Study and Revision Guide

Christopher Talbot
ANSWERS Richard Harwood

2017 EDITION
i7 HODDER
EDUCATION
 FOR THE
IB DIPLOMA

Chemistry
Study and Revision Guide
Christopher Talbot
Richard Harwood

899713_FM_IBDip Chem_RG_i-viii.indd 1 09/05/17 8:17 pm

 Acknowledgements
We thank the following for their invaluable advice on the content of selected
chapters: Professor Norman Billingham, University of Sussex, Professor Jon Owen,
University of Southampton, Professor David Jenkins, University of York, Gordon
Wood, Dr. David Fairley, Overseas Family School, Singapore, Professor Stanley Furrow,
Pennsylvania State University, Professor Philip Walker, University of Surrey, Dr. David
Cooper, University of Liverpool, Professor Laurence Harwood, University of Reading,
Professor Mike Williamson, University of Sheffield and Dr. Jon Cooper, University
College, London.
Photo credits:
p.130 all © Richard Harwood

The Options and answers are free online at www.hoddereducation.com/IBextras

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© Christopher Talbot and Richard Harwood 2017
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ISBN: 9781471899713

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 Contents
How to use this revision guide vi
Getting to know Papers 1, 2 and 3 vi
Assessment objectives vii
Countdown to the exams viii

Topic 1 Stoichiometric relationships 1

n 1.1 Introduction to the particulate nature of matter and chemical change 1
n 1.2 The mole concept 6
n 1.3 Reacting masses and volumes 10
n 1.4 Gases 14

Topic 2 Atomic structure 19

n 2.1 The nuclear atom 19
n 2.2 Electron configuration 23

Topic 3 Periodicity 32
n 3.1 Periodic table 32
n 3.2 Periodic trends 34

Topic 4 Chemical bonding and structure 44

n 4.1 Ionic bonding and structure 44
n 4.2 Covalent bonding 49
n 4.3 Covalent structures 54
n 4.4 Intermolecular forces 60
n 4.5 Metallic bonding 62

Topic 5 Energetics/thermochemistry 66
n 5.1 Measuring energy changes 66
n 5.2 Hess’s law 71
n 5.3 Bond enthalpies 76

Topic 6 Chemical kinetics 79

n 6.1 Collision theory and rates of reaction 79

Topic 7 Equilibrium 90
n 7.1 Equilibrium 90

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 iv Contents

Topic 8 Acids and bases 99

n 8.1 Theories of acids and bases 99
n 8.2 Properties of acids and bases 102
n 8.3 The pH scale 103
n 8.4 Strong and weak acids and bases 105
n 8.5 Acid deposition 108

Topic 9 Redox processes 112

n 9.1 Oxidation and reduction 112
n 9.2 Electrochemical cells 122

Topic 10 Organic chemistry 127

n 10.1 Fundamentals of organic chemistry 127
n 10.2 Functional group chemistry 134

Topic 11 Measurement, data processing and analysis 144

n 11.1 Uncertainties and errors in measurements and results 144
n 11.2 Graphical techniques 151
n 11.3 Spectroscopic identification of organic compounds 154

Topic 12 Electrons in atoms 164

n 12.1 Electrons in atoms 164

Topic 13 The periodic table – the transition metals 171

n 13.1 First-row d-block elements 171
n 13.2 Coloured complexes 176

Topic 14 Chemical bonding and structure 186

n 14.1 Further aspects of covalent bonding and structure 186
n 14.2 Hybridization 190

Topic 15 Energetics/thermochemistry 198

n 15.1 Energy cycles 198
n 15.2 Entropy and spontaneity 202

Topic 16 Chemical kinetics 214

n 16.1 Rate expression and reaction mechanism 214
n 16.2 Activation energy 225

Topic 17 Equilibrium 227

n 17.1 The equilibrium law 227

Topic 18 Acids and bases 236

n 18.1 Lewis acids and bases 236
n 18.2 Calculations involving acids and bases 238
n 18.3 pH curves 244

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 Contents v

Topic 19 Redox processes 252

n 19.1 Electrochemical cells 252

Topic 20 Organic chemistry 264

n 20.1 Types of organic reactions 264
n 20.2 Synthetic routes 270
n 20.3 Stereoisomerism 273

Topic 21 Measurement and analysis 281

n 21.1 Spectroscopic identification of organic compounds 281

Option chapters and answers

Option chapters and answers appear on the website accompanying this book:
www.hoddereducation.com/IBextras

899713_FM_IBDip Chem_RG_i-viii.indd 5 16/05/17 7:16 pm

 Answers

1 Stoichiometric relationships
Quick check questions
 1 Substance Type of substance Nature of mixture
Smoke Mixture Homogeneous
Mercury Element
Bronze Mixture Homogeneous
Sucrose Compound
Dry ice Compound
Carbonated (fizzy) drink Mixture Homogeneous
Magnesium iodide Compound
Distilled water Compound
Air Mixture Homogeneous
Magnesium and sulfur powders Mixture Heterogeneous
Petrol and water Mixture Heterogeneous
Chalk and water Mixture Homogeneous

 2 Z is a compound.
 3 3Cl2(g) + 6NaOH(aq) ➝ 5NaCl(aq) + NaClO3(aq) + 3H2O(l)
MnO2(s) + 4HCl(aq) ➝ MnCl2(aq) + Cl2(g) + 2H2O(l)
2Cs(s) + 2H2O(l) ➝ 2CsOH(aq) + H2(g)
3CuO(s) + 2NH3(g) ➝ 3Cu(s) + N2(g) + 3H2O(l)
4Na(s) + O2(g) ➝ 2Na2O(s)
 4 Ag+(aq) + Br−(aq) ➝ AgBr(s)
H+(aq) + OH−(aq) ➝ H2O(l)
Zn(s) + Fe2+(aq) ➝ Zn2+(aq) + Fe(s)
Na2CO3(s) + 2H+(aq) ➝ CO2(g) + H2O(l) + 2Na+(aq)
Cu2+(aq) + 2OH−(aq) ➝ Cu(OH)2(s)
 5 Ca(s) + 2H+(aq) ➝ Ca2+(aq) + H2(g); redox
Ba2+(aq) + SO42−(aq) ➝ BaSO4(s); precipitation (double decomposition)
O2−(s) + 2H+(aq) ➝ H2O(l); acid-base
 6 238.03 g mol−1
146.07 g mol−1
207.2 g mol−1
132.17 g mol−1
 7 1.204 × 1024
2.408 × 1023
 8 2723 mg
 9 7.64 × 10−23 g
10 0.800 mol; 28.36 g; 4.816 × 1023

Chemistry for the IB Diploma Study and Revision Guide © Christopher Talbot and Richard Harwood 2017
 1 Stoichiometric relationships 2

11 40.00 g mol−1
12 39.9728
13 1.44 g
14 4.21 g
15 239 g
16 CH, CH2, PH3, BH3, NO2, Fe2O3 and CH
17 K2Cr2O7
18 CuS
19 C6H12O6
20 ZnSO4
21 CH4O
22 3CuO + 2NH3 ➝ 3Cu + N2 + 3H2O
CuO is the limiting reagent; NH3 is present in excess
23 The reaction is reversible, side reactions leading to formation of other products, mechanical
losses during purification, insufficient time for reaction to reach completion
24 0.08 mol dm−3; 3.20 g dm−3
25 0.004 dm−3 Al3+ and 0.006 mol dm−3 SO42−
26 0.79 g
27 138 g mol−1
28 12.20 mol dm−3 ; potassium
29 18%
30 88%
The sodium hydroxide solution absorbs water and carbon dioxide from the air if left to stand
for a period of time and is therefore not an accurate standard. The concentration of the
solution decreases with time.
31 0.534 mol dm−3
32 25.00 cm3
33 0.906 mol dm−3
34 10.6 g; 0.46 mol dm−3; 10 321 ppm
35 34%; 100%. The electrolytic method is far more efficient.
36 pressure increases; pressure decreases; pressure increases
37 250 kPa
38 79.0 cm3
39 a 11.7 kPa
b 40.4 g mol−1
40 2CO(g) + O2(g) ➝ 2CO2(g)
41 18 cm3 hydrogen and 64 cm3 nitrogen
42 6 dm3 (4.8 dm3 of NO2 and 1.2 dm3 O2)
43 500 cm3 O2 needed and 1000 cm3 of SO2 produced
44 5.675 dm3 and 34.05 dm3
45 45
46 72
47 64 g mol–1

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 2 Atomic structure 3

48 Gas molecules do not exert attractive forces on each other. Gas molecules are in constant
motion in an overall random direction and they frequently collide with each other elastically.
The total energy of the molecules in the system remains constant. The average kinetic energy
of the molecules is proportional to the absolute temperature of the gas. Any two gases at the
same temperature will have molecules with the same average kinetic energy.
49 Gas pressure is the result of collisions between molecules and the walls of their container and
is proportional to the number of molecules per unit volume of gas. Decreasing the volume of a
given amount of gas increases the number of molecules per unit volume and hence its collision
rate. Hence, at constant temperature the pressure of a gas is inversely proportional to its
volume.
50 Gases behave ideally at low pressure and high temperature. At high temperature, the gas
molecules possess high amounts of kinetic energy and this is greater than the intermolecular
forces of attraction. At low pressure, the molecules of gas (in average) are relatively far apart
and hence the intermolecular attractive forces are very small.
51 Hydrogen would behave the most ideally because it consists of small non-polar molecules
with low London (dispersion) forces of attraction. Hydrogen fluoride would show the greatest
deviation from ideal behaviour because although HF molecules are smaller than F2 molecules,
they are very polar and form strong hydrogen bonds. Fluorine molecules have stronger London
forces then hydrogen molecules due to the greater number of electrons present.

2 Atomic structure
Quick check questions
 1 a Sub-atomic particle Proton (p) Neutron (n) Electron (e)
Position within atom Nucleus Nucleus Energy levels (shells)
Relative mass (amu) 1 1 Very small
Relative charge +1 0 −1

b Protons and neutrons are nucleons.

 2 8, 8, 8; 8, 8, 9; 8, 8, 10; 8, 10, 8; 8, 2, 9; 16, 16, 16; 16, 15, 20
 3 199F–
 4 a Isotopes are atoms of the same element having the same number of protons (atomic
number) but different numbers of neutrons (mass or nucleon numbers).
b – –
– 3 electrons – 3 electrons

+ + 3 protons, + + 3 protons,
+ 3 neutrons + 4 neutrons
nucleus nucleus
– –

 5 melting point, boiling point, density and rate of diffusion

 6 a 121
Sb =55.2% and 123Sb=44.8%
b carbon-12 (126C)
 7 a 28
14
Si+, 29
14
Si+, 30
14
Si+
b Relative atomic mass of silicon = (28 × 92.20%) + (29 × 4.70%) + (30 × 3.10%) = 28.11
 8 63.5
 9 35Cl37Cl; 35Cl35Cl and 37Cl37Cl

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 2 Atomic structure 4

10 Red – higher wavelength; blue – lower wavelength; red – lower frequency; blue – higher
frequency; red – lower energy; blue – higher energy.
11 a 5.08 × 1014 s−1
b 522 nm; green
12 UV-B radiation has shorter wavelength (or higher frequency); hence UV-B radiation / photons
has higher energy.
Or UV-A radiation has longer wavelength (or lower frequency); less energy (in its photons or
rays).
13 An atom is in the ground state when all the electrons in the atom are in the lowest energy
levels. This is the most stable state for atom. An atom is in an excited state when one or more
of the electrons in the atom are promoted to higher energy levels. An atom in an excited state
rapidly emits photons and the excited electrons transition back to the lower energy levels.
14 a 4.55 × 10−8 m, 4.38 × 10−18 J mol−1
b 3.32 × 10−19 J
15 A continuous spectrum is a spectrum that consists of all electromagnetic wavelengths across
a range of wavelengths. A line spectrum consists of electromagnetic radiation of specific
wavelengths.
16 a Electrons in an atom are quantized and can only exist in specific energy levels. When an
atom has absorbed energy corresponding to the difference in energy levels, an electron
is excited to the higher energy level. This is an unstable excited state and the electron
will undergo a transition to a lower energy level emitting radiation / light / photon of a
specific energy corresponding to the difference in the two energy levels. A line spectrum is
produced because the electrons in atom have discrete values of energy. Each line represents
a specific frequency / wavelength / energy.
b n=4
n=3

n=2

n=1

17 Discrete or quantized energy levels; the energy gap or difference in energies between quantum
shells (main energy levels) decreases; the distance between adjacent quantum shells (main
energy levels) becomes smaller as the distance from the nucleus increases; the energy levels
converge at high frequency.
18 An orbital is a region of space around the nucleus of an atom in which there is a high
probability of finding an electron of a specific energy is a maximum.
19 a z z

y y

x x

s orbital px orbital

b The 2s and 3s orbitals are like all other s orbitals and can be described as spherically
symmetrical. A 3s orbital is larger than a 2s orbital. An electron in a 3s orbital has more
energy than an electron in a 2s orbital. The electron density is more diffuse in a 3s orbital.
20 50, 3, 6, 10 and 14

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 3 Periodicity 5

21 a The Aufbau principle states that the order of electron filling sub-levels is from the orbital
which has the lowest energy. Hund’s rule states when electrons are placed in degenerate
orbitals (same energy), the electrons must occupy them with parallel spins before they can
occupy the orbitals in spin pairs.
b 1s2 2s2 2p6 3s2 3p6 4s2 3d6 or 1s2 2s2 2p6 3s2 3p6 3d6 4s2

1s 2s 2p 3s 3p 3d 4s

22 1s 2s 2p 3s 3p 4s 3d 4p

1s 2s 2p 3s 3p 4s 3d 4p

1s2 2s2 2p6 3s2 3p6 4s2 3d10 4p4; 1s2 2s2 2p6 3s2 3p6 4s2 3d10 4p6
[Ar] 3d10 4s2 4p4; [Ar] 3d10 4s2 4p6
23 a Electronic configuration according to Aufbau principle: 1s2 2s2 2p6 3s2 3p6 4s2 3d9
Electronic configuration determined by experiment: 1s2 2s2 2p6 3s2 3p6 4s1 3d10
b Completely filled 3d orbitals (3d10) or half-filled orbital (3d5) are relatively stable compared
with partially filled orbitals.
24 Chromium; 1s2 2s2 2p6 3s2 3p6 4s1 3d5
25 [Ar]3d3 4s2 (or [Ar]4s2 3d3); [Ar]3d3; [Ar]3d2 and [Ar]3d1

3 Periodicity
Quick check questions
 1 They have the same outer shell electron configuration and the same number of valence
electrons. These are the electrons that take part in chemical reactions and hence the elements
undergo similar reactions.
 2 arsenic: 5 valence electrons, p block, 1s2 2s2 2p6 3s2 3p6 3d10 4s2 4p3; group 2 and period 4
calcium: 2 valence electrons, s block, 1s2 2s2 2p6 3s2 3p6 4s2; group 15 and period 4
 3 period 2, p block, group 15
period 3, p block, group 18
period 3, s block, group 2
period 4, d block, group 5
 4 a 4f 5d 6s

b Good thermal conductor; good electrical conductor; shiny (lustrous); cation formation;
basic oxide
 5 Periodicity of elements refers to the chemical, physical and atomic properties of the elements
that recur periodically when these elements are arranged in increasing order of their proton
number (atomic number).

Chemistry for the IB Diploma Study and Revision Guide © Christopher Talbot and Richard Harwood 2017
 3 Periodicity 6

 6 The atomic radius decreases across a period due to the increase in effective nuclear charge as
the proton number increases in each atom of the element across a period. The nuclear charge
increases rapidly but the shielding (electron–electron repulsion) increases more slowly, since
the additional electrons enter the same shell (main energy level). Consequently, all electrons
are pulled closer to the nucleus.
The size of atoms increases down a group due to the presence of additional electron shells
(main energy levels). The nuclear charge increases due to the presence of additional protons,
but this effect is more than outweighed by the presence of additional electrons shells with all
shells located further away from the nucleus.
 7 a Si4–
Atomic radius

Ionic radius
Si4+

Na Mg Al Si P S Cl Ar Na Mg Al Si P S Cl Ar

b Atomic radius decreases across the period because of rapidly increasing nuclear charge
(due to additional protons) and a small increase in shielding (electron–electron repulsion)
since the electrons enter the same shell. All the electrons are more strongly attracted to
the nucleus and therefore atomic radii decreases. Cationic radii and anionic radii decrease
across the period because of increased nuclear charge and a small increase in shielding
(electron–electron repulsion). However, the anionic radius is much larger than the cationic
radius because of electron–electron repulsion as additional electrons enter the valence shell.
 8 A13+ < Mg2+ < Na+
They are isoelectronic ions, having the same electronic configuration of 1s2 2s2 2p6. The proton
numbers, however, increase from sodium to aluminium. Since the number of electrons in the
ions remains constant the radius of the ions decreases with increasing nuclear charge, as all the
electrons are more strongly attracted to the nucleus.
Mg2+ < C1− < S2−
Mg2+ has the electron configuration 1s2 2s2 2p6. S2− and Cl− are isoelectronic ions (with the
electron configuration 1s2 2s2 2p6 3s2 3p6). S2− is large than Mg2+ because it has an additional
shell of electrons. Cl− is smaller than S2− due to a higher effective nuclear charge in Cl−.
 9 Magnesium has stronger metallic bonding than sodium because has magnesium has smaller
atomic / metallic / ionic radius; hence stronger electrostatic attraction between the nucleus
and the delocalized valence electrons. Magnesium has the electron configuration [Ne]3s2,
while sodium has the electron configuration [Ne]3s1; hence each sodium atom donates one
delocalized electron per atoms, while magnesium donates two.
Silicon has a giant covalent structure / giant three-dimensional network; strong Si–Si covalent
bonds extending through the entire structure; many or all these strong bonds need to be
overcome during melting. Sulfur, S8, has a simple molecular / simple covalent structure with
weak London (dispersion) forces operating between non-polar molecules. A small amount of
thermal energy is needed to overcome them and cause melting.
10 a The first ionization energy is the minimum energy required for the removal of 1 mole of
outermost electrons from 1 mole of gaseous atoms in its ground state to form 1 mole of
gaseous unipositive cations.
b K(g) ➝ K+(g) + e−
c K: 1s2 2s2 2p6 3s2 3p6 4s1 and K+: 1s2 2s2 2p6 3s2 3p6.
11 a Evidence for the existence of main levels: highest values (peaks) for noble gases (group 18)
/ lowest values (troughs) for alkali metals (group 1) / general increase across periods 2 and
3; (evidence for sublevels); decrease in first ionization energy from beryllium to boron /
magnesium to aluminium / group 2 to group 13; decrease in first ionization energy from
nitrogen to oxygen / phosphorus to sulfur / group 15 to group 16.

