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1 Physical chemistry
3.1.1 Atomic structure
Fundamental particles
1a There is a concentration of positive charge in the atom / nucleus is positive which
repelled the positive alpha particles / like charges repel.
Nucleus containing protons and neutrons in today’s model, no nucleus in plum pudding
model
Electrons in shells / energy levels in today’s model, but scattered throughout in plum
pudding model
b The nucleus is very dense / small / massive or The nucleus is positively charged.
6a
Atomic number 83
Mass number 209
Number of protons 83
Number of neutrons 126
Number of electrons 83
All correct
The atomic number gives the number of protons, which is equal to the number of electrons so
there are 83 of each. The number of protons plus the number of neutrons gives the mass
number, 83 + 126 = 209
b Bismuth, Bi
Using the atomic number of 83 and the periodic table, the element is bismuth, Bi.
12711.38
= = 127.1 to 1 decimal place
100
8a Cl(g) + e− → Cl+(g) + 2e− / Cl(g) → Cl+(g) + e−
35
b In a TOF spectrometer, the ions are accelerated to the same kinetic energy by an
electric field. They then enter ion drift, where there is no electric field and they are
separated due to their different velocities; smaller ions move faster than heavier ions.
The positively charged ions hit a negatively charged detector at different times due to
their different velocities and gain electrons from the plate. The movement of
electrons creates a current which is recorded. The size of the current gives a measure
of the number of ions (abundance) hitting the plate.
2.478 × 1013 = ½ × 37 × v2
9 A
Lighter ions, which are accelerated by an electric field, reach the detector, which is a negative
plate, first.
10 D
The molecular ion peak is the one with the largest m/z value.
Electron configuration
11 a 1s1
b Br−
c CaCl2
d Mg3N2
13 A
The alkali metals are Group 1 elements with one electron in the outer shell. It takes little energy
to remove this single electron from the outer shell, which is far from the attraction of the
nucleus.
14 C
The biggest difference in ionisation energies is between the third and fourth ionisation energies
(4000 kJ mol−1 to remove the third electron but 25000 kJ mol−1 to remove the fourth). This
suggests that the first three electrons are in an outer energy level and the fourth is in a filled
shell closer to the nucleus. This is a Group 3 element.
15 a i Rb(g) → Rb+(g) + e
Shielding is similar, as the electron is being removed from the same shell.
Outermost electron is held closer to the nucleus by the greater nuclear charge.
These repel.
The electron configuration of O is 1s2 2s2 2p4. In one of the 2p orbitals, there is one pair of
electrons which repel, meaning that it takes less energy to remove one of these electrons than it
does for the electrons of nitrogen, which occupy one orbital each. Hence the ionisation energy is
slightly less for oxygen.
Exam-style questions
1ai
y = 24.00
y = 24
The answer must be given to 2 significant figures, similar to the other mass number data.
iv Same number of electrons (in outer shell or orbital) / same electron configuration
Isotopes are atoms of the same element and they have the same number of electrons in the
outer shell and, as a result, react in similar ways.
1 2
Kinetic energy = mv . If the particles all have the same kinetic energy, then the speed will
2
depend on the mass, and heavier particles will move more slowly than lighter particles and reach
the detector later.
25 ×10−3
vi Mass = 23
= 4.15 × 10−26
6.022× 10
2 KE 2× 4.52 ×10−16
v2 = = = 2.178 × 1010
m 4.15 ×10
−26
v=
√ 2 KE = 1.476 × 105
m
d = vt
= (1.476 × 105) × (1.44 × 10−5) = 2.125 m = 2.1 m (2 sig fig)
b i Mg(g) → Mg+(g) + e−
The first ionisation energy is the energy needed to remove one mole of electrons from one mole
of gaseous atoms to form one mole of gaseous ions with one positive charge.
ii The electron is being removed from a positive ion and this therefore needs more
energy.
The electron being removed is closer to the nucleus and held more tightly.
2 D
As the mixture contains 2 moles of Al3+ which is from 1 mole of Al2(SO4)3, this contributes
3 moles of sulfate ions so the remainder of the 5 moles of sulfate ions come from the sodium
sulfate, Na2SO4. 2 moles of sulfate ions from Na2SO4 means 4 moles of Na+ ions.
