barium chloride is ionic (ionic bonding is stronger than any form of IMF),
HF is second because of its hydrogen bonding. CO > Ne >H2 because larger
mass = more dispersion = stronger attraction to overcome to reach boiling
point.

4. Which of the following would you expect to have the highest boiling point:
CH3CH3, CH3OH, or CH3CH2OH? Explain your answer.
CH3CH2OH. It will be greater than CH3CH3 because it has hydrogen
bonding. It will be greater than CH3OH because while they both have
hydrogen bonding, CH3CH2OH has a greater mass / more dispersion.
5. How can we use intermolecular forces to explain the fact that chlorine is a
gas at room temperature, while bromine is a liquid, and iodine is a solid?

In terms of mass, I2 > Br2 > Cl2. With the largest mass, iodine has stronger
dispersion attractions and stronger IMF. This makes it a solid at room
temperature. Bromine has weaker dispersion giving it less IMF and making
it a liquid. Chlorine is the lightest of the three and exhibits the weakest
attractions, making it a gas at room temperature.

6. Using your knowledge of intermolecular forces, explain why the boiling

point of NO (–151 °C) is higher than the boiling point of either O2 (–183 °C)
or N2 (–196°C)

All three have similar masses, but NO will be slightly polar. The dipole-
dipole attraction between NO molecules give it stronger IMF and a higher
boiling point.

7. Arrange the following in order of increasing melting point: RbF, CO2,

CH3OH, CH3Br. Explain how you arrived at your answer.

RbF > CH3OH > CH3Br > CO2

Rubidium fluoride has ionic bonds, giving it the highest melting point.
CH3OH has hydrogen bonding making it have the second strongest IMF /
second highest melting point. CH3Br > CO2 because it has a much higher
mass resulting in stronger dispersion forces between its molecules.

8. Dimethyl Ether (CH3OCH3) boils at -25 °C whereas Ethanol (CH3CH2OH)

boils at 79 °C. How can we account for this difference using intermolecular
forces?

When drawing the structures, the oxygen is connected to a hydrogen atom in

ethanol but not in dimethyl ether. This means that ethanol is capable of
forming hydrogen bonds, but dimethyl ether is not. Hydrogen bonding in
ethanol gives it much stronger intermolecular attraction and a much higher
boiling point as a result.

9. If you lived in Alaska, would it be better to keep methane (CH4), propane

(C3H8), or butane (C4H10) in an outdoor storage tank during the winter?
Explain your answer.
You would want to select the fuel that would remain a gas at the lowest
temperature (to avoid freezing when outside). The fuel that has the weakest
IMF would remain as a gas at the lowest temperatures because it has very
weak attractions to keep it’s molecules together. With its lower molar mass,
methane is the best choice because it has weaker disperions attractions than
either of the other two fuels.