2020 Y6 Timed Practice Question Paper

RAFFLES INSTITUTION
2020 YEAR 6 TERM 2 TIMED PRACTICE
Higher 2
CHEMISTRY 9729
24 March 2020
2 hours 30 minutes
Additional Materials: Multiple Choice Answer (OMR) Sheet
READ THESE INSTRUCTIONS FIRST
Write your name, index number and civics tutorial group in the spaces provided on the OMR Sheet
and the cover sheet on page 7.
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) [Shade your section A answer on the cover sheet on page 7]
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 three 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 two questions in this section. Answers to this section are to be written in the spaces
provided in the question 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 the examination, fasten your answers to Section C securely together. Answers to
Sections A, B and C are to be handed in separately.
The number
Thisofdocument
marks is given in brackets please
is copyrighted, [ ] at the
doend
notofreproduce
each question or part
it without question.
permission
This document consists of 21 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 statement concerning the Period 3 elements sodium to chlorine is incorrect?
A Aluminium has the highest electrical conductivity.

B Only phosphorus can exhibit an oxidation number of +5.
C The atomic radii of the elements decrease across the period.
D The elements become more electronegative across the period.
2 Aluminium and silicon are consecutive elements in Period 3 of the Periodic Table.
Which statement concerning the compounds of aluminium and silicon is incorrect?
A Both their chlorides are covalent.

B Both their oxides have high melting points.
C Both their oxides give neutral solutions when added to water.
D Both their chlorides give strongly acidic solutions when added to water.
3 Hydrazoic acid, HN3, is a weak monobasic acid (pKa = 4.72).
An aqueous sample contains 0.100 mol dm–3 of the acid at 298 K. Which statements are
correct?
[Data: Kw = 1.0  10–14 mol2 dm–6 at 298 K]
1 The pH of the sample is 2.86.

2 The concentration of N3– in the sample is 1.38  10–3 mol dm–3.
3 The concentration of OH– in the sample is 7.24  10–12 mol dm–3.
A 1, 2 and 3 C 2 and 3 only

B 1 and 2 only D 1 only
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3
4 A sample of aqueous ammonia is diluted using water at constant temperature. Which of the
following diagrams are correct?
1 2 3
pH of solution degree of ionisation Kb of NH3
0 0 0
volume of water added volume of water added volume of water added
A 2 and 3 only C 3 only

5 Which of the following mixtures will form a buffer solution?
1 50 cm3 of 1 mol dm–3 hydrochloric acid and 100 cm3 of 1 mol dm3 ammonia.
2 100 cm3 of 1 mol dm–3 sodium dihydrogen phosphate (NaH2PO4) and 50 cm3 of
1 mol dm3 sodium hydroxide.
3 100 cm3 of 1 mol dm–3 ethanoic acid and 50 cm3 of 1 mol dm3 calcium hydroxide.

6 How many isomers (including both constitutional and stereoisomers) are possible for
C4H10O?
A 5 B 6 C 7 D 8
7 Ethane reacts with chlorine gas in the presence of ultraviolet light to form a mixture of
products via free radical substitution.
Which statements about this reaction are incorrect?
1 Homolytic fission occurs only in the initiation step.

2 Bond formation occurs only in the termination step.
3 document
This Chloroethane is formed only
is copyrighted, in thedopropagation
please step.it without permission
not reproduce

4
8 Which of the following compounds reacts with HBr(g) under suitable conditions to give a
chiral product?
A CH3CH2CH(OH)CH2CH3 C (CH3)2C=C(CH3)2
B D
9 Which statements about benzene are correct?
1 Benzene undergoes substitution rather than addition reactions.

2 All C–C bond lengths in benzene are between those of C–C bonds in an alkane
and C=C bonds in an alkene.
3 The enthalpy change of hydrogenation of benzene is less exothermic than that
predicted for cyclohexatriene.

10 Benzene is a cyclic aromatic hydrocarbon with 6 π electrons.
For a cyclic hydrocarbon to be aromatic, the molecule must

 be planar
 contain overlapping p orbitals on adjacent carbon atoms
 contain (4n + 2) π electrons (n = 0, 1, 2, 3, and so forth)
Which of the following hydrocarbons are aromatic?
1 2 3