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 3 Periodicity 7

b Aluminium has a lower value of first ionization energy compared to magnesium because the
electron removed is from the 3p orbital which is of a higher energy level than the 3s orbital
from which the valence electron of magnesium is removed from. Since the 3p electron
is less strongly held, and experiences more shielding (electron–electrons repulsion) less
energy is required to remove it. Sulfur has a lower value of first ionization energy compared
to phosphorus because the electron removed is from a spin pair which experiences greater
electron–electron repulsion. Since the electron is more easily removed, less energy is
required to ionize the atom.
12 a Electronegativity is the ability of an atom / element to attract a pair of electrons towards
itself in a covalent bond. Electron affinity is the amount of energy released or absorbed
when 1 mole of gaseous atoms accepts 1 mole of electrons to form a mole of gaseous
uninegative ions.
b F(g) + e− ➝ F−(g); F−(g) + e− ➝ F2−(g)
c The first electron affinity is exothermic: the energy released by attraction between the
incoming electron and the nucleus is greater than the repulsion between incoming electron
and the electrons in the atom (neutral). The second electron affinity is endothermic
because of repulsion between the electrons and the negatively charged fluoride ion – this is
greater than the electrostatic attraction between the incoming electron and the nucleus.
d Electronegativity decreases because the atomic radii of the halogen atoms increases
(additional electron shells) and hence less attraction for the bonding pairs of electrons due
to the greater distance and increase in shielding. Electron affinity decreases for the same
reason except the attraction is for an incoming valence electron.
13 a An amphoteric oxide reacts with acids and bases.
b Ga2O3 (s) + 6HCl(aq) ➝ 2GaCl3(aq) + 3H2O(l)
Ga2O3 (s) + 2KaOH(aq) + 3H2O(l) ➝ 2KGa(OH)4(aq)
14 N2O5(g) + H2O(l) ➝ 2HNO3(aq);
hydrolysis; no change in oxidation state
15 a
14
pH

Na2O MgO Al2O3 SiO2 P4O10 SO3

b Na2O(s) + H2O(l) ➝ 2NaOH(aq) pH 12 or 14

SO3(l) + H2O(l) ➝ H2SO4(aq) pH 1 or 2
P4O10(s) + 6H2O(l) ➝ 4H3PO4(aq) pH 1 or 2
16 2Cs(s) + 2H2O(l) ➝ 2CsOH(aq) + H2(g)
2Cs(s) + F2(g) ➝ 2CsF(s)
4Cs(s) + O2(g) ➝ 2Cs2O(s)
Cs2O(s) + H2O(l) ➝ 2CsOH(aq)

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 4 Chemical bonding and structure 8

17 Reactivity increases as a result of an increased ease of ion formation as we move down the
group. The effective nuclear charge decreases due to the significant increase of the shielding
effect (electron–electron repulsion) over nuclear charge (increase in proton number). Atomic
radius increases and the valence electrons are less strongly attracted due to a greater distance
from the nucleus, so less energy is required to remove the valence electron resulting in the
decrease in the first ionization energy.
18 a Br2(aq) + 2I−(aq) ➝ I2(aq) + 2Br−(aq)
b Br2 is an oxidizing agent; I− is a reducing agent
c A yellow precipitate of silver(I) iodide will be observed when added to colourless iodide
ions.

4 Chemical bonding and structure

Quick check questions
 1 lithium atom (Li) 1s2 2s2; fluorine atom (F) 1s2 2s2 2p5
The ionic bond in lithium fluoride is formed by the transfer of an electron from a lithium atom
to a fluorine atom. When these two elements react, a lithium atom loses an electron from the
2s orbital to form the lithium ion, Li+. The electronic configuration of the lithium ion is the
same as that of the noble gas helium.
Li (1s22s1)  ➝ Li+ (1s2) + e−
lithium atom   lithium ion
The electron that has been lost by a lithium atom is now gained by a fluorine atom to form a
fluoride ion, F−, which has the electronic configuration of the noble gas, neon (Ne).
F (1s22s22p5) + e− ➝ F− (1s22s22p6)
fluorine atom     fluoride ion
The positive lithium ions, Li+, and the negative fluoride ions, F−, attract one another because
they have opposite charges. It is the electrostatic attraction between two oppositely charged
ions that is ionic bonding.

–
Li + F Li+ + F

The curved arrow indicates the transfer of an electron from the 2s orbital of lithium atom
(Li) to the 2p orbital of the fluorine atom (F). The formula is LiF [Li+ F−] which is electrically
neutral.
 2 Na2O, MgO, Al2O3, Mg3P2, NaCl, MgCl2, AlCl3, CrCl3, Cu2O, Fe2S3 and Al2S3
 3 covalent, ionic, covalent, covalent, covalent, covalent, ionic and ionic
 4 sodium sulfate, Na2SO4, sodium hydroxide, NaOH, sodium hydrogen sulfate, NaHSO4, sodium
carbonate, Na2CO3, sodium hydrogencarbonate, NaHCO3, sodium phosphate, Na3PO4,
magnesium nitrate, Mg(NO3)2, magnesium phosphate, Mg3(PO4)2, aluminium hydroxide,
Al(OH)3, aluminium phosphate, AlPO4 and ammonium sulfate, (NH4)2SO4
 5 a Lithium fluoride has low volatility which is a consequence of having a relatively high
melting and boiling point. This is due to the strong attractive electrostatic forces of
attraction operating between oppositely charged ions in the lattice. Large amounts of
thermal energy are required to break down the lattice.

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 4 Chemical bonding and structure 9

b Lithium fluoride is a non-conductor in the solid state: the ions are not free to move when
a voltage is applied. It becomes an electrical conductor when melted or when an aqueous
solution is formed. The electrical conductivity is due to the presence of mobile lithium and
fluoride ions.
c Lithium fluoride is soluble in water (a polar solvent) because both ions are hydrated by the
water molecules. The polar water molecules hydrate the lithium and fluoride ions via ion-
dipole forces. The attraction between water molecules and ions is energetically favourable
to break up the lattice and release hydrated ions.
 6 2–
F
F F
Si
+
F F O N O
F

 7 Cl Cl Cl Cl

Al × 2 Al Al

Cl Cl Cl Cl Cl
Aluminium is the acceptor;
chlorine is the donor

–
Cl Cl
–
Al + Cl Cl Al Cl

Cl Cl
Cl
Aluminium is the acceptor,
chlorine is the donor

 8 a CO CO2

C O O C O

CH3CH2CH2OH
H H H
H C C C O H
H H H

b CO < CO2 < C3H7OH. Triple bonds are shorter than double bonds which are shorter than
single bonds. The greater the number of shared pairs of electrons between the two nuclei
the stronger the electrostatic attraction so the shorter the bond.
 9 +δO–Fδ−; +δB–Fδ−; +δC–Clδ−; P–H (least polar – same electronegativities);
δ+
C=Oδ− ; δ−O–Hδ+; δ+H–Brδ− and δ+H–Fδ− (most polar)
10 H H H
N N N N
H
polar form non-polar form

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 4 Chemical bonding and structure 10

11 SO2:

S
O O

Correct representation of the bent / non-linear / V-shape and for showing the net dipole
moment, or explaining it in words (unsymmetrical distribution of bond dipole moments).
CO2:

O C O

Correct representation of the linear shape and for showing the two equal but opposite dipole
moments or explaining it in words (symmetrical distribution of bond dipole moments).
Allow either an arrow or an arrow with bar for the representation of dipole moment / correct
partial charges instead of the representation of the vector dipole moment.
12 ionic, covalent, polar covalent, ionic and polar covalent
13 The sodium ion, Na+, has a low charge density so therefore it has a low polarizing power.
Therefore, sodium compounds will be essentially ionic. However, the oxide ion, O2−, is a larger
and more highly charged ion than the fluoride ion, F−. Therefore, its electron cloud can be
more easily distorted and polarized towards the Na+ ion. Hence, Na2O has a higher degree of
covalent character than NaF.
14 Carbon dioxide, CO2, is simple molecular covalent with a linear structure; silicon dioxide,
SiO2, is giant three-dimensional solid/network solid/macromolecular structure with repeating
tetrahedral units.
Covalent bonds are present in CO2 and SiO2. Carbon dioxide has double bonds: C=O and
silicon dioxide has single bonds: –O–Si–O– bonds.
15 Diamond: three-dimensional array / network / lattice involving tetrahedral bonded carbons
/ each carbon atom joined to four other carbon atoms (except at surface) by single covalent
bonds;
Graphite: multi-layer structure involving trigonal (triangular) planar carbon atoms / with each
carbon atom joined to three others / with hexagonal (six-membered) rings of carbon atoms;
C60 fullerene: truncated icosahedron; or cage of carbon atoms with 32 faces, of which 12 are
pentagons (isolated) and 20 are hexagons.
Diamond: covalent bonds between carbon atoms; graphite: covalent bonds between carbon
atoms and the separate layers held together by (weak) London (dispersion) forces; fullerene-60,
C60: covalent bonds between carbon atoms and the approximately spherical cages are attracted
to one another by (weak) London (dispersion) forces.
16 Diamond-like form of BN: Extremely hard, insoluble in water, very high melting and boiling
point, electrical insulator.
Graphite-like form of BN: Soft, slippery, electrically conducting across layers and lower
melting and boiling points.
17 a
O O
and
O O O O

Bond angle is 117° ( but accept between 115 to 119°).

b The two pi electrons in the ozone molecules are delocalized over the three oxygen atoms.
The pi electrons are equally shared by all three oxygen atoms, hence giving two oxygen–
oxygen bonds that are equal in length.

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 4 Chemical bonding and structure 11

18 a Resonance occurs when two (or more) valid Lewis (electron dot) structures need to be
used to describe a molecule or ion (with pi bonds). The actual structure (hybrid) is a blend
(50% contribution from each) of both them with intermediate values of bond length/bond
strength (bond enthalpy).
b O H O H

C – C
O O O O
–

19 Order: PH2− < PH3 < PH4+

Between lone (non-bonding) pairs of electrons, there is a greater repulsion than bonding
(shared) pairs thus, the bond angle decreases with increasing number of lone pairs.
20 a H O N O

The N=O bond is the shorter of the two.

b 102 to 105°; lone / non-bonding pairs on the oxygen occupy more space and hence repel
more than a bonding / shared pair, hence decreasing the H–O–N bond angle (from 109.5°)
21 α β θ
104.5 °
120 °
109.5°

22 –
Cl

Cl B Cl

Cl

Lewis structure of BCl4 −

tetrahedral bond angle =109.5°

23 a Cl Be Cl
A BeCl2 molecule
b beryllium in the BeCl2 molecule is electron deficient – it has four valence electrons
c Cl Cl Cl

Be Be Be Be

Cl Cl Cl

bond angle approximately 109°

24 For the molecules H2S, H2Se and H2Te, as the molecular size and mass increases, London
(dispersion) forces increase in strength (and the boiling point increases). H2O experiences
hydrogen bonding which is stronger than London (dispersion) forces.
25 CCl4 is non-polar molecule and therefore insoluble in water (because it forms only weak
London forces with water molecules), whereas CH3CH2OH forms hydrogen bonds with water
molecules and readily dissolves in water.
Methanoic acid is soluble in water as it forms hydrogen bonds with water molecules and
undergoes ionization. However, octanoic acid is much less soluble in water despite the presence
of the carboxylic acid functional group that hydrogen bonds with water molecules because of the
long hydrophobic non-polar alkyl chain (C7H15) that does not interact with the solvent water
molecules (and the long alkyl chain also disrupts the hydrogen bonding that is present in water).
26 Lattice of cations (positive caesium ions); delocalized or mobile ‘sea’ of valence electrons;
electrostatic attraction between the two; electrons move when a voltage (potential difference)
is applied.

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 5 Energetics / thermochemistry 12

27 Aluminium is malleable as the lattice planes can slide over each other without the metallic
bonding being disrupted. In the alloy, the movement of planes of aluminium atoms is
prevented by the presence of the impurity copper alloying atoms. The electrical conductivity is
due to the presence of delocalized valence electrons which are supplied by both the aluminium
and copper atoms in the alloy.
28 a In potassium, only one valence electron contributes to the metallic bonding (electron ‘sea’),
in calcium, two and in titanium, more than two, because the electrons in both 3d and 4s
sub-levels are used for the formation of metallic bonds and hence the number of valence
electrons per atom increases from potassium to titanium.
Also, from potassium to titanium (across period 4), the atomic radius decreases. Hence, the
strength of metallic bonding increases. The density increases because the relative atomic
mass increases and the atomic size decrease and the increase in nuclear charge is greater
than the shielding effect.
b In going down (ascending) group 2, the boiling and melting points of the metals are
expected to decrease. This is because the strength of the metallic bonding is inversely
proportional to the metallic radius (size of cation). On going down group 2 the metallic
radius increases and shielding increases, hence the metallic bonding becomes weaker and
hence the boiling point and boiling points are expected to decrease.
The melting point increases because the strength of metallic bonding increases. The
strength of metallic bond is proportional to the number of valence (delocalized electrons
per metal atom) / metallic radius.
29 a CH3CN and CHI3 are both polar molecules and hence dipole–dipole interactions / forces
operate between molecules.
b CH3CN can dissolve in water because it can form hydrogen bonds with water molecules via
the lone-pair on the nitrogen atom and the hydrogen atom of water molecules.
30 Ca3N2 has a giant ionic structure held together by strong electrostatic attraction between Ca2+
and N3− ions. S4N4 has a simple molecular structure held together by weak London (dispersion)
forces. Hence, more thermal energy is required to overcome the strong electrostatic attractions
in Ca3N2 accounting for the higher boiling point.

5 Energetics / thermochemistry
Quick check questions
 1 exothermic; exothermic: endothermic; exothermic; endothermic
 2
H2(g) + O2(g)
Enthalpy (potential energy)

∆H 1f = –186 kJ mol–1

H2O2(l)
∆H = –98 kJ mol–1

H2O(l) + 1 O2(g)
2

Reaction pathway

 3 282 kJ
 4 1.43 × 106 kJ
1
 5  N2(g) + O2(g) ➝ NO2(g)
2
1
Na(s) +  Cl2(g) ➝ NaCl(s)
2
H2(g) + S(s) ➝ H2S(g)

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 5 Energetics / thermochemistry 13

 6 −222.5 kJ mol−1
1
 7 H2(g) + O2(g) ➝ H2O(l)
2
1
2K(s) + O2(g) ➝ K2O(s)
2
C2H4(g) + 2.5O2(g) ➝ 2CO2(g) + H2O(l)
C6H6(g) + 7.5O2(g) ➝ 6CO2(g) + 3H2O(l)
CH3OH(l) + 2O2(g) ➝ CO2(g) + 2H2O(l)
 8 0.498 g
 9 5058 kJ mol−1
10 a C3H7COOH(aq) + NaOH(aq) ➝ C3H7COONa(aq) + H2O(l)
b Some of the heat released released from the neutralization is used to break the –O–H bond
in the propanoic acid molecules and release hydrogen ions.
11 6.4 °C
12 −56.8 kJ mol−1
13 +5.23 kJ mol−1
14 450 J
2.5 × 1.0 × 4.18 × 40.0
15 = 0.418 kJ mol−1
1000
16 a 620 kJ mol−1
b heat loss to the surroundings / incomplete combustion; determine the heat capacity of
calorimeter and take the heat absorbed by the calorimeter into account / improve thermal
insulation / measure temperature against time and extrapolate graph to compensate for
heat loss
17 ΔH 1 = (y − x) kJ mol−1
18 DH 1
hydration
Na2S2O3(s) + 5H2O(l) Na2S2O3.5H2O(s)

DH 1
solution[Na2S2O3(s)] DH1 DH2 DH 1
solution[Na2S2O3.5H2O(s)]
= –7.6 kJ mol–1 = +47.4 kJ mol–1

Na2S2O3(aq)

ΔH1 = ΔH2
(−7.6 kJ mol−1) = ΔH1hydration + (+47.4 kJ mol−1) = −55.0 kJ
19 Cyclohexane has localized single bonds (bond order 1) of the same length and same strength.
Benzene exists as a resonance hybrid and contains delocalized bonds intermediate in length
and strength between single and double bonds (bond order 1.5). Bond enthalpies can be used
for cyclohexane but not benzene.
20 The energy change to break one mole of bonds in a molecule in the gaseous state; averaged
over similar or related compounds; the I–I bond is only present in one molecule, I2.
21 ∆H1f
N N(g) + 3H H(g) 2H N H(g)

H
∆H 1
∆H 2
E(N N)(g)
+ 3 × E(H H)(g) 2 × 3 × –E(N H)(g)

2N(g) + 6H(g)

enthalpy of reaction = −92 kJ (enthalpy of formation of ammonia = −46 kJ mol−1

22 –10 kJ mol–1

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 6 Chemical kinetics 14

23 a −1080 kJ mol−1
b The three nitrogen–nitrogen single bonds in the trinitramide molecule are longer than the
nitrogen–nitrogen triple bond in the nitrogen molecule; the bond in N2 is shorter because
there are three electron pairs versus one electron pair in the N–N bonds in trinitramide;
resulting in greater electrostatic attraction between the two nuclei and the bonding pairs.

6 Chemical kinetics
Quick check questions
 1 B
 2 1.00 × 10−3 mol dm−3 s−1
 3 a five times (5×) as fast
b rate of appearance of Br2 is half (0.5×) that of the disappearance of H+ ions.
 4 a follow the volume of oxygen gas produced (gas syringe), or loss in mass from flask
b follow the disappearance of I2 using a colorimeter, or by titration with sodium thiosulfate
c follow the disappearance of NaOH by titration with acid
d follow the disappearance of OH− by titration with acid, or the change in conductivity or pH
 5 a the reaction has stopped
b 2.8 × 10−5 mol dm−3 s−1
c and d  graph of [A] against time; then draw tangent at 100 s
1.5

slope = (1.13 – 0.55)/200

[A] × 102/mol dm–3

1.0

0.5

0
0 100 200 300
Time/s

(1.13 − 0.55) × 10−2

slope of tangent = = 2.90 × 10−5
200
instantaneous rate at 100 s = 2.90 × 10−5 mol dm−3 s−1
average rate for 0 to 100 s = 3.28 × 10−5 mol dm−3 s−1
note that the instantaneous rate has a lower value as the reaction is slowing down.
 6 D
 7 B
 8 A

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 7 Equilibrium 15

 9 At higher temperature the particles have more kinetic energy and therefore move faster. This
means that they collide more frequently. However, this has only a relatively small effect on the
reaction rate. The major effect arises from the fact that a greater proportion of the collisions
will involve particles whose total kinetic energy is greater than the activation energy for the
reaction. The Maxwell–Boltzmann distribution shows that at the higher temperature more
particles have kinetic energy greater than, or equal to, Ea.
Kinetic energy distribution

Ea Kinetic energy

temperature = T
Kinetic energy distribution

temperature = T + 100

Ea Kinetic energy

7 Equilibrium
Quick check questions
1 D
2 a Kc = [[Fe(SCN)]2+(aq)] / [Fe3+(aq)] [SCN−(aq)]
b Kc = [SO3(g)]2 / [SO2(g)]2 [O2(g)]
c Kc = [NO(g)]4 [H2O(g)]6 / [NH3(g)]4 [O2(g)]5
d Kc = [CO2(g)] [H2(g)]4 / [CH4(g)] [H2O(g)]2
3 C
1
4 Kc =  or 0.25
4
5 a Kc = 5.8 × 10−5
b Kc = 2.89 × 108
6 The change in pressure has lowered the proportion of products in the reacting mixture.
Therefore, to reach equilibrium again and the same value of Kc, the system must shift to the
right towards products.
7 a The equilibrium position will shift to the right (favouring the products) in order to lower
the concentration of Fe2+ ions again.
b No effect, the addition of water will lower all the concentrations equally.

