Combinepdf

Cambridge International AS & A Level
*8748629381*
CHEMISTRY9701/22
Paper 2 AS Level Structured Questions February/March 2022
1 hour 15 minutes
You must answer on the question paper.
No additional materials are needed.
INSTRUCTIONS
● Answer all questions.
● Use a black or dark blue pen. You may use an HB pencil for any diagrams or graphs.
● Write your name, centre number and candidate number in the boxes at the top of the page.
● Write your answer to each question in the space provided.
● Do not use an erasable pen or correction fluid.
● Do not write on any bar codes.
● You may use a calculator.
● You should show all your working and use appropriate units.
INFORMATION
● The total mark for this paper is 60.
● The number of marks for each question or part question is shown in brackets [ ].
● The Periodic Table is printed in the question paper.
● Important values, constants and standards are printed in the question paper.
This document has 16 pages.
IB22 03_9701_22/4RP
© UCLES 2022 [Turn over
2
Answer all the questions in the spaces provided.
1 Fig. 1.1 shows how first ionisation energies vary across Period 2.
A
ionisation
energy
Li Be B C N O F Ne
element
Fig. 1.1
(a) Construct an equation to represent the first ionisation energy of oxygen.

Include state symbols.
............................................................................................................................................... [1]
(b) (i) State and explain the general trend in first ionisation energies across Period 2.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(ii) Explain why ionisation energy A in Fig. 1.1 does not follow the general trend in first
ionisation energies across Period 2.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2022 9701/22/F/M/22

3
(c) Element E is in Period 3 of the Periodic Table.

The first eight ionisation energy values of E are shown in Table 1.1.
Table 1.1
ionisation 1st 2nd 3rd 4th 5th 6th 7th 8th

ionisation energy / kJ mol–1 577 1820 2740 11 600 14 800 18 400 23 400 27 500
Deduce the full electronic configuration of E.

Explain your answer.
full electronic configuration of E = ..............................................................................................
explanation .................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
[3]
[Total: 9]
© UCLES 2022 9701/22/F/M/22 [Turn over

4
2 Some oxides of elements in Period 3 are shown.
Na2O Al 2O3 P4O6 P4O10 SO2 SO3
(a) Na reacts with O2 to form Na2O. Na is the reducing agent in this reaction.
(i) Define reducing agent.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Write an equation for the reaction of Na2O with water.
........................................................................................................................................ [1]
(b) Al 2O3 is an amphoteric oxide found in bauxite.
(i) State what is meant by amphoteric.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Al 2O3 is purified from bauxite in several steps. The first step involves heating Al 2O3 with
an excess of NaOH(aq). A colourless solution forms.
Write an equation for this reaction.
........................................................................................................................................ [1]
© UCLES 2022 9701/22/F/M/22

5
(iii) Al 2O3 is used as a catalyst in the dehydration of alcohols.
tate the effect of using Al 2O3 as a catalyst in the dehydration of alcohols. Use the
S
Boltzmann distribution in Fig. 2.1 to help explain your answer.
number of
molecules
energy
Fig. 2.1
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(c) P4O6 is a white solid that has a melting point of 24 °C. Solid P4O6 reacts with water to form
H3PO3.
(i) Deduce the type of structure and bonding shown by P4O6. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Determine the oxidation number of P in H3PO3.
........................................................................................................................................ [1]

6
(iii) When P4O6(s) is heated with oxygen it forms P4O10(s).
P4O6(s) + 2O2(g) → P4O10(s) ∆Hr = –1372 kJ mol–1
The enthalpy change of formation, ∆Hf, of P4O10(s) is –3012 kJ mol–1.
Calculate the enthalpy change of formation, ∆Hf, of P4O6(s).
∆Hf of P4O6(s) = .............................. kJ mol–1 [1]
(iv) Write an equation for the reaction of P4O10 with water.
........................................................................................................................................ [1]
(d) SO2 and SO3 are found in the atmosphere.

The oxidation of SO2 to SO3 in the atmosphere is catalysed by NO2.
The first step of the catalytic oxidation is shown in equation 1.
equation 1 SO2(g) + NO2(g) SO3(g) + NO(g)
(i) Construct an equation to show how NO2 is regenerated in the catalytic oxidation of SO2.
........................................................................................................................................ [1]
(ii) NO2 can also react with unburned hydrocarbons to form photochemical smog.
State the product of this reaction that contributes to photochemical smog.
........................................................................................................................................ [1]
© UCLES 2022 9701/22/F/M/22

7
(iii) Fig. 2.2 shows how the temperature of the atmosphere varies with height from the ground.
110
100
90
80
70
60
height / km
50
40
30
20
10
0
–120 –100 –80 –60 –40 –20 0 20
temperature / C
Fig. 2.2
The equilibrium reaction in equation 1 has ∆Hr = –168 kJ mol–1.
Suggest how the position of this equilibrium differs at a height of 20 km compared with a
height of 50 km from the ground.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 16]

8
3 The hydrogen halides HCl, HBr and HI are all colourless gases at room temperature.
(a) The hydrogen halides can be formed by reacting the halogens with hydrogen.
Describe and explain the relative reactivity of the halogens down the group when they react
with hydrogen to form HCl, HBr and HI.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(b) HCl is a product of several different reactions. Some of these are shown in Fig. 3.1.
SiCl 4 NaCl
reaction 1 reaction 2
H2O concentrated H2SO4
HCl
Fig. 3.1
(i) Write an equation for reaction 1.
........................................................................................................................................ [1]
© UCLES 2022 9701/22/F/M/22

9
(ii) In reaction 2, NaCl reacts with concentrated H2SO4 to form HCl and NaHSO4.
When NaBr reacts with concentrated H2SO4, the products include Br2 and SO2.
Identify the type(s) of reaction that occur in each case by completing Table 3.1.
Explain the difference in these reactions.
Table 3.1
reactants type(s) of reaction
NaCl and concentrated H2SO4
NaBr and concentrated H2SO4
explanation ..........................................................................................................................
..............................................................................................................................................
[3]
(c) When heated with a Bunsen burner, HCl does not decompose, whereas HI forms H2 and I2.
Explain the difference in the effect of heating on HCl and HI.
.....................................................................................................................................................
............................................................................................................................................... [1]

10
(d) The hydrogen halides dissolve in water to form strong Brønsted–Lowry acids.
The concentration of a strong acid can be determined by titration.
(i) State what is meant by strong Brønsted–Lowry acid.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) On Fig. 3.2, sketch the pH titration curves produced when:

● 0.1 mol dm–3 NaOH(aq) is added to 25 cm3 of 0.1 mol dm–3 HBr(aq), to excess
● 0.1 mol dm–3 NH3(aq) is added to 25 cm3 of 0.1 mol dm–3 HBr(aq), to excess.
reaction of NaOH(aq) and HBr(aq) reaction of NH3(aq) and HBr(aq)

14 14
12 12
10 10
8 8
pH pH
6 6
4 4
2 2
0 0
0 5 10 15 20 25 30 35 40 45 0 5 10 15 20 25 30 35 40 45
volume of NaOH / cm3 volume of NH3 / cm3
Fig. 3.2
[3]
© UCLES 2022 9701/22/F/M/22

11
(e) HBr reacts with propene to form two bromoalkanes, CH3CH2CH2Br and (CH3)2CHBr.
(i) Complete the diagram to show the mechanism of the reaction of HBr and propene to form
the major organic product.
Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate.
Draw the structures of the intermediate and the major organic product.
H H
H
C C
H C H
H
H Br
[4]
(ii) Explain why the two bromoalkanes are not produced in equal amounts by this reaction.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) The reaction of CH3CH2CH2Br and NaOH is different depending on whether water or
ethanol is used as a solvent.
Complete Table 3.2 to identify the organic and inorganic products of the reaction of
CH3CH2CH2Br and NaOH in each solvent.
Table 3.2
solvent organic product(s) inorganic product(s)
water
ethanol
[2]
[Total: 20]

12
4 Compounds J and K are found in plant oils.
J K
O OH H COOH
C C CHO C C
H 3C CH3 H CH3
Fig. 4.1
(a) (i) Complete Table 4.1 to state what you would observe when J reacts with the reagents
listed.
Table 4.1
reagent observation with J
2,4-dinitrophenylhydrazine
(2,4-DNPH)
Tollens’ reagent
sodium metal
[3]
(ii)
J has two optical isomers.
Draw the three-dimensional structures of the two optical isomers of J.
[2]
© UCLES 2022 9701/22/F/M/22

13
(b)
K is used to make the addition polymer Perspex®. A synthesis of Perspex® is shown in Fig. 4.2.
K M
H COOH H COOCH3
reactant L
C C C C Perspex®
H CH3 H CH3
Fig. 4.2
(i) Identify L. State the conditions required for reaction 1.
L = .......................................................................................................................................
conditions = .........................................................................................................................
[2]
(ii) Draw one repeat unit of the addition polymer Perspex®.
[2]
(iii) Use information from Table 4.2 to suggest how the infrared spectra of M and Perspex®
would differ. Explain your answer.
..............................................................................................................................................
........................................................................................................................................ [1]
Table 4.2
bond functional group containing the bond characteristic infrared absorption range
(in wavenumbers) / cm–1
C–O hydroxy, ester 1040–1300
C=C aromatic compound, alkene 1500–1680
C=O amide 1640–1690
carbonyl, carboxyl 1670–1740
ester 1710–1750
C≡N nitrile 2200–2250
C–H alkane 2850–3100
N–H amine, amide 3300–3500
O–H carboxyl 2500–3000
hydroxy 3200–3650

14
(iv)
K can be made from propanone in the three-step synthesis shown in Fig. 4.3.
propanone K
O OH OH H COOH
step 1 step 2 step 3
C H3C C C N H3C C COOH C C
H 3C CH3
H CH3
CH3 CH3
Fig. 4.3
Complete Table 4.3 to identify the reagent(s) used and the type of reaction in each step.
Table 4.3
step reagent(s) type of reaction
3 Al 2O3
[5]
[Total: 15]
© UCLES 2022 9701/22/F/M/22

15
Important values, constants and standards
molar gas constant R = 8.31 J K–1 mol–1

Faraday constant F = 9.65 × 104 C mol–1
Avogadro constant L = 6.022 × 1023 mol–1
electronic charge e = –1.60 × 10–19 C
molar volume of gas Vm = 22.4 dm3 mol–1 at s.t.p. (101 kPa and 273 K)
Vm = 24.0 dm3 mol–1 at room conditions
ionic product of water Kw = 1.00 × 10–14 mol2 dm–6 (at 298 K (25 °C))
specific heat capacity of water c = 4.18 kJ kg–1 K–1 (4.18 J g–1 K–1)
© UCLES 2022 9701/22/F/M/22

© UCLES 2022
The Periodic Table of Elements
Group
1 2 13 14 15 16 17 18
1 2
H He
hydrogen helium
Key 1.0 4.0
3 4 atomic number 5 6 7 8 9 10
Li Be atomic symbol B C N O F Ne
lithium beryllium name boron carbon nitrogen oxygen fluorine neon
6.9 9.0 relative atomic mass 10.8 12.0 14.0 16.0 19.0 20.2
11 12 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
sodium magnesium aluminium silicon phosphorus sulfur chlorine argon
23.0 24.3 3 4 5 6 7 8 9 10 11 12 27.0 28.1 31.0 32.1 35.5 39.9
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
at www.cambridgeinternational.org after the live examination series.

K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
potassium calcium scandium titanium vanadium chromium manganese iron cobalt nickel copper zinc gallium germanium arsenic selenium bromine krypton
39.1 40.1 45.0 47.9 50.9 52.0 54.9 55.8 58.9 58.7 63.5 65.4 69.7 72.6 74.9 79.0 79.9 83.8
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
16
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
rubidium strontium yttrium zirconium niobium molybdenum technetium ruthenium rhodium palladium silver cadmium indium tin antimony tellurium iodine xenon
85.5 87.6 88.9 91.2 92.9 95.9 – 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
9701/22/F/M/22
55 56 57–71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
lanthanoids
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
caesium barium hafnium tantalum tungsten rhenium osmium iridium platinum gold mercury thallium lead bismuth polonium astatine radon
132.9 137.3 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 – – –
87 88 89–103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
actinoids
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
francium radium rutherfordium dubnium seaborgium bohrium hassium meitnerium darmstadtium roentgenium copernicium nihonium flerovium moscovium livermorium tennessine oganesson
– – – – – – – – – – – – – – – – –
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
lanthanoids La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
lanthanum cerium praseodymium neodymium promethium samarium europium gadolinium terbium dysprosium holmium erbium thulium ytterbium lutetium
138.9 140.1 140.9 144.4 – 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.1 175.0
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
actinoids Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
actinium thorium protactinium uranium neptunium plutonium americium curium berkelium californium einsteinium fermium mendelevium nobelium lawrencium
– 232.0 231.0 238.0 – – – – – – – – – – –
Assessment International Education Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download
To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge
*5046493367*
CHEMISTRY9701/22
Paper 2 AS Level Structured Questions May/June 2022
1 hour 15 minutes
INSTRUCTIONS
INFORMATION
This document has 16 pages. Any blank pages are indicated.
IB22 06_9701_22/5RP
2
1 (a) Magnesium has a melting point of 650 °C and high electrical conductivity.
Explain these properties of magnesium by referring to its structure and bonding.
.....................................................................................................................................................
............................................................................................................................................... [2]
(b) When magnesium is heated in air, magnesium oxide, MgO, is the major product. Smaller
amounts of magnesium nitride, Mg3N2, are also made.
(i) Calculate the oxidation number for magnesium and for the nitrogen species in Mg3N2 to
complete Table 1.1.
Table 1.1
species magnesium in Mg3N2 nitrogen in Mg3N2
oxidation number
[1]
(ii) Identify the type of reaction which takes place between magnesium and nitrogen.
..............................................................................................................................................
........................................................................................................................................ [1]
(iii) Define enthalpy change of formation.
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) When 3.645 g of Mg(s) burns in excess N2(g) to form Mg3N2(s), 23.05 kJ of energy is
released.
Calculate the enthalpy change of formation, ∆Hf, of Mg3N2. Show your working.
∆Hf (Mg3N2) = .............................................. [3]
[Total: 9]
© UCLES 2022 9701/22/M/J/22

3
Question 2 starts on the next page.
© UCLES 2022 9701/22/M/J/22 [Turn over

4
2 Radium, Ra, is an element found in Group 2 of the Periodic Table. It is a crystalline solid at room
temperature and conducts electricity.
Radium chloride, RaCl 2, has a melting point of 900 °C and is soluble in water.
(a) Predict the lattice structure of RaCl 2(s) based on the properties described.
............................................................................................................................................... [1]
(b) Draw a dot-and-cross diagram to show the arrangement of outer electrons in RaCl 2.
[1]
(c) Solid Ra and Ca show similar reactions with H2O, but the reactions occur at different rates.
Separate samples, each containing a single piece of solid Ra or Ca, are added to equal
volumes of cold water.
Each sample contains equal numbers of moles of solid and the H2O is in excess.
(i) Construct an equation for the reaction of Ra with H2O.
........................................................................................................................................ [1]
(ii) Identify which element, Ra or Ca, reacts with H2O at a faster rate. Suggest how the
observations of each reaction would differ.
..............................................................................................................................................
........................................................................................................................................ [1]
(iii) Suggest why these reactions occur at different rates.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2022 9701/22/M/J/22

5
(iv) One of the solutions is cloudy when the reaction has finished.
At the end of each reaction, universal indicator is added to each reaction mixture.
Suggest pH values of the solutions made in both reactions. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(d) A sample of aqueous calcium halide, CaX2(aq), contains either chloride, bromide or iodide
ions.
Complete Table 2.1 to describe a two-step process that could be used to identify the halide ion
present.
Table 2.1
observation observation observation

step method
with CaCl 2 with CaBr2 with CaI2
step 1
step 2
[3]
[Total: 11]

6
3 (a) 0.025 mol of HI(g) is added to a closed vessel and left to reach dynamic equilibrium. The total
pressure of the vessel is 100 kPa.
equation 1 2HI(g) H2(g) + I2(g)
(i) Explain what is meant by dynamic equilibrium.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Describe one difference in the initial appearance of the reaction mixture compared to the
mixture at equilibrium.
........................................................................................................................................ [1]
(iii) Write an expression for Kp for the reaction described in equation 1.
Kp =
[1]
(iv) At equilibrium the partial pressure of HI(g) is 86.4 kPa.
Calculate the amount of HI(g) present in the mixture at equilibrium. Show your working.
amount of HI(g) = .............................. mol [2]
© UCLES 2022 9701/22/M/J/22

7
(b) Use equation 1 and the bond energy values in Table 3.1 to calculate the change in enthalpy,
∆H, for the thermal decomposition of 1 mole of HI(g). Show your working.
Table 3.1
bond bond energy / kJ mol–1

H–H 436
I–I 151
H–I 299
∆H = .............................. kJ mol–1 [2]
(c) Describe the effect of increasing pressure on the value of Kp for the decomposition of HI(g).
............................................................................................................................................... [1]
(d) HCl (g) is prepared by adding NaCl (s) to concentrated H2SO4.
HI(g) is not prepared by adding NaI(s) to concentrated H2SO4 because the HI(g) produced
also reacts with concentrated H2SO4.
(i) Identify the type of reaction that occurs when NaI(s) reacts with concentrated H2SO4 to
form HI(g).
........................................................................................................................................ [1]
(ii) Write an equation for the reaction of HI(g) and concentrated H2SO4.
........................................................................................................................................ [1]
(iii) Explain why HI(g) reacts with concentrated H2SO4 whereas HCl does not.
........................................................................................................................................ [1]
[Total: 12]

8
4 (a) Bromine reacts with butane in the presence of ultraviolet light to form bromobutane.
Two structural isomers with the molecular formula C4H9Br are produced during this reaction.
(i) Draw the two structural isomers and state the systematic name of each isomer.
structural isomer 1 structural isomer 2
name .............................................. name ..............................................
[2]
(ii) Identify the type of structural isomerism shown in (a)(i).
........................................................................................................................................ [1]
(b) Halothane is an anaesthetic.
halothane
F Cl
F C C H
F Br
Fig. 4.1
(i) Identify the chiral centre in halothane and mark it with an asterisk (*). [1]
When halothane reacts in ultraviolet light, homolytic fission occurs and the C–Br bond is
broken.
(ii) Construct an equation to show the homolytic fission of halothane, CF3CHBrCl.
........................................................................................................................................ [1]
© UCLES 2022 9701/22/M/J/22

9
(iii) C
omplete Fig. 4.2 to show the arrangement of electrons in a bromine atom using the
electrons in boxes notation.
[Ar]
3d 4s 4p
Fig. 4.2
[1]
(c)
X is an addition polymer.
Cl
Fig. 4.3
(i) Draw the monomer of X.
[1]
(ii) Suggest one reason why the disposal of items made from X is difficult.
........................................................................................................................................ [1]
[Total: 8]

10
5 Fig. 5.1 shows three reactions of 2-bromopropane, CH3CH(Br)CH3.
CH3CH(Br)CH3
reaction 2
CH3CH(OH)CH3 CH3CH(NH2)CH3 H2C=CHCH3
Fig. 5.1
(a) Complete Table 5.1 for each reaction, by:
● s tating the reagent and conditions used

● identifying the type of reaction that occurs.
Table 5.1
reaction reagent and conditions type of reaction
[6]
(b) A sample of 2-iodopropane, CH3CH(I)CH3, reacts under the same conditions as reaction 1 to
produce CH3CH(OH)CH3.
Explain why 2-iodopropane reacts at a faster rate than 2-bromopropane.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
© UCLES 2022 9701/22/M/J/22

11
(c) Fig. 5.2 shows how butan-1-ol can be made from 1-bromopropane in three steps.
HO
N HO
Br step 1 step 2 step 3
O
Fig. 5.2
(i) In step 1, 1-bromopropane reacts with CN– to form butanenitrile.
omplete Fig. 5.3 to show the mechanism for step 1. Include charges, dipoles, lone pairs
C
of electrons and curly arrows as appropriate.
H H H H H H
H C C C Br H C C C C N
H H H H H H
Br –
C –
Fig. 5.3
[2]
(ii) In step 2, butanenitrile is heated with HCl (aq). A hydrolysis reaction occurs.
Construct an equation for the reaction in step 2.
........................................................................................................................................ [1]
(iii) Step 3 is a reduction reaction.
Construct an equation for the reduction reaction in step 3. Use [H] to represent one atom
of hydrogen from the reducing agent.
........................................................................................................................................ [1]
(iv) State the identity of a suitable reducing agent in step 3.
........................................................................................................................................ [1]
[Total: 13]

12
6
Z is a molecule which contains the elements carbon, hydrogen and oxygen only.
Z contains only alkene and carboxyl functional groups.

