2018 Y6 CT1 Question Paper PDF

RAFFLES INSTITUTION
2018 YEAR 6 MARCH COMMON TEST
Higher 2
CHEMISTRY 9729
22 March 2018
2 hours 30 minutes
Additional Materials: Multiple Choice Answer (OMR) Sheet
Writing Paper
Data Booklet
READ THESE INSTRUCTIONS FIRST
Write your name, index number and civics tutorial group in the spaces provided on the OMR Sheet,
the cover sheet on page 9, and the writing paper used for Section C.
Do not use staples, paper clips, highlighters, glue or correction fluid.
This paper consists of three sections, A, B and C.
Section A (15 marks)

Answer this section first. The OMR Sheet will be collected after the first 30 minutes.
There are fifteen questions in this section. For each question there are four possible answers
A, B, C and D. Choose the one you consider correct and record your choice in soft pencil on the
OMR Sheet.
Read the instructions on the OMR Sheet very carefully.

Each correct answer will score one mark. A mark will not be deducted for a wrong answer.
Any rough working should be done in the question paper.
Section B (35 marks)

There are four questions in this section. Answers to this section are to be written in the spaces
provided in the question paper.
Section C (40 marks)

There are three questions in this section. Answers to this section are to be written on the writing
paper provided. You are to begin each question on a fresh sheet of paper.
Write in dark blue or black pen. You may use a pencil for any diagrams or graphs.
You are reminded of the need for good English and clear presentation in your answers.
At the end of document

This the examination, fasten your
is copyrighted, answers
please to reproduce
do not Section C it
securely
withouttogether. Answers to
permission
Sections A, B and C are to be handed in separately.
The number of marks is given in brackets [ ] at the end of each question or part question.
This document consists of 23 printed pages.

2
Section A (15 marks)
For each question, there are four possible answers, A, B, C, and D. Choose the one you consider
to be correct.
1 Which of the following pairs of substances, when mixed in equal volumes, does not produce
a buffer?
A 0.1 mol dm–3 NH3(aq) and 0.1 mol dm–3 NH4Cl(aq)

B 0.1 mol dm–3 K2CO3(aq) and 0.1 mol dm–3 H2SO4(aq)
C 0.1 mol dm–3 CH3CO2Na(aq) and 0.05 mol dm–3 HCl(aq)
D 0.1 mol dm–3 HO2C–CO2H(aq) and 0.05 mol dm–3 NaOH(aq)
2 Use of the Data Booklet is relevant to this question.
The ionic product of water at 50 °C is 5.48  10–14 mol2 dm–6.
Which of the following statements is correct?
A The concentration of H+ ions is lower at 50 °C than at 25 °C.

B The pH of water decreases with increasing temperature.
C The self-ionisation of water is an exothermic process.
D Water is acidic at 50 °C.
3 An excess of Ag2SO4(s) was shaken in Na2SO4(aq) of concentration X mol dm–3 and allowed
to reach equilibrium. The undissolved Ag2SO4(s) was filtered off and the concentration of
Ag+ in the solution was found to be Y mol dm–3.
Which expression gives the Ksp of Ag2SO4?
A (Y)² (X + ½Y) C (2Y)² (X + Y)

B (Y)² (½Y) D (Y)² (X)
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© Raffles Institution 2018 9729/M/18 [Turn Over

3
4 The numerical values of the Ksp of some salts at 298 K are given.
compound AgCl AgI Ag2CrO4 PbI2

Ksp 2.0  10–10 8.3  10–17 1.1  10–12 7.1  10–9
Which of the following statements are correct?
1 The solubility of AgI is 9.1  10–9 mol dm–3.