5
11 A reaction scheme involving a substituted alkane is given below.
(CH3)2CCH2CH3 (I)
C5H10
X
Which of the following combinations will result in a successful conversion with a high yield of
the product?
–X (I) C5H10
A –Cl ethanolic NaOH, heat CH2=C(CH3)CH2CH3
B –OH cold, conc. H2SO4 (CH3)2C=CHCH3
C –Cl NaOH(aq), heat CH2=C(CH3)CH2CH3
D –OH excess conc. H2SO4, heat (CH3)2C=CHCH3
12 A halogenoalkane, S, produces an amine when heated in a sealed tube with excess

ammonia. A nitrile, T, produces an amine as well when reacted with LiAlH4 in dry ether.
Which of the following pairs of S and T give the same amine?
S T
A C6H5Cl C6H5CN
B CH3CH2Cl CH3CH2CN
C CH3CH(CH2Cl)CH3 CH3CH(CN)CH3
D CH3CH2CHClCH3 CH3CH(CN)CH3
13 An iodoalkane and sodium react when heated under reflux to form an alkane according to
the equation:
2RI + 2Na  R–R + 2NaI
In a reaction with sodium, a mixture containing equal amounts of two different iodoalkanes,
CH3CH2I and CH3CH(I)CH3, is used. Which of the following alkanes will be formed?
1 (CH3)2CHCH(CH3)2
2 CH3CH2CH(CH3)2
3 CH3CH2CH2CH3


6
14 Compound X was subjected to the following sequence of reactions.
Which of the following could be the structure of X?
A C
B D
15 Which of the following shows the compounds in order of increasing pKa?
CH3CH2OH CH3CH(Cl)OH
I II III IV
A II < I < III < IV

B I < II < IV < III
C IV < III < I < II
D III < IV < II < I

7
RAFFLES INSTITUTION
2020 YEAR 6 TERM 2 TIMED PRACTICE
Higher 2
COVER SHEET
Name: ( ) Class:
For Examiner’s Use Only
Section Marks
A / 15
B1 / 13
B B2 / 11
B3 / 11
C1 / 16
C
C2 / 24
Total / 90
Percentage / 100
Penalty
Overall / 100
Grade

8
Section B (35 marks) For
This section consists of 3 questions. examiner’s
use
Answer all the questions in this section in the spaces provided.
1 Lactic acid, also known as milk acid, is a chemical compound that plays a role in several
biochemical processes. Sodium lactate, the sodium salt of lactic acid, is commonly used as a
food preservative and a food acidity regulator.
lactic acid sodium lactate
(a) A buffer solution contains a mixture of lactic acid and sodium lactate.
Write equations to show how the lactic acid/sodium lactate buffer system regulates the
acidity on the addition of H+ and OH− ions.
on addition of H+ …………………………………………………………………………………..….
on addition of OH− ………………………………………………………………………….……..[2]
(b) In order to investigate the composition of a lactic acid/sodium lactate buffer solution of initial
pH 3.25, 25.0 cm3 of this buffer solution was titrated with 1.0 mol dm3 aqueous sodium
hydroxide. The graph below shows the titration curve obtained.
pH
pHequivalence
X
3.25 X
0 3x 8x
Volume of NaOH(aq) / cm3

9
Upon the addition of 3x cm3 of aqueous sodium hydroxide, the buffer solution functions at For
its maximum buffering capacity. The equivalence point of titration is attained when 8x cm3 of examiner’s
use
aqueous sodium hydroxide is added.
(i) Show that the ratio of [lactic acid] : [sodium lactate] is 4 : 1 in the original buffer
solution.
[3]
(ii) Determine the acid dissociation constant, Ka, of lactic acid.
[1]
(iii) With the aid of an equation, explain why the pH at equivalence point is above 7.
equation …………………………………………………………………..…………………….
explanation ……..…………..………………………………………..…………………………
………………………………..………………………………………..…………………………
………………………………..………………………………………..………………...……[2]

10
(c) The table below lists some properties of three samples of lactic acid, E, F and G, prepared For
from different natural sources. examiner’s
use
sample source effect on planepolarised light melting point / oC

E meat extract rotate clockwise 26
F fermentation of sucrose rotate anti-clockwise 26
G sour milk no effect 18
(i) With the aid of suitable three-dimensional structural formulae, explain why samples E
and F behave differently towards planepolarised light.
……………………………………………………………..…………………..…………………
………………………………………………………………………………..……………….[2]
(ii) Explain why sample G has no effect on plane−polarised light and hence suggest why
it has a different melting point from E.
……………………………………………………………..………………………..……………
……………………………………………………………..……………………..………………
……………………………………………………………..………………………..……………
……………………………………………………………..……………………..………………
.………………………………………………………………………………….…………….[2]
(d) When lactic acid, C3H6O3, is heated under reflux with a catalytic amount of concentrated
sulfuric acid, compound H with the molecular formula of C6H8O4 is formed. H does not react
with sodium. Suggest the structural formula of H.