(a) C
omplete Table 6.1 by describing the observations that occur when two different reagents are
added to separate samples of Z(aq).
Table 6.1
reagent added
observation
to Z(aq)
Br2(aq)
Na2CO3(s)
[2]
(b) Table 6.2 shows the percentage by mass of each element present in Z.
Table 6.2
element percentage by mass / %

carbon 41.38
hydrogen 3.45
oxygen 55.17
Using the data in Table 6.2, demonstrate that the empirical formula of Z is CHO.
Show your working.
[1]
© UCLES 2022 9701/22/M/J/22

13
(c) Fig. 6.1 shows the mass spectrum of Z.
45
100
80
relative 60
abundance
40
71
20
116
117
0
10 20 30 40 50 60 70 80 90 100 110 120
m/e
Fig. 6.1
(i) Deduce the molecular formula of Z. Explain your answer by referring to the molecular ion
peak in Fig. 6.1 and the empirical formula of Z.
[1]
(ii) Use Fig. 6.1 to suggest the formulae of the fragments with m / e peaks at 45 and at 71.
m / e 45 .................................................................................................................................
m / e 71 .................................................................................................................................
[2]
(iii) Suggest the structure of Z using relevant information from Table 6.1, (b) and (c).
[1]
[Total: 7]

14
BLANK PAGE
© UCLES 2022 9701/22/M/J/22

15

© UCLES 2022 9701/22/M/J/22

© UCLES 2022
Group
1 2 13 14 15 16 17 18
1 2
H He
hydrogen helium
Key 1.0 4.0
11 12 13 14 15 16 17 18
23.0 24.3 3 4 5 6 7 8 9 10 11 12 27.0 28.1 31.0 32.1 35.5 39.9

19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
39.1 40.1 45.0 47.9 50.9 52.0 54.9 55.8 58.9 58.7 63.5 65.4 69.7 72.6 74.9 79.0 79.9 83.8
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
16
85.5 87.6 88.9 91.2 92.9 95.9 – 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
9701/22/M/J/22
55 56 57–71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
lanthanoids
132.9 137.3 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 – – –
87 88 89–103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
actinoids
– – – – – – – – – – – – – – – – –
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
138.9 140.1 140.9 144.4 – 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.1 175.0
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
– 232.0 231.0 238.0 – – – – – – – – – – –
*1663220061*
CHEMISTRY9701/22
Paper 2 AS Level Structured Questions October/November 2022
1 hour 15 minutes
INSTRUCTIONS
INFORMATION
IB22 11_9701_22/3RP
2
1 Species such as NH4+, CO32– and PO43– are examples of molecular ions.
(a) Ionic and covalent bonds both involve an electrostatic attraction between different species.
Identify the species that are electrostatically attracted to one another in:
● an ionic bond
.....................................................................................................................................................
● a covalent bond.
.....................................................................................................................................................
[2]
(b) Complete Table 1.1 to show the total numbers of protons and electrons in the molecular ions
NH4+, CO32– and PO43–.
Table 1.1
molecular total number total number

ion of protons of electrons
NH4+
CO32–
PO43–
[3]
(c) NH4+ is a Brønsted–Lowry acid.
(i) Define Brønsted–Lowry acid.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) When NH4+(aq) is heated with NaOH(aq), a pungent gas is produced.
Write an ionic equation for this reaction.
........................................................................................................................................ [1]
© UCLES 2022 9701/22/O/N/22

3
(iii) The nitrogen atom in NH4+ is sp3 hybridised. sp3 orbitals form from the mixing of one 2s and
three 2p orbitals.
Sketch the shapes of a 2s and a 2px orbital on the axes in Fig. 1.1.
z z
y y
x x
2s 2px
Fig. 1.1
[2]
(d) There are many naturally occurring hydrated compounds that contain the anion PO43–.
(i) Name the anion PO43–.
........................................................................................................................................ [1]
(ii) Struvite is a soft hydrated mineral with Mr = 245.3. The anhydrous form of the mineral has
the formula NH4MgPO4.
Calculate the number of molecules of water of crystallisation in struvite.
Give your answer to the nearest integer. Show your working.
number of molecules of water of crystallisation = .............................. [2]
© UCLES 2022 9701/22/O/N/22 [Turn over

4
(e) OH–(aq) reacts with 2-bromo-2-methylpropane in an SN1 reaction.

The molecular ion (CH3)3C+ forms as the intermediate in this reaction.
(i) Draw the mechanism for the SN1 reaction of OH– with 2-bromo-2-methylpropane.
Include charges, dipoles, lone pairs of electrons and curly arrows as appropriate.
Draw the structures of the organic reactant and organic product.
H 3C + CH3
C
CH3
[3]
(ii) 2-bromo-2-methylpropane is a tertiary bromoalkane.
Define tertiary bromoalkane.
..............................................................................................................................................
........................................................................................................................................ [1]
(iii) Organic compound M forms when 2‑bromo‑2‑methylpropane is heated with ethanolic

OH–.
Draw the structure of M.
[1]
[Total: 17]
© UCLES 2022 9701/22/O/N/22

5
2 The chlorides of some of the Period 3 elements are shown in Table 2.1.
Table 2.1
Period 3 chloride NaCl Al Cl 3 SiCl 4 PCl 5 PCl 3 SCl 2
bonding C C
structure S S
oxidation state of Period 3 element
(a) Complete Table 2.1.
● Identify the bonding shown by each chloride under standard conditions.

Use C = covalent, I = ionic, M = metallic.
● Identify the structure shown by each chloride under standard conditions.

Use G = giant, S = simple.
● Deduce the oxidation state of the Period 3 element in each chloride.

[4]
(b) Write equations for the reactions of NaCl and PCl 5 with water.
Include state symbols in both equations.
NaCl ...........................................................................................................................................
PCl 5 ............................................................................................................................................
[3]

6
(c) In the gas phase, Al Cl 3(g) exists at equilibrium with Al 2Cl 6(g) as shown.
equation 1 2Al Cl 3(g) Al 2Cl 6(g) ∆Hr = –63 kJ mol–1
(i) Complete the dot-and-cross diagram to show the bonding in Al 2Cl 6.
Cl
Al
Cl

[2]
(ii) S
tate the effect of an increase in temperature on the equilibrium mixture in equation 1.
..............................................................................................................................................
........................................................................................................................................ [1]
(d) A 3.30 g sample of a Period 3 chloride is heated to 500 K in a sealed flask.

At this temperature, the chloride is a gas of volume 250 cm3 and the pressure in the flask is
323 kPa.
Use the ideal gas equation pV = nRT to calculate the Mr of the Period 3 chloride.
Deduce its formula.
Mr = ..............................
formula of Period 3 chloride = ..............................

[3]
© UCLES 2022 9701/22/O/N/22

7
(e) (i) An excess of Cl –(aq) is added to 1 cm3 of Br2(aq).
Describe what is observed. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) SCl 2 has Mr = 103.1 and is a liquid at room temperature. SBr2 has Mr = 191.9 and is a gas
at room temperature.
xplain the difference in the physical state of SCl 2 and SBr2. Give your answer in terms of
E
intermolecular forces.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(f) Bismuth is a dense metal in the same group as phosphorus.
(i) Draw a labelled diagram to show the bonding in bismuth metal.
[2]
(ii) Bismuth reacts with chlorine to form BiCl 3.

BiCl 3 is a solid at room temperature. It melts when heated gently.
BiCl 3 reacts vigorously with water at room temperature to form an acidic solution.
Suggest the type of bonding and structure shown by BiCl 3. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 21]

8
3 Organic compounds can be distinguished using chemical tests and analytical techniques.
(a) Table 3.1 shows four pairs of organic compounds.
Table 3.1
positive result of
organic compounds reagent chemical test on
identified compound
A1 A2
O O
B1 B2
O O
C1 C2
O O
D1 D2
CH3 OH
OH
(i) Complete Table 3.1 to:

● identify a reagent which can distinguish between the compounds in each pair
● give the positive result of the chemical test and identify which compound shows this
result.
Use a different reagent for each test. [8]
(ii)
A1 and A2 are structural isomers.
Define structural isomers.
..............................................................................................................................................
........................................................................................................................................ [1]
© UCLES 2022 9701/22/O/N/22

9
(iii) Give the systematic name of B2.
........................................................................................................................................ [1]
(iv) Deduce the molecular formula of D1.
........................................................................................................................................ [1]
(b)
D2 forms polymer Z when heated gently.
(i) Identify the type of polymer that forms from D2.
........................................................................................................................................ [1]
(ii) Draw one repeat unit of polymer Z.
[2]

10
(c) Organic compound E contains three carbon atoms.

E reacts with cold dilute acidified KMnO4(aq) to form a single compound F with Mr = 154.9.
Fig. 3.1 shows the infrared spectrum of E.
Fig. 3.2 shows the infrared spectrum of F.
E
100
transmittance
/% 50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
Fig. 3.1
F
100
transmittance
/% 50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
Fig. 3.2
© UCLES 2022 9701/22/O/N/22

11
Table 3.2
bond functional group containing the bond characteristic infrared absorption range
(in wavenumbers) / cm–1
C–O hydroxy, ester 1040–1300
C=C aromatic compound, alkene 1500–1680
C=O amide 1640–1690
carbonyl, carboxyl 1670–1740
ester 1710–1750
C≡N nitrile 2200–2250
C–H alkane 2850–3100
N–H amine, amide 3300–3500
O–H carboxyl 2500–3000
hydroxy 3200–3650
oth spectra show absorptions between 2850 and 2950 cm–1 owing to C–H bonds in each
B
molecule.
(i) Use the two infrared spectra and Table 3.2 to identify the functional group present only
in E.
Explain your answer, referring only to absorptions at frequencies greater than 1500 cm–1.
functional group ...................................................................................................................
explanation ..........................................................................................................................
..............................................................................................................................................
[1]
(ii) Use the infrared spectrum of F to identify the functional group formed when E reacts with
cold dilute acidified KMnO4(aq).
Explain your answer, referring only to absorptions at frequencies greater than 1500 cm–1.
functional group ...................................................................................................................
explanation ..........................................................................................................................
..............................................................................................................................................
[1]
(iii) The mass spectrum of E shows a molecular ion peak and an M+2 peak of approximately
equal abundance at m/e = 120 and 122.
Deduce the relative molecular mass, Mr, of E.
Mr = .............................. [1]

12
(iv) Use the information in 3(c) to suggest a structure for E.
[1]
(v) Complete the equation for the reaction of E with cold dilute acidified KMnO4(aq) to form F.
In the equation, [O] represents cold dilute acidified KMnO4(aq).
H2O + [O] + ........................................... → ....................................................................

[1]
(d)
C2 can be synthesised using A1 as a single organic reactant.
A1 C2
O O
H O
Devise a multi-step synthetic route to form C2 from A1.

Identify relevant reagents and conditions, and state the organic products of each step.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [3]
[Total: 22]
© UCLES 2022 9701/22/O/N/22

13
BLANK PAGE
© UCLES 2022 9701/22/O/N/22

14
BLANK PAGE
© UCLES 2022 9701/22/O/N/22

15

© UCLES 2022 9701/22/O/N/22

© UCLES 2022
Group
1 2 13 14 15 16 17 18
1 2
H He
hydrogen helium
Key 1.0 4.0
11 12 13 14 15 16 17 18
23.0 24.3 3 4 5 6 7 8 9 10 11 12 27.0 28.1 31.0 32.1 35.5 39.9
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36

39.1 40.1 45.0 47.9 50.9 52.0 54.9 55.8 58.9 58.7 63.5 65.4 69.7 72.6 74.9 79.0 79.9 83.8
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
16
85.5 87.6 88.9 91.2 92.9 95.9 – 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
9701/22/O/N/22
55 56 57–71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
lanthanoids
132.9 137.3 178.5 180.9 183.8 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 – – –
87 88 89–103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
actinoids
– – – – – – – – – – – – – – – – –
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
138.9 140.1 140.9 144.4 – 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.1 175.0
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
– 232.0 231.0 238.0 – – – – – – – – – – –
*9722650000*
CHEMISTRY9701/22
1 hour 15 minutes
You will need: Data booklet
INSTRUCTIONS
● You should show all your working, use appropriate units and use an appropriate number of significant
figures.
INFORMATION
IB21 03_9701_22/2RP
2
1 The rate of chemical reactions is affected by changes in temperature and pressure.
(a) (i) D
raw a curve on the axes to show the Boltzmann distribution of energy of particles in a
sample of gaseous krypton atoms at a given temperature.
Label the curve T1 and label the axes.
[2]
(ii) O
n the diagram in (a)(i), draw a second curve to show the distribution of energies of the
krypton atoms at a higher temperature.
Label the second curve T2.[1]
(b) The Boltzmann distribution assumes that the particles behave as an ideal gas.
(i) State two assumptions of the kinetic theory as applied to an ideal gas.
1 ...........................................................................................................................................
..............................................................................................................................................
2 ...........................................................................................................................................
..............................................................................................................................................
[2]
(ii) 2.00 g of krypton gas, Kr(g), is placed in a sealed 5.00 dm3 container at 120 °C.
alculate the pressure, in Pa, of Kr(g) in the container.

