YISHUN INNOVA JUNIOR COLLEGE

2020 JC1 H1/H2 CHEMISTRY

TUTORIAL 3
INTERMOLECULAR FORCES

A Types of Intermolecular Forces

[Refer to lecture notes pages 3, 5, 11 12 and 14  15]

1. For each of the molecule below, describe the type of intermolecular forces present among its
molecules and explain how they arises. Use diagrams where appropriate to illustrate your answer.

 CO2,
 HCl, and
 NH3

 CO2
CO2 has a simple molecular structure and is non-polar. Instantaneous dipole – induced dipole
interactions are present between the CO2 molecules.

As electrons are always in random motion, at any point in time, there is an uneven distribution of
electrons in a molecule. This separation of charges creates an instantaneous dipole in the CO2
molecule. This instantaneous dipole can induce the formation of dipoles in the neighbouring
unpolarised CO2 molecules. As a result, a weak electrostatic forces of attraction, known as
instantaneous dipole – induced dipole interactions, forms between these two dipoles.

instantaneous induced
dipole dipole
e- d+ d- d+ d-
e-
e- e- e- e- e- e -
e- e-
e- e-
O C O O C O O C O e- O C O e-
e- e- e- e- e-
e- e- e-
e- e-

instantaneous dipole - induced dipole

interactions
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 HCl
HCl has a simple molecular structure and is polar. Permanent dipole – permanent dipole
interactions are present between the HCl molecules.

As there is an uneven distribution of electrons in polar bonds, permanent separation of charges

(dipole) is found within polar molecules.
The permanent dipoles in neighbouring polar molecules attract each other. The weak
electrostatic attraction forms between these dipoles, is known as permanent dipole – permanent
interactions.

permanent dipole permanent dipole

d+ d- d+ d-

H Cl H Cl

permanent dipole - permanent dipole

interactions

 NH3
NH3 has a simple molecular structure and is polar. Hydrogen bonds are present between the NH3
molecules.

N atom, being more electronegative than H atom, attracts the bonding electrons in the HN bond
closer to itself. As a result, it is more “electron rich” and gains a partial negative charge (). The H
atom, on the other hand, acquires a partial positive charge () and is almost a bare proton of the
hydrogen nucleus.

This electrostatic attraction between the H atom covalently bonded to N atom of one NH3 molecule
and the lone pair of electrons on N atom on the other NH3 molecule, is known as hydrogen bond.

d+ d+
H N H
d-

hydrogen bond H
d+

d+ d+
H N H
d-
H
d+

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B Instantaneous Dipole – Induced Dipole Interactions

[Refer to lecture notes pages 5  11]

2. Arrange the following compounds in increasing order of boiling points.

CH3CH(CH3)CH2CH3, CH3CH2CH2CH2CH3, CH3C(CH3)2CH3

2-methylbutane pentane 2,2-dimethylpropane

Explain your answer.

Increasing order of boiling point: CH3C(CH3)2CH3 < CH3CH(CH3)CH2CH3 < CH3CH2CH2CH2CH3,

All three compounds have simple molecular structure and are non-polar with instantaneous dipole
– induced dipole interactions (id-id) between the molecules.

Pentane is a straight-chain hydrocarbon while 2-methylbutane has one branching and 2,2-
dimethylpropane has 2 branching.

Hence, pentane is more linear than 2-methylbutane which is in turn more linear than 2,2-
dimethylpropane. Thus, pentane has the largest surface area for contact followed by 2-
methylbutane and 2,2-dimethylpropane has the smallest surface area for contact.

Pentane forms the most extensive id-id interactions between its molecules. Thus, requires the
most amount of energy to overcome the strongest id-id between pentane molecules. 2-
methylbutane forms the least extensive id-id interactions between its molecules and therefore
requires the least amount of energy to overcome them.

C Permanent Dipole – Permanent Dipole Interactions

[Refer to lecture notes pages 11  14]

3. PCl3 boils at 76 oC while SiCl4 boils at 58 oC.

Explain the difference in the boiling points in terms of structure and bonding.

PCl3 has a higher boiling point than SiCl4.

Both PCl3 and SiCl4 have simple molecular structure. PCl3 is polar with permanent dipole –
permanent dipole (pd-pd) interactions between the molecules. SiCl4 is non-polar and has
instantaneous dipole – induced dipole (id-id) interactions between the molecules.

