Cambridge International Examinations

Cambridge International Advanced Subsidiary and Advanced Level

*8488148240*

CHEMISTRY (11 A / B / C ) 9701

AS Level Structured Questions Wednesday, 28 August 2019

45 minutes
Candidates answer on the Question Paper.
Additional Materials: A Periodic Table

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.

Knowledge with understanding (1-10 + 1-5*) :

Handling, applying and evaluating information (11-13 + 6-9*) :
Critical Thinking (14-15 + 10-11*) :

This document consists of 9 printed pages with a periodic table

IB17 03_9701_42/6RP
© UCLES 2019 [Turn over
For each question there are four possible answers, A, B, C, and D. Choose the one you consider to
be correct. Use of the periodic table may be appropriate for some questions.

1 A slow stream of water from a tap can be deflected by an electrostatically charged plastic rod
because water is a polar molecule.

Why is a water molecule polar?

A Molecules are bonded together by hydrogen bonds.
B The oxygen and hydrogen atoms have different electronegativities.
C The oxygen atom has two lone pairs of electrons.
D Water is able to dissociate into ions.

2 The ability of an atom in a covalent bond to attract electrons to itself is called its electronegativity.
The greater the difference between the electronegativities of the two atoms in the bond, the more
polar is the bond.
Which pair will form the most polar covalent bond between the atoms?
A chlorine and bromine
B chlorine and iodine
C fluorine and chlorine
D fluorine and iodine
3 Which substance in a vehicle exhaust results from incomplete combustion of a hydrocarbon fuel?
A CO
B H2O
C N2
D NO

4 A compound X has all of the following properties:

it is a liquid at room temperature and atmospheric pressure;
it does not mix with water;
it does not react with HCl even at higher temperature,
it does not react with NaOH,
It is a relatively unreactive organic compound

What could X be?

A hexane
 B ethanoic acid
C ethanol
D methanal
5 Many reactions take place in the engine and catalytic converter of a car.
Which pair of substances is produced both by the reactions in a car engine and in a catalytic
converter?
A carbon dioxide and unburnt hydrocarbons
B carbon dioxide and water
C carbon monoxide and nitrogen
D carbon monoxide and unburnt hydrocarbons

6 The Russian composer Borodin was also a research chemist who discovered a reaction in which
two ethanal molecules combine to form a compound commonly known as aldol (reaction I). Aldol
forms another compound on heating (reaction II).

Which of the following best describes reactions I and II?

7 Which pollutant is formed in the internal combustion engine and, if not removed by the catalytic
converter, may become involved in the formation of acid rain?
AC B C8H18 C CO D NO
8 Methane, CH4 , and ethane, CH3CH3, have the same homologous series.
Their boiling points are given.
Methan -161.5 oC
e
Ethane -89 oC

What is responsible for this difference in boiling points?

A CH4 has a larger Mr than CH3CH3.
B CH3CH3 has a permanent dipole, CH4 does not.
C CH3CH3 has a strong C–C bond, CH4 does not.
D CH3CH3 has stronger van der waals forces than CH4
9 The complete combustion of alkanes to produce carbon dioxide and water is an important
exothermic reaction. Which line on the graph shows the relationship between the number of
carbon atoms in the alkane and the number of moles of oxygen gas needed for complete
combustion of the alkane?

10 Chlorofluoroalkanes, commonly known as CFCs, undergo homolytic fission by ultraviolet

irradiation in the stratosphere. The table of bond energies in polyatomic molecules (these are average
values) are given.

Which radical could result from this irradiation of CHFClCF2Cl?

11 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution. In a propagation step the free radical X• is formed.
 How many different forms of X• are possible?
A1 B2 C3 D4

12 3-methylbut-1-ene can undergo different types of reaction.

Which row correctly identifies the reaction types?