2.45
3a Number of oxygen atoms = × 6.022 × 1023 × 2 = 9.22 × 1022
32.0
0.0500
b Number of oxygen atoms = × 6.022 × 1023 = 1.67 × 1021
18.0
c Mass of ethanol = 1.50 × 0.790 = 1.185 g
1.185
Number of oxygen atoms = × 6.022 × 1023 = 1.55 × 1022
46.0
45500
d Number of oxygen atoms = × 6.022 × 1023 × 4 = 1.22 × 1027
90.0
4a Moles of caffeine = 9.12 × 1019/6.022 × 1023 = 1.514 × 10−4
0.0294
Mr = = 194
1.514 ×10−4
b H10N4O2 = 98
194 = (x × 12) + (10 × 1) + (4 × 14) + (2 × 16) = 12x + 98 so 12x = 96 and x =8
0.0150
7 Moles of H2 = = 0.00750
2
nRT 0.00750× 8.31 ×310
V= = = 1.84 × 10−4 m3
p 105000
Volume of H2 = 184 cm3
0.172
8 Moles of C6H12 = = 2.048 × 10−3
84.0
nRT 2.048× 10−3 ×8.31 ×350
V= = = 4.963 × 10−5 m3
p 120000
Volume of C6H12 = 49.6 cm3
Ca P O
Mass/g 2.41 1.24 2.56
Ar 40.1 31.0 16.0
Moles 0.06 0.04 0.16
Ratio 1.5 × 2 = 3 1×2=2 4×2=8 ü
C H
Mass/g 5 1
12 a
C H Cl
Mass/g 24.7 2.1 73.2
Ar 12.0 1.0 35.5
Moles 2.058 2.1 2.062
Ratio 1 1 1
145.5
b =3
48.5
Molecular formula = C3H3Cl3
13 a
C H O
Mass/g 0.720 0.0900 0.960
Ar 12.0 1.0 16.0
Moles 0.06 0.09 0.06
Ratio 1×2=2 1.5 × 2 = 3 1×2=2
1.77
Mr = = 118
0.0150
118
=2
59
Molecular formula = C4H6O4
24.75× 0.425
15 a Moles of KOH = 1000 = 0.01052 mol
0.01052
Amount (in moles) of H2SO4 = = 0.00526 mol
2
Concentration of H2SO4 = 0.00526 × 40 = 0.210 mol dm−3
Add deionised water until the bottom of the meniscus is on the line of the flask.
11.3× 0.126
16 a Moles of NaOH = 1000 = 1.4238 × 10−3 mol
50.0× 1.00
Moles of HCl added initially = = 0.05 mol
1000
Moles of HCl which reacted with CaCO3 = 0.05 − 0.014238 = 0.035762 mol
0.035762
Moles of CaCO3 = = 0.017881 mol
2
Mass of CaCO3 = 0.017881 × 100.1 = 1.7899 g
1.7899
Mass of CaCO3 in one tablet = = 0.3580 g = 358 mg
5
b Mass of one tablet = 500 mg
358
% of CaCO3 in one tablet = × 100 = 71.6 %
500
17 a Weigh empty container (evaporating basin / crucible).
1.96
b Moles of CuCl2 = 134.5 = 0.01457 mol
Mass of water lost = 2.48 − 1.96 = 0.52 g
0.450
18 a Moles of FeCl3.6H2O = moles of FeCl3 = 270.3 = 1.665 × 10−3 mol
Moles of Cl− = 1.665 × 10−3 × 3 = 4.995 × 10−3 mol
45.0 ×0.120
Moles of AgNO3 = moles of Ag+ = = 5.40 × 10−3 mol
1000
AgNO3 is in excess.
6.00
19 a Moles of H2O = 18.0 = 0.3333 mol
4.85
Moles of Mg3N2 = = 0.04807 mol
1000
Moles of H2O required for 0.04807 mol of Mg3N2 = 0.2884 mol
Water is in excess.