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Since pd-pd interactions are stronger than id-id interactions, a greater amount of energy is thus
required to overcome the stronger pd-pd interactions between the PCl3 molecules compared to the
weaker id-id interactions between the SiCl4 molecules.

D Hydrogen Bonding
[Refer to lecture notes pages 14  26]

4 (a) N08/P2/Q1(a)(ii)
Ethane-1,2-diol, (CH2OH)2, is an important solvent.

H H

H O C C O H

H H

ethane-1,2-diol

Draw a diagram to show how hydrogen bonding occurs between two molecules of ethane-
1,2-diol.

H H
d-
hydrogen
O C C O H
bond

H d+ H H
H H

d-
H O C C O

H H H
d+

(b) Hydrazine, N2H4, has a boiling point of 114 oC, ammonia, NH3, has a boiling point of −30 oC
and hydrogen fluoride, HF has a boiling point of 20 oC.

Suggest reasons for the low boiling point of ammonia compared to hydrazine and hydrogen
fluoride.

All three compounds have simple molecular structure and are polar. All three compounds have
intermolecular hydrogen bonds among their molecules.

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Ammonia has a lower boiling point compared to hydrazine because it can form less extensive
hydrogen bonding (1 hydrogen bond per NH3 molecule) compared to hydrazine (2 hydrogen bonds
per N2H4 molecule). Hence a smaller amount of energy is required to overcome the less extensive
intermolecular hydrogen bonds between its molecules.

Ammonia has a lower boiling point than hydrogen fluoride because the dipole moment of the H-N
bond is smaller than that of H-F bond and thus the intermolecular hydrogen bonds formed between the
NH3 molecules are weaker than those formed between HF molecules. Hence, a smaller amount of
energy is required to overcome the weaker hydrogen bonds between NH3 molecules.

5 (a) 1,2-dihydroxybenzene has a boiling point of 518 K but its isomer 1,4-dihydroxybenzene has
a boiling point of 558 K.

OH
OH

OH

OH
1,2-dihydroxybenzene 1,4-dihydroxybenzene

Explain the difference in the boiling points of the two isomers.

Both isomers have simple molecular structure and are polar.

Due to the close proximity of the two OH in 1,2-dihydroxybenzene, they form intramolecular
hydrogen bonds. This limits the number of sites available for intermolecular hydrogen bonding.

In 1,4-dihydroxybenzene, the two OH groups are further from each other and form intermolecular
hydrogen bonds.

Hence, less energy is required to overcome the less extensive intermolecular hydrogen bonds
between the 1,2-dihydroxybenzene.

(b) The apparent Mr of propanoic acid, CH3CH2COOH is twice as expected when it exists as a
vapour than when dissolved in water.

Explain, with the aid of a diagram, the observation above.

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In the vapour phase, propanoic acid undergoes dimerisation through the formation of hydrogen
bonds between two propanoic acid molecules.
hydrogen bond

d+ d-
O H O

CH3CH2 C C CH2CH3

O H O
d- d+

hydrogen bond

However, when dissolved in water, each propanoic acid molecule is surrounded by water molecules,
and hence the propanoic acid molecules forms hydrogen bonds extensively with water molecules,
and does not undergo dimerisation.

E Integrated questions
6 The bond energies and the boiling points of the halogens show a trend as follows.

halogen bond energy / kJ mol−1 boiling point / C

Cl2 244 34

Br2 193 59
I2 151 184

Explain why the bond energy of the halogens decreases down the group but the reverse was
observed for the boiling point.

 The bond energy of the halogens decreases because the size of the valence orbital of the atoms
increases down the group from Cl to Br to I. This result in a less effective overlap between the
orbitals from Cl2 to Br2 to I2. Hence, the covalent bond formed between the atoms is weaker and has
lower bond energy.

 The halogens have simple molecular structure and are non-polar with instantaneous dipole –
induced dipole interactions (id-id) between the molecules. The size of the electron cloud
increases and thus the electron cloud becomes more polarisable from Cl2 to Br2 to I2. Hence, the
strength of the id-id interactions between the halogen molecules increases and more energy is
required to overcome the stronger id-id interactions from Cl2 to Br2 to I2.

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7 Data about HF, HCl, HBr and HI are given below.

HX bond energy / kJ mol1 boiling point / C

HF 562 +20
HCl 431 85
HBr 366 66
HI 297 34

(a) Explain why the boiling of HCl, HBr and HI increase down the Group.