[1]
[Total: 13]

11
2 Halogens and their compounds are important intermediates in many reactions and are used For
extensively in industries. examiner’s
use
(a) With the aid of relevant equations, explain the following statement.
The difference in oxidising power of chlorine and iodine is evident from their reactions with
aqueous sodium thiosulfate.
………………………………………………………………………………………………………..…
……………………………………………………………………………………………………..……
……………………………………………………………………………………………………..……
……………………………………………………………………………………………………..……
………………………………………………………………………………………………………..…
……………………………………………………………………………………………………..……
……………………………………………………………………………………………….………[3]
(b) 1-bromobutane, CH3CH2CH2CH2Br, can react with ammonia to form 1-butanamine,

CH3CH2CH2CH2NH2.
(i) Excess ammonia is used in the reaction to reduce the amount of undesired products
such as dimethylamine, (CH3)2NH.
Suggest another role of ammonia in this reaction.
……………………………………………………………..……………………..………………
.……………………………………………………………………………….……………….[1]
(ii) Ammonia is soluble in both water and ethanol.
Suggest why ethanol, instead of water, is used as the solvent for this reaction.
……………………………………………………………..………………………..……………
……………………………………………………………..…………………………..…………
……………………………………………………………..…………………………..…………
.……………………………………………………………………………………….……….[2]

12
(c) Trimethylbutylammonium iodide, [(CH3)3NCH2CH2CH2CH3]+I−, can be prepared by the For
alkylation of methylamine. examiner’s
use
(i) Suggest the structural formulae of compounds P and Q in the following scheme.
P Q
[2]
Trimethylbutylammonium iodide is heated with moist silver(I) oxide to form a quaternary

ammonium hydroxide, which reacts further to produce but-1-ene and trimethylamine.
[(CH3)3NCH2CH2CH2CH3]+OH CH2=CHCH2CH3 + (CH3)3N + H2O
(ii) State the type of reaction that has occurred.
………………………………………………………………………………………………...[1]
(iii) When heated, the following quaternary ammonium hydroxide undergoes a similar
reaction to form two alkenes, R and S.
Draw the structural formulae of R and S.
R S

[2]
[Total: 11]
13
3 The flowchart below shows reactions involving some calcium compounds. For
examiner’s
use
(a) Coal-fired power stations emit flue gases, which contain the oxides of nitrogen, carbon and
sulfur. To reduce sulfur dioxide emission, such power station is fitted with a flue gas
desulfurisation (FGD) plant which uses a slurry of compound D to extract sulfur dioxide
gas from the flue gases.
(i) Suggest the identity of compound D. Hence write an equation for its reaction with
sulfur dioxide, given that one of the products produced is a sulfite.
compound D is ……………………………..………..
equation ………………………………………………………………………………….…[2]
(ii) With the aid of equation(s), suggest why solution E has a pH of 7 whereas a solution
of beryllium chloride has a pH of approximately 3.
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………….
………………………………………………………………………………….……………[3]

14
(b) Using relevant data from the Data Booklet, explain why calcium carbonate has greater For
thermal stability than magnesium carbonate. examiner’s
use
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
……………………………………………………………………………………………………...[2]
(c) Use of the Data Booklet is relevant to this question.
A solder is an alloy of metals which is used to join other metal pieces together.
A specialist solder that can be used to join together pieces of aluminium is made from a
mixture of zinc, aluminium and copper.
Outline how you would extract from the mixture each of the following in sequence;
(i) the copper metal, Cu,
(ii) the aluminium as aluminium hydroxide, Al(OH)3,
(iii) the zinc as zinc hydroxide, Zn(OH)2.
You are provided with

 a sample of this solder,
 dilute sulfuric acid, H2SO4,
 aqueous ammonia, NH3.
No other reagents should be used and no details regarding use of specific glassware are
required.
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
…………………………………………………………………………………………………………
……………………………………………………………………………………………………...[4]
[Total: 11]
15
Section C (40 marks) For
This section consists of 2 questions. examiner’s
use
Answer all the questions in this section in the spaces provided.
1 Compound X is an isomer of jasmone, a natural organic compound extracted from jasmine

flowers.
compound X
(a) Explain why X does not exhibit cis-trans isomerism.
………………………………...………………………………………………………………………
………………………………...………………………………………………………………………
……………………………………………………….…..……………………………………………
………………………………………………………………………………...…………………...[2]
(b) Give the structures of the organic products formed when X is reacted with
(i) cold, alkaline KMnO4(aq);
(ii) hot, acidified KMnO4(aq).