34.0
b % atom economy = 208.9 × 100 = 16.3%
3.25
20 a Moles of Cr(NO3)3 = 238.0 = 0.01366 mol
0.01366
b Moles of H2O2 required = 2 × 3 = 0.0205 mol
0.0205× 1000
Volume = = 35.3 cm3
0.580
0.01366
c Moles of K2Cr2O7 = 2 = 6.83 × 10−3 mol
1.42
d % yield = 2.01 × 100 = 70.7%
e Not all crystallised / side reactions / incomplete reaction
0.1
% uncertainty = × 100 = 0.6%
16.8
c Lower concentration of hydrochloric acid
Higher titre
17.2× 0.120
d Moles of HCl = 1000 = 2.064 × 10−3 mol
−3
2.064 ×10
Moles of Na2CO3 in 25.0 cm = 3
= 1.032 × 10−3 mol
2
Moles of Na2CO3 in 250 cm3 = 0.01032 mol
2.58
Mr of Na2CO3.xH2O = = 250.0
0.01032
Mr due to water = 250.0 − 106.0 = 144.0
144.0
x= =8
18.0
Exam-style questions
1 C
3000
Moles of Fe2O3 = 159.6 = 18.8 mol
300
Moles of C = 12 = 25 mol
25
Moles of Fe formed = 3 × 4 = 33.33 mol
Mass of Fe formed = 33.33 × 55.8 = 1860 g = 1.86 kg
0.500
2a Moles of NaN3 = 65.0 = 7.692 × 10−3 mol
Moles of Na = 7.692 × 10−3 mol
Mass of Na = 7.692 × 10−3 × 23.0 = 0.177 g
−3
7.692×10
b Moles of N2 = 2 × 3 = 0.01154 mol
4.8235
Moles of benzene = = 0.06184 mol
78.0
Theoretical yield, moles of 1,3,5-tribromobenzene = 0.06184 mol
11.58
% yield = × 100 = 59.5%
19.46
Density = mass/volume where, if the density is given in g cm−3, the mass is in grams and the
volume is in cm3. Be careful that you understand the difference between a liquid and a solution.
A liquid is a pure substance. A solution contains a solute dissolved in a solvent. Density is used
to convert between the volume (in cm3) and mass (in g).
2.27
4a Moles of Ba(OH)2.8H2O = −3
315.3 = 7.20 × 10 mol
7.20× 10−3
3
Moles of Ba(OH)2 in 25.0 cm = = 1.80 × 10−4 mol
40
Moles of HCl required = 1.80 × 10−4 × 2 = 3.60 × 10−4 mol
21.7 ×0.0200
b Moles of HCl = 1000 = 4.34 × 10−4 mol
−4
4.34 × 10
Moles of Ba(OH)2 in 25.0 cm =
3
= 2.17 × 10−4 mol
2
Moles of Ba(OH)2 in 1 dm3 = 2.17 × 10-4 × 40 = 8.68 × 10−3 mol
2.27
Mr of Ba(OH)2.xH2O = −3 = 261.5
8.68 ×10
Mr of xH2O = 261.5 − 171.3 = 90.2
90.2
x= =5
18.0
5 Mass of MgSO4 = 27.26 − 24.25 = 3.01 g
3.01
Moles of MgSO4 = = 0.025 mol
120.4
Mass of H2O = 29.96 − 27.26 = 2.7 g
0.15
x= =6
0.025
Compound Formula
Copper(II) nitrate Cu(NO3)2
c Ionic
b Tl2SO4
4 B
The Mg2+ ion and the N3− ion both have the same electron configuration as Ne (1s2 2s2 2p6). Al3+
and O2− also have this electron configuration but the charges are 3+ and 2− as opposed to 2+
and 3−.
6a
b 1+ / +
N2 0 0 1
NH3 3 0 0
CH4 4 0 0
C2H4 4 1 0
CO2 0 2 0
HCN 1 0 1
8 B
There are a total of four single covalent bonds, one double covalent bond and one triple covalent
bond, meaning nine pairs of electrons shared between atoms.
Metallic bonding
9a 1s2 2s2 2p6 3s2 3p6 3d10 4s1
Remember that copper has an unusual electron configuration. It has a more stable filled 3d
subshell. It does not end in 3d9 4s2.
Note that the particles must be regularly arranged and there must be a + or 2+ (as shown here).
10 C
11 D
13
Weak intermolecular forces / van der Waals forces between the molecules
When solid, carbon dioxide is a molecular crystal with weak van der Waals forces between the
molecules. These weak forces break below room temperature, and carbon dioxide is a gas.
15 a Ionic bonding
Ionic lattice
2+ and 2− charges
17 a B
b C
d A
Does not conduct electricity when solid but does when molten.