C
Assume Kr(g) behaves as an ideal gas.
Show your working.
pressure = ........................................ Pa [3]
© UCLES 2021 9701/22/F/M/21

3
(iii) State and explain the conditions at which krypton behaves most like an ideal gas.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(c) K
rypton reacts with fluorine in the presence of ultraviolet light to make krypton difluoride,
KrF2(g).
Kr(g) + F2(g) → KrF2(g)
activation energy for the reaction, Ea = +385 kJ mol–1
enthalpy change of formation of KrF2, ∆Hf = +60.2 kJ mol–1
(i) U
se this information to complete the reaction profile diagram for the formation of KrF2.
Label Ea and ∆Hf on the diagram.
Assume the reaction proceeds in one step.
energy reactants
/ kJ mol–1
progress of reaction
[2]
(ii) E
xplain, in terms of activation energy, Ea, and the collision of particles, how an increase in
temperature affects the rate of a chemical reaction.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 14]

4
2 Chlorine, Cl 2, is a reactive yellow-green gas. It is a strong oxidising agent.
(a) State how Cl 2 is used in water purification.
.....................................................................................................................................................
............................................................................................................................................... [1]
(b) Chlorine has the highest first ionisation energy of the Period 3 elements Na to Cl.
(i) Construct an equation for the first ionisation energy of chlorine.
........................................................................................................................................ [1]
(ii) Explain the general increase in the first ionisation energies of the Period 3 elements.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2021 9701/22/F/M/21

5
(c) The halide ions, X– (where X = Cl, Br, I), show clear trends in their physical and chemical
properties.
(i) State and explain the relative thermal stabilities of the hydrogen halides, HX.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
The halide ions react easily with concentrated H2SO4.
The main sulfur-containing product of each reaction is shown in the table.
halide ion Cl – Br – I–
main sulfur-containing product of

HSO4– SO2 H 2S
reaction with concentrated H2SO4
oxidation number of sulfur
(ii) C
omplete the table to show the oxidation number of sulfur in each of the sulfur-containing
products.[1]
(iii) E
xplain why different sulfur-containing products are produced when each of these halide
ions reacts with concentrated H2SO4.
..............................................................................................................................................
........................................................................................................................................ [1]
(d) Cl 2 reacts with aqueous sodium hydroxide in a disproportionation reaction.
(i) State what is meant by disproportionation.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Write an equation for the reaction of Cl 2 with cold aqueous sodium hydroxide.
........................................................................................................................................ [1]

6
(e) Aluminium reacts with chlorine to form aluminium chloride.
luminium chloride can exist as the gaseous molecule Al 2Cl 6(g). This molecule contains
A
coordinate bonds.
(i) Draw a diagram that clearly shows all the types of bond present in Al 2Cl 6(g).
[2]
(ii) Describe what you would see when solid aluminium chloride reacts with water.
Name the type of reaction that occurs.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(f) 0.020 mol of element Z reacts with excess Cl 2 to form 0.020 mol of a liquid chloride.
The liquid chloride has formula ZCl n, where n is an integer.
ZCl n reacts vigorously with water at room temperature to give an acidic solution and a white

solid.
When excess AgNO3(aq) is added to the solution, 11.54 g of AgCl (s) forms.
(i) Suggest the type of bonding and structure shown by ZCl n.
........................................................................................................................................ [1]
(ii) Calculate the value of n in ZCl n.
n = .............................. [2]
© UCLES 2021 9701/22/F/M/21

7
(g) Dichloromethane, CH2Cl 2, is widely used as an organic solvent.
CH2Cl 2 can be prepared by reacting CH3Cl and Cl 2 at room temperature.
The reaction proceeds via several steps, as shown.
initiation
Cl 2 2Cl •
propagation 1
Cl • + CH3Cl HCl + •CH2Cl
propagation 2
Cl 2 + •CH2Cl products
final step
Cl • + •CH2Cl CH2Cl 2
(i) Give the name of the mechanism of this reaction.
........................................................................................................................................ [1]
(ii) State the essential condition required for the initiation step to take place.
........................................................................................................................................ [1]
(iii) Give the electronic configuration of Cl •.
1s2 .................................................................................................................................. [1]
(iv) Identify the products of the step labelled propagation 2.
........................................................................................................................................ [1]
(v) Name the type of reaction shown in the final step.
........................................................................................................................................ [1]
(vi) S
uggest the identity of another organic molecule that is a product of the reaction of CH3Cl
and Cl 2 under the same conditions.
........................................................................................................................................ [1]
[Total: 23]

8
3 Compounds P, Q and R have all been found in the atmosphere of one of Saturn’s moons.
P Q R
H H
N C C C C N H C C C N C C
H C
(a) The equation for the complete combustion of P, C4N2(l), is shown.
C4N2(l) + 4O2(g) → 4CO2(g) + N2(g) ∆H = –2036 kJ mol–1
(i) The enthalpy change of formation, ∆Hf, of CO2(g) is –384 kJ mol–1.
Calculate the enthalpy change of formation, ∆Hf, of P, in kJ mol–1.
∆Hf of P = ............................. kJ mol–1 [2]
(ii) One of the products of the complete combustion of P is nitrogen gas, N2(g).
Explain the lack of reactivity of nitrogen.
........................................................................................................................................ [1]
© UCLES 2021 9701/22/F/M/21

9
(b)
Q forms when HCN reacts with ethyne, H C C H.
(i) Ethyne, HCN and Q are all weak Brønsted–Lowry acids.
Explain what is meant by the term weak Brønsted–Lowry acid.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Ethyne, HCN and Q all contain triple bonds between two atoms.
A triple bond consists of one sigma (σ) and two pi (π) bonds.
Draw a labelled diagram to show the formation of one pi (π) bond.
[2]
(c)
P and Q can be detected in the atmosphere by infrared spectroscopy.
Identify two absorptions, and the bonds that correspond to these absorptions, that will appear
in the infrared spectra of both P and Q.
1 ..................................................................................................................................................
.....................................................................................................................................................
2 ..................................................................................................................................................
.....................................................................................................................................................
[2]

10
(d) The flow chart shows some reactions of R.
R
H H H H dilute H2SO4(aq)
heat under reflux
C C C C S
H C H C
N
N
reaction 3 H2(g)
T
CH3CH2CH2NH2
(i) Name the type of reaction shown in reaction 1.
........................................................................................................................................ [1]
(ii) Draw the structure of S, the organic product of reaction 2.
[1]
(iii) Name T.
........................................................................................................................................ [1]
(iv)
T can also be formed by the reaction of CH3CH2CH2Br with ammonia.
State the necessary conditions of this reaction.
........................................................................................................................................ [1]
[Total: 13]
© UCLES 2021 9701/22/F/M/21

11
4 Hydroxyethanal, HOCH2CHO, has been observed in dust clouds near the centre of our galaxy.
hydroxyethanal
H O
HO C C
H H
(a) Predict the bond angles labelled x and y in the diagram of hydroxyethanal.
H O
x
HO C C y
H H
x = ..............................°
y = ..............................°
[2]
(b) H
ydroxyethanal reacts separately with 2,4-dinitrophenylhydrazine (2,4-DNPH) and with Tollens’
reagent.
State what you would observe in each reaction.
reaction with 2,4-DNPH ..............................................................................................................
reaction with Tollens’ reagent .....................................................................................................

[2]
(c) H
ydroxyethanal is converted to ethanedioic acid, (CO2H)2, when it reacts with excess acidified
dichromate(VI) ions, Cr2O72–.
(i) State the role of acidified Cr2O72– in this reaction.
........................................................................................................................................ [1]
(ii) State and explain any other necessary conditions for this reaction to be successful.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]

12
(d) Hydroxyethanal can be reduced to ethane-1,2-diol, (CH2OH)2, as shown.
hydroxyethanal ethane-1,2-diol
H O H H
[H]
HO C C HO C C OH
H H H H
(i) Write an equation for the reduction of hydroxyethanal to (CH2OH)2.
Use [H] to represent an atom of hydrogen from the reducing agent.
........................................................................................................................................ [1]
(ii) Identify a reagent for this reduction reaction.
........................................................................................................................................ [1]
(iii) ( CH2OH)2 also forms when an alkene A reacts with cold, dilute, acidified manganate(VII)
ions.
Name A.
........................................................................................................................................ [1]
[Total: 10]
Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every
reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the
publisher will be pleased to make amends at the earliest possible opportunity.
Cambridge Assessment International Education is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of the University of
Cambridge Local Examinations Syndicate (UCLES), which itself is a department of the University of Cambridge.
© UCLES 2021 9701/22/F/M/21

*6703041968*
CHEMISTRY9701/22
1 hour 15 minutes
INSTRUCTIONS
figures.
INFORMATION
IB21 06_9701_22/4RP
2
1 A Group 2 metal combines with bromine to form a crystalline solid, MBr2.
Excess aqueous AgNO3 is added to a solution of MBr2 and a precipitate forms. The mixture is
filtered. The precipitate is dried and the mass of the precipitate is recorded.
(a) State the formula and colour of the precipitate.
............................................................................................................................................... [2]
(b) Complete the equation to represent the reaction between MBr2 and AgNO3.
......MBr2 + ......AgNO3 → ................................................................... [1]
(c) A 0.250 g sample of pure MBr2 contains 8.415 × 10–4 mol MBr2.
Calculate the relative formula mass, Mr, of MBr2. Use this to identify M.
Show your working.
Mr = ..............................
M = ..............................
[3]
(d) A sample of MBr2 is dissolved in water. Chlorine gas is then bubbled into the solution.
(i) Describe the observations for this reaction.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Name the type of reaction that occurs when MBr2 reacts with chlorine gas.
........................................................................................................................................ [1]
© UCLES 2021 9701/22/M/J/21

3
(e) Compound Y is a pure insoluble solid which contains halide ions.
A single reagent is added directly to compound Y to determine the halide ion present.
Identify the reagent added. State the observation which would confirm that Y contains bromide
ions.
reagent .......................................................................................................................................
observation .................................................................................................................................
[2]
(f) Separate 1.0 g samples of three different magnesium salts are tested in order to identify the
anion present in each sample.
(i) Explain how the action of heat is used to identify which sample is:
● MgCO3
● Mg(NO3)2
● MgO.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(ii) Complete the electron configuration of the magnesium cation present in these salts.
1s2 .................................................................................................................................. [1]
(g) A sample of MgCO3(s) is distinguished from a sample of Mg(OH)2(s) by adding a small amount
of each solid to HCl (aq).
State one similarity and one difference in these two reactions.
similarity ......................................................................................................................................
.....................................................................................................................................................
difference ....................................................................................................................................
.....................................................................................................................................................
[2]
[Total: 16]

4
2 The strength of interaction between particles determines whether the substance is a solid, liquid or
gas at room temperature.
(a) Lithium sulfide, Li2S, is a crystalline solid with a melting point of 938 °C. It conducts electricity
when it is molten.
(i) Give the formulae of the particles present in solid lithium sulfide.
........................................................................................................................................ [1]
(ii) Explain, in terms of the structure of the crystalline solid, why lithium sulfide has a high
melting point.
..............................................................................................................................................
........................................................................................................................................ [2]
(b) Carbon monoxide, CO, is a gas at room temperature and pressure. It contains a coordinate
bond.
(i) Explain what is meant by coordinate bond.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Draw a ‘dot-and-cross’ diagram to show the arrangement of outer electrons in CO.
Show the electrons belonging to the C atom as ×.
Show the electrons belonging to the O atom as ●.
[2]
© UCLES 2021 9701/22/M/J/21

5
(c) Nitrogen, N2, is also a gas at room temperature and pressure. Neither CO nor N2 is an ideal
gas.
(i) State two assumptions that are made about the behaviour of particles in an ideal gas.
1 ...........................................................................................................................................
..............................................................................................................................................
2 ...........................................................................................................................................
..............................................................................................................................................
[2]
(ii) Explain why N2 does not behave as an ideal gas at very high pressures.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Complete the table by naming all the types of intermolecular forces (van der Waals’) in
separate samples of N2(g) and CO(g).
N2(g) CO(g)
number of electrons per molecule 14 14
presence of a dipole moment  
boiling point / °C –195.8 –191.5
intermolecular forces (van der Waals’)
[2]
(iv) Suggest why the bond in a molecule of CO contains a dipole moment.
........................................................................................................................................ [1]
[Total: 13]

6
3 A large excess of 2-bromo-2-methylpropane is added to 0.0010 mol of NaOH(aq), which contains

a few drops of phenolphthalein indicator. A stopwatch is started as soon as the substances are
mixed. The time taken for the pink colour to disappear is recorded.
The experiment is repeated at different temperatures, keeping all concentrations and volumes of
reagents constant.
temperature time taken for

/ °C pink colour to disappear / s
20 300
25 65
35 20
(a) Explain what is meant by the term rate of reaction.
.....................................................................................................................................................
............................................................................................................................................... [1]
(b) The graph shows the energy distribution of molecules in a sample of 2‑bromo‑2‑methylpropane
at 25 °C.
Ea represents the activation energy for the reaction.

proportion
of molecules
with a given
energy
0
0 Ea
molecular energy
(i) Label the graph to show the proportion of 2‑bromo‑2‑methylpropane molecules which
have sufficient energy to react. [1]
(ii) Use the same axes to sketch the distribution of energies of molecules in a sample of
2‑bromo‑2‑methylpropane at 50 °C.[2]
(iii) State the effect of an increase in temperature on Ea for this reaction.
........................................................................................................................................ [1]
© UCLES 2021 9701/22/M/J/21

7
(c) (i) Draw the mechanism to show the reaction of 2‑bromo‑2‑methylpropane with OH–(aq).
Show the intermediate formed in this reaction.
Include all charges, partial charges, lone pairs and curly arrows as appropriate.
CH3
Br
C
CH3
H 3C

[3]
(ii) Name the mechanism for this reaction.
........................................................................................................................................ [1]
(d)
The original experiment is repeated at 25 °C with 2‑chloro‑2‑methylpropane instead of
2‑bromo‑2‑methylpropane. All other variables remain constant.
Predict the effect of using 2‑chloro‑2‑methylpropane compared to 2‑bromo‑2‑methylpropane

on the time taken for the pink colour to disappear. Explain your answer.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
[Total: 11]

8
4 (a)
The table shows the structural formulae of four compounds, A, B, C and D, with molecular
formula C4H8.
(i) Complete the table by giving the systematic name of A, B, C and D.
structural formula name

A CH3CH2CH=CH2
H H
B C C
H3C CH3
H3C H
C C C
H CH3
D CH2=C(CH3)2
[4]
(ii) Explain what is meant by stereoisomerism.
..............................................................................................................................................
........................................................................................................................................ [1]
(b)
W is an alkene with formula C4H8. It reacts with HBr to form two possible carbocations,
CH3C+(H)(CH2CH3) and H2C+CH2CH2CH3.
(i) Identify W as compound A, B, C or D.
........................................................................................................................................ [1]
© UCLES 2021 9701/22/M/J/21

9
(ii) Draw the skeletal formula of the major organic product formed when HBr reacts with W.
Explain why this is the major organic product.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[3]
(c) A sample of propan‑1‑ol reacts with concentrated sulfuric acid to form propene.
Identify the role of concentrated sulfuric acid in this reaction.
............................................................................................................................................... [1]
(d) Alcohol Y reacts completely when warmed with acidified Cr2O72– to form Z.
Z is distilled from the reaction mixture as soon as it is made.

Tollens’ reagent is added to a sample of Z and warmed. A silver mirror forms.
(i) Name the type of reaction that occurs when Y reacts to form Z.
........................................................................................................................................ [1]
(ii) Identify with a tick () the functional group(s) present in Z.
functional group present in Z
aldehyde
ketone
carboxylic acid
[1]
[Total: 12]

10
5
S is a secondary alcohol with molecular formula C4H10O.
(a) Draw the displayed formula of S.
[1]
(b)
S is converted to V in a three‑step reaction sequence.
S step 1 T step 2 U step 3 V

C4H10O PBr3 C4H9Br C4H9CN dilute
acid
In step 1, the secondary alcohol S reacts with PBr3 to produce T, which has molecular formula
C4H9Br.
(i) Give the systematic name of T.
........................................................................................................................................ [1]
(ii) Name the type of reaction that occurs in step 1.
........................................................................................................................................ [1]
(iii) State the reagent(s) and conditions for step 2.
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) Step 3 involves heating C4H9CN with dilute acid to form V.
Complete the equation for this reaction.
.....C4H9CN + .....H+ + .....H2O → ........................................ [2]
© UCLES 2021 9701/22/M/J/21

11
(v) An unlabelled sample contains either S, T or U.
The sample produces the infrared spectrum shown.
100
transmittance
/% 50
0
4000 3000 2000 1500 1000 500
wavenumber / cm–1
Explain how this spectrum confirms that the unknown sample contains U.
In your answer identify one relevant absorption in the infrared spectrum and the bond that
corresponds to this absorption in the region above 1500 cm–1.
..............................................................................................................................................
........................................................................................................................................ [1]
[Total: 8]

12
BLANK PAGE
© UCLES 2021 9701/22/M/J/21

*2578092005*
CHEMISTRY9701/22
1 hour 15 minutes
INSTRUCTIONS
figures.
INFORMATION
IB21 11_9701_22/4RP
2
1 Hydrogen iodide, HI, is a colourless gas at room temperature.
(a) (i) Explain why HI has a higher boiling point than HCl and HBr.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) The bar chart shows the boiling points of HCl, HBr and HI. The boiling point of HF is not
shown.
300
280
260
boiling 240
point / K 220
200
180
160
HF HCl HBr HI
Hydrogen bonds form between HF molecules.
Draw a bar on the bar chart to predict the boiling point of HF.
..............................................................................................................................................
........................................................................................................................................ [2]
(b) The standard enthalpy change of formation, , of HI(g) is +26.5 kJ mol–1.
Define the term standard enthalpy change of formation.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
© UCLES 2021 9701/22/O/N/21

3
(c) HI(g) can be formed by reacting H2(g) with I2(g). The reaction is reversible, and an equilibrium
forms quickly at high temperatures.
H2(g) + I2(g) 2HI(g)
(i) Construct an expression for the equilibrium constant, Kp, for the reaction of H2(g) and I2(g)
to form HI(g).
Kp =
[1]
(ii) The equilibrium partial pressures of the gases at 200 °C are as follows.
pH2(g) = 895 Pa
pI2(g) = 895 Pa
pHI(g) = 4800 Pa
Calculate Kp for this reaction.
Kp = .............................. [1]
(iii) State how the value of Kp would change, if at all, if the reaction were carried out at 100 °C
rather than 200 °C.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]

4
(d) HI reacts with oxygen to form iodine and water.
(i) Construct an equation for the reaction of HI with oxygen.
........................................................................................................................................ [1]
(ii) Explain, with reference to oxidation numbers, why this reaction is a redox reaction.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(e) HI(g) can also be formed by the reaction of I2(g) with hydrazine, N2H4(g).
2I2(g) + N2H4(g) → 4HI(g) + N2(g)
State the change in pressure that would occur when 2 mol I2(g) fully reacts with 1 mol N2H4(g)
in a sealed container at constant temperature. Explain your answer.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
© UCLES 2021 9701/22/O/N/21

5
(f) In the laboratory, HI(aq) can be formed in a two-step process.
step 1 3I2(s) + 2P(s) → 2PI3(s)
step 2 PI3(s) + 3H2O(l) → H3PO3(aq) + 3HI(aq)
(i) Draw a ‘dot-and-cross’ diagram of a PI3 molecule.
[2]
(ii) Name the type of reaction in step 2.
........................................................................................................................................ [1]
(iii) H3PO3(aq) and HI(aq) are both strong Brønsted–Lowry acids.
Give the meaning of the term strong Brønsted–Lowry acid.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) Give the formula of the conjugate base of H3PO3.
........................................................................................................................................ [1]

6
(g) HI(g) reacts with propene, CH3CH=CH2(g) to form a mixture of 1-iodopropane and
2-iodopropane.
(i) Identify which of 1-iodopropane and 2-iodopropane is the major product of this reaction.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Complete the diagram to show the mechanism of the reaction between HI and CH3CH=CH2
that forms the major product identified in (g)(i).
Include curly arrows, lone pairs of electrons and charges as necessary.
H 3C H
C C
H H
H I
+ –
[3]
[Total: 26]
© UCLES 2021 9701/22/O/N/21

7
2 (a) Table 1 gives physical data for some of the Period 3 elements.
Table 1
atomic number, Z 11 12 13 14 15 16 17
bonding present in element M C
first ionisation energy / kJ mol–1 494 736 577 786 1060 1000 1260
maximum oxidation number +7
anionic radius / nm – – – 0.271 0.212 0.184 0.181
(i) Complete the row in the table labelled ‘bonding present in element’.
Use C = covalent, I = ionic, M = metallic, as appropriate. [1]
(ii) E
xplain the difference between the first ionisation energies of the elements with atomic
numbers 11 and 17.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) E
xplain the difference between the first ionisation energies of the elements with atomic
numbers 15 and 16.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) Complete the row in the table labelled ‘maximum oxidation number’. [1]
(v) Explain the variation in anionic radius for the elements with atomic numbers 14 to 17.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]