13 Which compounds decolourise bromine water?

14 A molecule of geraniol is shown.

What is formed when geraniol is reacted with an excess of cold, dilute, acidified manganate(VII)
ions?
15 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to
provide heat for power stations.
Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated?
A It destroys the ozone layer.
B It does not burn easily.
C It is easily biodegradable.
D Its combustion products are harmful.
16 Which product can be made from bromoethane by a free radical substitution of bromine?
A ethanol
B 1,2-dibromoethane
C bromomethane
D ethane

17 Propene, bromine and hydrogen bromide are mixed in the dark. A number of products are
formed, some in very small quantities. Which substance will not be present in the mixture of
products?
A 1-bromopropane
B 2-bromopropane
C 1,1-dibromopropane
D 1,2-dibromopropane

18 Bromine reacts with ethene in an addition reaction.

Which statements about this reaction are correct?

1 It is the basis of a test for unsaturation in alkenes.

2 It leads to an increase in each of the H–C–H bond angles.
3 A nucleophile attacks the C=C bond in ethene.
19 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does
not allow gases to pass through. It is used as cling wrapping.
Which sequence appears in a short length of the polymer chain?

20 Which reactions are examples of nucleophilic substitution?

21 In which reactions are occurred inside a catalytic converter?

22 Limonene is an oil formed in the peel of citrus fruits.

Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room
temperature in the dark?

23 Which environmental problem is not made worse by the release of oxides of nitrogen from car
engines?
A acidification of lakes
 B corrosion of buildings
C photochemical smog
D the hole in the ozone layer

24 Textiles for use in aircraft are treated with a finish containing a halogenoalkane.
What is the reason for this?

1 The textile burns less easily, improving safety.

2 The fabric forms hydrogen bonds to water more readily, making the fabric easier to wash.

3 The halogenoalkane undergoes addition polymerisation, stiffening the fabric.

25 Swimming pool water can be kept free of harmful bacteria by adding aqueous sodium chlorate(I),
NaOCl. This reacts with water to produce HOCl molecules which kill bacteria.

In bright sunshine, the OCl– ion is broken down by ultra-violet light.

What are the types of bond breaking in those two reactions respectively?
A Both are homolytic fission
B Both are heterolytic fission
C The first is homolytic fission, while the second is heterolytic fission
D The first is heterolytic fission, while the second is homolytic fission

26 In which species is an electrophile?

27 At 550 °C nitrogen dioxide reacts with unburnt hydrocarbon fragments such as CH3 in the
catalytic converter of a motor vehicle.

Which row gives the right enabling factors for this reaction to happen?

A At 550°C, methyl radical is produced

B The catalyst Ni lowers the Activation Energy
C The nitrogen dioxide is acidic
D The products have stronger bond energy than the bond
energy in the reactant.

28 Some polluting gases are removed from car exhaust fumes using a catalytic converter.
 Platinum or palladium can be used as the catalyst. The reactions are faster when platinum is the
catalyst than they are when palladium is the catalyst.
Which statements are correct?
1 Platinum acts as a heterogeneous catalyst in these reactions.
2 The palladium-catalysed reactions have higher activation energies than the
platinum-catalysed reactions.
3 The platinum-catalysed reactions are more spontaneous than the palladium-catalysed
reactions.
29 The diagrams show a compound.

How many chiral carbons are produced when this compound react with a bromine molecule
(Br2) via electrophilic addition?
A0
B1
C2
D3
30 What is the structural formula of the major product when hydrogen bromide reacts with
2-methylbut-2-ene?

31 A carbon chain is called an alkyl group –R. What do you call a CH3CH2- group?
A Propyl
B Butyl
C Ethyl
D Methyl
32 How many total carbon atoms in a molecule of pentan-2-ol?
A5
B6
C7
D8
33 What is the tetrahedral bond angle of H-C-H in CH3Cl?
A 1200
B 1800
C 109.50
D 1070
34 What do you call the two or more compounds with the same molecular formula but have
different structures?
A Isomers
B Isotopes
C Isoelectronic
D Isobars
35 How many hydrogen atoms are presented in the following skeletal formula of a cycloalkane?