2 AgCl has a higher solubility than Ag2CrO4.
3 When equal volumes of 0.1 mol dm–3 KI and 1.0  10–6 mol dm–3 Pb(NO3)2
are mixed, a yellow precipitate of PbI2 will form.
A 1 only C 2 and 3 only

B 1 and 3 only D 1, 2 and 3
5 Caryophyllene is commonly found in clove oil and is used for acne treatment.
caryophyllene
What are the numbers of chiral centres and sp3 hybridised carbon atoms in caryophyllene?
number of chiral centres number of sp3 hybridised carbon atoms

A 2 8
B 2 11
C 3 8
D 3 11

4
6 Use of the Data Booklet is relevant to this question.
A non-cyclic organic compound commonly found in mushrooms has the following features.
• It contains carbon, hydrogen and oxygen atoms only.
• It reacts with hydrogen gas in a 1:1 ratio.
• It reacts with sodium metal in a 1:1 ratio.
• It has a relative molecular mass of 128.
• It does not contain C=O.
How many carbon atoms are there in one molecule of this compound?
A 5 C 7
B 6 D 8
7 -D-glucose has the following structure.
-D-glucose
Which of the following oxidation states are present in the carbon atoms of -D-glucose?
1 –1
2 0
3 +1

B 1 and 2 only D 1, 2 and 3

5
8 Which of the following alkanes will not be formed in the termination step when propane
undergoes monochlorination?
A C
B D
9 The Diels-Alder reaction can occur between a conjugated diene and an alkene as shown
below.
conjugated diene alkene
What is the product formed when the following compounds undergo the Diels-Alder
reaction?
A C
B D

6
10 Which of the following shows the correct intermediate when ethylbenzene undergoes
reaction in the dark with bromine in the presence of iron filings?
A C
B D
11 Which of the following hydrocarbons will liberate 2 moles of carbon dioxide when 1 mole of
the compound is treated with an excess of hot acidified potassium manganate(VII)?
A 1, 2 and 3 C 2 and 3 only

B 1 and 3 only D 2 only

7
12 Iodoethane can be made by warming chloroethane with sodium iodide dissolved in

propanone according to the equation below:
CH3CH2Cl + NaI ⇌ CH3CH2I + NaCl equilibrium 1
The table below shows properties of reactants or products in equilibrium 1.
property X=I X = Cl
bond energy of CX / kJ mol1 240 340
electronegativity of X 2.5 3.0
solubility of NaX in propanone / g per 100 g of solvent 39.9 4.2  105
melting point of NaX / oC 661 801
Which of the following explains why the reaction goes almost to completion?
A CH3CH2Cl is more polar than CH3CH2I.

B CCl bond is stronger than the CI bond.
C NaCl has a higher melting point than NaI.
D The concentration of Cl in propanone is much lower than that of I.
13 One mole of each of the following compounds was heated with excess NaOH(aq), and then
excess dilute HNO3(aq) and AgNO3(aq) were added.
Which compound will produce the largest mass of silver halide precipitate?
A C
B D

8
14 Which set of reagents and conditions can be used to distinguish between the two isomers
below?
1 hot acidified KMnO4

2 hot acidified K2Cr2O7
3 anhydrous PCl5

B 2 only D 1, 2 and 3
15 Eugenol can be used as a local antiseptic and anaesthetic.
eugenol
Which of the following statements about eugenol is correct?

You may assume that the –OCH3 group is chemically inert.
A Eugenol forms an ester when heated with ethanoic acid and concentrated H2SO4.
B 1 mol of eugenol reacts completely with 1.5 mol of Br2 in CCl4.
C There are two sp2 hybridised carbon atoms in eugenol.
D There are four lone pairs of electrons in eugenol.