8
(b) Use the axes to sketch a graph that shows the trend in melting points of the elements with
atomic numbers 11 to 17.
melting point
of element
11 12 13 14 15 16 17
atomic number, Z
[2]
(c) Dmitri Mendeleev published the first Periodic Table in 1869.
Mendeleev used his knowledge of chemical periodicity to propose the properties of gallium,
31Ga, a Group 13 element.
Table 2 gives some chemical and physical data of elements in Group 13.
Table 2
density boiling point cationic radius

element
/ g cm–3 / K / nm
5 B 2.34 3930 0.020
13 Al 2470 0.050
31 Ga 5.91 2400
49 In 7.30 0.081
81 Tl 11.8 1460 0.095
Complete the table by predicting values for the missing data. [3]
© UCLES 2021 9701/22/O/N/21

9
(d) Indium and aluminium are elements in Group 13 of the Periodic Table.
Indium has very similar chemical properties to aluminium.
● Indium reacts vigorously with hydrochloric acid to form a colourless gas and a salt in
solution.
● Indium oxide, In2O3, is amphoteric.
● Gaseous indium bromide has the formula In2Br6. This molecule contains coordinate bonds.
(i) Identify the formula of the salt formed when indium reacts with hydrochloric acid.
........................................................................................................................................ [1]
(ii) Construct an equation for the reaction of In2O3 with excess aqueous NaOH.
........................................................................................................................................ [1]
(iii) Draw a diagram that clearly shows the types of bond present in In2Br6(g).
[2]
[Total: 17]

10
3 Compound T is an isomer of C6H12.
(a) Name T.
............................................................................................................................................... [1]
(b)
Draw the skeletal formula of a structural isomer of T that shows cis-trans (geometrical)
isomerism.
[1]
(c) Each carbon atom in T forms a sigma (σ) bond to at least one other carbon atom, as shown.
H 3C CH3
C C
H3C CH3
(i) On the diagram, draw the orbitals that represent the pi (π) bond that is also present in T.
[1]
(ii) State the hybridisation of the two carbon atoms between which the pi (π) bond forms.
........................................................................................................................................ [1]
(d) A reaction scheme starting with T is shown. Reaction 2 occurs in the presence of a catalyst;
knowledge of the mechanism for this reaction is not required.
T U V
reaction 1 HO OH reaction 2
O
catalyst
(i) Give the reagent(s) and conditions for reaction 1.
........................................................................................................................................ [1]
© UCLES 2021 9701/22/O/N/21

11
(ii) State and explain how 2,4-dinitrophenylhydrazine (2,4-DNPH) can be used to detect the
presence of V as a product of reaction 2.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) The progress of reaction 2 can be monitored by infrared spectroscopy.
The absorption caused by O–H bonds is always present because water is used as a
solvent.
Identify two absorptions, and the bonds responsible for these absorptions, whose
appearance will change significantly during the reaction.
1 ...........................................................................................................................................
..............................................................................................................................................
2 ...........................................................................................................................................
..............................................................................................................................................
[2]
(e)
V is used in a wide range of organic reactions.
Some reactions of V are shown.
V W
reaction 3
O O
alkaline
aqueous I2 O–
reaction 4 NaBH4
X Y
OH Z
dehydration addition
polymerisation
(i)
V and W are colourless and soluble in water.
State what you would observe in reaction 3.
........................................................................................................................................ [1]

12
(ii) Reaction 3 is a redox reaction.
Identify which of the reactants is reduced in this reaction.
........................................................................................................................................ [1]
(iii) Construct an equation for reaction 4.
Use [H] in the equation to represent an atom of hydrogen from NaBH4.
C6H12O + �� [1]
(iv)
X is a mixture of two optical isomers.
Draw the two optical isomers in the boxes provided.
[2]
(v) Both optical isomers of X can be dehydrated to form a single product, Y.
Give the reagent(s) and conditions required for reaction 5.
........................................................................................................................................ [1]
(vi)
Y can form an addition polymer Z.
Draw one repeat unit of Z.
[1]
(vii) Reaction 6 does not proceed quickly at room temperature.
Suggest why this is the case.
..............................................................................................................................................
........................................................................................................................................ [1]
[Total: 17]
© UCLES 2021 9701/22/O/N/21

*0464412317*
CHEMISTRY9701/22
1 hour 15 minutes
INSTRUCTIONS
●● Answer all questions.
●● Use a black or dark blue pen. You may use an HB pencil for any diagrams or graphs.
●● Write your name, centre number and candidate number in the boxes at the top of the page.
●● Write your answer to each question in the space provided.
●● Do not use an erasable pen or correction fluid.
●● Do not write on any bar codes.
●● You may use a calculator.
●● You should show all your working, use appropriate units and use an appropriate number of significant
figures.
INFORMATION
●● The total mark for this paper is 60.
●● The number of marks for each question or part question is shown in brackets [ ].
This document has 16 pages. Blank pages are indicated.
IB20 03_9701_22/4RP
2
1 Group 2 metals form alkaline solutions in water.
(a) (i) Write the equation for the reaction of calcium oxide with water.
........................................................................................................................................ [1]
(ii) Identify the ion that causes an aqueous solution to be alkaline.
........................................................................................................................................ [1]
(b) The table shows the melting points of some Group 2 metal oxides.
compound melting point / °C

MgO 2825
CaO 2613
SrO 2531
BaO 1923
Explain the trend in the melting points of the oxides down Group 2.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(c) Oxygen reacts readily with some metals, but each Group 2 metal requires strong heating to
start the reaction with oxygen.
Suggest why strong heating is required to start these reactions.
.....................................................................................................................................................
............................................................................................................................................... [1]
(d) Beryllium oxide reacts with hydrochloric acid to form molecules of BeCl 2.
Deduce the bond angle in BeCl 2.
.............................. [1]
© UCLES 2020 9701/22/F/M/20

3
(e) Unlike the other oxides of Group 2 metals, beryllium oxide is amphoteric.
(i) Give the meaning of the term amphoteric.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Beryllium oxide and aluminium oxide have similar chemical properties.
The Be(OH)42– anion is a product of the reaction between beryllium oxide and excess
concentrated OH–(aq).
Construct an equation for this reaction.
........................................................................................................................................ [1]
(f) Magnesium oxide reacts reversibly with chlorine according to the following equation.
2MgO(s) + 2Cl 2(g) 2MgCl 2(s) + O2(g)
Under certain conditions, a dynamic equilibrium is established.
(i) State two features of a reaction that is in dynamic equilibrium.
1 ...........................................................................................................................................
2 ...........................................................................................................................................
[2]
(ii) The equilibrium constant, Kp, is given by the following expression.
pO
Kp = 2
2
pCl 2
At 1.00 × 105 Pa and 500 K, 70% of the initial amount of Cl 2(g) has reacted.
Calculate Kp and state its units.
Kp = ..............................
units = ..............................
[3]

4
(g) Magnesium peroxide, MgO2, is made in the following reaction.
MgO(s) + H2O2(l) MgO2(s) + H2O(l) ∆H = –96 kJ mol–1
enthalpy change of
compound
formation, ∆Hf / kJ mol–1
MgO(s) –602
H2O2(l) –188
H2O(l) –286
(i) The peroxide ion is O22–.
Deduce the average oxidation number of oxygen in the peroxide ion.
........................................................................................................................................ [1]
(ii) Define the term enthalpy change of formation.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Use the data given to calculate the enthalpy change of formation of MgO2(s).
∆Hf MgO2(s) = .............................. kJ mol–1 [2]
© UCLES 2020 9701/22/F/M/20

5
(iv) Magnesium peroxide decomposes slowly to form magnesium oxide and oxygen.
1
MgO2(s) MgO(s) + 2 O2(g)
Use your answer to (g)(iii) and the data in the table to calculate the enthalpy change of
this reaction.
If you were unable to obtain an answer to (g)(iii), use the value ∆Hf = –550 kJ mol–1. This

is not the correct answer.
enthalpy change of reaction = .............................. kJ mol–1 [1]
[Total: 19]

6
2 The Group 17 elements, chlorine, bromine and iodine, are non-metals that show trends in their
physical and chemical properties.
(a) Describe the trend in the colour of the Group 17 elements down the group.
.....................................................................................................................................................
............................................................................................................................................... [1]
(b) The Group 17 elements can oxidise many metals to form halides.
(i) Describe the relative reactivity of the elements in Group 17 as oxidising agents.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Chlorine reacts with hot tin metal to form tin(IV) chloride, SnCl 4.
SnCl 4 is a colourless liquid at room temperature that reacts vigorously with water to form
an acidic solution.
Suggest the type of structure and bonding shown by SnCl 4. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(c) The Group 17 elements form soluble halides with sodium.
(i) Describe what is seen when dilute AgNO3(aq) is added to NaBr(aq) followed by aqueous
ammonia.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2020 9701/22/F/M/20

7
(ii) NaCl reacts with concentrated H2SO4 to form HCl and NaHSO4.
Explain the difference between the reactions of concentrated H2SO4 with NaCl and with
NaI. Your answer should refer to the role of the sulfuric acid in each reaction.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(d) The hydrogen halides are useful reagents in organic and inorganic reactions.
(i) Describe and explain the trend in the boiling points of the hydrogen halides, HCl, HBr and
HI.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Describe and explain the trend in the thermal stabilities of the hydrogen halides, HCl, HBr
and HI.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]

8
(e) Lucas’s reagent is a mixture of HCl and ZnCl 2. Primary, secondary and tertiary alcohols can
be distinguished by their reaction with Lucas’s reagent.
Alcohols react with the HCl in Lucas’s reagent to form halogenoalkanes.
ZnCl 2 acts as a homogeneous catalyst for these reactions.
(i) Explain the meaning of the term homogeneous.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Pentan-3-ol, C2H5CH(OH)C2H5, reacts slowly with HCl to form a secondary halogenoalkane.
Complete the equation for this reaction using structural formulae.
C2H5CH(OH)C2H5 + �� [1]
(iii) The fastest reaction shown by Lucas’s reagent is with a tertiary alcohol.
Draw the structure of the tertiary alcohol that is an isomer of pentan-3-ol.
[1]
(iv) Tertiary alcohols tend to react with Lucas’s reagent using the same mechanism as in their
reaction with HCl.
Suggest the type of reaction shown by tertiary alcohols with Lucas’s reagent.
........................................................................................................................................ [1]
[Total: 17]
© UCLES 2020 9701/22/F/M/20

9
3 Glycerol, CH2(OH)CH(OH)CH2OH, is widely used in the food industry and in pharmaceuticals.
(a) A series of reactions starting from glycerol is shown.
P Q
CH2OH HOOC COOH
NaCN and HCN
H C OH C O NC C OH
CH2OH HOOC COOH
(i) Suggest the reagent(s) and conditions for reaction 1.
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Name the reaction mechanism for reaction 2.
........................................................................................................................................ [1]
(iii) Give the observation you would make when 2,4-dinitrophenylhydrazine is added to P.
........................................................................................................................................ [1]
(iv)
Q does not show optical isomerism.
Explain why.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [1]
(v) When Q is heated with excess aqueous ethanoic acid in the presence of a catalytic amount
of sulfuric acid, two reactions take place to form compound R.
R
COOH
HOOC C OCOCH3
COOH
Identify the two types of reaction that occur.
1 ...........................................................................................................................................
2 ...........................................................................................................................................
[2]

10
(b) Glycerol can be used as a starting material in the manufacture of nitroglycerine, C3H5N3O9.
Nitroglycerine decomposes rapidly on heating to form a mixture of gases.
4C3H5N3O9(l) 12CO2(g) + 10H2O(g) + 6N2(g) + O2(g)
A sample of nitroglycerine decomposes, releasing 1.06 dm3 of O2(g) at 850 K and 1.00 × 105 Pa.
(i) Calculate the mass of nitroglycerine that decomposes.
mass of nitroglycerine = .............................. g [3]
(ii) Calculate the total volume of gas released by this decomposition at 850 K and 1.00 × 105 Pa.
total volume of gas = .............................. dm3 [1]
© UCLES 2020 9701/22/F/M/20

11
(c) Fats are compounds made from glycerol and unsaturated carboxylic acids.
4-pentenoic acid is an example of an unsaturated carboxylic acid.
4-pentenoic acid
(CH2)2COOH
H
H
H
(i) Give the molecular formula of 4-pentenoic acid.
........................................................................................................................................ [1]
(ii) Draw the repeat unit of the addition polymer that can be formed from 4-pentenoic acid.
[1]
(iii) Unsaturated acids are often brominated before being added to soft drinks.
Complete the mechanism for the addition of Br2 to 4-pentenoic acid.
●● Include the structures of the intermediate and the product of the reaction.
●● Include all charges, partial charges, lone pairs and curly arrows.
In the mechanism, R has been used to represent (CH2)2COOH.
R
H
H
H
Br
Br
[4]

12
(d) A reaction of another unsaturated carboxylic acid, T, is shown.
T U
C6H13 C6H13
HOOC HOOC
Br Br
(i)
T is one of a pair of geometrical (cis-trans) isomers.
Draw the other geometrical isomer of T and explain why the molecules exhibit this form of
isomerism.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[3]
(ii) Identify the reagent used to convert T to U.
........................................................................................................................................ [1]
© UCLES 2020 9701/22/F/M/20

13
(iii) The C–Br bond has an absorption between 500 cm–1 and 600 cm–1 in an infrared spectrum.
The infrared spectra for both T and U have absorptions between 2850 cm–1 and 2950 cm–1.
These correspond to C–H bonds.
Identify:
●● two other absorptions that would be seen in the infrared spectra of both T and U
●● one other absorption that would only be seen in the infrared spectrum of T.
For each absorption, give the range of the absorption and the bonds that correspond to
these absorptions.
absorption 1 present in both spectra ...................................................................................
..............................................................................................................................................
..............................................................................................................................................
absorption 2 present in both spectra ...................................................................................
..............................................................................................................................................
..............................................................................................................................................
absorption only present in spectrum of T ............................................................................
..............................................................................................................................................
..............................................................................................................................................
[3]
[Total: 24]

14
BLANK PAGE
© UCLES 2020 9701/22/F/M/20

15
BLANK PAGE
© UCLES 2020 9701/22/F/M/20

16
BLANK PAGE
© UCLES 2020 9701/22/F/M/20

*2460000734*
CHEMISTRY9701/22
1 hour 15 minutes
INSTRUCTIONS
●● Answer all questions.
●● Use a black or dark blue pen. You may use an HB pencil for any diagrams or graphs.
●● Write your name, centre number and candidate number in the boxes at the top of the page.
●● Write your answer to each question in the space provided.
●● Do not use an erasable pen or correction fluid.
●● Do not write on any bar codes.
●● You may use a calculator.
●● You should show all your working, use appropriate units and use an appropriate number of significant
figures.
INFORMATION
●● The total mark for this paper is 60.
●● The number of marks for each question or part question is shown in brackets [ ].
IB20 06_9701_22/3RP
2
1 Gallium is an element in Group 13.
A sample of gallium is analysed using a mass spectrometer. The mass spectrum produced is
shown.
60.11%
39.89%
% relative
abundance
mass 69 71
(a) Explain what is meant by the term relative atomic mass.
.....................................................................................................................................................
............................................................................................................................................... [2]
(b) C
alculate the relative atomic mass of gallium in this sample. Give your answer to 4 significant
figures.
Show your working.
relative atomic mass = .............................. [2]
(c) Complete the table which describes a gaseous atom of gallium.
total number type of orbital which

nucleon
isotope of electrons in contains the electron in
number
lowest energy level the highest energy level
71
Ga
[3]
© UCLES 2020 9701/22/M/J/20

3
(d) When gallium is heated in excess chlorine, gallium trichloride, GaCl 3, is made.
Draw the shape of the gallium trichloride molecule and suggest the Cl –Ga–Cl bond angle.
shape of molecule
bond angle .................................................................

[2]
(e) Gallium oxide, Ga2O3, and aluminium oxide react in the same way with HCl (aq) and with
NaOH(aq).
(i) Suggest the equation for the reaction between Ga2O3 and HCl (aq).
........................................................................................................................................ [1]
(ii) Suggest an equation for the reaction between gallium oxide and NaOH(aq).
........................................................................................................................................ [2]
[Total: 12]

4
2 Nitric acid can be made in a 3-stage process.
Stage 1 Ammonia is oxidised by oxygen from the air, to form nitrogen monoxide and water. This
reaction is carried out at 10–13 atmospheres pressure and 900 °C in the presence of a
platinum catalyst.
Stage 2 Nitrogen monoxide reacts with more oxygen to form nitrogen dioxide.
2NO + O2 2NO2 ∆H = –114 kJ mol–1
Stage 3 Nitrogen dioxide reacts with water to make nitric acid and nitrogen monoxide.
3NO2 + H2O → 2HNO3 + NO
(a) Write an equation to show the reaction occurring in stage 1.
............................................................................................................................................... [1]
(b) Draw a ‘dot-and-cross’ diagram to show the arrangement of outer electrons in a molecule of
ammonia.
[1]
(c) (i) In the boxes, give the oxidation numbers of nitrogen in the nitrogen-containing species for
the reaction in stage 3.
3NO2 + H2O → 2HNO3 + NO

[2]
(ii) Explain why the reaction in stage 3 is described as a disproportionation reaction.