A 3 B 4 C 5 D 6
36 How many total sigma bonds are present in a molecule of propanone, CH3COCH3?
A 7 B 8 C 9 D 10
37 The diagram shows a molecule that has σ bonds and π bonds. A π bond is composed of two
electrons.

How many π electrons are present in this molecule?

A3 B4 C5 D6

38 Which of the following is NOT a correct condensed structural formula of a compound?

A C(CH3)4 B CH3(OH)CH3(OH) C CH2Cl2 D CH3CH(CH3)CH3
39 Hybridization is the idea that atomic orbitals fuse to form newly hybridized orbitals, which in turn,
influences molecular geometry and bonding properties. Here is an example of an alkene
molecule.

What are the hybridizations of the carbons (labeled 1 and 2) in the respective structure?
A sp2 and sp
B sp2 and sp3
C both are sp2
D sp and sp3
40 Fructose is a sugar with more than one chiral centre. The fructose molecule is shown with X, Y
and Z indicating three carbon atoms.
 Which carbon atoms are chiral centres?
A X, Y and Z B X and Y only C X only D Y only
41 Which of the following statements is NOT true of propene, CH3CH=CH2?
A All carbon atoms are planar
B The empirical formula is CH2
C It can be either cis or trans
D It contains a phi bond

42 A σ bond is made between a carbon and a hydrogen atom in a molecule of ethane, CH3CH3.
Which diagram shows the orbital overlap that occurs to form this bond?
The outer shells of H is 1s1 and C is 2s2 2p2

43 Which row correctly contains a primary, a secondary and a tertiary alcohol?

primary secondary tertiary

CH2OH CH2OH CH2OH

A CH2 CHOH CHOH

CH3 CH3 CH2OH

CH2OH CH3 CH3

 B CH3 C H CH3 C OH CH3 C H

CH3 CH3 CH2OH

CH2OH CH2OH CH2OH

C CH3 C H CH3 C CH2OH CH3 C CH2OH

H H CH2OH

H CH3 CH3

D CH3 C OH CH3 C OH CH3 C OH

H H CH3

44 Which pair of alcohols are isomers of each other?

A butan-1-ol and 2,2-dimethylpropan-1-ol
B butan-2-ol and 2-methylpropan-2-ol
C pentan-1-ol and 2-methylpropan-2-ol
D propan-2-ol and 2-methylpropan-2-ol

[turn over]

45 When octane is subjected to catalytic cracking, which compounds can be obtained?

46 A new jet fuel has been produced that is a mixture of different structural isomers of compound Q.

Which skeletal formula represents a chain structural isomer of Q?

 [turn over]

Answer all the questions in the spaces provided.

1 The process of cracking produces useful substances from oil. Explain why cracking is useful.

....................................................................................................................................................... [1]
2 Explain the main difference in the products of thermal and catalytical cracking of a long chain
hydrocarbon
 ....................................................................................................................................................... [2]
3 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.

....................................................................................................................................................... [3]
4 Explain the main differences in the product of thermal and catalytical cracking

5 Explain the alkane is unreactive

.................................................................................................................................................... [1]
6 During the first stage in the substitution reaction chlorine forms chlorine free radicals.
Explain what is meant by the term free radical.

........................................................................................................................................ [1]
7 Explain the term homolytic bond breaking

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

........................................................................................................................................ [2]
8 Name the stage of the reaction mechanism which occurs when a methane molecule reacts
with a chlorine free radical.

........................................................................................................................................ [1]
9 Complete the equation for the reaction which occurs when a methane molecule reacts
with a chlorine free radical.

10 Write one equation to show how both carbon monoxide, CO, and nitrogen dioxide, NO 2,
are removed from the exhaust.

........................................................................................................................................ [1]
11 State the environmental consequence of allowing unburnt hydrocarbons to enter the
atmosphere.

........................................................................................................................................ [1]
12 Describe how NO2 is also produced inside the car engine.

..............................................................................................................................................
........................................................................................................................................ [2]
13 State one natural cause of NO2 being formed in the atmosphere.