19 D
BeCl2 is linear (bond angle of 180°), BCl3 is trigonal planar (bond angle 120°), SiH4 is tetrahedral
(bond angle 109.5°) and SF6 is octahedral (bond angle 90°).
c Ammonia
21
b i Bonding pairs = 3
Lone pairs = 11
The I atom has 3 bonding pairs of electrons and 2 lone pairs of electrons, but each Cl atom also
has 3 lone pairs of electrons.
ii T-shaped
24 B
Ignoring the noble gases, moving across a period, electronegativity increases and moving down
a group, it decreases.
Carbon dioxide: linear equally polar bonds / dipoles cancel each other out.
e Water molecules are held further apart in ice than in liquid water as hydrogen bonds
are fixed.
26 a
IF3
BF3
Exam-style questions
1a P4 + 6Br2 → 4PBr3
Melting breaks the weak intermolecular forces between the molecules which does not
require much energy.
Phosphorus tribromide is a compound between two non-metals, hence is a molecular crystal
with covalent bonding between the atoms and weak intermolecular forces between the
molecules. The weak intermolecular forces do not need much energy to break and so the melting
point is low.
c P has five electrons in its outer shell and shares three electrons with Br (eight e − total in
outer shell).
b Ionic
Strong attractions
b Ammonia: 10
Hydrogen chloride: 18
c Hydrogen chloride has induced dipole–dipole / van der Waals forces / London forces
and permanent dipole–dipole attractions between molecules.
Ammonia has induced dipole–dipole / van der Waals forces / London forces and
hydrogen bonds between molecules.
107°
b i 8Mg + S8 → 8MgS
ii
Magnesium sulphide: ions / charge carriers cannot move and carry charge
c i S has six electrons in its outer shell and shares six with F (twelve e − total in outer shell
of S); six bonding pairs
Electron pairs repel each other as far away as possible; bonding pairs repel each other
equally.
Octahedral shape
ii
c i +572 kJ
ii −788 kJ
iii +2822 kJ
Calorimetry
4a Heat energy (q) = 2021000 × 0.0232 = 46887.2 J
q = mcΔT
46887.2 = 200 × 4.18 × ΔT
ΔT = 56.1°C
b Any two from: heat loss to surroundings / heat loss by evaporation / heat absorbed in
heating the beaker / incomplete combustion
1.00
5 Moles of propanone = 58.0 = 0.01724 mol
ΔT = 64.3 − 18.8 = 45.5°C
28528.5
ΔH = = − 1654.8 kJ mol−1
0.01724 ×1000
6a
Extrapolated to 4 minutes
ΔT = 4.5°C
10.0
b Moles of KI = 166.0 = 0.06024 mol
q = mcΔT = 50 × 4.18 × 4.5 = 940.5 J
940.5
ΔH = = + 15.6 kJ mol−1
0.06024 ×1000
c Heat exchange with surroundings or container / evaporation
−828
Per mole of lead(II) sulfide = = −414 kJ mol−1
2
Bond enthalpies
13 D
Bonds broken: (C=C) + 4(C–H) + 3(O=O) = 611 + 4(412) + 3(496) = 3747
Bonds made: 4(C=O) + 4(O–H) = 4(803) + 4(463) = 5064
ΔH = 3747 − 5064 = −1317 kJ mol−1
−1389 = −3(O–H)
O–H = 463 kJ mol−1
b Mean bond enthalpy values are not specific to the molecules in the reaction / averaged
over many molecules containing the bond.
Exam-style questions
0.400
1a Moles of ethanol = 46.0 = 0.008696 mol
8569
ΔH = = − 985.4 kJ mol−1
0.008696 ×1000
b Bonds broken: (C–C) + 5(C–H) + (C–O) + (O–H) + 3(O=O)
= 348 + 5(412) + 360 + 463 + 3(496) = 4719
4(C=O) = 3212
C=O = 803 kJ mol−1
c i The enthalpy change in a reaction is independent of the route taken and depends only
on the initial and final states.
c All assumed to be gases when using bond enthalpy values / mean bond enthalpy
values are not specific to the molecules in the reaction / mean bond enthalpy values
are averaged across molecules containing the bond.
