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Pearson Edexcel International Advanced Level

Time 1 hour 30 minutes
Paper
reference WCH11/01
Chemistry
 

International Advanced Subsidiary/Advanced Level

UNIT 1: Structure, Bonding and Introduction to
Organic Chemistry
You must have: Total Marks
Scientific calculator, ruler

Instructions
• Use black ink or ball‑point pen.
• centrethe
Fill in boxes at the top of this page with your name,
number and candidate number.
• Answer all questions.
• Answer the questions in the spaces provided
– there may be more space than you need.

Information
• The total mark for this paper is 80.
• The marks for each question are shown in brackets
– use this as a guide as to how much time to spend on each question.
• You will be assessed on your ability to organise and present information, ideas,
descriptions and arguments clearly and logically, including your use of grammar,
punctuation and spelling.
• A Periodic Table is printed on the back cover of this paper.

Advice
• Read each question carefully before you start to answer it.
• Show all your working in calculations and include units where appropriate.
• Try to answer every question.
• Check your answers if you have time at the end.
Turn over

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SECTION A

Answer ALL the questions in this section.

You should aim to spend no more than 20 minutes on this section.

For each question, select one answer from A to D and put a cross in the box . If you change
your mind, put a line through the box and then mark your new answer with a cross .

1 Which mixture results in a displacement reaction?

A iron and copper(II) sulfate solution

B lead(II) nitrate solution and sodium iodide solution

C dilute hydrochloric acid and sodium hydroxide solution

D zinc and magnesium sulfate solution

(Total for Question 1 = 1 mark)

2 Which mixture results in a precipitation reaction?

A dilute sulfuric acid and potassium hydroxide solution

B iron and calcium chloride solution

C chlorine water and potassium bromide solution

D silver nitrate solution and potassium bromide solution

(Total for Question 2 = 1 mark)

3 An atom of 157 N forms a nitride ion, N3–.

What are the numbers of protons, neutrons and electrons in this ion?

Protons Neutrons Electrons

A 7 8 7

B 7 8 4

C 7 8 10

D 8 7 10

(Total for Question 3 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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4 What is the total number of orbitals in a sulfur atom which contain at least
one electron?

A 3

B 5

C 8

D 9

(Total for Question 4 = 1 mark)

5 Which structure has the name E‑2‑bromo‑3‑chloropent‑2‑ene?

Br

Cl

Br

B Cl

Cl

Br

Br

Cl
(Total for Question 5 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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6 The partial oxidation of butane in the presence of a catalyst has been investigated as
a possible source of hydrogen.

C4H10(g) + 2O2(g) → 4CO(g) + 5H2(g)

(a) What is the most significant hazard associated with the pollutant CO(g)?
(1)
A it is a major contributor to the formation of acid rain

B it strongly absorbs infrared radiation

C it is toxic at low concentrations

D it is the main cause of ozone layer depletion

(b) A mixture of 40 cm3 of butane and 20 cm3 of oxygen reacts in a sealed system to
form carbon monoxide and hydrogen.
What is the total volume of gas in the system at the end of the reaction, in cm3 ?
(1)
A 30
B 60

C 90

D 120

(Total for Question 6 = 2 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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7 Octane, C8H18 , reacts with bromine in the presence of ultraviolet radiation.

(a) What is the role of ultraviolet radiation in the reaction?

(1)
A to break the Br Br bond only

B to break a C H bond only

C to break a C C bond only

D to break both the Br Br and a C H bond

(b) One of the steps of the reaction is shown.

C8H17• + Br2 → C8H17Br + Br •

What is the name of this step and the type of bond breaking that takes place in
the bromine molecule?

(1)
Name of step Type of bond breaking
A initiation heterolytic
B initiation homolytic
C propagation heterolytic
D propagation homolytic

(c) What is the overall equation for the reaction of octane with bromine?
(1)
A C8H18 + Br2 → C8H16Br2 + H2

B C8H18 + Br2 → C8H17Br + HBr

C C8H18 + Br2 → 2C4H9Br

D C8H18 + 3Br2 → 2C4H7Br + 4HBr

(Total for Question 7 = 3 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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8 A stream of liquid from a burette is deflected by a charged rod.

burette

charged rod
+++++++

beaker

Which substance, in its liquid state, will be deflected the most?

A C5H12

B CCl 4

C BCl 3

D CH2Cl 2

(Total for Question 8 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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9 A piece of copper is shown.

4 cm

8 cm

12 cm

How many moles of copper atoms are there in this piece of copper?
[Density of copper = 8.96 g cm–3 ]

A 0.675

B 1.48

C 6.05

D 54.2

(Total for Question 9 = 1 mark)

Use this space for any rough working. Anything you write in this space will gain no credit.

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10 Mass spectrometers are used in chemical analysis.