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 8 Acids and bases 16

8 a i will shift equilibrium position to the left (in the exothermic direction), favouring the
reactants
ii will shift equilibrium position to the right (in the endothermic direction), favouring
the products
iii no effect
iv will shift equilibrium position to the left (to lower the hydrogen concentration again),
favouring reactants
b i will lower Kc
ii will increase Kc
iii no change
iv no change
9 a i will shift equilibrium position to the left (in the direction of that side of the equation
involving fewer moles of gas molecules), favouring the reactants
ii no change as both sides of the equation involve the same number of moles of gas
molecules
b i will shift equilibrium position to the right (in the direction of that side of the equation
involving more moles of gas molecules), favouring the products
ii will shift equilibrium position to the right (in the direction of that side of the equation
involving more moles of gas molecules), favouring the products
10 a will shift equilibrium position to the left (in the endothermic direction), favouring the
reactants; Kc value lowered
b will shift equilibrium position to the right (in the endothermic direction), favouring the
products; Kc value increased
c will shift equilibrium position to the left (in the endothermic direction), favouring the
reactants; Kc value lowered

8 Acids and bases

Quick check questions
 1 It is not an acid–base reaction (under Arrhenius theory) because HCl(g) does not contain H+
ions and NH3(g) does not contain OH− ions. There is no water present so no ions are released
into aqueous solution.
 2 An amphiprotic species is both a proton donor (Brønsted–Lowry acid) and a proton acceptor
(Brønsted–Lowry base).
HSeO4−(aq) + H+(aq) ➝ H2SeO4(aq)
HSeO4−(aq) ➝ H+(aq) + SeO42−(aq)
 3 Acids: HClO2(aq) and HCOOH2+(aq)
Bases: ClO2−(aq) and HCOOH(aq)

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 8 Acids and bases 17

 4 Acid – a proton donor; base – a proton acceptor

Reaction Acid Conjugate base Base Conjugate acid

I H2O(l) OH − (aq) NH3 (aq) NH4+(aq)
II HCO2H(aq) HCOO (aq)
−
C6H5O (aq)
−
C6H5OH(aq)

Stronger base in reaction II: phenoxide ion, C6H5O – Kc value is large – equilibrium favours
−

forward reaction; product favoured – better proton / hydrogen ion acceptor / stronger affinity
for protons/hydrogen ions.
 5 Equation that shows accepting a proton, e.g. reacting with hydrochloric acid.
CH3NH2(aq) + HCl(aq) ➝ CH3NH3+(aq) + Cl−(aq) / accept CH3NH3Cl;
CH3NH2(aq) + H2O(l) ➝ CH3NH3+(aq) + OH−(aq)
 6 H2O is the acid; OH− is the conjugate base
NH3 is the base; NH4+ is the conjugate acid
 7 F−, NO3−, SO42−, HS− and N2H4
 8 NH3, H3O+, PH4+, C2H5OH2+, H2O and HCOOH
 9 Colourless and odourless gas released; heat released to surroundings; colourless solution formed;
magnesium consumed / used up / reacted
Mg (s) + 2H+(aq) ➝ Mg2+(aq) + H2(g)
10 The hydrogen gas would be released at a slower rate / rate of reacting of magnesium will be
slower, since the concentration of hydrogen ions (protons) is less/acid partially dissociates or
ionizes.
11 Any three from: 2CH3COOH(aq) + Ca(s) ➝ (CH3COO)2Ca(aq) + H2(g)
2CH3COOH(aq) + CaCO3(s) ➝ (CH3COO)2Ca(aq) + CO2(aq) + H2O(l)
CH3COOH(aq) + KOH(aq) ➝ CH3COOK(aq) + H2O(l)
2CH3COOH(aq) + 2Na(s) ➝ 2CH3COONa(aq) + H2(g)
12 lithium hydroxide and nitric acid; sodium sulfate; neutralization / acid–base reaction / proton
transfer; exothermic.
13 [H+](aq) = 10−pH; [H+(aq)]HNO = 10−2 (mol dm−3)
3

and
[H+(aq)]HCN = 10−6 (mol dm−3)
10 000 / 104 : 1
14 Amount of NaOH = 0.05 dm3 × 0.50 mol dm−3 = 0.025 mol
Amount of HCl = 0.20 dm3 × 0.10 mol dm−3 = 0.02 mol
NaOH(aq) + HCl(aq) ➝ NaCl(aq) + H2O(l)
Excess NaOH is 0.005 mol in 250 cm3 of solution; concentration of NaOH = 0.02 mol dm−3
pOH = −log10 [OH−(aq)] = 1.69 = 1.7; pH = 14.0 − 1.7 = 12.3
15 104
16 pH = 0.43
17 pH = 0.90
18 NaHCO3(s) + HCOOH(aq) ➝ HCOONa(aq) + H2O(l) + CO2(g)
[H+] = 3.7 × 10−3mol dm−3
19 Increases by one pH unit
20 pH = 11.64
21 0.40 g
22 12.7 and 12.7

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 9 Redox processes 18

23 [H+(aq)] [OH−(aq)] Type of solution

0.1 1 × 10 −13
Acidic
1 × 10 −3 1 × 10 −11 Acidic
1 × 10 −5 1 × 10 −9 Acidic
1 × 10 −7 1 × 10 −7 Neutral
1 × 10 −9
1 × 10 −5
Alkaline
1 × 10 −11 1 × 10 −3 Alkaline
1 × 10 −13 0.1 Alkaline

24 [OH−] = 2.0 × 10−13 mol dm−3

25 Monoprotic: one proton donated per molecule of acid in aqueous solution.
Strong acid completely dissociated / ionized and weak acid partially dissociated / ionized.
H2O(l) + HClO4(aq) ➝ H3O+(aq) + ClO4−(aq)
H2O(l) + HCN(aq) ⇌ H3O+(aq) + CN−(aq)
26 0.20 mol dm−3 H2SO4(aq) < 0.20 mol dm−3 HCl(aq) < 0.020 mol dm−3 HCl(aq), < 0.020 mol dm−3
CH3CH2COOH, < 0.002 mol dm−3 CH3CH2COOH < 0.0020 mol dm−3 NH3(aq) < 2.0 mol dm−3
NH3(aq) < 2.0 mol dm−3 NaOH(aq)
27 HCl/A is strong and CH3COOH/C is weak;
HCl/A is fully dissociated and CH3COOH is slightly dissociated;
[H+] is greater in HCl/A than in CH3COOH/C; by a factor of 100
28 Bubbling/ effervescence/ dissolving of CO2 / colourless and odourless gas released (do not
accept CO2 produced). The rate of release is faster with sulfuric acid and the time taken for
completion of the reaction is less.
29 Normal rainwater has a pH less than 7.0 because of dissolved carbon dioxide and other acidic
gases from natural sources.
Acid rain (deposition) is rainwater that is below pH 5.6.
30 Limestone is a mineral form of calcium carbonate; this reacts with acid, as do all carbonates, to
produce a salt, water and carbon dioxide. So the limestone is eroded away over time.
31 N2(g) + O2(g) ➝ 2NO(g)
2NO(g) + O2(g) ➝ 2NO2(g)
Nitrogen(IV) oxide reacts with water in the air to produce a mixture of nitric(III) acid and
nitric(V) acid.
2NO2(g) + H2O(l) ➝ HNO3(aq) + HNO2(aq)
A further reaction in the presence of water can convert nitrogen(IV) oxide to nitric(V) acid by
oxidation; the reaction involving oxygen directly.
4NO2(g) + 2H2O(l) + O2(g) ➝ 4HNO3(aq)

9 Redox processes
Quick check questions
 1 2H2O2 ➝ 2H2O + O2; −1, −2 and 0; is a redox reaction in which both oxidation and reduction
of the same species occurs (in this example, oxygen).
 2 2N2H4(g) + N2O4(g) ➝ 3N2(g) + 4H2O(l); hydrogen is oxidized, nitrogen reduced.
 3 4NH3(g) + 5O2(g) ➝ 4NO(g) + 6H2O(l); ammonia is oxidized; oxygen reduced.

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 9 Redox processes 19

 4 Li ➝ Li+ + e− (oxidation)
H2 ➝ 2H+ + 2e− (oxidation)
4e− + 2O ➝ 2O2− (reduction)
Cu+ ➝ Cu2+ + e− (oxidation)
e−+ Cr3+ ➝ Cr2+ (reduction)
e− + Fe3+ ➝ Fe2+ (reduction)
Al ➝ Al3+ + 3e− (oxidation)
2Cl− ➝ Cl2 + 2e− (oxidation)
−1
 5 −3, 0, −3, −2, −2, +2, +1, +3, +5, +3, +5, −3, +5, +3, 3 , −1
 6 Element–element (homopolar) bonds are ignored in terms of oxidation state and hence the
terminal sulfur atom is regarded as S=S and hence each sulfur atom has an oxidation state of
zero.
The central sulfur atom is less electronegative than oxygen and hence assigned a positive
oxidation state – it forms four bonds with oxygen – the bond to sulfur is not counted.
 7 Cr6+ refers to a hypothetical ion formed by the loss of six valence electrons from a chromium
atom; the +6 oxidation state refers to the idea that oxidation numbers assign the more
electronegative atom the electrons in the bonds – and chromium is forming two Cr=O bonds
and two Cr–O− bonds; oxygen is more electronegative than chromium.
 8 +5, −2, −1; +1, −1, +3, −2; +1, −2; +1, −1; +7, −2; +1, −1; +2, −3; and +1, −1.
 9 a 4K(s) + O2(g) ➝ 2K2O(s)
b K: 1s2 2s2 2p6 3s2 3p6 4s1 and O: 1s2 2s2 2p4; K+: 1s2 2s2 2p6 3s2 3p6 and O2−: 1s2 2s2 2p6
c Oxygen is reduced since it has gained electrons / reduced since the oxidation number has
decreased (from 0 to −2).
10 a potassium sulfate(IV), sodium sulfate(VI), iron(III) nitrate, iron(II) nitrate, copper(II)
sulfate, copper(I) oxide, chromium(III) oxide, copper(I) sulfate, manganese(VII) oxide and
manganese(IV) oxide.
b NaOCl, Fe2O3, CsNO3, PCl3, SCl4 and NaClO3
11 +3, +2, +2 and +1
12 2FeI2 + I2 ➝ 2FeI3
(Iron in) FeI2 is oxidized because its oxidation number increases / changes from +2 to +3; iodine
reduced because it gains electrons / I2 + 2e− ➝ 2I− and its oxidation number/state decreases /
changes from 0 to –1
13 no change in oxidation number; precipitation (double decomposition)
14 a silver(I) nitrate or silver(I) ions
b oxidation or replacement; Pb (s) ➝ Pb2+(aq) + 2e−
c silver solid forms; silver atoms produced as the silver ions gain electrons and are reduced:
Ag+ + e− ➝ Ag
15 Cl2(g) + 2Br−(aq) ➝ 2Cl−(g) + Br2(aq)
There is a change in oxidation number / electron transfer occurs.
A pale green gas and colourless solution becomes an orange brown solution.
16 Cr2O72−(aq) + 3SO2(aq) + 2H+(aq) ➝ 2Cr3+(aq) + 3SO42−(aq) + H2O(l)
17 Ti3+(aq) + e− ➝ Ti2+(aq)
Ag(s) ➝ Ag+(aq) + e−
Ti3+(aq) + Ag (s) ➝ Ti2+(aq) + Ag+(aq)
18 Copper(II) ions are an oxidizing agent and iodide ions are a reducing agent.
It is a redox reaction because there is a change in oxidation number in iodine and copper.

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 9 Redox processes 20

19 3I3− + 3H2O ➝ IO3− + 8I− + 6H+

20 n(Cr2O72−) = (21.50/1000) dm3 × 0.100 mol dm−3 = 0.00215 mol
n(Fe2+) in 25.00 cm3 = 0.00215 mol × 6 = 0.0129 mol
n(Fe2+) in 250.00 cm3 = (0.0129/25.00) × 250.00 = 0.129 mol
mass of iron in iron ore = 0.129 mol × 55.85 g mol−1 = 7.20 g
% mass of iron in iron ore = 7.20/12.25 × 100% = 58.81% or 58.8%
21 a HOCl(aq) + 2I−(aq) + H+(aq) ➝ Cl−(aq) + I2(aq) + H2O(l)
b Amount of sodium thiosulfate/thiosulfate ions = (16.85/1000) dm3 × 0.152 mol dm−3
= 0.0025612 mol
Amount of iodine = 0.0025612 mol/2 = 0.0012806 mol
0.0012806 mol × 250
c Amount of NaOCl in original bleach solution = = 0.0160075 mol
20
Mass of NaOCl = 0.0160075 mol × 74.44 g mol = 1.19159 g
−1

Concentration of NaOCl = 1.19159 / 0.025 = 47.6 g dm−3

22 n(S2O32−) = (12.5/1000) dm3 × 0.00200 mol dm−3 = 0.000025 mol
n(I2) = (0.000025/2) mol = 0.0000125 mol
n(Mn(OH)3) = 2 × 0.0000125 mol = 0.000025 mol
n(O2) = (0.000025/4) mol = 0.00000625 mol
mass of O2 in 24.50 cm3 = 0.00000625 × 32.00 = 0.0002 g
mass of O2 in 1000 cm3 = (
0.0002
24.5 (
× 1000 = 0.00816 g dm−3 = 8.16 mg dm−3 or ppm

23 a electron
voltmeter
flow
V

salt bridge

magnesium gold
electrode electrode
(anode –) (cathode +)

Mg2+(aq) Au+(aq)

b Cathode: Mg(s) ➝ Mg2+(aq) + 2e−; anode: Au+(aq) + e− ➝ Au(s)

c Allows cations and anions to flow through it / to complete the circuit / to maintain
electroneutrality. KCl/KNO3/NaNO3
24 a
ammeter
conventional A
e–
current
electron
flow
e–

anode (+) cathode (–)

+
electrolyte
– +
– (molten lead(II)
– + bromide)
+

+ = cation Pb2+(l)
– = anion Br–(l)

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 10 Organic chemistry 21

b Electrons flow through connecting wires in the external circuit and ions move in the
molten electrolyte to their respective electrodes and lose / gain electrons on the surfaces.
c Pb2+(l) + 2e− ➝ Pb (s); 2Br−(l) ➝ Br2(l) + 2e−.
d It means energy has to be supplied to make the electrolytic processes occur. Electrical to
chemical energy. Mobile ions are able to move under the influence of an applied voltage.
25 a electrical energy to chemical energy
b The electrolysis only occurs in the molten state as the ions present must be able to move
laterally. In the solid the only motion of the ions taking place is vibration about a fixed
point.
c Cathode: Sr2+(l) + 2e− ➝ Sr(l); reduction
Anode: 2Br−(l) ➝ Br2(g) + 2e−; oxidation (also accept 2Br ➝ Br2)
d To prevent the re-oxidation of hot strontium by oxygen (air).

10 Organic chemistry
Quick check questions
 1 D
 2 a CH3CH2COOCH3
b CH3CH2CHCHCH3
c CH3CH2CH(OH)CH3
d (CH3CH2)3N
e CH3CH2COCH3
f CH3CH2CONH2
 3 a H b H H O H
H
H H O H H C C C C C
O
H C C C C H H H H
H C H
H H H H
H

c H O H H H d H H H H

H C C C C C H Cl C C C C C

H H H H H H H
H C H

e H H

H C C C H

 4 a 3; CH2CHCH2CH3 ; CH3CHCHCH3 ; CH2C(CH3)2

b 4; CH3CH2CH2CH2Br ; CH3CH2CHBrCH3 ; CH3CH(CH3)CH2Br ; CH3CBr(CH3)CH3
c 6; CH3CH2CH2CH2OH ; CH3CH2CH(OH)CH3 ; CH3CH(CH3)CH2OH; CH3C(OH)
(CH3)CH3 ; CH3CH2OCH2CH3 ; CH3OCH2CH2CH3

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 11 Measurement, data processing and analysis 22

 5 a butanamide
b ethyl propanoate
c diethylamine
d ethyl ethanoate
e ethyl methanoate
f ethyl-1-methylethanoate
g 2,2-dimethylpropanenitrile
h pentanenitrile
 6 a propane
C3H8 + 5O2 ➝ 3CO2 + 4H2O
2C3H8 + 7O2 ➝ 6CO + 8H2O
butane
2C4H10 + 13O2 ➝ 8CO2 + 10H2O
2C4H10 + 9O2 ➝ 8CO + 10H2O
b ethanol
C2H5OH + 3O2 ➝ 2CO2 + 3H2O
 7 a CH3CH2CH2OH(l) + CH3COOH(l) ➝ CH3COOCH2CH2CH3(l) + H2O(l)
b CH3CH2CH2CH2OH(l) + HCOOH(l) ➝ HCOOCH2CH2CH2CH3(l) + H2O(l)
c CH3CH2COOH(l) + CH3CH2OH(l) ➝ CH3CH2COOCH2CH3(l) + H2O(l)
 8 CH3CH3(g) + Cl•(g) ➝ CH3CH2Cl(g) + •CH3CH2(g)
•CH3CH2(g) + Cl2(g) ➝ CH3CH2Cl(g) + Cl•(g)
 9 a partial oxidation: propanal CH3CH2CHO
complete oxidation: propanoic acid CH3CH2COOH
b complete oxidation: propanone CH3COCH3
c no oxidation as this is a tertiary alcohol
d partial oxidation: butanal CH3CH2CH2CHO
complete oxidation: butanoic acid CH3CH2CH2COOH
10 50:50 mixture of concentrated nitric acid (HNO3) and concentrated sulfuric acid (H2SO4);
the active electrophile is +NO2, the nitronium ion (note the positive charge is on the nitrogen
atom)

11 Measurement, data
processing and analysis
Quick check questions
 1 a yes
b no
 2 Precision refers to how close the experimental measurements of the same physical quantity are
to each other. Accuracy refers to how close an individual reading is to the true, accepted or
literature value.
 3 5 s.f.; 4 s.f.; 1 s.f.; 6 s.f.; 3 s.f.; 6 s.f.; 1 s.f.; 6 s.f.

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 11 Measurement, data processing and analysis 23

 4 a 13.5 m3 (3 s.f.)
b 1900 g J mol−1 (2 s.f.)
c 1.02 g cm−3
d 2.00 J mol−1 (3 s.f.)
 5 a ΔG = –766 –
376 × 19.6
1000 (
= −733 kJ mol−1 (
Absolute uncertainty of ΔG = ± 20 +
≈ 30 kJ mol−1 (rounding up)
0.5
+
0.7
373 19.6 ( [(
×
373 × 19.6
1000 ( [( = ±20.3

ΔG = (−773 ± 30) kJ mol−1

[−773 −(−785)]
b % error = × 100% = 1.528% = 1.53%
−785
 6 a Amount of HCl = (24.40/1000) × 0.140 = 3.416 × 10−3 mol
Amount of KOH = 3.416 × 10−3 mol
b Concentration of KOH(aq) = 0.140 × 24.40/20.00 = 0.171 mol dm−3
c % error in volume of HCl = (0.04/24.40) × 100 = ±0.16%
% error in concentration of HCl = (0.002/0.140) × 100 = ±1.43%
% error in volume of KOH = ±0.2%
% error in concentration of KOH = 0.17% + 1.43% + 0.2% = 1.79% = ±1.9%
Concentration of KOH = 0.171 ± 0.003 mol dm−3
 7 magnesium does react directly with water, but very slowly; magnesium may have been oxidized
due to the large surface area; heat is lost to the surroundings and not accounted for in
calculation; assumption that the density of solution is 1 g cm−3 and specific heat capacity is the
same as that of pure water; heat is absorbed by the apparatus and thermometer repeating the
experiment many times and using only precise and temperature changes for averaging

Δq = 2080 
( Δm
m
+
( ΔT)
 (
T
or = 2800 ( 0.10 1
+
50.0 10.0(
 .0
= 212.16 = 220 J

(1367 − 855)
8 % error = × 100 ≈ 37.5% (37.45427%)
1367
The heat (thermal energy) gained by the copper container is not taken into account (via
knowing its specific heat capacity) / the burning wick may not transfer all the heat to the
water/ incomplete combustion (soot formation)
 9
0.7

0.6

0.5
Absorbance

0.4

0.3

0.2

0.1

0
0 0.1 0.2 0.3 0.4 0.5
Concentration/mol dm–3

concentration = 0.44 mol dm−3

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 11 Measurement, data processing and analysis 24

10

P2

V/dm3 P1

T/K

11 IHD = (14 − 12)/2 = 1

Cl
Cl Cl

Cl
or and many more

12 IHD values = 2, 1, 3, 2, 3 and 2

13 [CH3CH2CHO]+ ➝ [CH3CH2]+ + •CHO or ➝ CH3CH2• + [CHO]+
m/z = 29 m/z = 29
[CH3CH2CHO]+ ➝ [CH3CH2CO]+ + H• or ➝ CH3CH2CO• + H+
m/z = 57 m/z = 1
14 A: C2H535Cl+ and C2H537Cl+;
B: C2H479Br2+, C2H481Br2+, C2H479Br81Br+;
C2H5+
15 Cyclohexane
16 The bond angle (H–P–H) changes as bending occurs. The lengths of the P–H bonds change as
stretching occurs. The dipole moment of the phosphine molecule changes.
17 Mode of
vibration O C O O C O
O C O

IR active or IR IR inactive IR active IR active

inactive

18 Infrared waves have a smaller frequency and less energy and a lower wavenumber but longer
wavelength than red light waves.
19 4.08 × 10−7 m; 7.353 × 1014 s−1; 2.45 × 106 m−1
20 Carbon–carbon triple bond is stronger / shorter / more energy needed to vibrate it / cause resonance.
21 Ethene 1610–1680 cm−1 (>C=C<)
Ethane-1,2- diol 3200–3600 cm−1 (–O–H)
Ethane-1,2-dioic acid 2500–3300 cm−1 (–O–H in carboxylic acids) or 1700–1750 cm−1 (>C=O)
22 two wavenumber ranges common to the IR spectrum of both compounds:
(>C=O) 1680 to 1750 (cm−1);
(C–O) 1050 to 1410 (cm−1);
(C–H) 2840 to 3100 (cm−1);
one wavenumber range found only in the spectrum of one compound:
(–OH) 2500 to 3300 cm−1 (in methyl propanoic acid only)
23 It is a complicated region with many absorptions due to the large number of molecular
vibrations. This part of the infrared spectrum is totally unique to a particular molecule and so
can be used to identify and distinguish between compounds.