3a
Extrapolated to 4 minutes
ΔT = 12.5°C
50.0× 2.00
c Moles of H2O = moles of NaOH = 1000 = 0.100 mol
5225
ΔH = = −52.3 kJ mol−1
0.1× 1000
e Heat loss to surroundings / heat loss by evaporation / heat loss to container
2a 80 cm3
The volume of gas in the second time period (10–20 s) is calculated by subtracting the volume of
gas at 20 s from the volume of gas at 10 s, which is 65 − 40 = 25 cm3. This process continues for
the other time periods. The rate is calculated by dividing the volume of gas by the interval of the
time periods, which is 10 s, giving a rate in cm3 s−1.
e Curve labelled A starts at (0, 0) and stays higher than 25°C curve but levels off sooner
at 80 cm3.
f Curve labelled B starts at (0, 0) and stays lower than 25°C curve but levels off later at
80 cm3.
b Activation energy
c Peak moved to the right and lower; crosses other curve once.
d Many more particles with energy greater than the activation energy
e Lower value
5a B
b D
c A
d Peak moved to the left and higher; crosses other curve once
Exam-style questions
1a Rate increases as particles pushed closer together
iii Starts at 60 cm3; stays lower than the other curve; levels off earlier at 40 cm3
Ea = activation energy
b i Ea decreases.
iii X decreases.
b 1.5 mol of gas forms 1 mol of gas. (1.5 mol of gas on left and 1 mol of gas on right)
Position of equilibrium moves to the right to lower the pressure / oppose the increase in
pressure.
Position of equilibrium moves to the left to decrease the temperature / oppose the
increase in temperature.
d No effect
Catalyst speeds up the rates of the forward and reverse reactions equally.
3a A
Fewer moles of gas on the right-hand side / smaller gas volume on right-hand side
Position of equilibrium moves to the right to lower the pressure / oppose the increase in
pressure.
b B
c D
Position of equilibrium moves to the right to decrease the temperature / oppose the
increase in temperature.
Position of equilibrium moves to the right to lower the pressure / oppose the increase in
pressure.
Position of equilibrium moves to the right to lower the pressure / oppose the increase in
pressure.
Position of equilibrium moves to the left to lower the temperature / oppose the increase
in temperature.
5a A system at equilibrium will respond to oppose any changes imposed upon it.
Position of equilibrium moves to the right to lower the temperature / oppose the
increase in temperature.
Position of equilibrium moves to the left to lower the pressure / oppose the increase in
pressure.
iii No effect
Catalyst increases the rates of the forward and reverse reactions equally.
iv Position of equilibrium moves to the right to remove the added B / oppose the increase
in concentration of B.
8 D
Moles of A present at equilibrium = mol of B = 0.25
Moles of A which reacted = 0.75
Moles of C formed = 2 × 0.75 = 1.5
[C] 2 (1.5)2
=¿
Kc = [ A ] [B] (0.25)(0.25) = 36
2 4
[C] [D]
9a Kc = 2 3
[ A ] [B ]
b i Moles of B which reacted = 2.1
2.1
Moles of A which reacted = × 2 = 1.4
3
1.1
ii Concentration of A at equilibrium = = 0.055 mol dm−3
20
0.90
Concentration of B at equilibrium = = 0.045 mol dm−3
20
1.4
Concentration of C at equilibrium = = 0.070 mol dm−3
20
2.8
Concentration of D at equilibrium = = 0.14 mol dm−3
20
All correct (Each error −)
c i 3E + 2F ⇌ G + 2H
ii Endothermic
Position of equilibrium moves to the right to lower the temperature / oppose the
increase in temperature.
10 a i 2x
2
[HI ]
iiKc = [ H ¿¿ 2][ I 2 ]¿
2
(2 x )
¿
iii = ( 2−x ) (2−x ) = = 50
2x
(
2−x
) = √ 50 = 7.07
2x = 7.07 × (2 − x)
2x = 14.14 − 7.07x
9.07x = 14.14
14.14
x= = 1.56
9.07
iv 2x = 3.12
3.12
[HI] = = 0.624 mol dm−3
5
Starts at origin.
[N ¿¿ 2]¿ ¿ ¿
c Kc = mol dm−3
(0.60)(1.20)2
d Kc = (0.40)2 = 5.4 (mol dm−3)
e Kc decreases.
Position of equilibrium moves to the left to lower the temperature / oppose the increase
in temperature.
Position of equilibrium moves to the left to lower the temperature / oppose the increase
in temperature.
Kc decreases.
Position of equilibrium moves to the right to lower the pressure / oppose the increase in
pressure.