(a) In which region of this mass spectrometer are the ions accelerated?
(1)

P Q electromagnet

vaporised
sample to vacuum
pump

S
amplifier
chart
recorder

A region P

B region Q

C region R

D region S

(b) Four iron ions are present in a stream of ions in a mass spectrometer.
The paths of these ions are shown.

path 4

stream of
ions

path 3

path 1
path 2

Which of these ions will follow path 1 through the mass spectrometer?
(1)
54 +
A Fe
54
B Fe2+
56
C Fe+
56
D Fe2+

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(c) Naturally‑occurring chlorine has two isotopes, 35Cl and 37Cl.

How many peaks due to the singly-charged molecular ions are seen in the
mass spectrum of chlorine, Cl 2?
(1)
A 1

B 2

C 3

D 4

(Total for Question 10 = 3 marks)

Use this space for any rough working. Anything you write in this space will gain no credit.

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11 The graph shows the first ionisation energies of some consecutive elements from
Periods 2 and 3 of the Periodic Table.
The letters used to label the elements are not their chemical symbols.

W
First U
ionisation
T
energy V
S
Z

Atomic number

(a) Which element has only one p orbital containing a pair of electrons?
(1)
A element U

B element V

C element W

D element X

(b) Which element is the least reactive?

(1)
A element S

B element X

C element Y

D element Z

(c) Which element has the greatest second ionisation energy?

(1)
A element S

B element T

C element X

D element Y

(Total for Question 11 = 3 marks)

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12 A mass of 4.08 g of hydrated copper(II) sulfate, CuSO4∙5H2O, was dissolved in

deionised water to form 250 cm3 of solution.

What is the concentration of the copper(II) sulfate solution formed, in mol dm–3?

A 0.0163

B 0.0256

C 0.0654

D 0.102

(Total for Question 12 = 1 mark)

13 A mass of 2.50 g of sodium chloride reacts with excess lead(II) nitrate solution forming
lead(II) chloride with a yield of 95 %.
What is the mass of lead(II) chloride, PbCl 2 , formed?

2NaCl + Pb(NO3)2 → PbCl 2 + 2NaNO3

[Mr values:   NaCl = 58.5   PbCl 2 = 278.2]

A 5.65 g

B 5.94 g

C 11.3 g

D 11.9 g

(Total for Question 13 = 1 mark)

TOTAL FOR SECTION A = 20 MARKS

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SECTION B

Answer ALL the questions. Write your answers in the spaces provided.

14 This question is about barium and barium compounds.

(a) The graph shows the first eight ionisation energies of barium.

12 000

10 000

Ionisation 8 000
energy
6 000
/ kJ mol–1
4 000

2 000

0
0 2 4 6 8 10
Electron removed

(i) Write an equation, including state symbols, for the third ionisation energy
of barium.
(1)

(ii) State how the graph confirms that barium is in Group 2 in the Periodic Table.
(1)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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(b) An acidified aqueous solution of barium chloride, BaCl2 , is used to test for
sulfate ions.
(i) Draw a dot‑and‑cross diagram for barium chloride.
Show the outer electrons only.
(2)

(ii) Calculate the mass of barium chloride needed to form 150 cm3 of BaCl2(aq)
with a concentration of 0.200 mol dm–3.
Give your answer to an appropriate number of significant figures.
(2)

(iii) The barium chloride solution is acidified to prevent carbonate ions giving a
false positive result.
Write the ionic equation for the reaction of hydrochloric acid with
carbonate ions. State symbols are not required.
(1)

(c) Give a reason why solid barium chloride does not conduct electricity.
(1)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(Total for Question 14 = 8 marks)

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15 This question is about hydrocarbons obtained from crude oil.

(a) Petrol used in cars has a high proportion of the alkane iso‑octane.
Iso‑octane can be formed by heating octane to 400 °C in the presence of
a catalyst.

octane iso‑octane

(i) Give the IUPAC name for iso‑octane.

(1)

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(ii) Name the industrial process used to convert octane into iso‑octane.
(1)

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(iii) Give a reason why petrol needs a high proportion of iso‑octane.

(1)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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(b) Another way to produce iso‑octane is by reacting iso‑butane

with 2‑methylpropene.

iso‑butane 2‑methylpropene iso‑octane

Draw the skeletal formulae of four isomers of 2‑methylpropene.