(b) Suggest why the boiling point of HF is much higher than those of the others.

(a) The HX have simple molecular structure and are polar and have permanent dipole –
permanent dipole (pd-pd) interactions and instantaneous dipole – induced dipole (id-id)
interactions between the molecules.

The size of the electron cloud increases and thus the electron cloud becomes more
polarisable from HCl, HBr to HI. Hence, the strength of the id-id interactions between the HX
molecules increases down the Group and more energy is required to overcome the stronger id-
id interactions from HCl, HBr to HI.

(b) HF has a simple molecular structure and is polar. The intermolecular hydrogen bonds
between the HF molecules are stronger than the pd-pd interactions and id-id interactions
between the other HX molecules. Hence, a lot more energy is required to overcome the much
stronger intermolecular hydrogen bonds between the HF molecules.

8 N09/P3/Q4(b)
The molecules of ammonia and methane contain the same number of electrons, and have
approximately the same size and mass. Their boiling points differ widely, however.

compound boiling point / C

CH4 164
NH3 33

Suggest an explanation for the difference in boiling points.

Methane and ammonia have simple molecular structure.

Methane is a non-polar with weak intermolecular instantaneous-dipole induced  dipole

interactions. Ammonia is polar with intermolecular hydrogen bonds.

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A larger amount of energy is required to overcome the stronger hydrogen bonds in ammonia thus
its boiling point is higher.

F Physical Properties of Compounds based on Structures and Bonding

[Refer to Chemical Bonding lecture notes pages 4  24 and Intermolecular Forces lecture notes]

9 Explain why iodine solid is insoluble in water but dissolves in benzene, C6H6.

Iodine is insoluble in water because the energy evolved when the iodine molecules form
instantaneous dipole-induced dipole interactions with the water molecules is insufficient to
overcome the hydrogen bonds between water molecules and the instantaneous dipole-induced
dipole interactions between the iodine molecules.

The energy evolved when the iodine molecules form instantaneous dipole-induced dipole
interactions with the benzene molecules is sufficient to overcome the instantaneous dipole-
induced dipole interactions between the benzene molecules and the instantaneous dipole-
induced dipole interactions between the iodine molecules.

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10 N07/P3/Q4(b)(i)
The melting point of beryllium nitrate, Be(NO3)2, is 60 °C, whereas that of calcium nitrate is 561 °C.
Use these data to suggest the nature of the bonding in beryllium nitrate and in calcium nitrate,
explaining your answer.

Be(NO3)2 has a simple molecular structure since it has a low melting point. A small amount of energy
is required to overcome the instantaneous-dipole induced dipole between Be(NO3)2 molecules.

Ca(NO3)2 has a giant ionic structure since it has a high melting point. A large amount of energy is
required to overcome the strong electrostatic forces between Ca2+ and NO3− ions.

F Additional Questions

11. N17/P3/Q1(b)
The table gives the melting points, in oC, of the fluorides and chlorides of two elements in Period
3.

magnesium silicon
fluoride 1261 −90
chloride 714 −70

Explain, in terms of structure and bonding, the differences in melting point between

(a) MgCl2 and SiCl4,

(b) SiF4 and SiCl4,

(c) MgF2 and MgCl2.

(a) MgCl2 has a higher melting point than SiCl4.

MgCl2 has a giant ionic structure with strong electrostatic forces of attraction between Mg2+
and Cl− whereas SiCl4 has a simple molecular structure and is non-polar and has
instantaneous dipole – induced dipole (id-id) interactions between SiCl4 molecules. A
greater amount of energy is required to overcome the much stronger ionic bonds in MgCl2 than
the weak id-id interactions between SiCl4 molecules.

(b) SiF4 has a lower melting point than SiCl4.

Both SiF4 and SiCl4 have simple molecular structure and with weak id-id interactions between
the molecules since they are both non-polar. SiCl4 has a higher melting point than SiF4 as it has
a larger electron cloud and hence its electron cloud is more easily polarised and the strength
of id-id interactions between SiCl4 molecules are stronger. A greater amount of energy is required
JC1 H2 Chemistry Tutorial 3: Intermolecular Forces

to overcome the much stronger id-id interactions between SiCl4 molecules than that between
SiF4 molecules.

(c) MgF2 has a higher melting than MgCl2.