0.85
[P] = = 0.34 mol dm−3
2.50
0.90
[Q] = = 0.36 mol dm−3
2.50
1.1
[R] = = 0.44 mol dm−3
2.50
All 3 concentrations correct
2
[R ]
2
b Kc = [ P ] [Q]
2
(0.44)
c Kc = (0.34)( 0.36)2 = 4.4 mol dm
−1 3
d No effect
Position of equilibrium moves to the left to oppose the increase in volume / larger
volume means lower concentration of gas.
Position of equilibrium moves to the right to lower the temperature / oppose the
increase in temperature.
3 C
b Iodine is oxidised.
Electron acceptor
Each error −
8a Potassium sulfate(IV)
d Potassium ions
Chloride ions
b Fe2+ → Fe3+ + e−
c Electron acceptors
11
All correct
Exam-style questions
1 a i HNO3 +5 NO2 +4
d Sulfate ions
Potassium ions
And to +4 in MnO2
b MnO4− + e− → MnO42−
2 D
Hence there are stronger van der Waals forces between the molecules and so they are
held more tightly together and need more energy to break.
4 Silicon is a giant covalent structure and more energy is needed to break the many
strong covalent bonds than is needed to break the weaker metallic bonds in
aluminium.
5a The energy required to remove one mole of electrons from one mole of gaseous atoms
to form one mole of gaseous ions with a single positive charge.
c Al(g) → Al+(g) + e
d i Increased nuclear charge / more protons electrons removed from same shell / similar
shielding and so outer electron held closer to nucleus.
2a Ba2+
CO32−
d MgSO4
e It is taken as a ‘barium meal’ as it absorbs x-rays and allows the gut to be seen. / It is
insoluble and so, although toxic, is safe to use.
f In magnesium the delocalised electrons are closer to cations, as the cation has fewer
electron shells and is smaller.
Hence there is a stronger attraction between the cations and the delocalised electrons
and stronger metallic bonding.
3a Increases
More shells
b i Increases
c Decreases
d Decreases
2 D
3 Dissolve in water , add a few drops of silver nitrate and then some dilute ammonia
Therefore Br− ions are more easily oxidised / lose an electron more easily.
Cream precipitate
Remains colourless
White precipitate
7 C
Exam-style questions
1 B
2 B
3a Mg + 2H2O → Mg(OH)2 + H2
Titanium is reduced.
ii Mg + H2SO4 → MgSO4 + H2
The magnesium sulfate is soluble and the Ti solid can be filtered off.
b To remove any carbonate ions which may interfere with the test.
c Magnesium / calcium
5a Decreases
b i Increases
c i Increases
B 1,3-dichloropropane
C 2-chloropropane
D (2-)methylpropane
E 2-chloro-2,3,3-trimethylpentane
F 3,3-dichloro-2,2,4-trimethylhexane
G 2-bromo-1-chloro-3-ethylpentane
H Propan-2-ol
I Propanal
J Pentan-3-one
K Butanoic acid
L Propene
M But-2-ene
N 4-bromobutanoic acid
O Propan-1-ol
P (2-)methylpropene
Q (2,2-)dimethylpropane
R Buta-1,3-diene
2a
3a CnH2n+1OH
b CnH2n+2
c CnH2n
4a C5H12 C5H12
b C4H8O2 C2H4O
5a Butane alkane
b But-1-ene alkene
d Butan-1-ol alcohol
e Pentan-2-one ketone
f Propan-2-ol alcohol
Isomerism
6a C6H13 CnH2n+2
b 2,2,3,3,4,4-hexamethylhexane chain
7 C
8 C
9a Pent-2-ene
10 For each part for completely correct name; allow for correct E/Z.
a E-1-bromo-2-chloropropene
b Z-1-chlorobut-1-ene
d Z-1-bromo-1,2-dichloroethene
Exam-style questions
1 B
2 B
3 B
4a C=C OH / hydroxyl
Z E
d Structural isomers are compounds with the same molecular formula but different
structural formulae.
5 The right-hand carbon of the double bond has a C attached which has a higher atomic
number than H so the CH2Br has higher priority.
The left-hand carbon of the double bond has a carbon attached in each group, so
consider the atoms one bond further away. The C H H from the top propyl group are
attached to one carbon and have higher atomic number than the H H H attached to
the carbon of the methyl group. The propyl group has priority.
The highest priority groups, –CH2CH2CH3 and –CH2Br, are on the same side so it is a Z
isomer.
(Z)-1-bromo-3-methylhex-2-ene.