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 12 Electrons in atoms 25

24 An alkyne (hex-1-yne); C≡C and C–H

25 1, 3, 2, 1, 2
26 1, 3, 2, 5, 8
27 a Number of signals: the number of different hydrogen or proton environments. Integration
trace: the relative numbers or ratio of hydrogen / protons in each environment. Chemical
shift: effect of the neighbouring atoms, e.g. oxygen atom shifts the proton / hydrogen atoms
signal downfield (due to its high electronegativity).
b H H O
H C C C H

H H O C H

H
methyl propanoate

H O
H C C H H

H O C C H

H H
ethyl ethanoate

28 a number of signals in 1HNMR spectrum. 3; ratio of signals in 1H NMR spectrum. 2:3:3;

radio waves
b m/z 57: [CH3CH2CO]+; m/z 43: [CH3CO]+

12 Electrons in atoms
Quick check questions
 1 The two species are isoelectronic. Both have the same electronic configuration in the valence
shell: 3s2 3p3. As S+(g) has a higher nuclear charge (due to a greater number of protons in the
nucleus), the valence electrons in the S+(g) species will experience a greater attractive force.
Hence sulfur’s second ionization energy is larger than the first ionization energy of phosphorus.
 2 a Each letter represents an orbital orientated along the x-, y- or z-axis.
b The p orbitals are arranged mutually at right angles.
c Electrons are placed singly in degenerate orbitals before pairing occurs in one orbital
(to form a spin pair with electrons of opposite spin). This is known as Hund’s rule.
 3 The ‘4p’ orbitals should be labelled ‘3p’. Hund’s rule states that electrons will occupy degenerate
orbitals singly before any orbital is doubly filled (with a spin pair).
1s 2s 2px 2py 2pz 3s 3px 3py 3pz

 4 a He(g) ➝ He+(g) + e−
b 380 kJ mol−1 (±20 kJ mol−1)
c The noble gas atoms have the smallest radii (for their period) and the valence electrons
experience the highest effective nuclear charge.
d The group 1 metal atom has the largest radius (for their period) and has the smallest
effective nuclear charge in that period.

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 12 Electrons in atoms 26

e Each new energy level (shell) means a larger radius (less attraction for the valence electron)
and provides a greater shielding effect and hence reduced attraction by the nucleus.
There is a rapid increase in nuclear charge and the slight decrease in atomic radius from
lithium to neon atoms makes the attraction of the nucleus for outer electrons greater. The
effective nuclear charge increases across the period.
f A beryllium atom has the configuration 1s22s2 but a boron atom has the configuration
1s22s22p1. The valence electron in the boron atom is in a higher energy sub-level, further
away from the nucleus and more effectively shielded.
The electron removed from oxygen during ionization is from a spin pair in the 2p sub-level.
This experiences more repulsion than removal of the electron in a singly occupied 2p
orbital from nitrogen.
 5 Group 13. The first large change is between the third and the fourth ionization energies.
 6 5.5
5.0
4.5 two electrons in
n=1
log10∆Hi (N)

4.0
eight electrons in
3.5
n=2
3.0
2.5
two electrons in n = 2

1 2 3 4 5 6 7 8 9 10 11 12
Number of the electron removed (N)

As the electrons are successively removed from a gaseous atom, the protons increasingly
outnumber the remaining electrons. The effective nuclear charge experience by the remaining
electrons increase and they are all pulled closer to the nucleus.
 7 a Ti: 1s2 2s2 2p6 3s2 3p6 3d2 4s2, from the 3d sub-level
b The 5th electron is removed from 3p sub-level compared to the 4th electron from the 3d
sub-level. The electrons in the 3p sub-level are closer to the nucleus than the 3d sub-level,
hence the 4th electron experiences weaker forces of electrostatic attraction.
The 11th electron is removed from 3s sub-level compared to the 10th electron which is
from the 3p sub-level which is further away from the nucleus, hence the 10th electron
experiences weaker forces of electrostatic attraction.
 8 6.604 × 10−7 m
 9 1312.9 kJ mol −1
10 2.04 × 102 kJ mol −1
11 4.87 × 1014 s −1; 9 × 109 m; 3.23 × 10 −19 J
12 493 nm
13 74.42 nm; ultraviolet
14 a n = 1 to n = 4; n = 3 to n = 4
b III, I, II

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 13 The periodic table – the transition metals 27

13 The periodic table

– the transition metals
Quick check questions
 1 Ti: 1s22s22p63s23p63d24s2
Ti2+: 1s22s22p63s23p63d2
Ti4+: 1s22s22p63s23p6
 2 1s 2s 2p 3s 3p 4s 3d

Copper is a d-block element because it has 3d electrons in its outer main energy level. It
is a transition element because the copper(II) ion has unpaired 3d electrons; it has the
configuration d9.
 3 Scandium can form compounds with cations with an incompletely filled d sublevel; zinc only
forms Zn2+ with the 3d sublevel filled (d10).
 4 5; 4; 2 and 0.
 5 (NH4)2Cr2O7(s) ➝ N2(g) + 4H2O(g) + Cr2O3(s)
Cr2O72−: +6 and Cr3+: +3 and NH4+: −3 and N2: 0
 6 a Ti(g) ➝ Ti+(g) + e−; Ti3+(g) ➝ Ti4+(g) + e−
b 4th electron removed from 3d sublevel and 5th electron removed from the 3p sublevel;
electrons removed from lower energy level / energy level closer to nucleus and are attracted
more strongly.
 7 The calcium atom will lose two 4s electrons to form the calcium cation, Ca2+, resulting in a
stable ion with a noble gas configuration. A third ionization energy would involve the removal
of an electron in an inner 3p sublevel much closer to the nucleus which would be energetically
unfavourable. Transition metals are capable of forming a range of stable cations due to the
presence of 4s and 3d electrons, whose energy levels are relatively close in energy.
 8 Paramagnetic; the copper(II) ion, Cu2+, contains an unpaired electron in its 3d orbitals
(3d9 configuration). Diamagnetic: the zinc ion, Zn2+, does not contain any unpaired 3d
electrons (d10 configuration).
 9 Typical properties of transition metals are variable oxidation states, form complex ions with
ligands, have coloured compounds and display catalytic and magnetic properties. Iron forms
compounds with different oxidation states: +2 and +3. Magnesium only forms compounds with
an oxidation state of +2. Iron forms coloured compounds: iron(II) compounds are often pale
green; iron(III) compounds are often reddish-brown. Magnesium forms colourless compounds
(unless the anion is coloured). Iron forms many complex ions and complexes with well-
defined stoichiometry with ligands, but magnesium does not. Iron and its compounds often
show catalytic behaviour, but magnesium and its compounds do not. Iron(II) and iron(III)
compounds are paramagnetic, due to the presence of unpaired electrons. Magnesium and its
compounds are diamagnetic (due to the presence of spin pairs of electrons).
10 V3+; [Ar] 3d3 and Zn2+ [Ar] 3d10; V3+ not it in highest oxidation state (+5; +4 also stable) and can
be oxidized (by an oxidizing agent); Zn2+ in its highest oxidation state and cannot be oxidized
(to a higher oxidation state).
11 +7,+2 and +2 and +3; MnO4− and Fe2+
12 2+
H2O 2−
Cl
H2O OH2
−
Cu NC Ag CN
Cl Cu
H2O OH2
Cl
Cl
H2O

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 13 The periodic table – the transition metals 28

13 a [Ti(H2O)6]3+; 3+
b [CuCl4]2 −; 2−
c [CoI4]2 −; 2−
d [Cu(H2O)2(NH3)4]2+; 2+
e [Fe(SCN)(H2O)5]2+; 2+
f [Cu(CN2)2]; 0
g [Fe(CO)5]; 0
14 a Hydroxide ion, OH− and choride ion, Cl−, oxidation state of chromium is +3
b Cr3+ has the configuration 1s2 2s2 2p6 3s2 3p6 3d3; 3 unpaired electrons
15 [Co(H2O)6]2+ + 6Cl − ➝ [CoCl6]2 − + 6H2O
[Fe(H2O)6]3+ + SCN − ➝ [Fe(H2O)5SCN]2+ + H2O
There is no change in oxidation number.
16 a 6; +2
b molecules or anions with at least one lone pair of electrons; ligands use their lone pair
of electrons to form a coordinate covalent bond with the empty 3d and 4s orbitals of the
Cu2+ ion
c hexaquacopper(II) ion and pentaaquabromocopper(II) ion
17 [Ni(NH3)6]2+(aq) + 3H2NCH2CH2NH2(aq) ➝ [Ni(H2NCH2CH2NH2)3]2+(aq) + 6NH3(aq)
There is an increase in the number of ions on the right. The ammonia will form ammonium
ions.
18 bidentate; bidentate and bidentate
19 N O O
Cu

O O N

N N
Cu

O O O O

20 Optical isomerism / enantiomerism / stereoisomerism

Both will rotate plane-polarized light to the same extent / degree / angle but in opposite
directions.
21 a Diamminedichloroplatinum(II)
Cl NH3 H3N Cl
Pt and Pt
Cl NH3 Cl NH3
cisplatin transplatin

b Cl NH3 H3N Cl
M Pt and Pt
Cl NH3 Cl NH3
cisplatin M=0
transplatin
cis: polar and trans: non-polar

c X-ray crystallography / diffraction of X-rays

22 [Cu(H2O)6]2+ ➝ [Cu(H2O)5OH]+ + H+
The copper(II) ion is relatively small with +2 charge and hence has some polarizing power. It
will polarize a water molecule and cause the loss of a proton and retention of a hydroxide ion.
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 13 The periodic table – the transition metals 29

23 [Ti(H2O)6]3+appears violet because it absorbs yellow light / rays / complementary colour

24 It has partially filled 3d orbitals and the d sublevel splits into two energy levels (d–d*) in the
presence of ligands, allowing a d electron from the lower energy 3d orbital to absorb energy
from the visible spectrum and be excited to the higher energy 3d orbital. The colour observed
is complementary to the colour absorbed.
25 The ammonia ligand, NH3, causes a greater degree of d–d splitting resulting in a larger energy
gap between the two sets of d orbitals; hence the wavelength absorbed is shorter (blue) whereas
the water ligands, H2O, cause a smaller degree of d–d splitting and radiation (light) of a longer
wavelength (orange) is absorbed.
26 The electronic configuration of Zn2+ is [Ar] or [Ar] 3d10 / fully filled d sub-level. Hence, there
d–d transitions cannot occur as all the d orbitals are fully occupied with spin pairs of electrons.
27 Fe3+ (because of its greater positive charge) pulls the water ligands closer (to the central
cation); the energy levels of the two sets of 3d orbitals are split wider with a larger energy gap;
d electrons absorb higher frequency / energy / violet light when then undergo a transition from
lower energy level to higher energy level.
28 The gaseous reactants molecules are adsorbed on the surface / increases surface concentration
/ bonds weakened / products formed and desorb. The catalyst lowers the activation energy
barrier by providing an alternative pathway or mechanism for reaction.
29 a 2I −(aq) + S2O82 −(aq) ➝ I2(aq) + 2SO42 −(aq)
b The uncatalysed reaction involves a step involving two anions, which experience repulsion.
c 2Fe2+(aq) + S2O82 −(aq) ➝ 2Fe3+(aq) + 2SO42 −(aq)
2Fe3+(aq) + 2I −(aq) ➝ 2Fe2+(aq) + I2(aq)
30 CrF64− contains Cr2+ (d4)

small

The fluoride ion, F−, must be a weak field ligand to produce high-spin configuration.
31 a Nature / identity of metal ion (cation); oxidation state / oxidation number charge of metal
ion (cation); nature of ligands; molecular geometry of complex ion / coordination number
of metal ion (cation).
b [FeX6]2+ [FeX6]2+
eg eg

t2g t2g

CrF64− ➝ Cr2+ (d4)

The fluoride ion, F −, must be a weak field ligand to produce high-spin configuration.
Y since the coordination number is 6 but with 3 ligands; hence each ligand forms 2
coordinate bonds with the iron(II) cation.
c X < Y < Z; complex ion with ligand X absorbs light at longest wavelength hence smallest
ΔE in complex / Complex with ligand Z absorbs light at shortest wavelength hence largest
ΔE in complex / Complex with ligand X is paramagnetic which implies a small value of ΔE
thus maximum spin while in Z, ΔE is large hence minimal spin.
d
small

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 14 Chemical bonding and structure 30

14 Chemical bonding
and structure
Quick check questions
 1 O
F
F
Xe
F F

square pyramidal, 90°

F F
Br
F F

square planar, 90°

 2 Number of electron domains is five: four bonding pairs and one lone pair, n = 1.
 3 linear, 180°; bent / V-shaped / non-linear, between 90° and 109°
−
 4
I − I − I

linear
 5 a N

O O

Bent/V-shaped/ angular; 109.5° < θ < 120°;

b Bond angle: 109.5° < θ < 120°; less than 120° because of the added repulsion of the lone
pair
Resonance structures:
−1 −1
O N O O N O

N δ+

δ− O O δ−

 6 a Electron domain geometry; molecular shape: trigonal pyramidal and O–Cl–O bond angle.
b In Lewis structure I, the FC of Cl is 0 while O is −1; in Lewis structure II, the FC of Cl is −1
while O is 0. Structure II does not obey the octet rule, but chlorine is in period 3 (row 3) of the
Periodic Table and can accommodate an expanded valence shell.
 7 a

−3 +1 +1 − −2 +1 0 − −1 +1 −1 −
C N O C N O C N O

b The circled structure is more stable; D formal charge is closest to zero.

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 14 Chemical bonding and structure 31

8
N O

Formal charge (FC) on nitrogen: 0 and formal charge (FC) on oxygen: 0

 9 Sigma bonds are formed by end on / axial overlap of orbitals with electron density between the
two carbon atoms / nuclei; pi bonds are formed by sideways overlap of parallel p orbitals with
equal regions of electron density above and below the inter-nuclear axis / sigma bond.
10 a mixing / joining together / combining / merging of atomic orbitals to form the same
number of molecular orbitals / new orbitals / orbitals of equal energy / identical shape
b sp hydridized; one sigma and two pi (bonds).
11 12 sigma bonds; 2 pi bonds
12 a H H

C C
H H

b sp2; 5 σ bonds and 1 π bond

c the sigma bond is formed by head-on overlap and merging of hybridized sp2–sp2 of the two
carbon atoms / sp2 hybridized orbitals of carbon and 1s hydrogen orbitals along the inter-
nuclear axis; a pi bond is formed by the side-on overlap and merging of parallel p-orbitals
13 a Conjugation refers to a system of alternating carbon–carbon double (triple) and carbon–
carbon single bonds. Delocalization refers to molecules or ions that have p orbitals
extending over three or more atoms with delocalized pi electrons;
b sp2 hybridization
c longer than the C=C bond but shorter than the C-C bond / between 0.134 to 0.154 nm
d 4 pi electrons are delocalized / resonance.
Ground state configuration Excited state configuration
of carbon atom of carbon atom
promotion
of one 2s sp2
ENERGY

2p electron 2p hybridization 2p

2s 2s
three sp2
hybrid orbitals

14 a O N Cl

b bent; V-shaped, non-linear; bond angle: between 119° and 107°

c Hybridization refers to the mixing and merging of atomic orbitals (to form the same number
of new bonding/molecular orbitals); nitrogen is sp2 hybridized and chlorine is sp3 hybridized.
15 sp3, sp2 and sp2
16 a 8 sigma bonds, 10 lone pairs, 4 pi bonds
b 104° (accept from 103 to 106°)
c sp2 hybridization; nitrogen has 3 electron domains.
d S N
N S

S N
N S

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 15 Energetics/thermochemistry 32

17 molecule sp hybridized sp2 hybridized sp3 hybridized

Butanal CH3(CH2)2CHO 1 3

Pentane, C5H12 5
Ethylbenzene, C6H5-C2H5 0 6 2

18 H N H
N N

Trigonal planar, <109 °, sp3, sp2 and sp2, 5 sigma bonds and 1 pi bond
19 a 8 sigma bonds and 1 pi bond
b
C C C C C C
CH3 CH3 CH3

c The two p orbitals overlap sideways to form one localized pi bond over two carbon atoms.
The bond is localized as the electron cloud is just over the two bonded atoms.
20 a 2O3(g) ➝ 3O2(g)
b O• + NO• ➝ NO2 or O3 + NO ➝ NO2 + O2
NO2 + O3 ➝ 2O2 + NO or NO2 + O3 ➝ NO + 2O2
21 a O=O bond = 498 kJ mol−1
  = 498 000 J; 1 mol = 6.02 × 1023
Energy of O=O bond = 498 000 J /(6.02 × 1023 mol−1);
E = hv and c = vλ , therefore λ = hc/E ;
1
λ = 6.63 × 10−34 mol−1 × 3.00 × 108 m s−1 × × 6.02 × 1023 mol−1
498 000
= 2.40 × 10−7 m = 240 nm
b Bond order in ozone (1.5) is lower than oxygen (2); the lower bond order and hence weaker
bonding in ozone is due to the delocalization of pi electrons (or resonance).
22 Cl• + O3 ➝ ClO• + O2,
ClO• + O3 ➝ Cl• + 2O2 ,
Overall equation: 2O3 ➝ 3O2;
The chlorine atom / radical Cl• is a catalyst as it is consumed and regenerated in the process.