9
RAFFLES INSTITUTION
2018 YEAR 6 MARCH COMMON TEST
Higher 2
CANDIDATE
NAME
CLASS INDEX NUMBER
CHEMISTRY 9729
22 March 2018
Section Marks
3B
0B A / 15
B1
2B / 10
B2 /6
B
1B
B3 /7
B4 / 12
4B
C1 / 15
C C2 / 11
C3 / 14
Total / 90
Overall / 100
This document isGrade
copyrighted, please do not reproduce it without permission

10
Section B (35 marks) For
examiner’s
This section consists of 4 questions. use
Answer all the questions in this section in the spaces provided.
1 There are few naturally occurring organic compounds that contain fluorine.
The South African plant Dichapetalum cymosum contains fluoroethanoic acid, FCH2CO2H,
and malonic acid, HO2CCH2CO2H. Data about these acids is given below.
Table 1.1
acid formula pKa1 pKa2

malonic HO2CCH2CO2H 2.85 5.70
fluoroethanoic FCH2CO2H 2.57 –
(a) (i) Define the term Brønsted-Lowry acid.
………………………………………………………………………………………. [1]
(ii) Write the equation for the ionisation of FCH2CO2H in water, and identify the
conjugate acid-base pairs that are present.
equation: …………………………..………………………………………………….
acid: …………………… conjugate base: …………..........
base: ………………….. conjugate acid: …………………

[2]
(iii) Calculate the pH of a 0.10 mol dm–3 solution of malonic acid (ignore the effect
of pKa2 on the pH).
[2]

11
(b) The pH–volume curve when 30 cm3 of 0.10 mol dm–3 NaOH is added to 10 cm3 of For
examiner’s
0.10 mol dm–3 malonic acid is shown below. use
pH
A
7
volume of NaOH
0 added / cm3
(i) Using your answer from (a)(iii) and the information provided in Table 1.1, label
various key points on the axes above. [2]
(ii) With the aid of an equation, explain why the pH at point A on the graph has a
value greater than 7.
……….……………………………………………………………………….…
…..……….……………………………………………………………………..
……….……..……….………………………………….………………………
………………………..……….………………………………………………..
…………………………….……..……….………………………………… [2]
(iii) Calculate the pH of a solution that contains 0.50 mol of HOOCCH2COO– and
0.20 mol of –OOCCH2COO– dissolved in 1.0 dm3 of water.
This document is copyrighted, please do not reproduce it without permission [1]
[Total: 10]

12
2 (a) Silver chloride has many applications, including its use as an antidote for mercury For
examiner’s
poisoning. Silver bromide is primarily used in the manufacture of photographic use
emulsions. Their solubility products, at 298 K, are given below.
compound AgCl AgBr

2
Ksp / mol dm –6
2.0  10 –10
4.1  10–13
An experiment on selective precipitation was carried out.

Solid silver nitrate was added gradually to a 1 dm3 solution containing 0.10 mol of
NaCl and 0.15 mol of NaBr until the first precipitate was seen.
(i) With relevant calculations, show that AgBr is the first precipitate to form.
[2]
Solid silver nitrate was added until AgCl just started to precipitate.
(ii) Determine the concentration of Br– in the solution.
[1]
(iii) Calculate the percentage of Br– precipitated out and hence comment on the
effectiveness of using silver nitrate to separate the halide ions.
[1]

13
(b) The solubility of silver chloride in aqueous solutions containing different For
examiner’s
concentrations of Cl– is based on the following equilibria: use
(I) AgCl(s) ⇌ Ag+(aq) + Cl–(aq) Ksp = 2.0  10–10 mol2 dm–6

(II) Ag+(aq) + 2Cl–(aq) ⇌ AgCl2–(aq) Kc = 1.8  105 mol–2 dm6
The graph of solubility of AgCl against concentration of Cl– is shown below.
solubility of AgCl
/ mol dm–3
0 concentration of Cl– / mol dm–3
Using the above information and Le Chatelier’s principle, explain how the solubility
of AgCl changes as the concentration of Cl– increases.
……….……………………………………………………………………………..…
…….…………………………………………………………………………….…….
.……….………………………………….……………………………………………
…..……….……………………………………………………………………………
.……..……….………………………………….………………………….……… [2]
[Total: 6]