6a Propanal CH3CH3CHO
Propanone CH3COCH3
b Prop-2-en-1-ol
or prop-1-en-2-ol
High pressure
High temperature
Propane
Zeolite
Fractional distillation
Hence it has stronger van der Waals forces between the molecules.
Catalytic cracking and thermal cracking both take place at high temperature.
Thermal cracking takes place at high pressure and catalytic cracking at a slight
pressure.
Combustion of alkanes
4 C
They show similar chemical properties / they show a gradual change in physical
properties from propane to butane.
c CnH2n+2
d Saturated: only contains single C–C bonds / there are no C=C bonds.
h Sulfur dioxide
Neutralisation
i Nitrogen(IV) oxide: The pressure and high temperature in the combustion engine
cause the normally unreactive nitrogen in the air to react with oxygen. /
N2 + 2O2 → 2NO2
Harm caused: react with unburned hydrocarbons to produce smog / dissolve in water to
form acid rain.
Chlorination of alkanes
6 B
7 C
8 D
b i Cl2 → 2Cl•
ii UV light
Level 3 All stages are covered and each Stage 1: states and explains the condition.
(5–6 stage is generally correct and
UV light is the condition.
marks) virtually complete. Answer
communicates reasoning It is needed to break the Cl–Cl bond.
coherently and shows a logical Stage 2: describes initiation and
progression through the propagation.
mechanism with correct
equations. Chlorine radicals are formed.
Substitution as one atom (H) is replaced by
Level 2 Two stages are covered or parts another (Cl).
(3–4 of three stages (if two stages are
marks) covered, they must be complete Initiation: Cl2 → 2Cl•
Octane
Exam-style questions
1a C3H8 + Br2 → C3H7Br + HBr
2-bromopropane
b Fractional distillation
Platinum or rhodium
3 C
2a The reaction is exothermic, and adding concentrated acid slowly with stirring controls
the reaction and prevents dangerous spitting.
b Bromine
The solid potassium bromide reacts with the concentrated sulfuric acid to form
hydrogen bromide which is further oxidised by the concentrated sulfuric acid to form
bromine.
c Anti-bumping granules
Shake
Allow to settle, remove stopper and run off bottom layer – discard the aqueous layer.
h To remove water
b Equal amounts of each halogenoalkane are placed in separate test tubes in a water
bath at 50°C. A test tube containing a mixture of ethanol and aqueous silver nitrate is
heated in the same water bath.
When all tubes reach the same temperature, equal volumes of the mixture are added to
each halogenoalkane and the clock is started.
The halide ions react with the silver ions in silver nitrate and form a precipitate.
Iodoethane forms a precipitate fastest, then bromoethane and then chloroethane.
The time taken for a precipitate to form in each test tube is recorded.
b Elimination
c Propene
Base / accepts H+
Ozone depletion
5a A species with an unpaired electron
b UV light
c Cl• + O3 → O2 + ClO•
is regenerated
d Ozone absorbs UV radiation which can cause sunburn / cancer / ageing of skin.
2 B
3a 1-iodobutane
The C–I bond has the lowest bond enthalpy / weakest bond.
Bond enthalpy decreases down the group with increasing size of the halogen atom.
But-1-ene
c Elimination
e 2-methylbut-1-ene
2-methylbut-2-ene
Butan-1-ol
g Nucleophilic substitution
The electrons in the covalent bond are attracted more to the halogen and form a partial
negative charge on the halogen.
4a Dichlorodifluoromethane
c O2 → 2O•
O2 + O• → O3
d Cl• + O3 → O2 + ClO•
Propylhydrogensulfate
2,3-dibromobutane
Bromopropane
2,3-dibromohexane
2 A
3a But-1-ene:
Butane:
b The double bond is a centre of high electron density and can undergo attack by
electrophiles.
c Bromine water
2,3-dibromobutane
ii Electrophilic addition
E Z
Addition polymers
4 Poly(but-2-ene)
5a
Fluoroethene
d Poly(chloroethene)
e Plasticiser
Exam-style questions
1 C
2 C
3 A
4a A: 1-bromopropane
B: Propan-1-ol
C: Propene
D: 2-bromopropane
d Step 1
Step 4
ci
ii It contains a C=C which can break and allow molecules to add on.
6a Isoprene
Limonene
b C5H8
c C5H8
iii
b Yeast produces an enzyme which converts glucose to ethanol and carbon dioxide.
A temperature of 35°C. The enzyme in yeast works best around this temperature.