Include reference to transfer of electrons in your answer.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2020 9701/22/M/J/20

5
(d) The release of nitrogen monoxide into the atmosphere causes atmospheric pollution.
State and explain the effect of nitrogen monoxide gas in contact with moist air.
.....................................................................................................................................................
............................................................................................................................................... [2]
(e) The nitric acid made in stage 3 can then be reacted with ammonia to form ammonium nitrate.
Stage 3 3NO2 + H2O → 2HNO3 + NO
NH3 + HNO3 → NH4NO3
Calculate the volume of nitrogen dioxide, measured at room temperature and pressure,

required to make 40 tonnes of ammonium nitrate.
[1 tonne = 1000 kg]
Show your working.
volume of nitrogen dioxide = .............................. [3]
(f) State one use of ammonium nitrate.
............................................................................................................................................... [1]
[Total: 12]

6
3 Sucrose, C12H22O11, reacts with water to form glucose and fructose in reaction A.
glucose fructose
O H O CH2OH
C C
H C OH HO C H
C12H22O11 + H2O HO C H + H C OH
H C OH H C OH
H C OH CH2OH
CH2OH
reaction A
(a) Suggest a name for this type of reaction.
............................................................................................................................................... [1]
(b) Explain in detail, why glucose and fructose are a pair of structural isomers. Your answer should
refer specifically to these two molecules.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(c) Reaction A occurs faster in the presence of an enzyme. This is reaction B.
(i) The activation energy for reaction B is +29 kJ mol–1.
Predict a value for the activation energy of reaction A.
........................................................................................................................................ [1]
(ii) The enthalpy change for reaction A is –14 kJ mol–1.
Predict a value for the enthalpy change for reaction B.
........................................................................................................................................ [1]
© UCLES 2020 9701/22/M/J/20

7
(iii) Sketch a labelled energy level diagram for reaction B. Use relevant values from (c)(i) and
(c)(ii).
energy
/ kJ mol–1
[2]
(d) 1.00 g of sucrose, C12H22O11, is completely combusted. The heat energy produced is used to
increase the temperature of 250 g of water inside a calorimeter from 25.0 °C to 40.7 °C.
These data can be used to calculate the enthalpy change of combustion of sucrose.
(i) Explain what is meant by the term enthalpy change of combustion of sucrose.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Use the Data Booklet to calculate the enthalpy change, in kJ mol–1, for the combustion of
sucrose.
Assume that all of the heat energy produced is transferred to the water.
Show your working.
enthalpy change of combustion of sucrose = .............................. kJ mol–1

[3]
[Total: 12]

8
4 (a) An unlabelled bottle contains a straight-chain halogenoalkane, Q. The molecular formula of Q
is C5H11X, where X is a halogen; bromine, chlorine or iodine.
A test is carried out to identify the halogen present in Q.

A sample of Q is added to NaOH(aq) and warmed. Dilute nitric acid is then added followed by
a few drops of aqueous silver nitrate. A cream precipitate is observed.
(i) Suggest the identity of X.
........................................................................................................................................ [1]
(ii) Write an ionic equation to describe the formation of the cream precipitate. Include state
symbols.
........................................................................................................................................ [1]
(iii) Describe a further test which would confirm the identity of X.
test .......................................................................................................................................
expected result ....................................................................................................................

[2]
(b) The reaction of Q with NaOH(aq) tends to proceed via an SN2 mechanism.
(i)
Suggest the structural formula of the straight-chain halogenoalkane Q.
[1]
(ii)
Explain why the reaction tends to proceed via an SN2 mechanism rather than an SN1
mechanism.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2020 9701/22/M/J/20

9
(c) Two different halogenoalkanes, P and R, both with the molecular formula C4H9Cl, are separately
dissolved in ethanol and heated under reflux with sodium hydroxide.
The major organic product of each of these reactions is methylpropene.
(i)
Name the type of reaction occurring.
........................................................................................................................................ [1]
(ii)
Write an equation, using molecular formulae, to represent the reaction occurring.
........................................................................................................................................ [1]
(iii) Draw the skeletal formula of methylpropene.
[1]
(iv) Give the names of P and R.
........................................................................................................................................ [2]
[Total: 12]

10
5 The reaction sequence shows how ethene, C2H4, can be converted into other organic molecules.
C 2H 4
reaction 1
reaction 5
OH Cl
O NH2
reaction 3
HO
reaction 4
heat with dilute acid
(a) Complete the table to give

●● the name of the reaction mechanisms of reactions 1 and 6
●● the reagents and conditions required for reactions 1, 2 and 6.
name of name of reagents

reaction
mechanism and conditions
[6]
© UCLES 2020 9701/22/M/J/20

11
(b) In reaction 3 the organic molecule reacts with HCN and a KCN catalyst.
(i) Complete the diagram to show the mechanism of the reaction occurring.
Include all relevant dipoles, lone pairs and curly arrows in your answer.
H H H
–
C O H3C C O H 3C C OH
H 3C CN CN
C– H
C
N C–
N
N
[3]
(ii) Name the functional groups present in the product of reaction 3.
........................................................................................................................................ [2]
(c)
Draw the structure of the organic molecule W formed in reaction 4.
[1]
[Total: 12]

12
BLANK PAGE
© UCLES 2020 9701/22/M/J/20

*1309098231*
CHEMISTRY9701/22
1 hour 15 minutes
INSTRUCTIONS
figures.
INFORMATION
IB20 11_9701_22/3RP
2
1 Atoms contain the subatomic particles electrons, protons and neutrons. Protons and electrons
were discovered by observations of their behaviours in electric fields.
(a) The diagram shows the behaviour of separate beams of electrons and protons in an electric
field.
protons
charge on plate electrons charge on plate

......................... .........................
source
(i) Complete the diagram with the relative charge of each of the electrically charged plates.
[1]
(ii) On the diagram, draw a line to show how a separate beam of neutrons from the same
source behaves in the same electric field. [1]
(b) Electrons in atoms up to 36Kr are distributed in s, p and d orbitals.
(i) State the number of occupied orbitals in an isolated atom of 36Kr.
type of orbital s p d
number of orbitals
[3]
© UCLES 2020 9701/22/O/N/20

3
(ii) Complete the diagram to show the number and relative energies of the electrons in an
isolated atom of 14Si.
4s
3p
3s
2p
2s
1s
[2]
(iii) The diagram shows a type of orbital.
State the total number of electrons that exist in all orbitals of this type in an atom of 9F.
........................................................................................................................................ [1]
(iv) The first ionisation energies of elements in the first row of the d block (21Sc to 29Cu) are
very similar. For all these elements, it is a 4s electron that is lost during the first ionisation.
Suggest why the first ionisation energies of these elements are very similar.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(c)
Hydron is a general term used to represent the ions 11H+, 12H+ and 13H+.
State, in terms of subatomic particles in the nucleus, what is the same about each of these ions
and what is different.
same ...........................................................................................................................................
different .......................................................................................................................................
[1]
[Total: 12]

4
2 The Period 3 elements, Na to S, all react with oxygen to form oxides.
(a) State the trend in acid/base behaviour of the oxides of the Period 3 elements, from Na to S.
.....................................................................................................................................................
............................................................................................................................................... [1]
(b) State and explain the trend, from Na to S, in the maximum oxidation number of the Period 3
elements in their oxides.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(c) Sodium oxide and phosphorus(V) oxide both react with water.
Name the product of each reaction.

reaction product
sodium oxide with water
phosphorus(V) oxide with water
[2]
(d) Explain why phosphorus(V) oxide has a low melting point of approximately 300 °C but
magnesium oxide has a high melting point of approximately 2850 °C.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [3]
© UCLES 2020 9701/22/O/N/20

5
(e) Aluminium oxide, Al 2O3, reacts separately with both acids and alkalis.
(i) Write an equation for the reaction of aluminium oxide with excess aqueous hydrochloric acid.
........................................................................................................................................ [1]
(ii) Write an equation for the reaction of aluminium oxide with excess aqueous sodium hydroxide.
........................................................................................................................................ [1]
(f) Describe the lattice structure of silicon(IV) oxide.
Your answer should include reference to the arrangement of the silicon and oxygen atoms and
the bonds between them.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(g) Sodium oxide and silicon(IV) oxide react to form sodium silicate(IV), Na2SiO3.
Sodium oxide is obtained from the thermal decomposition of sodium carbonate.
Write equations for the following reactions:
(i) sodium oxide with silicon(IV) oxide
........................................................................................................................................ [1]
(ii) the thermal decomposition of sodium carbonate, forming sodium oxide and carbon dioxide.
........................................................................................................................................ [1]
[Total: 14]

6
3 PCl 5, PCl 3 and NCl 3 are halides of Group 15 elements.
(a) PCl 5 can be formed from the reaction of phosphorus with chlorine. PCl 5 has a melting point of
161 °C.
(i) Write an equation for the formation of PCl 5 from the reaction of phosphorus and chlorine.
........................................................................................................................................ [1]
(ii) State the type of structure and bonding shown by liquid PCl 5.
........................................................................................................................................ [1]
(b) A small amount of PCl 5 is added to excess water. The PCl 5 reacts vigorously to form a
colourless solution.
(i) Give one other observation you would make when PCl 5 reacts with excess water.
........................................................................................................................................ [1]
(ii) Write the equation for the reaction of PCl 5 with excess water.
........................................................................................................................................ [1]
(iii) Estimate the pH of the resulting solution.
........................................................................................................................................ [1]
(c) PCl 3 is used to convert alcohols to chloroalkanes, such as compound T.
Cl
Cl
A possible synthesis of T is shown.
reaction 1 using PCl 3

O OH Cl
HO HO Cl
OH
(i) Identify a reagent that could be used in reaction 1.
........................................................................................................................................ [1]
© UCLES 2020 9701/22/O/N/20

7
(ii) T exhibits optical isomerism.
Explain what is meant by the term optical isomer and circle any atom(s) in T that give rise
to optical isomerism.
Cl
Cl
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[2]
(iii)
T is a minor product in the reaction of compound S with excess HCl.
Draw the structure of the major product of the reaction of S with excess HCl.
[1]

8
(d) NCl 3 is a yellow liquid that can be used to bleach flour.
(i) Predict the shape of the NCl 3 molecule and the Cl –N–Cl bond angle.
shape ...................................................................................................................................
bond angle ...........................................................................................................................

[2]
(ii) NCl 3 reacts with water to form HOCl, a weak Brønsted-Lowry acid.
Explain fully what is meant by the term weak Brønsted-Lowry acid.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) NCl 3(l) decomposes according to the equation shown.
2NCl 3(l) → N2(g) + 3Cl 2(g)
A sealed container of volume 250 cm3 contains an unreactive gas at a pressure of

1.00 × 105 Pa.
0.241 g of NCl 3(l) was injected into the sealed container.
The sealed container was heated to make the NCl 3(l) decompose fully and then cooled to
20 °C.
Calculate the final total pressure inside the sealed container at 20 °C after the NCl 3(l) has
fully decomposed.
final total pressure = .............................. Pa

[4]
[Total: 17]
© UCLES 2020 9701/22/O/N/20

9
4
Some reactions of compound G are shown.
G
O O
reaction 3
OH Tollens’ reagent OH
H HO
reaction 1 H2SO4, heat

reaction 2 Na reaction 4
under reflux
HOOC(CH2)2COOH
H
O
O
(a) (i) State the type of reaction that occurs in reaction 1.
........................................................................................................................................ [1]
(ii) Suggest the reagent(s) and conditions required for reaction 1.
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Draw the structure of the organic product, H, from reaction 2.
[1]
(iv) State what you would observe in reaction 3.
........................................................................................................................................ [1]
(v) Give the type of reaction shown by reaction 4.
........................................................................................................................................ [1]

10
(b)
G and J are structural isomers of each other.
G J
O O OH
OH
H H
(i) Name the type of structural isomerism shown by G and J.
........................................................................................................................................ [1]
(ii) Suggest one chemical test that can distinguish G from J. Give the result of the test with
each compound.
test .......................................................................................................................................
result with G .........................................................................................................................
result with J .........................................................................................................................

[2]
In the reaction schemes below, G and J are converted into organic compound K.
G J
NaBH4 NaBH4
Al 2O3 Al 2O3
HO(CH2)3CH2OH K HO(CH2)2CH(OH)CH3
heat heat
(iii) State the role of NaBH4 in the reactions with G and J.
........................................................................................................................................ [1]
(iv) Identify the organic product K.
........................................................................................................................................ [1]
© UCLES 2020 9701/22/O/N/20

11
(c)
P and Q have the same molecular formula as G.
P Q
O O
HO
OH
Complete the table with the expected observations for the reactions of P and Q with the named
reagents.
reagent result with P result with Q
Br2(aq)
2,4-dinitrophenylhydrazine
aqueous sodium carbonate
[3]

12
(d) The structure of compound L is shown. R represents a hydrocarbon chain.
O R
O
A student was asked to deduce the full structure of L.
The student analysed L using infrared spectroscopy. The following spectrum was obtained.
100
transmittance
% 50
X Y Z
0
4000 3000 2000 1500 1000 500
wavenumber / cm –1
(i) Identify the bonds responsible for the absorptions marked X and Z.
X ..........................................................................................................................................
Z ..........................................................................................................................................
[1]
© UCLES 2020 9701/22/O/N/20

13
Absorption Y shows that L has a C=C bond present in the R group.
The student decided to treat L with hot concentrated acidified potassium manganate(VII). The
products of the reaction are shown.
O
L
hot concentrated O OH
O
acidified KMnO4
+
O R
O
M
CH3(CH2)4COOH
(ii) Name M.
........................................................................................................................................ [1]
(iii) Use the information in (d) to deduce the molecular formula of L.
molecular formula of L = .............................. [1]
[Total: 17]

14
BLANK PAGE
© UCLES 2020 9701/22/O/N/20

15
BLANK PAGE
© UCLES 2020 9701/22/O/N/20

16
BLANK PAGE
© UCLES 2020 9701/22/O/N/20

Cambridge Assessment International Education
Cambridge International Advanced Subsidiary and Advanced Level
*6417226760*
CHEMISTRY 9701/22
1 hour 15 minutes
Candidates answer on the Question Paper.
Additional Materials: Data Booklet
READ THESE INSTRUCTIONS FIRST
Write your centre number, candidate number and name on all the work you hand in.
Write in dark blue or black pen.
You may use an HB pencil for any diagrams or graphs.
Do not use staples, paper clips, glue or correction fluid.
DO NOT WRITE IN ANY BARCODES.
Answer all questions.

Electronic calculators may be used.
You may lose marks if you do not show your working or if you do not use appropriate units.
A Data Booklet is provided.
At the end of the examination, fasten all your work securely together.
The number of marks is given in brackets [ ] at the end of each question or part question.
This document consists of 14 printed pages and 2 blank pages.
IB19 03_9701_22/3RP
2
1 Nitrogen, N2, is the most abundant gas in the Earth’s atmosphere and is very unreactive.
(a) State why N2 is very unreactive.
............................................................................................................................................... [1]
(b) Magnesium and lithium both form nitrides with N2. These compounds both contain the N3– ion.
(i) Write an equation for the reaction of magnesium with N2 to form magnesium nitride.
........................................................................................................................................ [1]
(ii) Solid lithium nitride, Li3N, reacts with water according to the following equation.
Li3N(s) + 3H2O(l) 3LiOH(aq) + NH3(aq)
State one observation you would make during this reaction.
........................................................................................................................................ [1]
(c) (i) State the industrial importance of ammonia.
........................................................................................................................................ [1]
(ii) One method of producing NH3 is by heating ammonium chloride, NH4Cl, with CaO.
2NH4Cl + CaO 2NH3 + CaCl 2 + H2O
Explain why the reaction of NH4Cl with CaO produces ammonia.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2019 9701/22/F/M/19

3
(d) Three oxides of nitrogen, NO, NO2 and N2O, can be formed under different conditions.
(i) Complete the table to give the oxidation numbers of nitrogen in NO and NO2.
compound NO NO2
oxidation number of N
[1]
(ii) NO2 can be formed by different chemical reactions.
Write equations for the formation of NO2 by:
● the reaction of N2 with O2
..............................................................................................................................................
● the thermal decomposition of magnesium nitrate.
..............................................................................................................................................
[2]
(iii) Molecules of N2O can be formed by the reaction between N2 and O2. The bond between
the N and O atoms (N O) is a co-ordinate (dative covalent) bond.
2N2(g) + O2(g) 2N≡N O(g)
The enthalpy change of reaction for this reaction is +82 kJ mol–1.
Calculate the bond enthalpy, in kJ mol–1, of the N O bond.
Use relevant data from the Data Booklet to answer this question.
bond enthalpy of the N O bond = ............................. kJ mol–1

[2]

4
(e) Nitrosyl chloride, NOCl, is a reactive gas that is sometimes formed when NO reacts with Cl 2.
nitrosyl chloride
δ+
O N
Cl
δ–
NOCl is a strong electrophile and readily undergoes an addition reaction with alkenes.
Complete the diagram to show the mechanism of the electrophilic addition reaction of NOCl
with ethene.
Include all necessary charges, lone pairs and curly arrows, and the structure of the organic
intermediate.
H H
C C
H H
H H
H C C H
δ+ N Cl
O N
O
Cl
δ–
[2]
[Total: 13]
© UCLES 2019 9701/22/F/M/19

5
2 The elements in Group 17 of the Periodic Table are called the halogens. They form stable compounds
with both metals and non-metals.
The table gives some data about F2, HCl and CaF2.
F2 HCl CaF2
boiling point / K 85 188 2773
relative formula mass 38.0 36.5 78.1
(a) (i) State what is meant by the term relative formula mass.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) F2 and HCl are both covalent molecules.
Suggest why the boiling point of HCl is higher than that of F2.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Explain why CaF2 has a very high boiling point.
..............................................................................................................................................
........................................................................................................................................ [1]
(iv) CaF2(aq) can be made by the reaction of calcium carbonate with hydrofluoric acid, HF(aq).
Write an equation for this reaction. Include state symbols.
........................................................................................................................................ [2]

6
(b) (i) Complete the electronic configuration of a chloride ion.
1s2 .................................................................................................................................. [1]
(ii) When Cl 2 is passed over hot iron, FeCl 3 is formed.
However, when I2(g) is passed over hot iron, the following reaction occurs.
Fe(s) + I2(g) FeI2(s)
State what you would observe during the reaction between Fe and I2. Explain why FeI2(s)
is formed rather than FeI3(s).
observation ..........................................................................................................................
..............................................................................................................................................
explanation ..........................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[2]
(iii) FeI2 is soluble in water.
student carries out a chemical test to confirm that a solution of FeI2 contains aqueous
A
iodide ions, I–(aq). The student adds a single reagent and a precipitate forms.
Identify the reagent the student uses. State the colour of the precipitate that forms.
reagent ................................................................................................................................
colour of precipitate .............................................................................................................