15 Energetics/thermochemistry
Quick check questions
 1 Work has to be done (energy absorbed) to pull the ions away from each other and overcome
the attractive electrostatic forces.
 2 MgO(s) ➝ Mg2+(g) + O2−(g)
AlF3(s) ➝ Al3+(g) + 3F–(g)
K2S(s) ➝ 2K+(g) + S2–(g)
Na2O2s) ➝ 2Na+(g) + O22−(g)

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 15 Energetics/thermochemistry 33

1 1
 3 a N (g) ➝ N(g); Ba(s) ➝ Ba(g); I2(g) ➝ I(g); Sc(s) ➝ Sc(g)
2 2 2
b It is zero for neon because it exists in the form of gaseous atoms under standard conditions.
 4 a The lattice enthalpy is the energy required to convert one mole of ionic solid into gaseous
ions.
b Enthalpy of atomization for M: M(s) ➝ M(g); enthalpy of atomization for X: X(s) ➝ X(g); first
ionization energy of M: M(g) ➝ M+(g) + e−; first electron affinity of X: X(g) + e− ➝ X−(g) and
enthalpy of formation of MX: M(s) + X(s) ➝ MX(s).
 5 Mg2+(g) + O2−(g)
∆H 12nd EA(O) = +753
Mg2+(g) + O(g) kJ mol−1

∆H 12nd IE(Mg) ∆H 11st EA(O) = –141

kJ mol−1
= +1451 kJ mol−1 2+ −
Mg (g) + O (g)
Mg+(g) + O(g)

∆H 1Ist IE(Mg) = +738 kJ mol−1

Mg(g) + O(g)

∆H 1at(O2) = +249 kJ mol−1 ∆H 1IE(MgO)

Mg(g) + 1 O2(g)
2

∆H 1at(Mg)
= +148 kJ mol−1
Mg(s) + 1 O2(g)
2

∆H 1f(MgO) = –602 kJ mol−1

MgO(s)

 6 a Ba2+(g) + 2e− + 2Br(g)

(IE2) 965 kJ mol−1 (EA) =

2 × 325 kJ mol−1
Ba+(g) + e− + 2Br(g)

(IE1) 503 kJ mol−1

Ba(g) + 2Br(g) Ba2+(g) + 2Br−(g)

(BDE) 193 kJ mol−1

Ba(g) + Br2(g)
(LE)
1950 kJ mol−1
(SE) 175 kJ mol−1

Ba(s) + Br2(g)
(∆Hf ) − 764 kJ mol−1

BaBr2(s)

b Lattice enthalpy = [2 × (−325)] + 965 + 503 + 193 + 175 − (−764) = 1950 kJ mol−1

 7 a Enthalpy of formation of AuCl2(s) = +368 + 890 + 1980 + 242 + 2(−349) − 2180
= 602 kJ mol−1
b This large positive formation enthalpy means that AuCl2(s) is energetically unstable.
 8 The charges remain constant, but there is an increase in ionic size from fluoride to iodide. The
larger ions have smaller charge densities, which reduce the attraction to the sodium ions and
hence reduces the lattice enthalpy.
 9 Size of ions and charge of ions; the charge on the calcium ion Ca2+ is twice that of the
potassium K+ ion; the size of Ca2+ is smaller than of the K+ ion. Therefore, the lattice enthalpy of
potassium chloride, KCl will be less endothermic compared to that of calcium chloride, CaCl2.
10 −123 + (1650) + (−2255) = −728
ΔHhydration Cl−(g) = −728/2 = −364 kJ mol−1

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 15 Energetics/thermochemistry 34

11 The chloride ion has a smaller radius than the bromide ion and hence its charge / size ratio
is greater. Water molecules are polar and therefore chloride ions interact with the partially
positive hydrogen atoms in the water molecules. This interaction (ion–dipole attraction) with
chloride ions is stronger than the interactions between water molecules and bromide ions.
Hence more energy is released to the surroundings by chloride ions compared to bromide ions.
12 Solubility depends on the balance of energy required to destroy the solid structure, the
lattice energy (enthalpy) and the energy released when ions are hydrated by water molecules
(hydration enthalpy). So a compound like M2O3 is expected to have a significantly larger
lattice energy due to its higher charges: (3+)(2−) versus (1+)(1−) in MX. This will make the
enthalpy for dissolution likely much more positive and unfavorable.
13 A spontaneous process occurs by itself, whereas a non-spontaneous process requires a
continuous input of energy to make it occur. It is possible to cause a non-spontaneous
process to occur, but the process stops once the energy source is removed. A reaction that is
spontaneous at one temperature, may become spontaneous at a different temperature.
14 The low molar entropy of ice indicates that the structure is very organized into a regular,
repeating lattice; in water there is less structure and no long range organization in the structure
and the much higher value for steam because of a very disordered and constantly changing
random arrangement of molecules.
15 a decrease
b increase
c decrease
d decrease
e increase
f increase
g decrease
h increase
i decrease
16 a 16
b 1/16
c 87.5%
17 The entropy is low at the start because the water molecules are arranged into a regular
repeating lattice in the form of ice crystals and so there is a relatively small number of ways
to arrange the molecules and a relatively small number of ways to distribute quanta within
the molecule. As the ice melts, the water cools, and any given water molecule can be found
anywhere in the glass. Now there are many more ways to arrange the molecules and distribute
their quanta in energy levels due to the broadening of temperature. The entropy is now much
higher and is maximized once equilibrium is achieved.
18 ΔSsurroundings = −ΔH/T = −17 800 J mol−1 / 300 K = −593.3 J K−1 mol−1
ΔStotal = ΔSsurroundings + ΔSsystem = −593.3 J K−1  mol−1 + 160.4 J K–1 mol−1 = −433 J K−1 mol−1
The reaction is not spontaneous at 300 K.
ΔSsurroundings = −ΔH/T = −17 800 J/1200 K = −148.3 J K−1 mol−1
ΔStotal = ΔSsurroundings + ΔSsystem = −148.3 J K−1 mol−1 + 160.4 JK−1 mol−1 = +12.1 J K−1 mol−1
The reaction is spontaneous at 1200 K.
19 a The two gases gradually diffuse into each other until the concentrations of each gas are the
same at all points in both bulbs.
b ΔH = 0, ΔS is positive and ΔG is negative.
c Yes, it is consistent.
20 ΔG = −TΔSuniverse and the second law of thermodynamics states that all spontaneous reactions
involve an overall increase in entropy. If ΔSuniverse is positive then −TΔSuniverse must be negative.

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 16 Chemical kinetics 35

21 Non-spontaneous under standard conditions, therefore ΔG > 0

22 Steam condenses to water when ΔG < 0; ΔH = TΔS;
ΔS = 189 − 70 = 119 J K−1 mol−1; ΔH = 373 × 119 = 44 kJ mol−1
23 diamond ➝ graphite ΔS = +3 J K−1 mol−1 since ΔH < 0, ΔG is always < 0 kinetics: large
activation energy, Ea, makes reaction extremely slow: kinetically hindered
24 CaO(s) + CO2(g) ➝ CaCO3(s)
ΔS = 90 − (214 + 40) = −164 J K−1 mol−1
ΔG = ΔH – TΔS
and to be spontaneous ΔG < 0.
Temperature at which – TΔS > 178 is 1085 K.
25 a ΔG = ΔH – TΔS; ΔH = c and (−)ΔS = m / ΔH and ΔS are constants; ΔH is the intercept,
and (−)ΔS is the slope / gradient
b because the entropy change / ΔS is positive / TΔS becomes larger/ −TΔS becomes more
negative
c not feasible / unfeasible / not spontaneous
26 ΔG1 = ΔG1f (CuO(s)) − ΔG1f (H2O(g)) = (−129.7 kJ mol−1) − (−228.6 kJ mol−1)
ΔG1 = 98.9 kJ mol−1; the positive sign indicates that the reaction is non-spontaneous; that is, the
reverse reaction is spontaneous.
27 because bromine is a liquid under standard thermodynamic conditions
28 ΔG1 = −RTlnK = − (8.31 J K−1 mol−1) × (298 K) × (ln 1.8 × 10−5) = 2.7 × 104 J mol−1 or
2.7 × 101 kJ mol−1
29 2.22 × 106
30 An equilibrium constant less than 1 indicates the equilibrium mixture contains very little
product. The reaction is not spontaneous in the forward direction and ΔG is a relatively large
positive value.
31 A large negative value for ΔG indicates that the reaction is spontaneous and goes almost to
completion. The equilibrium mixture will contain a high concentration of product, so Kc > 1.
The reaction quotient, Q, depends on initial conditions, not equilibrium conditions, so its
value cannot be predicted from ΔG.
32 The equilibrium position; ΔG

16 Chemical kinetics
Quick check questions
 1 A
 2 C
 3 Plot gives a straight line passing through the origin / shows a directly proportional relationship
between rate and [I−(aq)] / reaction is first order with respect to [I−(aq)]
 4 a Plot of rate against [H2O2(aq)] gives a straight line / the reaction is first order with respect to
[H2O2(aq)]
b gradient of the line = rate constant k = 7.4 × 10−4 s−1

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 17 Equilibrium 36

 5 a first order / second order / third order overall

Rate = k [A] [B]2
b k = 1.21 × 10−2 dm6 mol−2 s−1
c rate = 8.65 × 10−6 mol dm−3 s−1
 6 rate = k[NO]2 [O2]
k = 71.1 dm6 mol−2 s−1
 7 a rate = k [NO]2
b intermediate
Ea for step 1
Ea for step 2
reactants
Potential energy

ΔH
products

Progress of reaction

 8 H2O2 ➝ 2OH
 9 a C + B2 ➝ BC + B
A + B ➝ AB
b A + B ➝ AB
A + AB ➝ A2B
c NO + H2 ➝ H2O + N
NO + N ➝ N2 + O
H2 + O ➝ H2O
10 43 kJ mol−1
11 41.6 kJ mol−1
12 a A small amount of catalyst greatly increase the rate of reactions; undergoes no permanent
chemical change or change in mass; the catalyst provides an alternative reaction pathway
of lower activation energy; the catalyst does not increase the equilibrium constant, but
equilibrium is reached faster.
b The catalyst and reactants are in the same physical state.
c +1 and 4
d The presence of a lone pair of electrons on the phosphorus atom.
e C6H10 + H2 ➝ C6H12
f Bubble through bromine – if there is no loss of colour or reduction in intensity then the
reaction has gone to completion.
g The ability of transition metals to interconvert between two or more stable cations via
redox reactions.

17 Equilibrium
Quick check questions
 1 a Kc = [NH3(g)]2 / [N2(g)] [H2(g)]3
b Kc = 2.09

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 18 Acids and bases 37

 2 a Kc = [NO]2[Cl2] / [NOCl]2 or Kc = [NO(g)]2[Cl2(g)] / [NOCl(g)]2

b at 503 K: Kc = 4.5 × 10−3
at 738 K: Kc = 9.2 × 10−2
c The value of Kc is greater at 738 K; Kc increases with temperature, with the forward reaction
being favoured to increase the proportion of products in the equilibrium mixture. This
suggests that the forward reaction is endothermic.
 3 a CO(g) + H2O(g) ⇌ H2(g) + CO2(g)
b Kc = [H2] [CO2] / [CO] [H2O] or Kc = [H2(g)] [CO2(g)] / [CO(g)] [H2O(g)]
Kc = 1.84
 4 Kc = 33
5 [CH3OH(g)] = 2.4 × 10−3 mol dm−3
6 [H2(g)] = 5.2 × 10−7 mol dm−3
 7 ΔG1 = −33.3 = kJ mol−1
 8 a ΔG1 = 0
b ΔG1 = +69.73 kJ mol−1
 9 a K = e−1.79 = 0.166
b The equilibrium constant value is less than 1.00 and so the equilibrium is well to the
reactants side of the equation.

18 Acids and bases

Quick check questions
 1 Water acts as a base in both reactions; HBr is a Brønsted–Lowry base / proton acceptor;
Fe3+(aq) is a Lewis base / electron pair donor.
 2 Brønsted–Lowry base: a substance that accepts a proton (H+); Lewis base: a substance that
donates an electron pair to form a coordinate bond.
 3 Boric acid acts as a Lewis acid because it accepts an electron pair from the hydroxide ion
released by the water molecule. It is not a Brønsted–Lowry acid because it does not donate a
proton to the water molecule; it acts as a hydroxide ion acceptor.
 4 B(CH3)3 (electrophile), OH− (nucleophile), HOCH3 (nucleophile), CN− (nucleophile)
CH3CH2O− (nucleophile) C6H5–CH2+ (electrophile) and HI (electrophile).
 5 CH3COO−, Cl− and NH3 are Lewis bases in a, b and c respectively.
[NH4+][OH−]
6 Kb = 10−4.75 = 1.78 × 10−5; Kb = /[OH−(aq)] = √(Kb[NH3])
[NH3]
[OH−(aq)] = √(1.78 × 10−5 × 0.121); pOH = 2.83; pH = 14.00 − 2.83 = 11.17
 7 4.5 × 10−4
 8 1.77 × 10−5
 9 9.8 × 10−3 mol dm−3; 2.01
10 4.30 × 10−3 mol dm−3
11 HClO and C6H5NH2
12 R > Q > P > S
13 [H+] = √(5.0 × 10−10 × 0.2) = 10−5 mol dm−3
14 [OH−(aq)] = 1.0 × 10−2 mol dm−3; 1.0 × 10−2 = √(Kb × 0.15); Kb = 6.7 × 10−4
15 Kw = 5.60 × 10−13 mol2 dm−6 = [H+][OH−]; pH = −log10 √(5.60 × 10−13) = 6.13

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 18 Acids and bases 38

16 [H+] = 5.60 × 10−13/0.100 = 5.60 × 10−12 mol dm−3; pH = 11.3

17 The ionization / dissociation of water to H+ / H3O+ and OH− / H2O ⇌ H+ + OH−;
2H2O ⇌ H3O+ + OH−; the forward reaction is an endothermic process due to –O–H bond
cleavage;
By applying Le Châtelier’s Principle, raising the temperature will shift the position of
equilibrium to the right, resulting in a higher concentration of H3O+/H+ and OH–; neutral
because for water, [H+] = [OH−]
18 Amount of KOH = 0.05 dm3 × 0.50 mol dm−3 = 0.025 mol
Amount of HCl = 0.20 dm3 × 0.10 mol dm−3 = 0.02 mol
0.005  mol of excess KOH/OH− present in 250 cm3 of solution
Concentration of KOH = 0.02 mol dm−3
pOH = −log10 [OH−(aq)] = 1.69 = 1.7; pH = 14.0 − 1.7 = 12.3
19 1.90; 12.10
20 11.6; 2.4
[CH3CH2NH3+][OH–] [ OH–]2
21 Kb =  ; 10–3.35 =
[CH3CH2NH2] 0 .500
[OH−] = 0.0149 mol dm−3; pOH = 1.83 ; pH = 12.17
22 [NH4Cl] = 53.30 g/53.50 g mol−1 = 1.00 mol dm−3; amount of NH3 = 14 mol dm−3 × 0.4 dm3
= 6 mol; [NH3] = 5.60 mol dm−3
23 A buffer solution is one that resists changes in pH when a small amount of acid or base
is added to it; the conjugate base, CH3COO− removes the added acid by reacting with it:
CH3COO− + HCl ➝ CH3COOH + Cl− or CH3COO− + H+ ➝ CH3COOH; the ethanoic acid
molecules remove the added KOH by reacting with it: CH3COOH + KOH ➝ CH3COO−K+ +
H2O or CH3COOH + OH− ➝ CH3COO− + H2O.
24 a 20.00 cm3
b at the half-equivalence point of 10.00 cm3, pH = pKa; pKa is 4.75 hence the acid is ethanoic
acid
c Owing to negative inductive effect of chlorine (relatively electronegative atom) the
ionization of chloroethanoic acid increases and its Ka value is higher than ethanoic acid.
25 basic; neutral; basic; basic; acidic; neutral
26 Potassium ions have only a +1 charge and a relatively large size and hence low charge density
with low polarizing power. They are unable to polarize the O–H bond in the water ligand
strongly enough to release H+ ions (protons) in solution.
27 Slightly acidic due to hydrolysis / polarizing effect of Cu2+ which has a charge density sufficient
to dissociate water molecules.
[Cu(H2O)6]2+(aq) + H2O(l) ➝ [Cu(OH)(H2O)5]+(aq) + H3O+(aq)
neutral; Ba(NO3)2 is formed from a neutralization reaction involving a strong base Ba(OH)2
and a strong acid (HNO3) and the ions of the salt do not undergo hydrolysis; alkaline because
HCO3− is a weak base: and undergoes hydrolysis with water molecules:
HCO3−(aq) + H2O(l) ➝ H2O(l) + CO2(aq) + OH−(aq) / HCO3−(aq) + H2O(l) ➝ H2CO3(aq) +
OH−(aq)
28 HIn(aq) ⇌ H+(aq) + In−(aq);
colour A     colour B
in presence of acid / H+, equilibrium shifts to the left, colour A predominates;
in presence of base / OH−, equilibrium shifts to the right, colour B predominates;
bromophenol blue / bromocresol green / methyl red
29 yellow, colourless and green (yellow and blue)
30 orange (a mixture of red, yellow and colourless)
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19 Redox processes
Quick check questions
 1 Platinized platinum electrode; H2 gas at 100 kPa; [H+(aq)] = 1 mol dm−3 HCl/0.5 mol dm−3 H2SO4;
temperature = 298 K / 25 °C
 2 A A solution of ReO4− (aq) at 298 K and 1 mol dm−3
B Platinum electrode (coated with a layer of rhenium)
C Salt bridge
D Hydrogen gas at 209 K and 100 kPa
E H+ /HCl/H3O+ at 1 mol dm−3

From SHE to the rhenium half cell (left to right); to complete the circuit / allows movement
of anions and cations between electrolytes / maintain electroneutrality; saturated aqueous
potassium nitrate/potassium chloride
 3 When an aluminium half-cell which consists of an aluminium electrode in contact with
a 1 mol dm−3 aqueous solution of Al3+(aq) connected to the SHE, the potential difference
measured will be +1.66 V. Aluminium atoms have a higher tendency to lose electrons
than hydrogen molecules. Electrons will flow from the aluminium half-cell to the SHE:
Al3+(aq) + 3e− ➝ Al(s).
When a copper cell is connected to a SHE, the electrode potential measured is −0.34 V and
the electrons will flow from the SHE to the copper half-cell. Hydrogen molecules have a greater
tendency to lose electrons than copper atoms: Cu2+(aq) + 2e− ➝ Cu(s).
 4 silver(I) ions, Ag+(aq)
 5 Zn(s) ➝ Zn2+(aq) + 2e−; 2e−+ Pb2+(aq) ➝ Pb (s)
2e− + 2H+(aq) ➝ H2(g); Ca (s) ➝ Ca2+(aq) + 2e−
 6 Al(s) | Al3+(aq) || Ag+(aq) | Ag(s); Al(s) + 3Ag+(aq) ➝ Al3+(aq) + 3Ag(s)
E1 = (1.66 V) + (0.80 V) = +2.46 V
 7 MnO4−(aq) + 8H+(aq) + 5Fe2+(aq) ➝ Mn2+(aq) + 4H2O(l) + 5Fe3+(aq)
Pt(s) | Fe2+(aq), Fe3+(aq) || MnO4−(aq), Mn2+(aq) | Pt(s)
 8 E1cell = 0.77 V − (−0.26 V) = 1.03 V: yellow/brown to green at Fe3+/Fe2+ half-cell; nickel electrode
decreases in mass / size; nickel ion concentration increasing;
2Fe3+ + Ni ➝ 2Fe2+ + Ni2+
9 E1cell = +1.56 V; ΔG1 = − (2) (9.65 × 104 C mol−1) (+1.56 V) = −301 kJ mol−1
10 3.2
11 VO2+(aq); species most readily gains electrons (in aqueous solution) to form VO2+(aq) and
H2O(l) / most positive E1 value; Zn(s); species most readily loses electrons (in aqueous solution)
to form zinc ions, Zn2+(aq); Zn(s) + 2VO2+(aq) + 4H+(aq) ➝ Zn2+(aq) + 2VO2+(aq) + 2H2O(l); a
positive cell potential implies a spontaneous reaction and hence a negative value of negative
ΔG1 due to the relationship: ΔG1 = −nFE1.
12 E1cell = (+0.77 V) − (0.00 V) = +0.77 V; electrons will flow from the hydrogen half-cell to the
Fe3+/Fe2+ half-cell through the external circuit. H2(g) + 2Fe3+(aq) ➝ 2H+(aq) + 2Fe2+(aq); when
the concentration of the Fe3+ ion is increased the reaction will be shifted towards the right
hand side, making the cell potential more positive (> 0.77 V).
13 Mn2+ is a weaker oxidizing agent than H2O and H+ will be discharged to form H2, in preference
to Mn2+.
14 Dilute sodium chloride: 2H2O ➝ O2 + 4H+ + 4e−; 4OH− ➝ O2 + 2H2O + 4e−
Concentrated sodium chloride: 2Cl− ➝ Cl2 + 2e−
15 Sulfuric acid is formed which results in a decrease in pH: 2H2O ➝ O2 + 4H+ + 4e−

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16 Anode: Ag (s) ➝ Ag+(aq) + e−; cathode: Ag+(aq) + e− ➝ Ag (s)

17 Molten sodium chloride releases mobile Na+ and Cl− ions; Na+ migrates towards the cathode
and undergoes reduction: Na+ + e− ➝ Na. In aqueous sodium chloride, since the E1 H+/H2 > E1
Na+/H2, it is hydrogen gas which is produced at the cathode: 2H+ + 2e− ➝ H2.
18 item to be
+ power –
nickel plated at
anode supply cathode

Ni2+
Ni Ni2+
SO42–
SO42– Ni2+ Ni
SO42–
Ni2+
SO42–

19 a Electrode X
b Electrode X: Cr3+(aq) + 3e− ➝ Cr (s); Electrode Y: Cr (s) ➝ Cr3+(aq) + 3e−;
c because H+ ions are discharged / H2 gas is produced instead / standard reduction
potential of aluminium is relatively negative
20 Anode: Cu ➝ Cu2+ + 2e−; cathode: Cu2+ + 2e− ➝ Cu
Q = 2.40 A × (25 × 60) s = 3600 C
Amount of electrons = 3600 C/96 500 C mol−1 = 3.73 × 10−2 mol
3.73 × 10−2
Mass of copper = ( ) × 63.58 g mol−1 = 1.186 g
2
21 2:2:1
22 1:4
23 Ag+(aq) + e− ➝ Ag (s); amount of silver atoms = 0.200 g/107.87 g mol−1 = 0.00185 mol; amount
of electricity needed to deposit 0.00185 mol of Ag = 96 500 C mol−1 × 0.00185 mol = 178.53 C;
178.53 C = I × 1200 s; I = 0.149 A = 149 mA