14
3 An old bottle of methanoic acid solution was found in a laboratory. For
examiner’s
use
It is known that methanoic acid decomposes slowly according to the following equation.
HCO2H  CO + H2O
You are to design an experiment to determine the concentration of methanoic acid

remaining in the bottle using a titration method.
You may assume that the following are available:

• 150 cm3 of the partially decomposed solution from the bottle (FA1)
• 0.200 mol dm–3 NaOH (FA2)
• 250 cm3 graduated flask
• deionised water
• thymolphthalein and methyl orange indicators
• the equipment and materials normally found in a school or college laboratory
The solutions were tested and it was found that 20 drops of FA1 required 4 drops of FA2
for complete reaction. FA2 was too concentrated and required dilution.
(a) Write a plan for the volumetric analysis of FA1.
In your plan you should give:
details, including quantities, for the preparation of FA3 (diluted FA2);
the essential details of the titration procedure.
Present your plan as a sequence of numbered steps. FA1 is in the conical flask and
is titrated against FA3.
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...

………………………………………………………………………………………………...
………………………………………………………………………………………………...

15
For
examiner’s
………………………………………………………………………………………………... use
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………………………………………………………………………………………………...
………………………………………………………………………………………………...
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………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
………………………………………………………………………………………………...
……………………………………………………………………………………………...[5]
(b) The label on the bottle reads “0.1 mol dm–3 methanoic acid”.
Show how the experimental results may be used to determine the percentage
decomposition of methanoic acid in the sample. Assume that the average titre value
is 𝒙 cm3.

[2]
[Total: 7]

16
4 Alkenes are often used to manufacture polymers. The following table shows the data for For
examiner’s
various polymers. use
Table 4.1
name monomer polymer example of use

Teflon tetrafluoroethene −(CF2CF2)n− non-stick utensils
polychloroethene chloroethene −(CHClCH2)n− pipes, doors
food containers,
polypropene propene −(CH(CH3)CH2)n−
water bottles
cis-polybutadiene rubber tyres
buta-1,3-diene −(CH2CH=CHCH2)n−
trans-polybutadiene golf balls
conductive organic
polyacetylene ethyne −(CH=CH)n− polymer, electrical
capacitors
(a) The use of Teflon in non-stick utensils is related to the chemical inertness of the
carbon-fluoro polymer.
With reference to the Data Booklet, explain why Teflon is chemically inert as
compared to polychloroethene.
..…………………………………………………………………………………..….............
…………………..………………………………………………………………..….............
………..…………………………………………………………………………..….............
……..……………………………………………………………………………………….[2]
(b) (i) Explain why propene tends to undergo electrophilic addition reactions, but
polypropene does not.
…...………………………………………………………………………………..…..
…...………………………………………………………………………………..…..
…...………………………………………………………………………………..…..
…...………………………………………………………………………………..…..
…...………………………………………………………………………………..…..
…………...………………………………………………………………………....[2]

17
(ii) Give the skeletal formula of the major product, A, formed when propene For
examiner’s
undergoes electrophilic addition with hydrogen chloride. use
[1]
(iii) Describe the mechanism for the formation of A from propene and hydrogen
chloride. Show curly arrows, charges, dipoles and any relevant lone pairs.
[2]
(c) (i) Buta-1,3-diene undergoes electrophilic addition with gaseous hydrogen

chloride to form 1-chlorobut-2-ene.
The structure of the carbocation intermediate of the reaction is shown below.
Explain why this carbocation intermediate is stable.
………………………………………………………………………….…………..…
………………………………………………………………………….…………..…
………………………………………………………………………………….…..…
………………………………………………………………………..……...……..[1]