[2]
(iv) Compounds containing I– are often contaminated by bromide ions, Br –.
Identify a further reagent that the student could use to show that the precipitate formed in
(iii) contained iodide ions.
........................................................................................................................................ [1]
© UCLES 2019 9701/22/F/M/19

7
(c) HOF is the only known molecule that contains only the elements hydrogen, oxygen and fluorine.
(i) Draw a ‘dot-and-cross’ diagram to represent the bonding in a molecule of HOF.
Show the outer shell electrons only.
[2]
(ii) HOF can be made by the reaction of F2 with ice at – 40 °C. The reaction is similar to the
reaction of Cl 2 with cold water.
Suggest an equation for the reaction of F2 with ice.
........................................................................................................................................ [1]
(iii) HOF is an unstable compound and decomposes to form HF and O2.

1
HOF → HF + 2 O2 ΔH = –139 kJ mol–1
Draw a fully labelled reaction pathway diagram on the axes provided to show the
decomposition of HOF into HF and O2.
enthalpy
[2]

8
(iv) Pure HF is a colourless liquid at 273 K. The liquid contains HF molecules that have strong
hydrogen bonds between them.
Draw a fully labelled diagram to suggest how a hydrogen bond can form between two HF
molecules.
[3]
(d) Interhalogen compounds, such as BrCl or IF5, contain two or more different halogen atoms
that are covalently bonded.
D is an interhalogen compound that contains only chlorine and fluorine.

At 0 °C and 101 325 Pa, 1 dm3 of D has a mass of 4.13 g.
(i) Use the general gas equation to calculate the relative molecular mass, Mr, of D.
Mr = ..............................
[3]
(ii) Use your answer to (i) to determine the molecular formula of D.
If you were unable to calculate the Mr in (i), assume that the Mr is 130.5. This is not the
correct value.
molecular formula of D = ..............................

[1]
[Total: 25]
© UCLES 2019 9701/22/F/M/19

9
Question 3 starts on the next page.

10
3
P, Q and R all contain five carbon atoms.
P Q R
OH O OHC H
H 3C C C N C C C
H 3C CH2CH2CH3
CH2CH3 H CH2CH3
A student carries out several tests to distinguish between P, Q and R.
(a)
Complete the table, identifying any observations for the reaction of each reagent with
P, Q and R.
If no reaction occurs, write ‘no reaction’.
observations with
reagent
P Q R
Na(s)
2,4-DNPH no reaction
acidified K2Cr2O7(aq) no reaction
[3]
(b)
Q is reduced by NaBH4.
Write an equation for the reaction of Q with NaBH4.
In your answer, use [H] to represent NaBH4.
C5H10O + ............................................................................................................................. [1]
© UCLES 2019 9701/22/F/M/19

11
(c)
R exists as a pair of stereoisomers.
Identify the type of stereoisomerism shown by R and draw the structure of the other stereoisomer.
type of stereoisomerism .................................................
stereoisomer of R
[2]
(d) The infra-red spectrum shown corresponds to one of P, Q or R.
100
transmittance
50
0
4000 3000 2000 1500 1000 500
wavenumber / cm –1
Deduce which of the compounds, P, Q or R, produces this spectrum. Explain your reasoning.
In your answer, identify any relevant absorptions in the infra-red spectrum and the bonds that
correspond to these absorptions in the region above 1500 cm–1.
compound ........................
explanation .................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
[3]
[Total: 9]

12
4 Allyl chloride is an important chemical used in the manufacture of plastics, pharmaceuticals and
pesticides.
allyl chloride
Cl
(a) Give the systematic name of allyl chloride.
............................................................................................................................................... [1]
(b) Allyl chloride can be produced by many different methods. The most common method is
chlorination of propene which proceeds via a free-radical substitution mechanism.
Cl 2 Cl
(i) The initiation step in this reaction is the formation of chlorine radicals (Cl ●) from Cl 2
molecules.
State the conditions required to initiate this reaction.
........................................................................................................................................ [1]
(ii) The propenyl radical, CH2=CHCH2●, is formed in the first propagation step of the reaction.
Write an equation to show the formation of CH2=CHCH2● in this propagation step.
........................................................................................................................................ [1]
(iii) Explain why the free-radical substitution reaction gives a low yield of allyl chloride.
..............................................................................................................................................
........................................................................................................................................ [1]
(iv) Allyl chloride can also be formed by the following substitution reaction.
OH reagent X Cl
Suggest the identity of reagent X.
........................................................................................................................................ [1]
© UCLES 2019 9701/22/F/M/19

13
(c) A series of reactions starting from allyl chloride is shown.
OH
Cl reaction 1 HO Cl
reaction 2
Y
CH3COO CH3COO
reaction 3
CH3COO Cl CH3COO CN
HCN and NaCN
(i) Suggest a reagent that can be used in reaction 1.
........................................................................................................................................ [1]
(ii) In reaction 2, the organic product of reaction 1 is mixed with concentrated H2SO4 and an
organic acid, and then heated under reflux.
State the role of the concentrated H2SO4. Identify the organic acid used.
role of the concentrated H2SO4 ............................................................................................
identity of the organic acid ...................................................................................................

[2]
(iii) State the name of the mechanism that occurs in reaction 3.
........................................................................................................................................ [1]
(iv) The organic product of reaction 3 is Y.
Y can be hydrolysed using excess aqueous H2SO4 to form Z.

The molecular formula of Z is C4H8O4.
Draw the structure of Z.
[2]

14
(d) 2-bromo-1-chloropropane, CH3CHBrCH2Cl, is the major product of the reaction of allyl chloride
with HBr.
major product minor product

Br
Cl HBr Cl Br Cl
and
Explain why 2-bromo-1-chloropropane is the major product of this reaction.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
[Total: 13]
© UCLES 2019 9701/22/F/M/19

15
BLANK PAGE
© UCLES 2019 9701/22/F/M/19

16
BLANK PAGE
© UCLES 2019 9701/22/F/M/19

*3472908311*
CHEMISTRY 9701/22
1 hour 15 minutes

IB19 06_9701_22/4RP
2
1 Methylpropane, (CH3)2CHCH3, is an isomer of butane, CH3(CH2)2CH3.
(a) (i) Explain why methylpropane and butane are a pair of isomers.
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Identify the type of isomerism shown by methylpropane and butane.
........................................................................................................................................ [1]
(b) When a sample of butane is heated to 373 K, in the presence of a catalyst, and allowed to
reach equilibrium the following reaction occurs.
CH3(CH2)2CH3(g) (CH3)2CHCH3(g) ∆H = –8.0 kJ mol–1
State and explain the effect on the composition of this equilibrium mixture when the temperature
is increased to 473 K.
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
© UCLES 2019 9701/22/M/J/19

3
(c) 1 mole of butane gas was added to a 1 dm3 closed system, at a constant temperature and
pressure. The amount of butane and methylpropane was measured at regular time intervals.
1.0
0.9
0.8
0.7
0.6
amount
0.5
/ mol
0.4
0.3
0.2
0.1
0
time
(i) Label the graph with a t to show the time taken to reach dynamic equilibrium. [1]
(ii) U
se the graph to find the concentration of butane and methylpropane in the mixture at
equilibrium.
concentration of butane = .................................... mol dm–3
concentration of methylpropane = ....................... mol dm–3

[1]
(iii) Write an expression for Kc for this reaction.
[1]
(iv) Calculate a value for Kc and state its units.
Kc = .............................. units = .............................. [2]
[Total: 10]

4
2 Group 17 elements are commonly referred to as the halogens.
(a) State and explain the trend in volatility of chlorine, bromine and iodine down the group.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [3]
Hydrogen gas reacts with the different halogens under different conditions.
(b) (i) State the conditions required for chlorine to react with hydrogen at room temperature.
........................................................................................................................................ [1]
(ii) On heating, iodine reacts with hydrogen in a reversible reaction.
Give the equation for this reaction. Include state symbols.
........................................................................................................................................ [2]
(c) Hydrogen chloride reacts with water.
HCl + H2O H3O+ + Cl –
(i) In this reaction, one of the reactants behaves as a Brønsted-Lowry acid.
What is meant by the term Brønsted-Lowry acid?
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Identify the reactant behaving as an acid and its conjugate base.
acid ......................................................................................................................................
conjugate base ....................................................................................................................

[1]
(iii) Name the type of bond formed between H+ and H2O to make H3O+.
........................................................................................................................................ [1]
(iv) For H3O+, predict its shape and the H–O–H bond angle.
shape ...................................................................................................................................
bond angle ...........................................................................................................................

[2]
[Total: 11]
© UCLES 2019 9701/22/M/J/19

5
3 Period 3 elements react with chlorine gas, Cl 2(g), to form chlorides.
(a) The table shows the differences in observations which occur when two Period 3 chlorides are
added to water.
observations when pH of solution

Period 3 chloride
added to water formed with water
White solid disappears.

NaCl 7
Colourless solution made.
Pale yellow solution forms.

SiCl 4 Bubbles form and the test-tube feels hot. 1–2
White precipitate forms.
(i) Write an equation for the reaction occurring when SiCl 4 is added to cold water. Include
state symbols.
........................................................................................................................................ [1]
(ii) Name the type of reaction occurring when SiCl 4 is added to water.
Ignore the exothermic/endothermic nature of the reaction.
........................................................................................................................................ [1]
(iii) Explain, in terms of bonding, why NaCl and SiCl 4 behave differently when added to water.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) Explain, in terms of electronegativity, why the bonding in NaCl is different from the bonding
in SiCl 4.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]

6
(b) Cl 2(g) dissolves in cold water and reacts with it.
Cl 2 + H2O HCl + HCl O
(i) Identify the oxidation number of chlorine in each of the chlorine‑containing species in this
reaction.
chlorine-containing species Cl 2 HCl HCl O

oxidation number of chlorine
[2]
(ii) Name the type of reaction occurring.
........................................................................................................................................ [1]
(iii) Explain why chlorine is used in the purification of water.
..............................................................................................................................................
........................................................................................................................................ [1]
(c) A mixture of HCl and HCl O is added to cold dilute NaOH. One of the products behaves as a
bleach.
Suggest the equation for the reaction occurring.
............................................................................................................................................... [2]
[Total: 13]
© UCLES 2019 9701/22/M/J/19

7
4 There are many different types of aliphatic and aromatic hydrocarbons.
(a) Name a naturally occurring source of aliphatic and aromatic hydrocarbons and outline how
different hydrocarbons are separated from this source.
name of source ...........................................................................................................................
outline of separation of hydrocarbons ........................................................................................
.....................................................................................................................................................
[2]
(b) When alkanes are heated to high temperatures, in the absence of air, the molecules can break
into smaller molecules.
(i) Identify the type of reaction occurring.
........................................................................................................................................ [1]
(ii) Write an equation which describes the reaction occurring when heptane, C7H16, is heated
in the absence of air, to form hexane, butane and ethene only.
........................................................................................................................................ [1]
(c) The equation for the complete combustion of ethene is shown.
C2H4 + 3O2 2CO2 + 2H2O
Calculate the volume, in dm3, of carbon dioxide formed in the complete combustion of 1.00 g
of ethene at room temperature and pressure.
volume of CO2 = .............................. dm3 [3]

8
(d) The table compares the reactivity of alkanes and alkenes with chlorine.
alkanes alkenes
name of the type of
substitution addition and substitution
reaction with chlorine
name of the type of electrophile and
free radical
reacting species free radical
(i) During the first stage in the substitution reaction chlorine forms chlorine free radicals.
Explain what is meant by the term free radical.
........................................................................................................................................ [1]
(ii) Name and explain the type of bond breaking which occurs to form chlorine free radicals.
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Name the stage of the reaction mechanism which occurs when a methane molecule reacts
with a chlorine free radical.
........................................................................................................................................ [1]
(iv) Complete the equation for the reaction which occurs when a methane molecule reacts
with a chlorine free radical.
H C H + •Cl +
H .................... ....................
[1]
(v) Carbon atoms can form σ and π bonds within hydrocarbon molecules.
Explain the following statement with reference to σ and π bonds.

Alkenes react with electrophiles but alkanes do not.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 14]
© UCLES 2019 9701/22/M/J/19

9
5 Many naturally occurring esters are used as flavourings in food.
(a) The structure of ester V is shown.
O O
V
(i) Name V.
........................................................................................................................................ [1]
V reacts with a reagent to form a salt of a carboxylic acid and an alcohol.

(ii) Identify a reagent that could be used in this reaction.
........................................................................................................................................ [1]
(iii) Draw the displayed formula of the alcohol made during this reaction.
[1]
(iv) State one other possible use for V, apart from as a food flavouring.
........................................................................................................................................ [1]
(b) Ester W is made up of 54.5% carbon, 9.1% hydrogen and 36.4% oxygen.
(i) Calculate the empirical formula of W.
[3]
(ii) State what additional information is required to determine the molecular formula of W.
........................................................................................................................................ [1]

10
(c) Compounds X, Y and Z are shown. They all have the same molecular formula.
X Y Z
O O
O O OH O
(i) Deduce the molecular formula of X, Y and Z.
........................................................................................................................................ [1]
(ii) In three experiments, sodium is added to separate samples of X, Y and Z.
Complete the table to show the observations for each of these three experiments. Ignore
any temperature changes which may occur.
experiment observations
Na + X
Na + Y
Na + Z
[2]
(d) Sodium carbonate solution reacts with methanoic acid.
Write the equation for this reaction.
............................................................................................................................................... [1]
[Total: 12]
© UCLES 2019 9701/22/M/J/19

11
BLANK PAGE
© UCLES 2019 9701/22/M/J/19

12
BLANK PAGE
© UCLES 2019 9701/22/M/J/19

*8474817039*
CHEMISTRY 9701/22
1 hour 15 minutes

IB19 11_9701_22/4RP
2
1 In the Periodic Table, the p block contains elements whose outer electrons are found in the
p subshell.
(a) E
lements in the p block show a general increase in first ionisation energy as the atomic number
increases.
(i) Draw the shape of a p orbital.
[1]
(ii) Write an equation to show the first ionisation energy of silicon.
........................................................................................................................................ [1]
(iii) E
xplain why there is a general increase in first ionisation energies of the elements across
Period 3.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2019 9701/22/O/N/19

3
(iv) Element A is in the p block.
The graph shows the successive ionisation energies for the removal of the first ten
electrons of A.
ionisation
energy
1 2 3 4 5 6 7 8 9 10
number of electrons removed
State and explain the group of the Periodic Table that element A belongs to.
group number .............................
explanation ..........................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[2]

4
(b) S
ilicon is found in many compounds in the Earth’s crust. Silicon has only three naturally
occurring isotopes, 28Si, 29Si and 30Si.
(i) The table shows data for 28Si, 29Si and 30Si.
28
Si 29
Si 30
Si
relative isotopic mass 28.0 29.0 30.0
A sample of silicon contains 92.2% 28Si. The total percentage abundance of 29Si and 30Si
in the sample is 7.8%.
The relative atomic mass, Ar, of silicon in the sample is 28.09.
Calculate the percentage abundance of 30Si.
Give your answer to one decimal place.
percentage abundance of 30Si = .............................. %

[3]
(ii) Silicon reacts with nitrogen gas to form Si3N4.
Si3N4 is a solid with a melting point of 1900 °C. It is insoluble in water and does not conduct
electricity when molten.
Suggest the type of bonding in and structure of Si3N4. Explain your answer.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
© UCLES 2019 9701/22/O/N/19

5
(c) Sulfur-containing compounds, such as C2H5SH, are found in fossil fuels, and produce SO2
when they are burned.
(i) Write the equation to show the complete combustion of C2H5SH.
........................................................................................................................................ [1]
(ii) S
tate why the presence of SO2 in the atmosphere has environmental consequences.
Describe one of the consequences on the environment.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(d) SO2 can react with ozone, O3, to form SO3 in two different reactions.
(i) In one reaction, SO2 reacts with O3 until a dynamic equilibrium is established.
SO2(g) + O3(g) SO3(g) + O2(g)
State and explain the effect of an increase in pressure on the composition of the equilibrium
mixture.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) In the other reaction, a different equilibrium is established at 300 K as shown.
3SO2(g) + O3(g) 3SO3(g) ΔH = +462.3 kJ mol–1
Suggest a temperature needed to increase the yield of SO3 at equilibrium.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 19]

6
2 xygen is the most abundant element in the Earth’s crust. It reacts with other elements to form
O
stable compounds, ions and molecules.
(a) Complete the table to give the formulae and acid/base behaviour of some of the oxides of the
Period 3 elements.
element sodium aluminium silicon phosphorus sulfur
formula of oxide Na2O SO3
acid/base behaviour amphoteric
[2]
(b) G
roup 2 elements form stable hydroxides, with general formula M(OH)2, where M is the Group 2
element.
(i) B
eryllium hydroxide, Be(OH)2, is an amphoteric compound that shows similar chemical
reactions to aluminium oxide.
State the meaning of the term amphoteric.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Write an ionic equation for the reaction of magnesium hydroxide, Mg(OH)2, with
hydrochloric acid.
........................................................................................................................................ [1]
(iii) Two methods of preparing strontium hydroxide are shown.
H2O strontium H 2O strontium

strontium
reaction 1 hydroxide reaction 2 oxide
State one difference between the observations you would make for reaction 1 and
reaction 2.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [1]
(iv) State how the solubility of the Group 2 hydroxides changes down the group.
........................................................................................................................................ [1]
© UCLES 2019 9701/22/O/N/19

7
(c) Sodium peroxide, Na2O2, reacts with CO2.