Both has giant ionic lattice structure with strong electrostatic forces of attraction between
Mg2+ and X−. While the size and charge of the Mg 2+ as well as the charge on the anions are the
same for both the ionic compounds, F− has a smaller ionic radius than Cl−. Hence more energy
is required to overcome the stronger ionic bonds between Mg2+ and F− than that between Mg2+
and Cl−.

12 Identify the type of intermolecular forces present among the molecules listed below.

 H2O  CHCl3  XeF4

 HBr  CH3CH2CH3  CH3COOH
 AlCl3  BF3  SO2
 CH3CH2OH  H2S  SO3 O

 CH3NH2  PF3  CH3CHO ( CH 3 C H )

 CCl4  CH3OCH3

molecule type of intermolecular forces

H2O hydrogen bonding
HBr pd-pd interactions
AlCl3 id-id interactions
CH3CH2OH hydrogen bonding
CH3NH2 hydrogen bonding
CCl4 id-id interactions
CHCl3 pd-pd interactions
CH3CH2CH3 id-id interactions
BF3 id-id interactions
H2S pd-pd interactions
PF3 pd-pd interactions
CH3OCH3 pd-pd interactions
XeF4 id-id interactions
CH3COOH hydrogen bonding
SO2 pd-pd interactions
SO3 id-id interactions
CH3CHO pd-pd interactions

13 For each of the substances listed below, complete the table by stating
 the type structure it has,
 the type of bond or interaction broken during the melting or boiling process (if the type of
interaction broken is intermolecular forces, specify the type of intermolecular forces).

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substance structure type of bond or interaction broken

SiO2 giant molecular covalent bonds between Si & O atoms
AlF3
AlCl3
AlBr3
graphite
Al2O3
Cu
NH4Cl
(CH3)3N
(CH3)2NH
diamond

substance structure type of bond or interaction broken

SiO2 giant molecular covalent bonds between Si & O atoms
AlF3 giant ionic lattice ionic bonds between Al3+ & F−
AlCl3 simple molecular id-id interactions between AlCl3 molecules
AlBr3 simple molecular id-id between AlBr3 molecules
graphite giant molecular covalent bonds between C atoms
Al2O3 giant ionic lattice ionic bonds between Al3+ & O2−
Cu giant metallic lattice metallic bonds between Cu2+ & delocalised electrons
NH4Cl giant ionic lattice ionic bonds between NH4+ & Cl−
(CH3)3N simple molecular pd-pd interactions between (CH3)3N molecules
(CH3)2NH simple molecular hydrogen bonds between (CH3)2NH molecules
diamond giant molecular covalent bonds between C atoms

14 Identify the type of intermolecular forces present among the molecules listed below.

 I2  SF6  HCN
 CH4  BF3  CH3CH(CH3)CH3
 N2  CO  SCl2
 S8  OF2  HF
 Br2  CS2

molecule type of intermolecular forces

I2 id-id interactions

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CH4 id-id interactions

N2 id-id interactions
Br2 id-id interactions
SF6 id-id interactions
CO pd-pd interactions
OF2 pd-pd interactions
CS2 id-id interactions
HCN pd-pd interactions
CH3CH(CH3)CH3 id-id interactions
SCl2 pd-pd interactions
HF hydrogen bonding

15 For each of the substances listed below, complete the table by stating
 the type structure it has,
 the type of bond or interaction broken during the melting or boiling process (if the type of
interaction broken is intermolecular forces, specify the type of intermolecular forces).

substance structure type of bond or interaction broken

Na
NaBr
HF
CH2Cl2
P4
Fe
HBr
CH3COONa
NH3

substance structure type of interaction broken

Na giant metallic lattice metallic bonds between Na+ & delocalised electrons
NaBr giant ionic lattice ionic bonds between Na+ & Br−
HF simple molecular hydrogen bonds between HF molecules
CH2Cl2 simple molecular pd-pd interactions between CH2Cl2 molecules
P4 simple molecular id-id interactions between P4 molecules
Fe giant metallic lattice metallic bonds between Fe2+ & delocalised electrons
HBr simple molecular pd-pd interactions between HBr molecules
CH3COONa giant ionic lattice ionic bonds between Na+ & CH3COO−

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NH3 simple molecular hydrogen bonds between NH3 molecules

16 N94/P1/Q3(b) (modified)
The table below shows the boiling points of five organic compounds.

formula relative molecular mass boiling point / oC

A CH3CH2OCH2CH3 74.0 35
B CH3CH2CH2CH2OH 74.0 117
C (CH3)3COH 74.0 82

By comparing A and B and B and C, suggest for the differences in the boiling points within each of
these two pairs.