18
(ii) Buta-1,3-diene can be polymerised to form cis- and trans-polybutadiene. The For
examiner’s
structure of trans-polybutadiene is given below: use
Draw the skeletal structure of cis-polybutadiene.
[1]
(iii) By considering their structures in (c)(ii), explain why trans-polybutadiene is

harder than cis-polybutadiene.
……………..……………………………………………………………………..…...
…………………..………………………………………………………………..…...
………………………..…………………………………………………………….[1]
(iv) Polyacetylene has a silvery appearance and high electrical conductivity.
Polyacetylene and polybutadiene are polymers with C=C double bonds. With
reference to their structures in Table 4.1, explain why polyacetylene is an
electrical conductor but polybutadiene is an electrical insulator.
…………………………………..………………………………………………..…...
…………………………………..………………………………………………..…...
………………………………..…………………………………………………..…...
………………………………..…………………………………………………..…...
…………………………………………..………………………………………….[2]
[Total: 12]

19
Section C (40 marks)
Answer all questions in this section.
Write your answers on the writing paper provided.
Begin each question on a fresh sheet of paper.
1 (a) Aluminium chloride is used as a catalyst in electrophilic substitution reactions. The

reaction occurs in a few steps.
 The first step is the reaction between Cl2 and AlCl3.
Cl2 + AlCl3  Cl+ + AlCl4‾
 The benzene ring is then attacked by the Cl+ cation in the second step.
Explain how AlCl3 behaves as a Lewis acid in the first step. [1]
(b) The following reaction scheme shows the synthesis of 5-amino-2-chlorobenzoic acid.
(i) Suggest a structure for compound A. [1]
(ii) Suggest reagents and conditions for steps 1, 2 and 3. [3]
(iii) State the type of reaction in step 4. [1]

20
(c) Compound B can react with bromine under different conditions to give compounds C, D
and E.
Suggest structures for compounds C, D and E. [3]
(d) Compound F, C9H12O3, does not rotate plane-polarised light. No carbon atom in F has
more than one oxygen atom joined to it.
1 mol of F reacts with

 1 mol of sodium hydroxide.
 excess sodium to produce 1.5 mol of hydrogen.
 aqueous bromine in the dark to produce G, C9H11O3Br.
 hot excess concentrated sulfuric acid to produce only one product, H.
Deduce the structures of F, G and H. Explain your reasoning clearly. [6]
[Total: 15]

21
2 Propylene glycol is used as an antifreeze to de-ice aircraft in cold weather. When sprayed
onto ice, the antifreeze and water forms a solution with a lower melting point than ice. This
prevents the ice from refreezing.
propylene glycol
The table below contains data about propylene glycol and other hydroxy compounds.
compound pKa melting point / oC

butan-1-ol 16.1 –89.8
propylene glycol 14.9 –59.0
phenol 10.0 40.5
(a) (i) Account for the much higher melting point of propylene glycol as compared to
butan-1-ol. [2]
(ii) Suggest why propylene glycol is more suitable for use as an antifreeze than
butan-1-ol. [1]
(b) (i) Explain why the pKa of phenol is much smaller than that of butan-1-ol. [2]
(ii) The following equation shows the dissociation of propylene glycol.
CH3CH(OH)CH2OH ⇌ CH3CH(OH)CH2O– + H+
With reference to the structure of the conjugate base, draw a suitable diagram
and use it to explain why the pKa of propylene glycol is much lower than that of
butan-1-ol. [2]
(c) (i) Propylene glycol can be produced from propene in a single step. State the
reagents and conditions for this conversion. [1]
(ii) Using the [O] notation, write a chemical equation for the reaction in (c)(i). [1]
(d) Suggest a simple chemical test to distinguish between butan-1-ol and propylene glycol.
[2]
[Total: 11]

22
3 (a) (i) Outline how chloroalkanes, RCl, are made from alcohols in the laboratory. [1]
(ii) Compare the reactivities of chlorocyclohexane and chlorobenzene with hot

aqueous NaOH. Explain your answer. [2]
(b) Suggest the structural formula for each of the compounds J to M in the following
schemes:
(i)
[1]
(ii)
[3]
(c) An epoxide is a cyclic ether with a 3-membered ring, exemplified by compound P as

shown below.
Like halogenoalkanes, it undergoes nucleophilic substitution reactions when reacted

with nucleophiles such as methoxide ions, CH3O–.
(i) Explain what is meant by the term nucleophile. [1]
The following reaction occurs when P is heated with sodium methoxide dissolved in
methanol:
The mechanism of Reaction I involves the following two steps:
Step 1: CH3O– donates an electron pair to Cx with a simultaneous breaking of the

This document
Cx–Oz is copyrighted,
bond to form anplease do notwith
intermediate reproduce it without
a negative charge permission
on Oz.
Step 2: Donation of an electron pair from Oz to CH3OH to form product Q and CH3O–.