20 Organic chemistry
Quick check questions
 1 a Polar aprotic solvents will not interact with the attacking nucleophile forming a ‘solvent
shell’. The nucleophile remains ‘naked’. A nucleophile with a solvent shell is going to
be slower in attacking the target molecule. By using an aprotic solvent and allowing the
nucleophile to react all of the time, we are greatly speeding up the reaction. SN2 reactions
performed with nucleophiles in polar aprotic solvents occur about 1000 times faster than
those in regular protic solvents.
b DMF is a better solvent for this reaction as it is a polar aprotic solvent whereas water is a
polar protic solvent which will shield the nucleophile by forming a solvent shell. Water has
hydrogen atoms that are attached to a highly electronegative element, oxygen.
 2 a CH3CHBrCH2CH3
b Cl is more electronegative than Br, so the Cl will be δ− and the Br δ+
CH3CH2CHBrC(CH3)2Cl
 3 a butan-1-ol
b 3-methylbutan-2-ol

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 4 a Reduction with LiAlH4 in diethyl ether; reflux; add dilute acid to complete reaction.
b Not a possible route.
c Reaction with bromine vapour (or in an organic solvent) in sunlight (UV light).
d Reaction with chlorine or bromine in an organic solvent (in dark).
e Heat with concentrated sulfuric acid and then add water.
f Reaction under reflux (50 °C) with a nitrating mixture of concentrated nitric acid and
concentrated sulfuric acid.
g Reflux with tin and concentrated hydrochloric acid.
h Warm with sodium dichromate(VI)/concentrated sulfuric acid in distillation apparatus.
 5 but-1-ene ➝ (react with HBr) ➝ 2-bromobutane ➝ (react with NaOH solution) ➝ butan-2-ol
➝ (oxidation with Na2Cr2O7 / concentrated H2SO4) ➝ butanone
or
but-1-ene ➝ (react with conc. H2SO4 /add water) ➝ butan-2-ol ➝ (oxidation with
Na2Cr2O7 / concentrated H2SO4) ➝ butanone
The second method may give the greater yield as it involves fewer stages
 6 1-chlorobutane ➝ (react with NaOH solution) ➝ butan-1-ol ➝ (oxidation with
Na2Cr2O7 / concentrated H2SO4 under reflux) ➝ butanoic acid
CH3CH2CH2CH2Cl + OH– ➝ CH3CH2CH2CH2OH
CH3CH2CH2CH2OH + 2[O] ➝ CH3CH2CH2COOH + H2O
 7 a and c show cis–trans isomerism, b does not
1-chlorobut-1-ene
Cl CH2CH3
C C Z-form
H H

H CH2CH3
C C E-form
Cl H

3-methylpent-2-ene
CH3CH2 CH3

C C Z-form

CH3 H

CH3 CH3

C C E-form

CH3CH2 H

 8 five
 9 D

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 21 Measurement and analysis 42

10 In each case decide the priority of the different groups attached to the carbon atoms making
the carbon–carbon double bond
A is the E-isomer as the high-priority groups are on different sides of the molecule (different
carbon atoms of the two forming the double bond).
B is the E-isomer as the high-priority groups are on different sides of the molecule.
C is the Z-isomer as the high-priority groups are on the same side of the molecule (attached to
the same carbon atom of the two forming the double bond).

21 Measurement and analysis

Quick check questions
 1 A doublet and a quartet and a sextet
 2 High-resolution 1H NMR spectrum for 2-chloropropanoic acid, CH3CHClCOOH

TMS

12 11 10 9 8 7 6 5 4 3 2 1 0
Chemical shift/ppm

High-resolution 1H NMR spectrum for 3-chloropropanoic acid, CH3CHClCOOH

TMS

12 11 10 9 8 7 6 5 4 3 2 1 0
Chemical shift/ppm

3 H C O
3

CH2
O CH3

three types of hydrogen / proton environments

two –CH3 groups (peak area 3) and one –CH2– group (peak area 2)
one of the –CH3 groups is next to an electronegative oxygen (at 4.1 ppm), proton/hydrogen
most deshielded / downfield signal
one of the –CH3 groups is adjacent to a carbon atom (at 0.9 ppm), proton / hydrogen atom most
shielded / upfield
the –CH2– group next to >C=O at 2 ppm, signal is in between the two extremes one of the
–CH3 groups, has no neighbouring protons / hydrogen atoms produces a singlet
one of the –CH3 groups next to –CH2– (2+1) produces a triplet
the –CH2– next to –CH3 / –C2H5 (3+1) produces a quartet

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 4 The IHD is zero which means that the compound contains no rings or double bonds. Six
equivalent hydrogen atoms usually implies two methyl groups. This is a doublet, so the six
hydrogen atoms have one neighbouring hydrogen atom which is logical since the other
hydrogen atom is a septet (seven peaks, six hydrogen atom neighbours). This gives the following
partial structure meaning the compound is 2-iodopropane.

H3C C CH3

 5 tetramethysilane / TMS
strong single peak (as there are 12 hydrogen atoms (protons) in identical chemical
environment); absorbs upfield / away from most other hydrogen atoms (protons);
low boiling point / bp / volatile (so easily removed from sample by evaporation);
non-toxic / unreactive / does not interfere or react with sample;
 6 It does not contain hydrogen atoms (protons) that will give rise to signals in the NMR
spectrum.
 7 Empirical formula is C4H10O; Mr is 74; mass spectrum gives peak of 74; IR spectrum indicates
presence of an –OH group, which is C4H9OH (3300 cm−1) as well as –CH3 and –CH2–
groups. NMR spectrum has four peaks showing hydrogen atoms are present in four different
environments. δ = 0.9 for R–CH3 (integration trace of 3), δ = 1.4 for R–CH2–R (integration
trace of 4), δ = 2.2 for R–CH2–O (integration trace of 2) and δ = 3.6 for R–OH (integration
trace of 1); this confirms the structure as CH3CH2CH2CH2OH.
 8 Non-invasive; low-energy radiation / no tissue damage
Magnetic resonance imaging (MRI) gives a three-dimensional view of organs in the human
body; protons (hydrogen atoms) in water molecules(/ lipids / carbohydrates) in human cells give
different signals depending upon their chemical environment
 9 An aromatic compound containing a benzene ring would give rise to the six equivalent sets of
rings. The slight ‘humps’ on two of these are hydrogen atoms, and the three large sets of circles
are the iodine atoms as they have a larger number of electrons. The last set of circles attached
to a carbon atom is an oxygen atom as it is slightly larger than the carbon atoms (contains
more electrons) and the slight ‘hump’ on it is a hydrogen atom, giving the –OH group.

22 Materials
Quick check questions
 1 Si2O88−, SiO44− and SiO56−
 2 Ceramics have ionic bonding and covalent structures; no delocalized electrons. Metals contain
fixed lattice of positive ions / cations in ‘sea’ of delocalized (or mobile) valence electrons.
 3 ionic bonding / ionic bonding with covalent character; giant covalent bonding
 4 Ductility, excellent electrical and thermal conductivity and malleability describe metals.
Ceramics can be characterized as being electrically and thermally insulating and brittle.
 5 polar covalent, ionic, metallic, metallic, metallic, polar covalent and covalent
 6 100% covalent, 0% ionic; 48–52% ionic, 48–52% covalent; 32–38% ionic, 62–68% covalent

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 22 Materials 44

 7 Difference in electronegativity = 2.0 − 1.3 = 0.7

2.0 + 1.3
Average = = 1.65
2
Ionic character approx. 15%
Metallic bonding
 8 2Fe2O3 + 3C ➝ 4Fe + 3CO2
2Al + Fe2O3 ➝ Al2O3 + 2Fe
Fe2O3 + 3H2 ➝ 2Fe + 3H2O
 9 limestone / CaCO3;
air (enriched with hydrocarbons, such as methane)
coke / C / carbon
contains too much carbon / 4% carbon by mass; (and so it is) brittle / has low malleability
10 a 3Fe + Sb2S3 ➝ 2Sb + 3FeS
b Fe ➝ Fe2+ +2e−
c 2Sb2S3 + 9O2 ➝ 2Sb2O3 + 6SO2
d Sulfur dioxide is used to make sulfuric acid.
11 Charge passed = 3.60 × 104 C; amount of electrons = 0.373 mol; Al3+ + 3e− ➝ Al; amount of
aluminium atoms = 0.124 mol; mass of aluminum = 3.35 g
12 Mass of manganese = [54.94 g mol−1 × 0.235 A × (250 × 60) s]/ [(2 × 96 500 C mol−1) = 1.00 g
13 a The electrolysis can be carried out at a much lower temperature; its presence lowers the
melting point of aluminium oxide (a physical effect).
b 2O2-➝ O2 + 4e−
c Oxygen produced at the anode reacts with the hot carbon electrode to form carbon
dioxide: C + O2 ➝ CO2.
d Aluminium oxide (alumina) reacts with sodium hydroxide to form a soluble product
(sodium aluminate); basic impurities, such as iron(III) oxide, do not react and dissolve.
e High electrical and thermal conductivity; resistance to corrosion; low density; high tensile
strength
f Aluminium has a greater affinity for oxygen compared to carbon / aluminium is more
reactive than carbon / higher up the reactivity or activity series
14 A homogeneous mixture of metals, or of a metal and a non-metal (for example carbon).
15 When these two metals form alloys with each other, the metallic bonding is weakened because
of their slightly different atomic and ionic radii and different ionization energies. This weaker
metallic bonding means that the melting points of the alloys are lower than those of the pure
metals.
16 FeO, paramagnetic; unpaired electrons present, so magnetic moments do not cancel out; ZnO;
diamagnetic; no unpaired electrons / all electrons are paired, so magnetic moments cancel out
17 The purpose of the plasma in ICP-OES is to atomize the sample and produce excited state
atoms.
18 It has a dual role of aerosol generation and droplet selection.

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 22 Materials 45

19 a 40

Intensity (λ = 216.5 nm)

30

20

10

0
0 10 20 30 40 50
Cadmium concentration (μg dm −3)

b cadmium concentration = 17.0 ppb (μg dm−3)

20 a It is a heterogeneous catalyst: the reactants (gas) are in a different physical state from the
catalyst (solid).
b Reactant gas molecules adsorbed onto the catalyst surface; covalent bonds broken in
reactants due to interactions with surface; new covalent bonds form; product molecules
released / diffuse away from surface.
c Lead particles are irreversibly adsorbed onto surface and occupy active sites, instead of
reactant molecules.
21 Pores / cavities / channels / holes / cage-like structures in zeolites have specific fixed shape /
fixed size or act as molecular sieves; only reactants with appropriate size / geometry fit inside
and are activated / reacted.
22 Rapid uptake by living organisms, unknown distribution pathways, unknown interactions
with living organisms, high reactivity, ability to penetrate cells and rapidly spread in the body
including along nerve cells.
23 Crystalline solid Nematic phase liquid crystal Pure liquid

Positional order of particles Yes No No

Directional order of particles Yes Yes No

24 The nitrile (cyanide) functional group –CN group make the molecule polar; the alignment/
orientation of molecules can be controlled by electric field / voltage is applied across a sample
of molecules. A liquid crystal is thermotropic if the order of its components is determined or
changed by temperature.
25 Liquid crystal molecules work over a limited temperature range; ability of liquid crystal
molecules to transmit light depends on molecular orientation of polar liquid crystal molecules
controlled by applying voltage (electric field) across a small section; areas of the material /
display that are dark and light can be controlled.
26 Isotatic and atactic / isotactic – chains exhibit greater stereoregularity (‘more regular’); chains
pack together more effectively; stronger attractive forces operating between chains; chains do
not move past each other easily, so the fibre is stronger.
27 Addition polymerization

CH3 H

C C

CH3 CH3

H3C H

C C

H CH2CH3

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28 The orientation of the monomer units along the chain (head-to-tail, head-to-head, random)
and the orientation of the methyl groups with respect to the polymer backbone (tacticity).
29 Thermosets are more rigid, brittle, capable of operating at higher temperatures, and cannot be
re-melted.
30 LDPE has a branched structure and is amorphous. HDPE is linear and highly crystalline. These
differences account for HDPE having higher density, stiffness and melting point.
31 Plasticizer molecules fit between the PVC chains / plasticizer molecules prevent chains from
forming crystalline regions (crystallites) / plasticizer molecules keeps PVC strands / chains /
PVC molecules separated / plasticizer molecules increase space / volume / distance between
PVC chains; weakens intermolecular / dipole–dipole / London / dispersion / instantaneous
induced dipole–induced dipole / van der Waals.
32 Polar C–Cl bonds in PVC leading to formation of dipole–dipole forces; stronger intermolecular
forces (than weaker London (dispersion) forces in polythene)
33 Iron does not rust / undergo corrosion
low density; thermal insulator / poor conductor of heat (thermal energy); electrical insulator /
poor conductor of electricity
(wood) easily moulded or decomposed; non-biodegradable / does not rot; low density
34 The main cylinder is made only from hexagons of sp2 hybridized carbon atoms (graphene), with
pentagons required to close the structure at the ends; single- or multiple-walled tubes made
from concentric carbon nanotubes can be formed; bundles of the aligned nanotubes have
high tensile strength; other substances (elements, small molecules, metal oxides, etc.) can be
inserted inside the nanotubes; strong two-dimensional covalent bonding / no weak bonds; the
behaviour of the delocalized π electrons depends on the length, diameter and arrangement
of hexagons of a nanotube and hence some forms are metallic conductors and some are
semiconductors.
35 iron (clusters) or iron(0) pentacarbonyl / Fe(CO)5; high temperature (1050 °C); high pressure
(30–100 atm); single-walled carbon nanotubes
36 possible toxicity of the cores of small airborne particles; unknown long-term health effects;
small particle size and hence large surface area may increase reactions rates; immune system /
allergy concerns; uncertain impact on the environment
37 Complete combustion of substances of PVC needs a very high temperature to vaporize them
into a gas and overcome surface area limitations; relatively large amounts of air and hence
oxygen are required; many fires take place in closed houses. PVC will decompose before
melting and release hydrogen chloride.
38 C2H3Cl + 2½O2 ➝ 2CO2 + H2O + HCl or
2C2H3Cl + 5O2 ➝ 4CO2 + 2H2O + 2HCl
HCl is produced when PVC is thermally decomposed; HCl is toxic and acidic in the presence
of water when hydrochloric acid is formed; no toxic products when polyethene is combusted.
39 Phthalates are highly lipophilic (fat soluble and non-polar). When used in PVC plastic, DEHP
is weakly interacting with the PVC chains and readily leaches into blood or other lipid-
containing solutions in contact with the plastic. It is chemically stable and accumulates within
the body.
40 Collisions between the delocalized valence electrons and positive ions (cations) in the lattice.
Collisions with impurities present in the metal also contribute to resistance.
41 The loss of magnetism that a superconductor displays when cooled to its transition temperature
in a magnetic field; the magnetic flux is excluded when it is in a superconducting state, except
for a thin layer at the surface.
42 Y2O3 + 4BaO + 6CuO ➝ 2YBa2Cu3O6.5
43 perovskite; type 2 superconductor
44 They have opposite spins and opposite momenta.

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45 Mercury is a superconductor; passing electrons deform the mercury lattice / displace positive
ions / cations and couple / form Cooper pairs / condense with other electrons; energy
propagates along the mercury lattice as waves (phonons); Cooper pair / electron condensate
moves through lattice freely; phonons (vibrational quanta) are perfectly elastic / cause no
energy loss / transfer.
46 a d = nλ/2 sinθ = (1 × 154 pm)/(2 sin (10.91°)) = 407 pm
b d = λ/2 sin; (1 × 154 pm)/(2 sin 14.22) = 313 pm = 3.13 × 10−10 m
47 monochromatic X-rays / X-rays of known frequency / wavelength / energy single crystal /
powder; sample rotated; X-rays diffracted by electrons in samples atoms; detected / recorded on
(photographic) film
48 a For a body-centred cubic lattice with one atom per lattice point, there are two atoms per
unit cell.
b For this type of lattice the atoms are in contact along a body diagonal and 4r = a√2,
where r is the metallic radius and a is the edge length of the cell. Thus, r = 0.433a
= 0.433 × 343 pm = 149 pm.
49 There are 4 uranium ions and 8 oxide ions per unit cell, and a U:O ratio of 4:8. The chemical
formula is therefore UO2.
50 Determine the volume of the unit cell (in cm3).
Volume = l3 = (4.09 × 10−10 m × 1 cm/10−2)3 = 6.842 × 10−2 cm3
Determine the mass of the unit cell (in g).
Mass of unit cell = 10.5 g cm−3 × 6.842 × 10−23 cm3 = 7.184 × 10−22 g
Deduce the number of atoms per unit cell.
4 atoms.
Determine the molar mass of X and the identify of X.
(7.184 × 10−22 g/ 4 atoms) = (1.796 × 10−22 g/atom) × 6.02 × 1023 atoms = 108 g mol−1; X is silver.
51 Cubic closest packed structures have an abcabc . . . pattern, and hexagonal closest packed
structures have an abab... pattern.
52 Volume of silver unit cell = (408.7 pm)3 = 6.83 × 10−23 cm3
Mass of 4 Ag atoms = 107.87 g mol−1/6.02 × 1023 mol−1 = 7.167 × 10−22 g; density
= 7.167 × 10−22 g/6.83 × 10−23 cm3 = 10.5 g cm−3
53 The rock salt (NaCl) structure has coordination number = 6, while the CsCl has coordination
number = 8.
54 Perovskite = 1 × Ti = Ti at centre; 8 Ca × 1/8th = 1 Ca; 6O × ½ = 3 O. Thus CaTiO3.
55 hexane-1,6-diamine or 1,6-diaminohexane or 1,6 hexan(e)diamine

(—)C (CH2)4 C N (CH2)6 N(—)

O O H H

56 Addition polymerization: unsaturated monomers containing >C=C< monomers with reactive

π bonds that add together without elimination / removal of any atoms (to form an addition
polymer)
Condensation polymerization: monomers have two reactive functional groups / are
bifunctional and produce a larger molecule with elimination / removal of a smaller molecule,
such as water or hydrogen chloride.