All three compounds have simple molecular structure and are polar.

A has permanent dipole – permanent dipole (pd-pd) interactions between its molecules, while B
and C have intermolecular hydrogen bonds between its molecules.

B has a higher boiling point than A because a greater amount of energy is required to overcome the
stronger hydrogen bonds between the molecules of B compared to the pd-pd interactions between
the molecules of A.

B has a higher boiling point than C because B is a straight chain molecule and hence more linear than
C which is branched and more spherical. B has a greater surface area of contact which leads to more
extensive instantaneous dipole – induced dipole (id-id) interactions between its molecules.
Hence a greater amount of energy is required to overcome the stronger id-id interactions between
the molecules of B.

17 N15/P2/Q2(c)
Methanol has the advantage of being a liquid at 25 oC, so it can be stored in conventional fuel
tanks.
Explain in terms of the intermolecular forces involved, two reasons why methanol has a significantly
higher boiling point than methane.

Both methanol and methane have simple molecular structure. While methanol is polar, methane is not
polar.

Methanol has strong hydrogen bonds between its molecules as compared to the weak
instantaneous dipole – induced dipole attractions between methane molecules.

In addition, the electron cloud present in methanol is larger than that in methane and this leads to
higher polarisability of the methanol molecules. A greater amount of energy is required to overcome

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the stronger hydrogen bonds and stronger intermolecular instantaneous dipole – induced dipole
interactions in methanol and hence it has a higher boiling point than methane.

18 N12/P3/Q4(c)(ii) (modified)
Sodium, silicon, phosphorus and chlorine are found in the Period 3 of the Periodic Table. These
four elements differ greatly in their melting points.

element sodium silicon phosphorus chlorine

melting point / K 371 1683 317 172

Describe how their melting points differ, and explain this variation.

melting point: Si > Na > P4 > Cl2

Silicon has a very high melting point due to its giant molecular structure. A large amount of energy
is required to break the strong and extensive covalent bonds between Si atoms / electrostatic forces
of attraction between the nucleus of the silicon atoms and the shared pair of electrons in the three-
dimensional tetrahedral network.

Sodium has giant metallic lattice structure. A large amount of energy is required to break the strong
electrostatic forces of attraction between the sea of delocalised electrons and the Na+ cations.
Sodium has a lower melting point than silicon because the metallic bonds in sodium is weaker than
the covalent bonds in silicon.

Phosphorus and chlorine have lower melting points since they have simple molecular structure and
with weak instantaneous-dipole induced-dipole between the molecules since they are both non-
polar. A lower amount of energy is required to overcome the weak intermolecular instantaneous-
dipole induced-dipole attractions.

Phosphorus has a higher melting point than chlorine as it has a larger electron cloud and hence its
electron cloud is more easily polarised and the strength of instantaneous-dipole induced-dipole
between P4 molecules are stronger. The instantaneous-dipole induced-dipole between P4
molecules is only marginally weaker than the metallic bonds in sodium and hence phosphorus and
sodium have relatively close melting points.

19 N13/P3/Q3(b) (modified)
The structures of oxides can be simple or giant, and their bonding can be covalent or ionic. Use
these terms to describe the structure and bonding in each of the oxides
W, X, Y and Z.

Explain your reasoning in each case.

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melting point electrical conductivity

oxide
/ C when molten
W 2850 good
X 1720 poor
Y 1280 good
Z 580 poor

W and Y are ionic oxide with giant ionic structure. They have high melting points because a large
amount of energy is required to overcome the strong electrostatic forces of attractions between
the oppositely charged ions. In the molten state, they have free ions acting as mobile charge carrier
to conduct electricity.

X is a covalent oxide with a giant molecular structure. It has a high melting point because a lot of
energy is required to overcome the strong and extensive covalent bonds / electrostatic forces of
attractions between the nucleus of X and O atoms and the shared pair of electrons. It is a poor electrical
conductor in the molten state as all the electrons are involved in bonding and there are no mobile charge
carriers.

Z is a covalent oxide with a simple molecular structure. It has a low melting point because lesser
amount of energy is required to overcome the weak intermolecular forces between the molecules.
It is a poor electrical conductor in the molten state as all the electrons are involved in bonding and there
is no mobile charge carrier.

CHEM~IS~TRY

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