........................................................................................................................................ [1]
14 Complete the table to give details of the mechanism

15 Complete the mechanism to show the reaction of methylpropene with HBr to form the
major product. Include the structure of the intermediate and all necessary charges, dipoles, lone
pairs and curly arrows. The structure of 2-bromo-2-methylpropane is not required.

16 Nitrosyl chloride, NOCl, is a reactive gas that is sometimes formed when NO reacts with Cl2.

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.
17 A case study
Analyze these two proposed mechanisms of ethanal, CH3CHO, with hydrogen cyanide, HCN, in
the presence of ethanolic solution of NaCN. The CN- works as a catalyst. The optimum
temperature of the reaction is 10 oC.
Which do you think is the correct mechanism?
Write your supporting arguments based on the concepts of bond fission, dipole, and bond energy.
A

……………………………………………………………………………………………………………[2]
18 Categorize the following chemical reactions based on their types.
The types of reaction available are substitution, elimination, redox, and addition.
One has been answered as an example.
CH3CH3 + Cl2  CH3CH2Cl + HCl …………..
CH2=CH2 + Br2  CH2BrCH2Br …………..
CH3CHO + [O]  CH3COOH Redox
CH3CH2Cl  CH2=CH2 + HCl …………..
[1]
19 State the number of primary, secondary, and quaternary carbon atoms in the given structure:

Primary Carbons ………………….

Secondary Carbons …………………..
Tertiary Carbons ………0……….
Quaternary Carbons ………………….
[3]

20 Omega-3 fatty acids are found in foods, such as fish and flaxseed, and in dietary supplements,
such as fish oil. Consuming linoleic acid as one of the omega-3 fatty acid is proven to prevent
heart attacks or strokes or any vascular disease outcomes. Omega-3 fatty acids are characterized
by the presence of a double bond three atoms away from the terminal (ending) methyl group
in their chemical structure. The structure is given.

How many total geometrical isomers of this omega-3 fatty acid can be possible (including the
structure given)?

…............................................................................................................................................... [1]
21 A cycloalkane has a restricted rotation on the C-C bonds, due to a bond angle strain in a ring.
This allows a cis or trans position in a dichlorocyclopropane. A structure of cis-1,2-
dichlorocyclopropane is given as an example. You are to draw the other dichlorocyclopropanes
that are trans and a structure neither cis nor trans.

trans-1,2-dichloropropane neither cis nor trans

[2]
22 Vitamin C, also known as ascorbic acid and l-ascorbic acid, is a vitamin found in various foods
and sold as a dietary supplement. Vitamin C is an essential nutrient involved in the repair of tissue
and the enzymatic production of certain neurotransmitters. It also functions as an antioxidant.

Give asterisk symbols ( * ) for the chiral carbons in the ascorbic acid.

[2]
[turn over]

23 Alanine is a small non-essential amino acid in humans. Alanine is one of the most widely used for
protein construction and is involved in the metabolism. Alanine is an important source of energy
for muscles and central nervous system, strengthens the immune system, helps in the metabolism
of sugars and organic acids.

The 2D displayed structure of alanine is given.

 The second carbon in the middle of the structure is a chiral carbon. Draw a pair of optical
isomers of alanine using 3D structure showing its dotted and bold lines.

[1]
24 Cis-platin is a well-known chemotherapeutic drug. It has been used for treatment of numerous
human cancers including bladder, head and neck, lung, ovarian, and testicular cancers. It is
effective against various types of cancers, including carcinomas, germ cell tumors, lymphomas,
and sarcomas. Its mode of action has been linked to its ability to crosslink with the purine bases
on the DNA; interfering with DNA repair mechanisms, causing DNA damage, and subsequently
inducing apoptosis in cancer cells. It is a square planar molecule.

This structure below is a trans-platin.

Draw the structure of cis-platin

….............................................................................................................................................. [1]
[turn over]

25 A polymer is a large molecule, or macromolecule, composed of many repeated subunits.

Polybutadiene is a polymer behind automobile tyres. Two structures of polybutadiene are given
here.

What is the relationship of these two structures?

..............................................................................................................................................[1]
 [end]
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