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57 H
H H
O
H C C C H
1 2 3
O
H H
H

O O

HO OH or Cl
or Cl

Condensation polymerization
58 polyester: terylene / PET; polyamide: Kevlar (or aromatic nylon); hydrogen bonding in second
polymer between amide linkages; stronger than dipole–dipole forces in the first polymer

O O
nH2N NH2 + n C C
HO OH
1,4-diaminobenzene –2nH2O terephthalic acid

N N C C
n
H H O O
amide link

59 a bullet-proof vests and cords to reinforce the walls of car tyres

b Hydrogen bonds form between adjacent chains from –NH– of one chain to >C=O of the
next chain, which were aligned into a crystalline fibre.
60 a The –NH– groups are protonated; disrupting the hydrogen bonds between adjacent Kevlar
chain; there is flexibility in the carbon chain in nylon, but not in the benzene ring in
Kevlar.
b The fibres of nylon can be stretched more easily without breaking bonds; it will therefore be
more elastic.
61 Polyamide link can be hydrolysed; polyalkenes cannot be hydrolysed.
OH− attacks polyamide link or electron deficient Cδ+; poly(ethene) is non-polar
62 Adsorption is the physical interaction between heavy metal ions and an inert solid surface
(for example, a zeolite or carbon) and the removal of the ions from solution.
Chelation is the reaction between a heavy metal ion and a multidentate ligand (chelating
agent) to form an insoluble complex.
63 CH2 2+

CH2 NH2 CH2

H2N NH2
CH2 Ni
H2N NH2

NH2 CH2
CH2

64 AlPO4 ⇌ Al3+ (aq) + PO43−(aq) Ksp = [Al3+] [PO43−]

BaSO4 ⇌ Ba2+ (aq) + SO42− (aq) Ksp = [Ba2+] [SO42−]
CdS ⇌ Cd2+ (aq) + S2 − (aq) Ksp = [Cd2+] [S2¯]

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65 The Ksp expression is: Ksp = [Ce4+][IO3−]4

There is a 1:4 ratio between the concentrations of the cerium(IV) ion and the iodate(V) ion.
There is a 1:1 ratio between the molar solubility and the cerium(IV) ion’s concentration.
Therefore: Ksp = (1.80 × 10−4) (7.20 × 10−4)4 = 4.84 × 10−17
66 The Ksp expression is: Ksp = [Mg2+]3 [PO43−]2. There is a 3:1 ratio between the concentration of
the magnesium ion and the molar solubility of the magnesium phosphate. There is a 2:1 ratio
between the concentration of the phosphate ion and the molar solubility of the magnesium
phosphate. Therefore: Ksp = (1.071 × 10−5)3 (7.14 × 10−6)2 = 6.26 × 10−26.
67 Convert to grams per 1000 cm3, then moles per cubic decimetre:
2.97 × 10−10 g/100 cm3 × (10/10) = 2.97 × 10−9 g/1000 cm3
2.97 × 10−9 g dm−3 divided by 90.77 g mol−1 = 3.27 × 10−11 mol dm−3
When NiS dissolves, it dissociates: NiS (s) ⇌ Ni2+ (aq) + S2− (aq)
The Ksp expression is: Ksp = [Ni2+] [S2−]
There is a 1:1 ratio between NiS and Ni2+ and there is a 1:1 ratio between NiS and S2−. This
means that, when 3.27 × 10−11 mole per cubic decimetre of NiS dissolves, it produces 3.27 × 10−11
moles per cubic decimetre of Ni2+ and 3.27 × 10−11 moles per decimetre of S2− in solution.
Ksp = (3.27 × 10−11) (3.27 × 10−11) = 1.07 × 1021
68 EDTA is a chelating (multidentate) ligand that forms very stable complexes by bonding its
six Lewis base groups to a cation. The Cu2+ in a solution containing EDTA is not toxic to
phytoplankton because the Cu2+ ion is fully complexed by the EDTA molecule.
69 Fe3+ + •O2− ➝ Fe2+ + O2; Fe2+ + H2O2 ➝ Fe3+ + •OH + OH−

23 Biochemistry
Quick check questions
 1 Catabolism – the breakdown of complex molecules into simpler molecules; with the release of
energy
Anabolism – the synthesis of more complex molecules from simpler precursor molecules -
requiring energy
Photosynthesis – catabolic
Respiration – anabolic
 2 a ethanol and carbon dioxide
b lactic acid
 3 2C3H8O3 + 7O2 ➝ 6CO2 + 8H2O
2C18H34O2 + 51O2 ➝ 36CO2 + 34H2O
 4 2H2O2 (aq) ➝ 2H2O (l) + O2 (g); catabolic; since it involves the decomposition of one molecule
into two smaller molecules
 5 3C6H12O6 ➝ C18H32O16 + 2H2O
By boiling with dilute aqueous acid; or reacting with the appropriate enzyme
 6 a Alanine is in the zwitterion form in the solid state (+H3NCH(CH3)COO−) and is therefore
essentially an ionic solid with relatively strong electrostatic forces between the ionic forms.
b At around neutral pH alanine is in the zwitterionic form and is soluble in a polar solvent
such as water.
 7 a the amino group, NH2

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b a peptide bond / amide link

c H
O
N
C N or C
H O

d hydrogen bonding between peptide link regions of the backbone of the protein chain
e secondary: folding of backbone of the chain into α-helix and/or β-pleated sheet
tertiary: folding of the polypeptide chain involving non-covalent interactions between the
R-groups of the amino acid residues
quaternary: folding and assembly of multiple subunits of a protein
 8 a H2NCHRCOOH
b Ala-Gly and Gly-Ala
H2NCH(CH3)CONHCH2COOH and H2NCH2CONHCH(CH3)COOH
water (H2O)
c six
 9 a concentrated HCl(aq); heat in a sealed tube for 6 hours (or overnight) the peptide bonds
(amide links) are hydrolysed
b A buffer solution is used as the electrolyte in electrophoresis. The amino acid molecules
are charged and move in an applied electric field, and separate predominantly according to
the charge on the molecules. The net charge on the amino acid depends on the pH of the
buffer. An amino acid will be positively charged if the pH of the running buffer is below its
isoelectric point, and negatively charged if the pH is above its isoelectric point.
10 +H3NCHCOO– in the solid state and in solution at pH 5.7

CH2OH

+
H3NCHCOOH at pH 1 H2NCHCOO– at pH 14

CH2OH CH2OH

11 Look closely at the R-groups along the chain; the sequence is Phe-Ser-His-Ala
H2N CH COOH

CH2

H2N CH COOH

Phe Ser CH2 OH

H2N CH COOH

CH2

N
H2N CH COOH
N
His H Ala CH3

12 see Figure 23.22

13 Maintain internal / core body temperature / thermal insulation (around organs and under the
skin); energy / respiratory source (during starvation); to transport and store fat-soluble vitamins
(A, D, E and K); phospholipids in cell membranes; maintain skin and hair

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14 a 57 carbon atoms
b mol iodine = 7.61 / 253.8 = 0.03 mol
molar ratio iodine : oil = 0.03:0.01 = 3:1
An average of three C = C double bonds in a molecule of the oil.
15 a CH2OH–CHOH–CH2OH
b carboxyl group; –COOH
CH3(CH2)6COOH
H H H H H H H O
H C C C C C C C C

H H H H H H H O H

c Saturated fatty acids contain only carbon–carbon single bonds in the chain; unsaturated
fatty acids contain at least one carbon–carbon double bond in the chain.
d Degree of unsaturation is determined by finding the iodine number of the oil or fat / the fat
or oil is reacted with a solution of iodine in a non-polar solvent (ethanol, for example) of
known concentration / the iodine number is the mass of iodine reacting with 100 g of the
fat or oil.
16 a Mol iodine reacting = 0.5 × 19 /1000 = 9.5 × 10−3 mol
Mass of iodine = 9.5 × 10−3 × 253.8 = 2.41 g
Iodine number = (100 / 25) × 2.41 = 96.4
b Mol vegetable oil = 2.5 / 865 = 2.89 × 10−3 mol
Molar ratio of iodine :  oil (to nearest whole number) = 3:1
An average of three C=C double bonds in a molecule of the oil.
c The vegetable oil will contain a mixture of different long-chain acid molecules
17 a i stearic acid
ii oleic acid
b i To prevent the chocolate manufactured melting too readily in the hotter climate.
ii They are likely to be made of longer chains and have a higher proportion of saturated fats.
18 a soya bean oil, highest proportion of unsaturated fats and with a high proportion of
linoleic acid
b soya bean oil: 6.1 / olive oil: 5.7 / beef fat: 0.69
c soya bean oil, highest proportion of unsaturated fats
19 a an alkenyl group and a ketone carbonyl group
b the four fused rings of the steroid ‘nucleus’
c Such steroids have medical uses in the treatment of growth disorders and muscle wasting
conditions / their production has medical benefit.
20 ketone = B; aldehyde = A and C; triose = C; pentose = A; hexose = B
21 a Both contain just carbon, hydrogen and oxygen and have the general formula Cx(H2O)y.
b P is an aldose (has an aldehyde group); Q is a ketose (has a ketone group).
22 a C6H12O6 + 6O2 ➝ 6CO2 + 6H2O
b Mr glucose = 180.18 g mol−1
amount of glucose = 15.0 / 180.18 = 0.083 mol
energy produced = 0.083 × 2803 = 233 kJ

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23 a α-1,4 and α-1,6 glycosidic links

b hydrolysis
c α-glucose
CH 2OH
H O H
H
OH H
HO OH
H OH

d amylopectin
e The polymer contains many glucose molecules which are not able to react while they are
‘stored’ in the polymer, whereas the monomer is readily able to react.
24 Starch contains α-glycosidic links which enzymes present in humans are able to hydrolyse
– hence starch is a useful dietary source of energy; cellulose contains β-glycosidic links and
humans do not have enzymes capable of hydrolysing such bonds. Cellulose is useful in human
diet as ‘dietary fibre’.
25 a i X
C B A
H OH
H
N OH
HO
H3C CH3 O O

ii Y
B A C
O
CH3

CH3

O CH3 CH3 CH3 CH3

b X is water-soluble; Y is fat-soluble
26 Vitamin C undergoes oxidation in the air, and it is soluble in water where it undergoes
oxidation and hydrolysis.
27 a A vitamin is an organic compound and a vital nutrient that an organism requires in
limited amounts.
b It is fat soluble because of the presence of a long hydrophobic alkyl chain and a benzene
ring.
c The process of adding vitamin K to foods to increase its content.
28 The oxonium ion fits into the crown ether interior and the attractive interactions are
maximised.

O O
H
+
O O H O
H
O O

29 a heating, dissolving in water, lowering the pressure

b The atoms are too small to interact strongly and they escape as gas.
c London (dispersion) forces

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30 advantage: the packaging is biodegradable / the packaging is made from a renewable resource
disadvantage: the packaging is not chemically resistant / packaging is relatively fragile
31 a Atom economy = (total mass of desired product formed / total mass of all products) × 100
Method 1: atom economy = (120.16 / 620.49) × 100 = 19.4%
Method 2: atom economy = (120.16 / 138.18) × 100 = 86.9%
b Consider: the use of highly corrosive chemicals such as sulfuric acid or the ease of
availability of any catalyst.
32 Enzymes lower the activation barrier of the reaction.
The free-energy difference between the initial and the final states is not affected.
The energy source is the binding energy, i.e. the energy released from enzyme-substrate
interactions.
33 a The presence of an enzyme behaves as a catalyst in providing an alternative reaction
pathway – via the ES intermediate – that has a lower activation energy than the
uncatalysed reaction.
The substrate binds to the enzyme at the active site and the interactions between the
enzyme and substrate facilitate the chemical reaction(s) that need to take place – mention
the ‘lock and key’ and/or induced-fit hypothesis.
b Competitive inhibition: the inhibitor (resembles the substrate in shape) competes with
the substrate for active sites on the enzyme thus slowing the rate of reaction / the rate will
eventually reach the same plateau value (Vmax) as that achieved without inhibitor.
Non-competitive inhibition: the inhibitor binds to a site on the enzyme other than the
active site, altering the conformation of the enzyme and reducing its activity / the rate will
not reach the same plateau value (Vmax) as the uninhibited enzyme.
34 a Ka = 1.74 × 10−5 = 0.250 × [H+] / 0.200
[H+] = (1.74 × 10−5) × 0.200 / 0.250 = 1.39 × 10−5
pH = −log10(1.39 × 10−5) = 4.86
b pH = pKa + log10 ([base]/[acid]) = 7.21 + log10 (0.045/0.055)
pH = 7.21 − 0.09 = 7.12
c pH = pKa + log10 ([base]/[acid]) = 8.30 + log10(0.750/0.650)
pH = 8.30 + 0.06 = 8.36
35 pH = pKa2 + log ([anionic form]/[zwitterion])
pH = 9.1 + log (0.2/0.8) = 9.1 + log 0.25
pH = 9.1 + (- 0.6) = 8.5
36 a Concentration = A/ε = 0.31/500 = 6.4 × 10−4 mol dm−3
b Concentration A/ε = 0.23/63.5= 3.6 × 10−3 mol dm−3
37 The phosphate groups of the backbone of the DNA molecule are negatively charged.
38 a Hydrogen bonds play a part in the recognition of the possible base pairs that can form / A
always pairs with T, and G with C / AT pairing involves two hydrogen bonds whereas GC
pairing involves three.
b After replication the daughter molecules contain one parent strand and one new
strand / each new molecule contains one old strand and one new strand.
c i hydrogen bonding (and London forces referred to as ‘base stacking’)
ii phosphodiester links

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 23 Biochemistry 54

39 a RNA contains the sugar, ribose / DNA the sugar, deoxyribose

RNA contains the base, uracil / DNA contains thymine
(RNA is single stranded / DNA is double stranded)
b i purine: adenine or guanine
pyrimidine: cytosine or thymine
ii I is a purine (with two rings); II is a pyrimidine (with one ring).
40 a The position of the phosphate groups on the inside of the structure would have led to the
chains repelling each other as under cellular conditions the phosphate groups would carry
negative charges.
b The hydrogen bonds between the nitrogenous bases in the two chains break so that the
chains can part.
41 Separate red blood cell DNA from other material (by centrifugation).
Cut DNA up (using restriction enzymes).
Separate DNA fragments by gel electrophoresis.
Method of detection (e.g. UV, radioactive probe, X-ray (autoradiograph)).
42 a i an RNA virus / the structure contains the base, U (uracil), not T (thymine)
ii single-stranded / the % composition of the bases in the structure do not correspond to
those expected for a double helical structure: A ≠ U and G ≠ C
b 5´ ACUGUGCGACAGU 3´
Since the sequence is a palindrome, it will form a double-strand RNA hairpin structure.
43 a A food from an animal or plant in which the DNA / genetic material has been altered by
artificial means.
Foods where biotechnology has been used to modify the plants used in food production.
Inter-species DNA transfer has been used and a wide range of genetically modified foods,
GM foods, are possible. The genetic modification may have been used to add a gene to
yield a new product, inactivate a gene to remove an undesired property or modify a gene for
higher yields of its protein.
b From the following lists
Benefits of GM foods:
● longer shelf-life
● improved flavour, texture and nutritional value
● increased resistance to diseases and pests, reducing the use of pesticides
● produce a supply of substances such as vitamins and vaccines
● increased crop yields
● tolerance of a wider range of growing conditions, such as drought resistance.
Concerns:
● lack of information about long-term effects
● changes to the natural ecosystem through cross-pollination
● possible links to increased allergies
● risk of altering natural composition of food
● concerns of breeding species that are resistant to control
● escape of modified genes into the environment; potential harm to natural ecosystem.
44 Bromine, Br2, reacts with the double bonds / the number of double bonds in the conjugated
system decreases as the bromine reacts / the absorbed energy shifts towards the violet end of
the spectrum / a higher energy in the visible region is absorbed; resulting in complementary
yellow colour.

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 23 Biochemistry 55

45 Benzene absorbs strongly in the UV region, but not at all in the visible region. The light absorbed
by benzene is lower in energy than the light absorbed by most non-conjugated molecules, but
it is still higher in energy than visible light. The degree of conjugation determines the actual
energy difference between the ground and excited states. The more highly conjugated the system
the lower the energy difference and the lower the required energy of light needed to excite the
electrons. Hence the pi transitions for pentacene are in the visible region.
46 a structure involves extensive conjugation
b water soluble since there are several hydroxyl groups (capable of hydrogen bonding) and
charged regions of the structure which will interact with the polar solvent, water
47 pH 2 – absorbs in the blue / green region so the solution will be red / orange
pH 11 – absorbs in the red / orange region so solution will be blue / green
48 a increased temperature – less oxygen binds
decreased pH (increased acidity) – less oxygen binds
higher levels of carbon dioxide – less oxygen binds
presence of carbon monoxide – CO binds more strongly, and irreversibly, to hemoglobin
instead of oxygen
b Fetal hemoglobin is a different form of hemoglobin only present in the blood of the
developing fetus. It has a higher affinity for oxygen than maternal hemoglobin (which
replaces it after birth). This adaptation allows the efficient transfer of oxygen from the
mother’s blood to the fetal blood in the placenta.
49 A is d-form / B is l-form / C is d-form.
50 a isomerism
b The several hydroxyl groups can all participate in hydrogen bonding with the water molecules.
c A is α-glucose as the –OH on carbon-1 is on the opposite side of the plane of the ring to
the carbon-6 / C is β-glucose.
51 a i C20H28O
ii Add the following to end of the molecule; the aldehyde group –CHO is converted to a
primary alcohol grouping –CH2OH

OH
iii A C = C double bond.
iv Heat alcohol with sodium dichromate(IV) / concentrated sulfuric acid in distillation
apparatus so that the aldehyde distils over as soon as formed; use an excess of the
alcohol to the oxidizing agent.
v 5 mol
b i cis arrangement here
CH3 H CH3 H
H
C C C
C C C
CH3
CH3 H H HC
3
C H

C
H O
11-cis-retinal

ii primary amine group (–NH2)

iii condensation reaction
iv O H

R C N opsin

H H

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 24 Energy 56

24 Energy
Quick check questions
 1 Specific energy = 7434 kJ mol−1 ÷ 156.31 g mol−1 = 47.56 kJ g−1
Volume of one mole of undecane = 156.31 g ÷ 0.740 g cm−3 = 211.23 cm3 = 0.2113 dm3
Energy density = 7434 kJ ÷ 0.2133 dm3 = 34 852 kJ dm−3
 2 a Specific energy = 2021.06 kJ mol−1 ÷ 60.11 g mol−1 = 33.62 kJ g−1
Volume of one mole of propan-1-ol = 60.11 g ÷ 0.803 g cm−3 = 74.86 cm3 = 0.07486 dm3
Energy density = 2021.06 kJ ÷ 0.07486 dm3 = 26997 kJ dm−3
b 2CH3CH2CH2OH(l) + 9O2(g) ➝ 6CO2(g) + 8H2O(l)
3 mol of CO2 produced per mole of propan-1-ol
 3 The amount of carbon dioxide released on complete combustion is equivalent to the amount of
carbon dioxide absorbed from the atmosphere by photosynthesis.
 4 Different solutions / approaches / statistical data / dependent data, e.g. efficiencies can be
compared / combined or best ideas / solution / best practices can be shared to arrive at global
/ national / local solutions or acceleration of pace or rate of research or discoveries and
findings become available to all scientists and engineers or improved confidence in validity /
reproducibility of results if many scientists with engineers / research groups are involved in a
similar project or money / resources / time is not wasted duplicating work other scientists and
engineers have already done
 5 a 2C(s) + O2(g) ➝ 2CO(g); S(s) + O2(g) ➝ SO2(g)
b Liquid fuel can be pumped; easy to mix with air and react with oxygen; easier to control the
rate of combustion.
 6 a boil / vaporize the crude oil (petroleum); (vapours / gases) rise up the fractionating column
or tower; vapours / gases condense / liquids form at different heights; the heights depend on
the boiling points which varies with the size of molecule
b residue / bitumen; refinery gas; gas oil; naphtha
 7 In winter more volatile components are incorporated into the petrol, so it vaporizes more
readily. However, in hot weather you do not want a large proportion of volatile components.
There will be loss of petrol from the petrol tank by evaporation.
 8 a calculate the weighted averages of the three components:
[(90/100) × 100] + [(5/100) × 0] + (5/100 × 114)] = 95.7; the fuel mixture has an octane rating
of about 96
b to increase the octane number; to favour complete combustion and hence release of more
heat (thermal energy)
 9 a C16H34 ➝ C11H24 + C2H4 + C3H6
b C12H26 ➝ C8H18 + C4H8
c C10H22 ➝ C8H18 + C2H4
10 a Catalytic cracking produces a mixture of alkanes and alkenes; hydrocracking produces
alkanes only.
b C7H16 ➝ C7H14 ➝ C7H8 + 4H2
11 2C(s) + 2H2O(g) ➝ CH4(g) + CO2(g) or 3C(s) + 2H2O(g) ➝ CH4(g) + 2CO(g)
12 a 9C(s) + 10H2(g) ➝ C9H20(l)
b 19H2(g) + 9CO(g) ➝ C9H20(l) + 9H2O(l)
13 4000 tonnes × 0.746 tonne carbon/tonne of coal = 2984 tonnes of carbon
Mass of carbon dioxide = 2984 tonnes of carbon × (44.01 ÷ 12.01) = 10 935 tonnes CO2/day

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 24 Energy 57

14 Gamma, beta and alpha

15 a 222
86
Rn ➝ 218
84
Po + 42He
b 49
21
Sc ➝ 4822Ti +−10e + 10n
c 14
6
C ➝ 147N + −10e
16 a 11H + 157N ➝ 126C + 42He + 00γ
b In radioactive decay, there is no bombardment, no collisions; transmutation involves the
collision of two particles.
17 The mass defect is the difference between the mass of the nucleus of an isotope and the sum of
the masses of the individual nuclear particles that make up that isotope. The binding energy is
the energy released when individual nucleons combine to form the nucleus of an isotope.
18 Δm = 8.45946 × 10−26 kg − [(23 × 1.67262 × 10−27 kg) + (28 × 1.677493 × 10−27 kg]
= −7.737 × 10−28 kg
ΔE = −7.737 × 10−28 kg × (3.00 × 108 m s−1)2
= 6.96 × 10−11 J
19 Similarity – some mass is converted to energy
Differences – (fission) one heavy / large nucleus / atom becomes two (or more) lighter ones;
(fusion) two light nuclei / atoms become one heavier nucleus
20 235
92
U + 10n ➝ 95
37
Rb + AZX + 310n
Applying the law of conservation of mass, A = 138, and applying the law of conservation of
charge Z = 55. Hence the nuclide is 13855Cs.
21 c = f × ν; 3 × 108 m s−1 = f × 587.562 × 10−9 m; ν = 5.10584 × 1014 Hz
E = hν; E = 6.63 × 10−34 J s × 5.10584 × 1014 Hz = 3.3852 × 10−19 J
E = (3.3852 × 10−19 J/1000) × 6.02 × 1023 mol−1 = 203.6 kJ mol−1
22 6CO2 + 6H2O ➝ C6H12O6 + 6O2
chlorophyll in chloroplasts
23 Ethanol may be too volatile to be used on its own in a hot country and the engine may not be
‘tuned’ to work on pure ethanol; ethanol and the molecules in petrol can interact with each
other and there is an increase in entropy upon mixing.
24 0, unsaturated; 1 unsaturated and 2 unsaturated.
25 CH3COOCH3 + HOCH2(CH2)8CH3 and 2 × CH3COOCH3 + HOCH2CH2OH
26 methanol or ethanol, concentrated sulfuric acid (H+) / concentrated sodium hydroxide (or
other strong base)
27 CO2(g) + H2O(l) ⇌ H+ (aq) + HCO3−(aq) or CO2(g) ⇌ CO2(aq) and CO2(aq) + H2O(l) ⇌ H+ (aq)
+ HCO3−(aq); with decreasing levels of carbon dioxide the equilibrium will shift to the left and
the pH increases.
28

bend

asymmetric C–O
stretch

29 lower energy / lower frequency / longer wavelength / infrared radiation reflected from the Earth
greenhouse gases absorb / retain / trap this energy as vibrational energy within the bonds of the
molecule
30 Voltage is the potential difference between the two electrodes; a measure of the energy carried
by each electron.