1
Na2O2(s) + CO2(g) Na2CO3(s) + 2 O2(g)
The partial pressure of CO2(g) in a 0.500 dm3 sample of air is 5.37 kPa at 20 °C.
(i) Calculate the amount, in moles, of CO2(g) present in the sample of air at 20 °C.
amount of CO2(g) = .............................. mol [2]
(ii) Calculate the mass of Na2O2(s) that would react fully with the amount of CO2(g) calculated
in (i).
mass of Na2O2(s) = .............................. g [1]
(iii) The peroxide ion, O22–, has a single covalent bond between the two oxygen atoms. Each
oxygen atom carries a negative charge.
Draw a ‘dot-and-cross’ diagram for the peroxide ion. Show outer electrons only.
[2]
[Total: 11]

8
3 A series of reactions for phosphorus and its compounds is shown.
excess Cl 2 H 2O NH3
P PCl 5 H3PO4 (NH4+)(H2PO4–)
reaction 1 reaction 2 reaction 3
(a) (i) State what you would observe in reaction 1.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) State the type of reaction that occurs in reaction 2.
........................................................................................................................................ [1]
(iii) H3PO4 can be produced by direct reaction of phosphorus with nitric acid.
P + 5HNO3 H2O + 5NO2 + H3PO4
Use oxidation numbers to show that this reaction is a redox reaction.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(b) Reaction 3 is a neutralisation reaction in which NH3 acts as a base.
(i) Explain how NH3 acts as a base in reaction 3.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Draw the three-dimensional shape of the ammonium ion, NH4+. Give the bond angle.
bond angle = .............................. ° [1]
(iii) State the industrial importance of compounds such as (NH4+)(H2PO4–).
........................................................................................................................................ [1]
© UCLES 2019 9701/22/O/N/19

9
(c) PCl 5 can be used to convert alcohols to halogenoalkanes.
(i) Write an equation for the reaction of C2H5OH with PCl 5 to form C2H5Cl.
........................................................................................................................................ [1]
(ii) State the type of reaction in (i).
........................................................................................................................................ [1]
(iii) H
alogenoalkanes can also be prepared by reacting alcohols with hydrogen halides, such
as HCl and HI.
● HCl is prepared using NaCl and concentrated H2SO4.

● I is prepared by reacting NaI with concentrated H3PO4.
H
Suggest why HI is not prepared by the reaction of NaI with concentrated H2SO4.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(iv) T
he rate of the hydrolysis reaction of halogenoalkanes with NaOH(aq) is dependent on the
halogen that is bonded to carbon.
tate and explain the order of reactivity when NaOH(aq) reacts separately with C2H5Cl,
S
C2H5Br and C2H5I.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 13]

10
4 renol is a naturally occurring organic molecule found in many fruits. It contains both an alkene and
P
an alcohol functional group.
prenol
H 3C H
C C
H 3C CH2OH
(a) Prenol can be formed by the reaction of G with NaOH(aq).
Complete the diagram to show the mechanism of the reaction between G and NaOH(aq) to
form prenol.
Include all relevant charges, partial charges, lone pairs and curly arrows.
G prenol
H 3C H H 3C H
C C C C
H 3C C Cl H3C CH2OH
H H
[2]
(b) Prenol reacts with steam to form a mixture of three isomers, J, K and L, of molecular formula
C5H12O2.
(i) When J is heated with excess acidified potassium dichromate(VI) it forms an organic
product which shows no reaction with 2,4‑DNPH.
Draw the structure of J.
[1]
© UCLES 2019 9701/22/O/N/19

11
K and L are stereoisomers with molecular formula C5H12O2.

K and L both react when heated with excess acidified potassium dichromate(VI) to form M,

C5H8O3.
M forms an orange precipitate on reaction with 2,4‑DNPH.

(ii) Give the structural formula of K and L.
........................................................................................................................................ [1]
(iii) Name the type of stereoisomerism shown by K and L.
........................................................................................................................................ [1]
(iv) Give the balanced equation to represent the reaction of K, C5H12O2, with acidified potassium
dichromate(VI) to form M, C5H8O3.
Use [O] to represent an atom of oxygen provided by the oxidising agent.
........................................................................................................................................ [1]
(c) (i) Prenol contains an alkene functional group.
escribe a chemical test to confirm the presence of an alkene functional group. Give the
D
result of the test.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Prenol can be polymerised to form poly(prenol).
Draw one repeat unit of poly(prenol).
[1]

12
(d) Isoprenol is a structural isomer of prenol.
isoprenol
H CH3
C C
H CH2CH2OH
The series of reactions shows how isoprenol can be used to form Q, a sweet-smelling liquid.
N acidified P
potassium O
H2 and Ni dichromate(VI)
isoprenol
reaction 1 OH heat under OH
reflux
C2H5OH heat under

and H2SO4 reflux
(i) Give the name of N.
........................................................................................................................................ [1]
(ii) Isoprenol is a liquid.
Ni acts as a catalyst for reaction 1.
Identify the type of catalysis shown by Ni in reaction 1.
........................................................................................................................................ [1]
(iii) Draw the skeletal formula of Q and suggest one commercial use of Q.
commercial use ...................................................................................................................

[2]
© UCLES 2019 9701/22/O/N/19

13
(e) P can be produced as shown.
O
HCl N H + / H 2O
reaction I Cl reaction II C reaction III
OH
P
(i) The progress of reaction I can be monitored using infra-red spectroscopy.
One absorption that can be used to monitor the progress of this reaction is that of C–Cl at
730 cm–1.
Identify another absorption that can be used to monitor the progress of this reaction. In
your answer, you should refer to the specific bond and its corresponding absorption range
in wavenumbers.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) State the reagent(s) needed for reaction II.
........................................................................................................................................ [1]
(iii) Name the type of reaction that occurs in reaction III.
........................................................................................................................................ [1]
(iv) The yield of reaction I is very low.
Explain why.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 17]

14
BLANK PAGE
© UCLES 2019 9701/22/O/N/19

15
BLANK PAGE
© UCLES 2019 9701/22/O/N/19

16
BLANK PAGE
© UCLES 2019 9701/22/O/N/19

Cambridge International Examinations
*3410012160*
CHEMISTRY 9701/22
1 hour 15 minutes
Write your Centre number, candidate number and name on all the work you hand in.

This document consists of 11 printed pages and 1 blank page.
IB18 03_9701_22/3RP
2
1 (a) T
he graph shows a sketch of the first ionisation energies of six successive elements in the
Periodic Table.
The letters are not the symbols of the elements.
first
ionisation
energy
A B C D E F
element
(i)
Explain what is meant by the term first ionisation energy.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
(ii) Suggest why the first ionisation energy of B is much less than that of A.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
© UCLES 2018 9701/22/F/M/18

3
(b)
P–T are successive elements in Period 3 of the Periodic Table.
The letters are not the symbols of the elements.
On the axes, sketch a graph to show the trend in the atomic radius of the elements P–T.
atomic radius
of the element
P Q R S T
element
explanation .................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
[3]
[Total: 9]

4
2 Carbon and silicon are elements in Group 14.
(a) C60 and diamond are allotropes of carbon.
(i) Describe the lattice structure of solid C60.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) C60 sublimes (turns directly from solid to gas) at about 800 K. Diamond also sublimes but
only above 3800 K.
Explain why C60 and diamond sublime at such different temperatures.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [4]
(b) C60 forms hydrocarbons with similar chemical properties to those of alkenes. One such
hydrocarbon is C60H18.
(i) State what is meant by the term hydrocarbon.
..............................................................................................................................................
........................................................................................................................................ [1]
© UCLES 2018 9701/22/F/M/18

5
(ii) D escribe a test to indicate the presence of double bonds between carbon atoms in C60H18.
Give the result of the test.
test .......................................................................................................................................
..............................................................................................................................................
result ....................................................................................................................................
..............................................................................................................................................
[2]
(c) 0.144 g of C60 was placed in a 100 cm3 container of hydrogen gas at 20 °C and 1.00 × 105 Pa.
The container was heated to make the C60 and hydrogen gas react.
The reaction occurred as shown in the equation.
C60(s) + xH2(g) C60H2x(s)
After the reaction, the container was allowed to cool to 20 °C. The pressure decreased to
2.21 × 104 Pa. All of the C60 had reacted.
(i) Name the type of reaction that occurred.
........................................................................................................................................ [1]
(ii) Calculate the amount, in moles, of C60 that reacted.
amount of C60 = .............................. mol [1]
(iii) Calculate the amount, in moles, of hydrogen gas that reacted with the C60.
amount of hydrogen gas = .............................. mol [2]
(iv) U
se your answers from (ii) and (iii) to deduce the molecular formula of the hydrocarbon,
C60H2x.
If you were unable to calculate the amount of hydrogen gas, assume that 0.00240 mol of
hydrogen gas reacted. This is not the correct value for the amount of hydrogen gas that
reacted.
molecular formula = .............................. [2]

6
(d) Silicon shows the same kind of bonding and structure as diamond.
(i) State the type of bonding and structure shown by silicon.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) When silicon reacts with magnesium, Mg2Si forms. Mg2Si is thought to contain the Si4– ion.
State the full electronic configuration of the Si4– ion.
1s2................................................................................................................................... [1]
(iii) S
olid Mg2Si reacts with dilute hydrochloric acid to form gaseous SiH4 and a solution of
magnesium chloride.
Write an equation to show the reaction of solid Mg2Si with dilute hydrochloric acid.
........................................................................................................................................ [2]
(iv) Predict the shape of the SiH4 molecule.
........................................................................................................................................ [1]
(v) SiH4 reacts spontaneously with oxygen to produce a white solid and a colourless liquid
that turns anhydrous copper(II) sulfate blue. No other products are formed.
Write an equation for the reaction of SiH4 with oxygen.
State symbols are not required.
........................................................................................................................................ [1]
[Total: 22]
© UCLES 2018 9701/22/F/M/18

7
3 Calcium and its compounds have a large variety of applications.
(a) Calcium metal reacts readily with most acids.
Write an equation for the reaction of calcium with dilute nitric acid. State symbols are not
(i)
required.
........................................................................................................................................ [1]
(ii) When calcium metal is placed in dilute sulfuric acid, it reacts vigorously at first.
fter a short time, a crust of calcium sulfate forms on the calcium metal and the reaction
A
stops. Some of the calcium metal and dilute sulfuric acid remain unreacted.
Suggest an explanation for these observations.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(b) C
alcium ethanedioate is formed when calcium reacts with ethanedioic acid, (CO2H)2. The
compound contains one cation and one anion.
(i) D
raw the ‘dot-and-cross’ diagram of the cation present in calcium ethanedioate. Show all
electrons.
[1]
(ii) Draw the displayed formula of the anion present in calcium ethanedioate.
[2]

8
alcium chlorate(I), Ca(Cl O)2, is used as an alternative to sodium chlorate(I), NaCl O, in some

(c) C
household products.
(i) Suggest a use for calcium chlorate(I).
........................................................................................................................................ [1]
(ii) The chlorate(I) ion is formed when cold aqueous sodium hydroxide reacts with chlorine.
Write an ionic equation for this reaction. State symbols are not required.
........................................................................................................................................ [1]
(iii) The chlorate(I) ion is unstable and decomposes when heated as shown.
Deduce the oxidation number of chlorine in each species. Complete the boxes.
3Cl O– 2Cl – + Cl O3–

oxidation number
+1
of chlorine:
[1]
(iv) In terms of electron transfer, state what happens to the chlorine in the reaction in (iii).
........................................................................................................................................ [1]
(d) C
alcium lactate is used in some medicines. It forms when lactic acid (2-hydroxypropanoic acid)
reacts with calcium carbonate.
OH
H 3C C H
CO2H
lactic acid
(i) Identify the two other products of the reaction of lactic acid with calcium carbonate.
........................................................................................................................................ [1]
© UCLES 2018 9701/22/F/M/18

9
Two possible methods of making lactic acid are shown.
O OH
reaction 1
C H3C C H
H3C H reaction 2
CN
OH
H 3C C H
CO2H
OH O lactic acid
H 3C C H C
H 3C CO2H
CH2OH
(ii) State suitable reagents and conditions for reactions 1 and 3.
reaction reagents and conditions
[4]
(iii) Name the type of reaction that occurs in reaction 2.
........................................................................................................................................ [1]
(iv) Reaction 4 uses NaBH4.
Identify the role of NaBH4 in this reaction.
........................................................................................................................................ [1]
(v) Lactic acid has a chiral centre.
State what is meant by the term chiral centre.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [1]
[Total: 18]

10
4 Cyclohexane is a colourless liquid used in industry to produce synthetic fibres.
A reaction scheme involving cyclohexane is shown.
Cl
(a) Reaction 1 involves a free radical substitution mechanism.
(i) State the essential condition required for reaction 1 to occur.
........................................................................................................................................ [1]
(ii) Complete the table to give details of the mechanism in reaction 1.
name of step reaction
................................. Cl 2 2Cl •
•
propagation + Cl • +
..............................
Cl
•
................................. + Cl 2 + Cl •
•
termination + Cl •
..............................
[4]
(b) Name the type of reaction that occurs in reaction 2.
............................................................................................................................................... [1]
© UCLES 2018 9701/22/F/M/18

11
(c) The product of reaction 2 is cyclohexene.
Cyclohexene can be converted into adipic acid (hexanedioic acid), HO2C(CH2)4CO2H.
(i) Identify the reagents and conditions for the conversion of cyclohexene into adipic acid.
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Suggest three main differences between the infra-red spectra of cyclohexene and
adipic acid.
In each case, identify the bond responsible and its characteristic absorption range (in
wavenumbers).
1 ...........................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
2 ...........................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
3 ...........................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
[3]
[Total: 11]

12
BLANK PAGE
Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable
effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will
be pleased to make amends at the earliest possible opportunity.
To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge International
Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after
the live examination series.
Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local
Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.
© UCLES 2018 9701/22/F/M/18

*5604890866*
CHEMISTRY 9701/22
1 hour 15 minutes

IB18 06_9701_22/6RP
2
1 Sodium and magnesium are the first two elements in the third period.
(a) S
odium and magnesium both react with cold water to produce the same type of product in
solution. With sodium the solution is clear but with magnesium it appears cloudy.
(i) Write an equation for the reaction of magnesium with cold water.
........................................................................................................................................ [1]
(ii) Suggest why the solution is cloudy after the reaction of magnesium with cold water.
..............................................................................................................................................
........................................................................................................................................ [1]
(b) G
roup 2 elements, including magnesium, react with oxygen and with dilute acids. There are
trends in both the physical and chemical properties of the elements and their compounds down
the group. Reactivity generally increases from Mg to Ba.
(i) Explain why there is a general increase in reactivity from Mg to Ba.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) Give two observations for the reaction of magnesium with oxygen. Write an equation for
this reaction. Include state symbols.
..............................................................................................................................................
..............................................................................................................................................
equation ...............................................................................................................................
[3]
(iii) Write an equation for the reaction of magnesium with sulfuric acid.
........................................................................................................................................ [1]
(iv) S
uggest why there is a general decrease in the melting points of the elements down
Group 2.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [3]
[Total: 11]
© UCLES 2018 9701/22/M/J/18

3
2 Ammonium iron(II) sulfate, (NH4)2Fe(SO4)2, has a relative formula mass, Mr, of 284.
(a) Define the term relative formula mass.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]
(b) One of the cations in ammonium iron(II) sulfate is the ammonium ion, NH4+.
(i) Draw a ‘dot-and-cross’ diagram of an ammonium ion. Show outer shell electrons only.
Use × to show electrons from nitrogen.

Use ● to show electrons from hydrogen.
[2]
(ii) Suggest the shape of an ammonium ion and predict the bond angle.
shape ...................................................................................................................................
bond angle ...........................................................................................................................

[2]
(c) In aqueous solution the ammonium ion acts as a weak Brønsted-Lowry acid.
(i) Explain the meaning of the term weak Brønsted-Lowry acid.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) W
rite an equation to show this behaviour of the ammonium ion in water. Include state
symbols.
........................................................................................................................................ [2]

4
(d) Mohr's salt, (NH4)2Fe(SO4)2•xH2O, is the hydrated form of ammonium iron(II) sulfate.
x represents the number of moles of water in 1 mole of the salt.

A student wanted to determine the value of x. 0.784 g of the hydrated salt was dissolved in
water and this solution was acidified.
ll of the solution was titrated with 0.0200 mol dm–3 potassium manganate(VII). 20.0 cm3 of this

A
potassium manganate(VII) solution was required for complete reaction with the Fe2+ ions.
(i) Use changes in oxidation numbers to balance the equation for the reaction taking place.
MnO4–(aq) + .....Fe2+(aq) + .....H+(aq) .....Mn2+(aq) + .....Fe3+(aq) + .....H2O(l)

[1]
(ii) State the role of the Fe2+ ions in this reaction.
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) Calculate the amount, in moles, of manganate(VII) ions that reacted.
amount = .............................. mol [1]
(iv) Calculate the amount, in moles, of Fe2+ ions in the sample of the salt.
amount = .............................. mol [1]
© UCLES 2018 9701/22/M/J/18

5
(v) Calculate the relative formula mass of (NH4)2Fe(SO4)2•xH2O.
relative formula mass = .............................. [1]
(vi) Calculate the value of x.
x = .............................. [1]
[Total: 17]

6
3 Most vehicle fuels contain hydrocarbons obtained from crude oil.
(a) (i) S
tate the name of the type of reaction that hydrocarbons undergo when being used as
fuels.
........................................................................................................................................ [1]
(ii) Write an equation for the reaction of octane, C8H18, as a fuel, as in (a)(i).
........................................................................................................................................ [2]
(b) T
he supply of material suitable for use as fuels directly from crude oil is not sufficient to meet
demand. A process is carried out to make some of the larger hydrocarbon molecules more
useful.
(i) Name this process.
........................................................................................................................................ [1]
As well as producing fuels, this process produces compounds suitable for use in the production
of polymers. An example of such a compound is but-2-ene, CH3CH=CHCH3.
(ii) Draw the repeat unit of the polymer that is produced from but-2-ene.
[2]
(iii) Name the type of polymerisation that occurs during the production of the polymer in (ii).
........................................................................................................................................ [1]
© UCLES 2018 9701/22/M/J/18

7
(c) G
ases produced in internal combustion engines include carbon monoxide, oxides of nitrogen
such as NO2, and unburnt hydrocarbons.
These gases are removed from the exhaust before they can enter the atmosphere.
(i) State what is used to remove these gases from the exhaust.
........................................................................................................................................ [1]
(ii) W
rite one equation to show how both carbon monoxide, CO, and nitrogen dioxide, NO2,
are removed from the exhaust.
........................................................................................................................................ [1]
(iii) S
tate the environmental consequence of allowing unburnt hydrocarbons to enter the
atmosphere.
........................................................................................................................................ [1]
(d) V
ehicle fuels are treated to remove sulfur. If sulfur is present in a fuel when it is burned, SO2 is
produced and may be released into the atmosphere where it can form acid rain.
(i) Acid rain can contribute to breathing difficulties.
Identify two other consequences of acid rain in the atmosphere.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) NO2 is involved in the production of acid rain from SO2.
Give two equations which describe how acid rain is formed by the action of NO2 with SO2.
..............................................................................................................................................
........................................................................................................................................ [2]
(iii) NO2 is described as a catalyst during this process.
Explain, with the use of an appropriate equation, why NO2 is described as a catalyst.
..............................................................................................................................................
........................................................................................................................................ [2]
[Total: 16]

8
4
W is CH3COCH2CH3.
(a) The reaction between W and alkaline aqueous iodine produces a yellow precipitate.
(i) Give the name of the compound formed as a yellow precipitate in this reaction.
........................................................................................................................................ [1]
(ii) Give the name of W.
........................................................................................................................................ [1]
(b) There are two structural isomers of W that are also carbonyl compounds.
Draw the structures of these two isomers of W.
[2]
Two reactions of W are shown.
reaction 1
CH3COCH2CH3 CH3CH(OH)CH2CH3
W
reaction 2
OH
H3C C CH2CH3
CN
X
(c) (i) Identify the type of reaction occurring in reaction 1.
........................................................................................................................................ [1]
(ii) Identify the reagent for reaction 1.
........................................................................................................................................ [1]
© UCLES 2018 9701/22/M/J/18

9
(d) Reaction 2 is carried out by adding a mixture of HCN and NaCN to W.