Include only one isomer that does not decolorise bromine water.
(4)

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(c) 2‑methylpropene reacts with hydrogen bromide to form two possible products.
(i) Draw the mechanism for the formation of the major product of the reaction
between 2‑methylpropene and hydrogen bromide, HBr.
Include curly arrows, and relevant lone pairs and dipoles.
(4)

(ii) Give the reason why your product in (c)(i) is the major product.
(1)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(d) Another component of petrol, compound X, contains 92.3 % carbon and

7.7 % hydrogen by mass.
(i) Calculate the empirical formula of compound X.
You must show all your working.
(2)

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(ii) A sample of compound X has a mass of 0.267 g and vaporises at 85.0 °C and
104 kPa to produce a gaseous sample with a volume of 98.0 cm3.
Calculate the molar mass of compound X.
You must show all your working.
[ pV = nRT    R = 8.31 J mol–1 K–1]
(4)

(iii) Deduce the molecular formula of compound X, using your answers to (d)(i)
and (d)(ii).
(1)

(Total for Question 15 = 19 marks)

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16 This question is about the Group 4 element germanium and some of its compounds.
(a) Naturally‑occurring germanium consists of five stable isotopes.
Explain what is meant by the term isotopes.
(2)

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................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(b) The mass spectrum of a sample of germanium is shown.

40 36.7

30 27.4
Percentage 20.6
abundance 20

10 7.7 7.6

0
70 71 72 73 74 75 76 77
m/z

Calculate the relative atomic mass of this sample of germanium.

(2)

(c) Give the electronic configuration of a germanium atom.

(1)

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(d) Germane is a compound with the formula GeH4 .

It can be formed by the reaction shown.

Na2GeO3 + NaBH4 + H2O → GeH4 + 2NaOH + NaBO2

(i) Calculate the atom economy, by mass, for the formation of germane.
Use Ar of Ge = 72.6
(2)

(ii) Germane can donate a proton to ammonia, forming the ion GeH3–.

NH3 + GeH4 → NH4+ + GeH3–

Draw a dot‑and‑cross diagram of the ion GeH3–. Show the outer electrons only.
(2)

(iii) Use your answer to (d)(ii) and electron‑pair repulsion theory to predict the
name of the shape and bond angle of the ion GeH3–.
(2)
Name of the shape

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Bond angle

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(iv) Germane is toxic and the maximum permitted concentration is

0.640 mg m–3 in air.
Calculate the maximum number of germane molecules permitted in a
laboratory with a volume of 231 m3.
[Avogadro constant (L) = 6.02 × 1023 mol–1]
(4)

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(e) A halide of germanium, GeX4 , reacts with water as shown.

GeX4 + 2H2O → GeO2 + 4HX

1.50 g of GeX4 was added to excess water.

The insoluble GeO2 was removed by filtration.
The solution of hydrogen halide formed was then added to
excess magnesium carbonate, forming 335.5 cm3 of carbon dioxide
at room temperature and pressure (r.t.p.).

MgCO3 + 2HX → MgX2 + CO2 + H2O

[Molar volume of a gas at r.t.p. = 24 000 cm3 mol–1]

(i) Calculate the number of moles of carbon dioxide formed.

(1)

(ii) Deduce the number of moles of HX formed when GeX4 reacted with the
excess water.
(1)

(iii) Deduce the number of moles of GeX4 that reacted with the excess water.
(1)

(iv) Calculate the molar mass of GeX4 and hence identify X.

(2)

(Total for Question 16 = 20 marks)

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17 Limonene is an oil extracted from the skin of citrus fruits such as oranges or lemons.
It is found in some cleaning products such as those used to remove chewing gum.
Limonene has the structure shown.

(a) Deduce the molecular formula of limonene.

(2)

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(b) (i) A few drops of acidified potassium manganate(VII) solution are mixed with a
sample of limonene.
State the colour change.
(1)
From . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ................................... to ................................................................................................ . . .

(ii) Draw the skeletal formula of the structure of the organic

product formed when the reaction in (b)(i) is carried out with
excess acidified potassium manganate(VII).
(1)

(iii) Name the type of reaction that limonene undergoes in (b)(i).

.(1)

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(c) On heating, limonene reacts to form two molecules of a smaller hydrocarbon, Q.

Q can be polymerised to form R, a polymer used to improve the grip of car tyres.
A section of R is shown.

H3C CH2 H3C CH2

 H C H C


 
 C C C C 
 
 
 H H H H

Section of polymer R

Draw the structure of Q.

(1)

(d) Give two ways in which chemists can help minimise problems caused by the
disposal of polymers.
(2)

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(e) Limonene is extracted from orange peel using a solvent.

Possible solvents are hexane and liquid carbon dioxide.
Liquid carbon dioxide can be obtained by allowing solid carbon dioxide to melt
under high pressure.
(i) Suggest one advantage and one disadvantage of using liquid carbon dioxide
rather than hexane to dissolve the limonene. Assume that the carbon dioxide
does not escape into the atmosphere.
(2)
Advantage

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Disadvantage

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ............................................................................................................................................ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

(ii) Orange peel contains 1.63 % of limonene by mass.

A chewing gum remover contains 30 cm3 of limonene per bottle.
Calculate the mass of orange peel, in kg, needed to obtain 30 cm3 of limonene.
[Density of limonene = 0.841 g cm–3]
(3)

(Total for Question 17 = 13 marks)

TOTAL FOR SECTION B = 60 MARKS

TOTAL FOR PAPER = 80 MARKS

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