23
(ii) Suggest why CH3O donates the electron pair to Cx rather than Cy in Step 1. [1]
(iii) Use the information above to draw out the mechanism for Reaction I. Show
clearly any intermediates that may be formed, relevant lone pairs and dipoles,
and use curly arrows to indicate the movement of electron pairs. [2]
(iv) Step 1 is the rate-determining step of the reaction.
Sketch a labelled energy profile diagram for Reaction I. [2]
(v) When P is heated in methanol acidified with H2SO4, the following reaction occurs.
The mechanism of Reaction II involves the heterolytic fission of the Cy–Oz bond
to form a carbocation intermediate with the positive charge on Cy.
Explain why the Cy–Oz bond breaks rather than the Cx–Oz bond. [1]
[Total: 14]
– END OF PAPER –

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RAFFLES INSTITUTION

2018 YEAR 6 MARCH COMMON TEST

READ THESE INSTRUCTIONS FIRST

Do not use staples, paper clips, highlighters, glue or correction fluid.

This paper consists of three sections, A, B and C.

Section A (15 marks)

Read the instructions on the OMR Sheet very carefully.

Section B (35 marks)

Section C (40 marks)

At the end of document

This document consists of 23 printed pages.

A 0.1 mol dm–3 NH3(aq) and 0.1 mol dm–3 NH4Cl(aq)

2 Use of the Data Booklet is relevant to this question.

The ionic product of water at 50 °C is 5.48  10–14 mol2 dm–6.

Which of the following statements is correct?

A The concentration of H+ ions is lower at 50 °C than at 25 °C.

Which expression gives the Ksp of Ag2SO4?

A (Y)² (X + ½Y) C (2Y)² (X + Y)

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

compound AgCl AgI Ag2CrO4 PbI2

Which of the following statements are correct?

1 The solubility of AgI is 9.1  10–9 mol dm–3.

A 1 only C 2 and 3 only

number of chiral centres number of sp3 hybridised carbon atoms

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

6 Use of the Data Booklet is relevant to this question.

7 -D-glucose has the following structure.

A 2 only C 1 and 3 only

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© Raffles Institution 2018 9729/M/18 [Turn Over

conjugated diene alkene

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

A 1, 2 and 3 C 2 and 3 only

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12 Iodoethane can be made by warming chloroethane with sodium iodide dissolved in

CH3CH2Cl + NaI ⇌ CH3CH2I + NaCl equilibrium 1

The table below shows properties of reactants or products in equilibrium 1.

A CH3CH2Cl is more polar than CH3CH2I.

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

1 hot acidified KMnO4

A 1 only C 2 and 3 only

15 Eugenol can be used as a local antiseptic and anaesthetic.

Which of the following statements about eugenol is correct?

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

CLASS INDEX NUMBER

© Raffles Institution 2018 9729/M/18 [Turn Over

Answer all the questions in this section in the spaces provided.

acid formula pKa1 pKa2

(a) (i) Define the term Brønsted-Lowry acid.

acid: …………………… conjugate base: …………..........

base: ………………….. conjugate acid: …………………

This document is copyrighted, please do not reproduce it without permission

© Raffles Institution 2018 9729/M/18 [Turn Over

This document is copyrighted, please do not reproduce it without permission [1]

© Raffles Institution 2018 9729/M/18 [Turn Over

compound AgCl AgBr

An experiment on selective precipitation was carried out.