Above this the enzyme is denatured, below this the reaction is too slow.
Air is kept out to prevent the oxidation of the ethanol formed to ethanoic acid (vinegar).
c i Fractional distillation
d i A carbon-neutral activity is one which has no net annual emissions of carbon dioxide to
the atmosphere.
ii Mention any process: for example, harvesting, planting, transport of materials, distilling
the ethanol solution, producing fertilisers for crops.
iv It uses up land which could be used for crops for food / production of crops is slow.
e i Electrophilic addition
ii Excess ethene or excess steam / water or remove the ethanol as it forms or recycle
the ethane
60 atm pressure
600 K temperature
c 2-methylpropan-2-ol
3 D
4a CH3CH2CH2CH2OH butan-1-ol
CH3CH(OH)CH2CH3 butan-2-ol
b CH3CH2CH2COOH
CH3CH2CH2CHO
CH3COCH2CH3
All 3 correct 2 correct
2-methylpropan-2-ol
Warm with Fehling’s solution / Tollens’ reagent / acidified potassium dichromate( VI)
No change in propanone
6a
b Hydrogen bonds can form between the lone pair on O of diol and polar hydrogen in
water or vice versa
c Primary
7a 3-methylbutan-2-ol
b i Elimination / dehydration
ii
c 3-methylbutan-2-one
e Pour distillate into a separating funnel and shake with sodium carbonate solution.
When cyclohexene goes clear, remove calcium chloride by filtration under reduced
pressure.
Exam-style questions
1a Same molecular formula but different structural formula
b Butan-1-ol
c i K2Cr2O7
ii CH3CH2CH2CHO
Butanal
iii CH3CH2CH2COOH
Butanoic acid
ii Orange to green
e 2-methylpropan-2-ol
4 : 10 : 1
2 C
2 D
D is a tertiary alcohol, so will not be oxidised with acidified potassium dichromate( VI) solution.
b Bromine water
With butanal, Fehling’s solution changes from a blue solution to form a red precipitate /
Tollens’ reagent changes to form a silver mirror.
With butanone, Fehling’s solution remains blue and Tollens’ reagent shows no change.
Blue Fehling’s solution gives a red precipitate / Tollens’ solution forms a silver mirror.
b Propenal / prop-2-enal
iii Oxidation
They have the same Mr (to 1 decimal place) and give the same molecular ion peak.
The molecular ion value gives the relative molecular mass – it is 44.00105. To show that this is
N2O, simply add together the precise relative atomic mass values of (2 × N) and (1 × O).
2(14.00307) + 15.99491 = 44.00105. You then need to calculate the relative atomic mass of each
of these molecules using the relative atomic masses given to 1 decimal place in your periodic
table:
Propane is C3H8 → (3 × 12.0) + (8 × 1.0) = 44.0
Carbon dioxide is CO2 → (1 × 12.0) + (2 × 16.0) = 44.0
Dinitrogen oxide is N2O → (2 × 14.0) + (1 × 16.0) = 44.0
They have the same Mr (to 1 decimal place) and would give the same molecular ion peak.
7a A: O–H
B: C–H
C: C=O
D: C–O
(Each error −)
b Compound Z
8a A: Pent-1-ene
B: Pentan-2-ol
C: 2-methylbutan-2-ol
D: 2-methylbutanoic acid
E: Butanone
F: 2-methylbutanal
b Bromine water
c Compound F
Aldehyde group
e Compound D
B is ethanoic acid as it has an OH absorption (acid) between 2500 and 3000 and a
C=O absorption between 1680 and 1750.
Exam-style questions
1 C
2a C3H6O
ii
2,3-dibromopropan-1-ol
70.6
Moles C = = 5.88
12.0
13.7
Moles H = = 13.7
1.0
15.7
Moles O = = 0.98
16.0
5.88 13.7 0.98
Ratio: = 6.0; = 14.0; = 1.0 so C6H14O
0.98 0.98 0.98
Hexan-1-ol
Hexan-2-ol
Hexan-3-ol
Vapour escapes from the liquid mixture, condenses and returns to the liquid mixture
where it is in contact with the oxidation agent again.
c Orange to green
d Change the apparatus for distillation. / Use a still head containing a thermometer with
the condenser horizontal.
or
Add Fehling’s solution Red precipitate
No effervescence observed
ii O–H absorption / C–O absorption for propanoic acid / different fingerprint region