The product, X, is formed as a mixture of two isomers.
(i) Complete the mechanism for this reaction.
Include the structure of the intermediate formed and all necessary charges, dipoles, lone
pairs and curly arrows.
O OH
W C CH3 H3C C CH2CH3
H 3C CH2
CN
CN– X
[4]
(ii) State the name of the type of isomerism shown by X.
........................................................................................................................................ [1]
(iii) Explain fully why X shows this type of isomerism.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
Question 4 continues on page 10.

10
(e) If X is treated with ammonia and the product hydrolysed, a compound, Y, is obtained that
contains 51.3% C, 9.40% H, 12.0% N and 27.3% O by mass.
(i) Show that the empirical formula of Y is C5H11NO2.
[2]
(ii) The empirical formula of Y is C5H11NO2 and the Mr of Y is 117.
Deduce the molecular formula of Y. You must explain your reasoning.
molecular formula = ..............................
..............................................................................................................................................
..............................................................................................................................................
[1]
[Total: 16]
© UCLES 2018 9701/22/M/J/18

11
BLANK PAGE
© UCLES 2018 9701/22/M/J/18

12
BLANK PAGE
© UCLES 2018 9701/22/M/J/18

*5824876239*
CHEMISTRY 9701/22
1 hour 15 minutes

IB18 11_9701_22/6RP
2
1 The model of the nuclear atom was first proposed by Ernest Rutherford. He developed this model
on the basis of results obtained from an experiment using gold metal foil.
(a) Complete the table with information for two of the particles in an atom of 197Au.
relative relative location total number in

particle
mass charge within atom an atom of 197Au
electron 0.0005 –1 79
neutron nucleus
[4]
(b) State the type of bonding in gold.
............................................................................................................................................... [1]
(c) A sample of gold found in the earth consists of only one isotope.
(i) Explain what is meant by the term isotopes.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) A different sample of gold contains more than one isotope.
uggest why this different sample of gold has the same chemical properties as the sample
S
found in the earth.
..............................................................................................................................................
........................................................................................................................................ [1]
© UCLES 2018 9701/22/O/N/18

3
(d)
Tumbaga is an alloy of copper and gold. A sample of tumbaga was analysed. The mass
spectrum of the sample is shown.
56.36
percentage
abundance 25.14
x
0
63 65 197
m/e
(i) Calculate the percentage abundance of gold, x, in the sample of tumbaga.
x = .............................. % [1]
(ii) C alculate the relative atomic mass, Ar , of the copper present in this sample.
Give your answer to two decimal places.
Ar (Cu) = .............................. [2]
[Total: 11]

4
2 The table gives some data for elements in the third period and some of their compounds.
element Na Mg Al Si P S
type of bonding metallic covalent covalent
formula of oxide P4O10 SO2
formula of chloride NaCl MgCl 2 SCl 2
(a) C
omplete the table to show the bonding in the elements, and the formulae of their oxides and
chlorides.[3]
(b) SCl 2 is formed in the following reaction.
S2Cl 2(l) + Cl 2(g) 2SCl 2(l) ΔH = – 40.6 kJ mol–1
(i) C
omplete the ‘dot-and-cross’ diagram to show the bonding in a molecule of SCl 2. Show
outer electrons only.
[1]
(ii) C
omplete and fully label the reaction pathway diagram for the reaction between S2Cl 2 and
Cl 2. Include labels for activation energy, Ea, and enthalpy change of the forward reaction,
ΔH.
S2Cl 2(l) + Cl 2(g)

energy
[2]
© UCLES 2018 9701/22/O/N/18

5
(c) (i) On the axes, sketch the trend in melting point of the elements Na to S.
melting point
of element
Na Mg Al Si P S
[1]
(ii) Give three statements to explain your sketch.
1 ...........................................................................................................................................
..............................................................................................................................................
2 ...........................................................................................................................................
..............................................................................................................................................
3 ...........................................................................................................................................
..............................................................................................................................................
[3]
(d) Write an equation for the reaction of P4O10 with water.
............................................................................................................................................... [1]
(e) SO2 can be released into the atmosphere when fossil fuels containing sulfur are burnt.
State and explain one environmental consequence of the release of SO2 into the atmosphere.
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
............................................................................................................................................... [2]

6
(f) T
he elements in the third period show a general increase in their first ionisation energies from
left to right.
Identify two pairs of successive elements in the third period that do not agree with this
statement.
For each pair, explain why the change in ionisation energy does not agree with this statement.

Use of the Data Booklet may help you to answer this question.
pair 1 ...........................................................................................................................................
explanation .................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
pair 2 ...........................................................................................................................................
explanation .................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
.....................................................................................................................................................
[4]
[Total: 17]
© UCLES 2018 9701/22/O/N/18

7
3 rihalomethanes are organic molecules in which three of the hydrogen atoms of methane are
T
replaced by halogen atoms, for example CHF3.
(a) The equation shows a reaction to produce CHF3.
CHI3(s) + 3AgF(s) CHF3(g) + 3AgI(s)
Use the data to calculate the enthalpy change of reaction, ΔHr , for this formation of CHF3.
enthalpy change of
compound
formation, ΔHf / kJ mol–1
CHI3(s) –182.1
CHF3(g) – 692.9
AgF(s) –204.6
AgI(s) – 61.8
enthalpy change of reaction, ΔHr = .............................. kJ mol–1 [3]

8
(b) T
he graph shows the relationship between pV and p at a given temperature for CHF3 and an
ideal gas.
CHF3
pV
ideal gas
0 200 400 600 800 1000

p / atm
(i) CHF3 is not an ideal gas.
State three basic assumptions that scientists make about the properties of ideal gases.
1 ...........................................................................................................................................
2 ...........................................................................................................................................
3 ...........................................................................................................................................
[3]
(ii) E
xplain why CHF3 deviates from the properties of an ideal gas at pressures greater than
300 atm.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
© UCLES 2018 9701/22/O/N/18

9
(c) A
different trihalomethane, CHCl 3, reacts with O2 to produce carbonyl dichloride. HCl (g) is also
released as a product of this reaction.
C
Cl Cl
carbonyl dichloride
(i) Write an equation for this reaction of CHCl 3 with O2.
........................................................................................................................................ [1]
(ii) T he conversion of CHCl 3 to carbonyl dichloride can be monitored by infra-red spectroscopy.

The infra-red spectrum of carbonyl dichloride is shown.
100
transmittance
50
0
4000 3000 2000 1500 1000 700
wavenumber / cm–1
n the infra-red spectrum of carbonyl dichloride identify with an X the absorption that
O
would not be present in an infra-red spectrum of CHCl 3.
..............................................................................................................................................
..............................................................................................................................................
[2]
(iii) Suggest another difference between the infra-red spectra of CHCl 3 and carbonyl dichloride.
..............................................................................................................................................
........................................................................................................................................ [1]
[Total: 12]

10
4 The diagram shows a reaction sequence starting from ethanal.
H
O OH
HCN and NaCN H2SO4(aq) H C
C P H3C C H C CO2H
reaction 1 reaction 2 reaction 3
H 3C H
CO2H H
ethanal
Q R
reaction 4
C
H 3C CO2H
(a) (i) Draw the displayed formula of P.
[1]
(ii) Name the type of chemical reaction that occurs in reaction 3.
........................................................................................................................................ [1]
(iii) Write an equation to represent reaction 4.
Use [O] to represent the oxidising agent.
........................................................................................................................................ [1]
(iv) State the reagents and conditions for reaction 4.
........................................................................................................................................ [1]
© UCLES 2018 9701/22/O/N/18

11
(b) Compound Q is formed as a mixture of two optical isomers.
(i) Explain what is meant by the term optical isomers.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Draw the two optical isomers of Q, showing clearly their three‑dimensional structures.
[2]
(c)
R can be used to make a polymer, W, in two steps.
addition intermediate NaOH(aq)

R polymer W
polymerisation
Draw one repeat unit of W.
[3]

12
(d) Compound Z, H2C=CHCH3, is produced from R.
Z can be used in a two-step process to produce 2-aminopropane.
(i) In the first step, Z reacts with HBr to form two products. The structure of the product
depends on which intermediate is formed, intermediate I or intermediate II.
H H H
C
+ + C C CH3
H 3C CH3 H H
intermediate I intermediate II
Explain why intermediate I is more likely to form than intermediate II.
..............................................................................................................................................
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [2]
(ii) When intermediate I forms, the product of the first step is T.
omplete the diagram to show the mechanism for the conversion of Z to T.

C
Include all relevant charges, partial charges, curly arrows and lone pairs.
Z T
H
H H
H C +
C H 3C C CH3
C CH3
H3C CH3
H Br
H
Br
[3]
(iii)
T can then be converted to 2-aminopropane.
T
H H
NH3
H 3C C CH3 H3C C CH3
ethanol
Br NH2
2-aminopropane
Name the mechanism for this conversion.
........................................................................................................................................ [1]
© UCLES 2018 9701/22/O/N/18

13
(e) (i) Compound S, CH3COCO2H, can be reduced by LiAl H4.
omplete the equation using structural formulae to represent this reaction.

C
Use [H] to represent the reducing agent.
CH3COCO2H + ............................................................................................................. [2]
ther reducing agents containing Group 1 metal cations include LiBH4, NaBH4 and KBH4.
O
The strength of the reducing agent depends on the size of its cation.
(ii) Give the electronic configuration of the Na+ cation.
1s2 .................................................................................................................................. [1]
(iii) Suggest why ionic radius increases down Group 1.
..............................................................................................................................................
..............................................................................................................................................
........................................................................................................................................ [1]
[Total: 20]

14
BLANK PAGE
© UCLES 2018 9701/22/O/N/18

15
BLANK PAGE
© UCLES 2018 9701/22/O/N/18

16
BLANK PAGE
© UCLES 2018 9701/22/O/N/18

Combinepdf

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Combinepdf

Uploaded by

Copyright:

Available Formats

Cambridge International AS & A Level

You must answer on the question paper.

No additional materials are needed.

This document has 16 pages.

Answer all the questions in the spaces provided.

1 Fig. 1.1 shows how first ionisation energies vary across Period 2.

(a) Construct an equation to represent the first ionisation energy of oxygen.

© UCLES 2022 9701/22/F/M/22

(c) Element E is in Period 3 of the Periodic Table.

ionisation 1st 2nd 3rd 4th 5th 6th 7th 8th

Deduce the full electronic configuration of E.

full electronic configuration of E = ..............................................................................................

© UCLES 2022 9701/22/F/M/22 [Turn over

2 Some oxides of elements in Period 3 are shown.

Na2O Al 2O3 P4O6 P4O10 SO2 SO3

(i) Define reducing agent.

(ii) Write an equation for the reaction of Na2O with water.

(b) Al 2O3 is an amphoteric oxide found in bauxite.

(i) State what is meant by amphoteric.

Write an equation for this reaction.

© UCLES 2022 9701/22/F/M/22

(iii) Al 2O3 is used as a catalyst in the dehydration of alcohols.

(ii) Determine the oxidation number of P in H3PO3.

© UCLES 2022 9701/22/F/M/22 [Turn over

(iii) When P4O6(s) is heated with oxygen it forms P4O10(s).

P4O6(s) + 2O2(g) → P4O10(s) ∆Hr = –1372 kJ mol–1

The enthalpy change of formation, ∆Hf, of P4O10(s) is –3012 kJ mol–1.

Calculate the enthalpy change of formation, ∆Hf, of P4O6(s).

 ∆Hf of P4O6(s) = .............................. kJ mol–1 [1]

(iv) Write an equation for the reaction of P4O10 with water.

(d) SO2 and SO3 are found in the atmosphere.

equation 1 SO2(g) + NO2(g) SO3(g) + NO(g)

State the product of this reaction that contributes to photochemical smog.

© UCLES 2022 9701/22/F/M/22

The equilibrium reaction in equation 1 has ∆Hr = –168 kJ mol–1.

© UCLES 2022 9701/22/F/M/22 [Turn over

(i) Write an equation for reaction 1.

© UCLES 2022 9701/22/F/M/22

reactants type(s) of reaction

NaCl and concentrated H2SO4

NaBr and concentrated H2SO4

Explain the difference in the effect of heating on HCl and HI.

© UCLES 2022 9701/22/F/M/22 [Turn over

The concentration of a strong acid can be determined by titration.

(i) State what is meant by strong Brønsted–Lowry acid.

(ii) On Fig. 3.2, sketch the pH titration curves produced when:

reaction of NaOH(aq) and HBr(aq) reaction of NH3(aq) and HBr(aq)

© UCLES 2022 9701/22/F/M/22

solvent organic product(s) inorganic product(s)

© UCLES 2022 9701/22/F/M/22 [Turn over

4 Compounds J and K are found in plant oils.

reagent observation with J

Draw the three-dimensional structures of the two optical isomers of J.

© UCLES 2022 9701/22/F/M/22

(i) Identify L. State the conditions required for reaction 1.

(ii) Draw one repeat unit of the addition polymer Perspex®.

© UCLES 2022 9701/22/F/M/22 [Turn over

step reagent(s) type of reaction

© UCLES 2022 9701/22/F/M/22

Important values, constants and standards

molar gas constant R = 8.31 J K–1 mol–1

© UCLES 2022 9701/22/F/M/22

at www.cambridgeinternational.org after the live examination series.

1 Fig. 1.1 shows how first ionisation energies vary across Period 2.

(a) Construct an equation to represent the first ionisation energy of oxygen.

(c) Element E is in Period 3 of the Periodic Table.

Deduce the full electronic configuration of E.

2 Some oxides of elements in Period 3 are shown.

(i) Define reducing agent.

(ii) Write an equation for the reaction of Na2O with water.

(b) Al 2O3 is an amphoteric oxide found in bauxite.

(i) State what is meant by amphoteric.

Write an equation for this reaction.

(iii) Al 2O3 is used as a catalyst in the dehydration of alcohols.

(ii) Determine the oxidation number of P in H3PO3.

(iii) When P4O6(s) is heated with oxygen it forms P4O10(s).

The enthalpy change of formation, ∆Hf, of P4O10(s) is –3012 kJ mol–1.

Calculate the enthalpy change of formation, ∆Hf, of P4O6(s).

∆Hf of P4O6(s) = .............................. kJ mol–1 [1]

(iv) Write an equation for the reaction of P4O10 with water.

(d) SO2 and SO3 are found in the atmosphere.

State the product of this reaction that contributes to photochemical smog.

The equilibrium reaction in equation 1 has ∆Hr = –168 kJ mol–1.

(i) Write an equation for reaction 1.

Explain the difference in the effect of heating on HCl and HI.

The concentration of a strong acid can be determined by titration.

(i) State what is meant by strong Brønsted–Lowry acid.

(ii) On Fig. 3.2, sketch the pH titration curves produced when:

4 Compounds J and K are found in plant oils.

Draw the three-dimensional structures of the two optical isomers of J.

(i) Identify L. State the conditions required for reaction 1.

(ii) Draw one repeat unit of the addition polymer Perspex®.

Explain these properties of magnesium by referring to its structure and bonding.

(iii) Define enthalpy change of formation.

∆Hf (Mg3N2) = .............................................. [3]

Radium chloride, RaCl 2, has a melting point of 900 °C and is soluble in water.

(i) Construct an equation for the reaction of Ra with H2O.

(iii) Suggest why these reactions occur at different rates.

(i) Explain what is meant by dynamic equilibrium.

(iii) Write an expression for Kp for the reaction described in equation 1.

(iv) At equilibrium the partial pressure of HI(g) is 86.4 kPa.

amount of HI(g) = .............................. mol [2]

∆H = .............................. kJ mol–1 [2]

(d) HCl (g) is prepared by adding NaCl (s) to concentrated H2SO4.

(ii) Identify the type of structural isomerism shown in (a)(i).

(b) Halothane is an anaesthetic.

(ii) Construct an equation to show the homolytic fission of halothane, CF3CHBrCl.

(i) Draw the monomer of X.

5 Fig. 5.1 shows three reactions of 2-bromopropane, CH3CH(Br)CH3.

(a) Complete Table 5.1 for each reaction, by:

● s tating the reagent and conditions used

Explain why 2-iodopropane reacts at a faster rate than 2-bromopropane.

(i) In step 1, 1-bromopropane reacts with CN– to form butanenitrile.

Construct an equation for the reaction in step 2.

(iii) Step 3 is a reduction reaction.

(iv) State the identity of a suitable reducing agent in step 3.

(b) Table 6.2 shows the percentage by mass of each element present in Z.

(c) Fig. 6.1 shows the mass spectrum of Z.

● an ionic bond

(c) NH4+ is a Brønsted–Lowry acid.

(i) Define Brønsted–Lowry acid.

(ii) When NH4+(aq) is heated with NaOH(aq), a pungent gas is produced.

Write an ionic equation for this reaction.

Sketch the shapes of a 2s and a 2px orbital on the axes in Fig. 1.1.

(i) Name the anion PO43–.

Calculate the number of molecules of water of crystallisation in struvite.