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 24 Energy 58

Power is the total quantity of electricity available; the product of the voltage and current.
Voltage is affected by the materials used to form the electrode.
Power is affected by the quantity of materials used.
31 a PbO2 + 4H+ + SO42− + 2e− ➝ PbSO4 + 2H2O;
PbO2 + 2H+ + H2SO4 + 2e− ➝ PbSO4 + 2H2O
b positive because reduction occurs / electrons gained; decrease in oxidation number
32 a Cathode: H+ (aq) + NiO(OH)(s) + e− ➝ Ni(OH)2 (aq)
Anode: Cd (s) ➝ Cd2+ (aq) + 2e−
b These NiCad cells can be recharged because the products of the discharge half reactions
remain in contact with the electrodes in a convertible form.
33 A hybrid vehicle uses a relatively cheap fuel (gasoline or petrol) in the internal combustion
engine and has good fuel economy but releases carbon dioxide. A hydrogen fuel-cell vehicle
does not release carbon dioxide (the reaction produces water) but requires a more expensive
and explosive fuel (hydrogen gas); current battery technologies incorporate materials that are
still very expensive and bulky.

34 E1 cell = 1.10 V − 0.0592 log10 0 .050 = 1.16 V

2 5 .00
35 a A concentration cell is one whose emf is generated solely because of a concentration
difference. In a standard voltaic cell the emf is generated because of a difference in the
reduction potentials of two electrodes.
b +0.0888 V
36 Let the rate of diffusion of oxygen be r(O2) = r1; the rate of diffusion of the unknown gas
r (x) = 4r

√
r(O2) M(x)
=
r(x) M(O2)
or

√
r1 M(x)
=
4r1 32
Squaring on both sides,
1 = M(x)
16 3 2

M(x) = 3 2 = 2
16
Gas is hydrogen, H2.
–
37 a OO superoxide radical

H O hydroxyl radical
–
H O hydroxide ion

b They both contain an unpaired electron in their outer energy levels.

38 Al(g) ➝ Al+(g) + e−; Si(g) ➝ Si+(g) + e−; aluminium
39 a group 13 element / Ga / In has three outer (valence) electrons; p-type semiconductor /
forms electron holes; group 5 element / As / P / Sb has five outer (valence) electrons; n-type
semiconductor / forms mobile electrons
b sunlight / photons interacts with the semiconductor surface to release electrons

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 25 Medicinal chemistry 59

40 a Light energy excites dye molecules

(excited) dye molecules inject electrons into TiO2 layer or
dye ➝ dye+ + e−
Oxidized dye molecules oxidized / convert I− to I3−; or 2 dye+ + 3I− ➝ I3− + 2dye, or dye+ +
e− ➝ dye and 3I− ➝ I3− + 2e−
Electrons flow through external circuit back to the counter electrode
Electrons reduce / convert I3− ions to I− (at the counter electrode) or I3− + 2e− ➝ 3I−
b Dye-sensitized cells can use light of lower energy / lower frequency / longer wavelength than
silicon cells; the advantage of nanoparticles is that they provide a large surface area.

25 Medicinal chemistry
Quick check questions
 1 oral – by mouth / swallowing pills/powders / drinking liquids/mixtures;
inhalation – administering drugs into respiratory tract / inhaling gases/vapours/sprays/powders;
rectal – introducing drugs into the rectum/colon via the anus / using suppositories/enemas;
transdermal – diffusion through the skin / skin patches / ointments / therapeutic baths
 2 drug design / discovery (often from plant extracts) / screening / identifying lead compound /
rational drug design process using computer studies of receptor; preparation of analogues
through combinatorial chemistry; characterization of the new compound / in vitro testing /
drug formulation / delivery / stability studies; pre-clinical (toxicology and pharmacokinetics)
tests / tests on animals / bacteria / cell cultures / determination of LD50 with test animals;
clinical tests/tests on humans; determination of ED50 to show improvements over existing drugs
 3 a Therapeutic index = 80/20 = 4;
Patients responding

100
therapeutic
toxic
effect
effect
therapeutic
50 window

0
0 20 80
Dose/mg kg –1

b The second drug has a higher therapeutic index hence the probability of toxicity / risk of
adverse effects due to over-dosage is not high.
 4 a Z; X and Y; X
b the range of dosages between the minimum amounts of the drug that produced the desired
effect and a medically adverse effect; a biologically inert substance used as a control when
testing a drug clinically
 5 a solubility in water
b how easily it is absorbed through the cells / membranes of the intestinal wall; susceptibility
to hydrolysis or being broken down by enzymes in the gut and liver and formulation of the
tablets.
 6 esterification or condensation (addition–elimination)
 7 Aspirin prevents the synthesis of enzyme prostaglandin synthase / cyclooxygenase (COX) and
hence interferes with the production of prostaglandins (‘local hormones’ / autacoids); this stops
the transmission of nerve impulses / action potentials from the site of the injury to the brain.

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 8 preventing (recurrence of) heart attacks / strokes / reduces blood clotting / thins the blood /
anti-inflammatory
 9 increases solubility in aqueous solution blood plasma; higher proportion of drug dosage reaches
target cells
solubility in water; increases how easily it is absorbed through the cells / membranes of the
intestinal wall; though converted back to un-ionized form in the stomach
10 (secondary) amide group / –CONH– / peptide; ring is strained / bond angles less than 109°;
ring breaks / hydrolyses easily so (the two fragments similar to cysteine and valine) then
bond(s) covalently to the enzyme (trans peptidase) that synthesizes the bacterium cell wall (so
blocking its action)
11 resistant to penicillinase enzyme / more resistant to bacteria breaking it down / effective
against bacteria that are genetically resistant (to penicillin G); resistance to breakdown by
stomach acid / hydrochloric acid (so it can be taken orally)
12 irregular / interrupted treatment allows more bacteria to be selected for and survive (and
mutate) / failure to complete full course; surviving bacteria develop / pass on genetic resistance
to the antibiotic
13 (CH3CO)2O; CH3COOH; or CH3COCl and HCl; or CH3COOH and H2O
14 Morphine has two hydroxyl / hydroxyl groups and diamorphine (heroin) has two ester /
ethanoate functional groups; morphine is more polar than diamorphine / heroin;
diamorphine / heroin crosses the blood–brain barrier more easily due to its lower polarity;
morphine is more soluble in blood plasma (aqueous solution) and diamorphine / heroin is more
soluble in lipids (lipophilic).
15 increasing amounts / doses needed to produce same effect; increasing amounts cause damage /
death
16 Both molecules have a tertiary amine group, a phenylethylamine structure and a benzene ring;
they have different shapes and different rigidities.
17 Mass of Mg(OH)2 = 0.960 g; amount Mg(OH)2 = 0.01646 mol; amount of HCl = 0.03292 mol;
volume of HCl neutralized = 220 cm3
18 a ionic and covalent
b kill bacteria / microorganisms; provides an acidic medium so enzymes for digestion can work
c Mg2Si3O8(s) + 4HCl(aq) ➝ 3SiO2 (s) + 2H2O(l) + 2MgCl2(aq)
The silicon dioxide is inert and dense and will prevent the acid from undergoing reflux.
19 Other factors to consider when deciding an antacid’s effectiveness include the neutralizing
action of the antacid over a prolonged period (30 minutes or 1 hour, for example), and whether
or not the antacid upsets the acid/ion balance in the stomach’s gastric juice. The presence and
nature of food in the stomach may also affect the neutralization reaction. Furthermore, some
brands claim to have a coating action on the stomach wall which might be unrelated to the
neutralizing action. There may also be side effects.
20 HCO3−(aq) + H3O+(aq) ➝ CO2(g) + 2H2O(l)
21 Acid / gastric juice from the stomach rises into the oesophagus and damages the cells.
22 Both compounds relieve symptoms of acid reflux / heartburn / indigestion / both raise the pH
of gastric juice; both may cause diarrhoea; omeprazole stops the production of hydrogen ions /
protons / hydrochloric acid; inhibits the action of the proton pump; the antacid neutralizes the
excess hydrogen ions / protons / hydrochloric acid in the gastric juice; omeprazole takes longer
than metal hydroxide-based antacids to provide relief; omeprazole is used to treat gastric ulcers
while metal hydroxide-based antacids are not. Omeprazole can prevent long-term damage
to the stomach lining and oesophagus from over-production of acid; metal hydroxide based
antacids do not. The magnesium ions affect the ionic/electrolyte balance in the body fluids and
omeprazole does not.
23 Ranitidine is a competitive, reversible inhibitor of the action of histamine at the histamine H2
receptors found in gastric parietal cells.
24 a Carbonic acid removes hydroxide ions from an alkali:

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 25 Medicinal chemistry 61

H2CO3 + OH− ➝ HCO3 − + H2O;

hydrogen carbonate ion removes protons / hydrogen ions from an acid:
HCO3 − + H+ ➝ H2CO3
salt [hydrogencarbonate]
b pH = pKa + log / 7.4 = 6.1 + log ;
acid [carbonic acid]
[hydrogencarbonate]
= 101.3 = 20
[carbonic acid]
Since the concentration of hydrogencarbonate ions is 20 times greater than the carbonic
acid concentration, the buffer is better at resisting the effects of acids rather than alkalis.
25 n(NaOH) = 20.00 g / 40.00 g mol −1 = 0.500 mol; ratio of HEPES to NaOH is 1:1
n(HEPES) consumed = 0.500 mol; n(anion) = 0.500 mol; n(HEPES) in original solution =
1.00 mol; n(HEPES) left = 0.500 mol; since [anion] = [HEPES]remaining; pH = pKa; pH = 7.5.
26 To catalyse the formation of double stranded DNA from single stranded viral RNA.
27 block enzyme activity within host cell / block reverse transcriptase;
alter host cell’s genetic material;
prevent virus from multiplying / replicating;
alter virus’s binding site on cell wall / prevent virus binding with cell wall; prevent virus from
entering / leaving cell
28 prevents virus from binding to host cell membrane; prevents the uncoating process (loss of
viral capsid) and thus the injecting of genetic material (DNA or RNA) into cell / inhibit
activity of enzyme in formation of new viral particles (viruses) / prevents virus from leaving
host cell
29 bacteria multiply by cell division / binary fission / (mitosis);
viruses insert DNA / RNA / genetic material into cells;
viruses lack a cellular structure and they can only replicate within the host cell; they mutate at
a high rate; antiviral agents must inhibit the host cell without damaging the host cells.
30 HIV virus mutates rapidly; HIV metabolism linked to that of host cell / HIV uses host cell;
retroviral drugs harm host cell as well as HIV / difficult to target HIV without damaging
host cell.
31 Leads to genetically determined bacterial resistance of antibiotics; antibiotics less effective;
increased side effects due to larger doses; proportion of genetically resistant bacteria increases;
kill useful / beneficial symbiotic bacteria replaced by more harmful (pathogenic) bacteria;
genetically resistance bacteria transfer the genes for resistance to the next generation of
bacteria.
32 a 2CH2Cl2 + 3O2 ➝ 2CO2 + 2H2O + 2Cl2
CH2Cl2 + O2 ➝ CO2 + 2HCl
b contamination of soil and ground water; stored in body fat and concentrated as they move
up food chain; toxic and often carcinogenic
33 low-level waste: short half-life; low activity
high-level waste: long half-life; high activity
34 O
H+ H O
+ + H2O
HO
H OH O
Mr (alcohol) = 74.0: Mr (methanoic acid) = 46.0; Mr (ester) = 102; Mr (H2O) = 18.0:
102.0
% atom economy = × 100% = 85.0%
(74.0 + 46.0)

35 the number of steps in the synthesis; the type of waste (toxicity (if chemical) / half-life activity
(if nuclear) produced in the synthesis; the amount of energy needed in the synthesis and the
nature of any solvents needed.

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 25 Medicinal chemistry 62

36 Less land used; faster due to high rate of bacterial binary fission; simpler extraction process
from bacteria; solvents not needed for extraction.
37 Not all pollution may be cleared up; energy will be wasted producing unwanted products; it is
better not to produce hazardous materials at all then there is no danger of them entering the
environment.
38 Using a catalyst (or more efficient catalyst) may mean that the process can be carried out at a
lower temperature, which saves energy. (It may also increase the yield of one product over that
of another, unwanted one.)
39 a ovarian, lung and breast cancers
b Production of the drug starts with a compound isolated from a natural source but the rest of
the steps in the production of Taxol uses organic chemistry synthesis conversions.
40 This means 50% of rats (in a large test sample) would die if Taxol concentrations in the body
tissues were 35.2 mg of Taxol for 1000 g of rat tissue.
41 One enantiomer may have a therapeutic effect; the other enantiomer may have no therapeutic
effect or have a harmful effect.
42 A chiral molecule is bonded to a non-chiral starting reagent to produce a chiral intermediate.
The presence of the auxiliary follows the reagent in the next stage of the synthesis and forces
the reaction to follow a path that produces one of the possible enantiomers. Chemical removal
of the chiral auxiliary follows to give a single enantiomer.
43 cheap to synthesize and readily available in both enantiomeric forms; easily attached; induce
stereochemistry; chemically inert; easily removed
44 need a point of attachment (limits structures); need a stoichiometric amount of the chiral
auxiliary; extra steps – installation and removal of chiral auxiliary.
45 equimolar mixture of a pair of enantiomers / 50% each of a pair of enantiomers
46 a refluxing of dried plant material; solvent extraction
b HO O H
O N

* * N * * O
H OH
OH NH2

24 = 16
c polarimeter; pass plane polarized light through a sample; analyser / second polarizer
determines the angle of rotation of the plane of polarized light
d each enantiomer will rotate the plane of plane polarized light in opposite directions by the
same angle (under the same experimental conditions)
47 a  60
27
Co ➝ 59
28
Ni +−10e + γ;
b A method for delivering a beam or of high-energy X-rays or ionizing radiation to a patient’s
tumour. Beams are generated outside the patient and are targeted at the tumour site.
48 the use of a carrier substance used to transport particular radioisotopes directly to cancer cell
which are killed by alpha radiation
Ac ➝ 221
225
89 87
Fr + 42He; short path length and highly ionizing
49 Targeted alpha therapy targets cancer cells by using monoclonal antibodies; monoclonal
antibodies can be made to target the cell surface proteins of a specific type of cancer cell and
can be labelled with an α-emitting radioisotope; the antibody reaches and interacts with the
target cancer cell carrying the α radioisotope with it.
50 Cancer patient given non-radioactive boron-10 atoms (in the form of a compound) at targeted
cancer cells; irradiation of patient with a neutron beam from outside the body; boron-10 atoms
(in boron compound) capture neutrons to form boron-11 atoms which undergo fission to
produce α particles and lithium nuclei.

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51 a    177
71
Lu ➝ 177
72
Hf +−10 e; λ = ln 2/t½ = 0.103 day−1; N/N0 = e −λt = 0.559
b mass of lutetium-177 = 0.0559 × 20 = 1.118 mg
52 Strontium has a similar electronic structure to calcium – both have an s2 valence configuration.
The Ca2+ and Sr2+ ions have the same charges and similar ionic radii.
53 Traditional radiotherapy – healthy tissues receive a similar dose of kinetic energy to cancerous
tissues; proton beam therapy – doctors can control the energy distribution of the protons
directed and deposited in tissue volumes in a three-dimensional pattern from each beam used.
Greater control and precision of the radiation.
54 99
42
Mo ➝ 99
43
Tc +−10 e
55 Appropriately short half-life allows time for production of nuclide, administration to patient,
and for it to accumulate in the tissue of interest. Activity is high enough to give good quality
image with small amount of nuclide. It is a gamma emitter – highly penetrating radiation that
can be detected outside the body and is not damaging to human tissue as it is non-ionizing.
Its chemical properties allow it to be incorporated into molecules that will be absorbed by the
organs to be investigated.
56 skin and nail damage; nausea; fatigue; sterility
57 risk versus benefit to the patient and the environment (and society); providing adequate
information and informed consent to patients about risks, doses and including likely side
effects; security concerns if radioactive material was acquired by terrorists (conventional
explosion involving nuclear material); cultural resistance / superstition; lack of education and
scientific awareness; potential exposure of health workers and technicians to ionizing radiation;
proper training in handling / disposal and storage of radioactive materials not given; proper
disposal of radioactive material.
58 a The vapour pressure is the pressure exerted by a vapour (or mixture of vapours) over a
liquid when they are in dynamic equilibrium.
b temperature / the composition of the mixture
59 Liquid X will have the higher vapour pressure at 50 °C as it has a lower boiling point than Y.
Liquid X is more volatile than liquid Y.
60 PA = P°A × XA = P°A (1 − XB)
XB = (P°A − PA)/P°A = (30 − 28)/30 = 0.067
61 Only a mixture containing hexane and heptane will obey Raoult’s law as the interaction
between heptane molecules will be similar to those between hexane molecules.
62 a Ketone (carbonyl), alkenyl and hydroxyl; C18H26O2
b increase in muscle mass, strength and stamina
c The chemicals are extracted from the urine sample then separated into various components
by gas chromatography (GC). Each band / component as it leaves the gas chromatography
column is passed directly into a mass spectrometer (MS) where it is analysed. The mass
spectra obtained are matched with a database to identify the compound.
63 Reduction: Cr2O72− + 14H+ + 6e− ➝ 2Cr3+ + 7H2O
Oxidation: C2H5OH + H2O ➝ CH3COOH + 4H+ + 4e− or C2H5OH + H2O ➝ CH3CHO +
2H+ + 2e−

Chemistry for the IB Diploma Study and Revision Guide © Christopher Talbot and Richard Harwood 2017