[3]

16
(c) Compound Y is an isomer of jasmone and it can be synthesised from compound Z. For
examiner’s
use
compound Y compound Z
[The –OCH3 group can be regarded as inert.]
(i) Suggest a simple chemical test that you could use to distinguish between
compounds Y and Z.
Test …………………………………………………………………………………...………
…………………………………………………………………………………………….…..
Observations…………………………………………………………………………………
…………………………………………………………………………………………….…..
…………………………………………………………………………………………….…..
………………………………………………………………………..…………………….[2]
(ii) State the reagents and conditions needed for the following conversions. Draw the
structure of the intermediate.
Reagents and conditions
Step 1.............................................................................................................
Step 2............................................................................................................. [3]

17
(iii) Compound Z can react with IBr in an inert organic solvent. For
examiner’s
use
Draw the mechanism of this reaction to form the major product.
Show all charges, dipoles and relevant lone pairs and show the movement of
electron pairs by using curly arrows.
You may represent Z as
[3]
(d) Aluminium oxide is employed industrially for many organic reactions. Compound Z is the
only organic product formed when compound W is heated over Al2O3.
(i) Draw the skeletal formula of compound W.
[1]
(ii) Aluminium oxide is amphoteric. With the aid of balanced equations, explain the
meaning of the term amphoteric.
…………………………………………………………………………………………….…..
…………………………………………………………………………………………….…..
…………………………………………………………………………………………….…..
This………………………………………………………………………..…………………….[2]
document is copyrighted, please do not reproduce it without permission
[Total: 16]

18
For
2 (a) Phenol can react with acyl chlorides to form esters. An example is given below. examiner’s
use
In this reaction, phenol acts as a nucleophile.
(i) Define the term nucleophile.
………………………………………………………………………………………………..
………………………………………………………………………………………..……[1]
(ii) Carboxylic acids can also act as the nucleophile in the reaction. Predict the product
when (CH3)2CHCOOH reacts in the above reaction in replacement of phenol.
[1]
An alcohol, such as ethanol, also acts as a nucleophile when it reacts with carboxylic
acids.
(iii) Unlike ethanol, phenol does not react directly with carboxylic acids.
Suggest and explain why this is so.
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………..……[2]

19
(b) The reaction scheme below starts with phenol. For
examiner’s
use
(i) State the reagents and conditions for steps 1 and 2.
Step 1.............................................................................................................
Step 2............................................................................................................. [2]
(ii) With the aid of an equation, explain why aluminium chloride can act as a Lewis acid
in step 3.
equation……………………….……………………………………………………………..
explanation…………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………..……[2]
(iii) Given that aluminium chloride acts as a catalyst and using your answer to (b)(ii),
describe the mechanism of the reaction in step 3.
[3]

20
(iv) Suggest why the yield in step 3 is lower than expected. For
examiner’s
use
………………………………………………………………………………………………..
………………………………………………………………………………………..……[1]
(c) A student proposed the following synthesis of a phenol-containing compound.
(i) Explain why step 1 does not produce compound G.
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………………..
………………………………………………………………………………………..……[2]
(ii) Using the symbol [O] to represent the oxidising agent, write the balanced equation
for step 2.
………………………………………………………………………………………..……[1]

21
(d) J (C9H12O) is a sparingly soluble compound that forms a violet complex with neutral For
aqueous iron(III) chloride. Upon heating with acidified potassium manganate(VII), K examiner’s
(C8H6O5) is produced. Adding aqueous chlorine to J yields L (C9H11OCl). use
M is an isomer of L and is formed from the reaction of J with chlorine in the presence of
ultraviolet light. M reacts with hot aqueous sodium hydroxide to form N (C9H11O2Na),
which gives a yellow precipitate when heated with aqueous alkaline iodine.
Deduce, with reasoning, the structures of compounds J to N.

[9]
[Total: 24]

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RAFFLES INSTITUTION

2020 YEAR 6 TERM 2 TIMED PRACTICE

READ THESE INSTRUCTIONS FIRST

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

Read the instructions on the OMR Sheet very carefully.

Section B (35 marks)

Section C (40 marks)

This document consists of 21 printed pages.

1 Which statement concerning the Period 3 elements sodium to chlorine is incorrect?

A Aluminium has the highest electrical conductivity.

A Both their chlorides are covalent.

3 Hydrazoic acid, HN3, is a weak monobasic acid (pKa = 4.72).

[Data: Kw = 1.0  10–14 mol2 dm–6 at 298 K]

1 The pH of the sample is 2.86.

A 1, 2 and 3 C 2 and 3 only

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

© Raffles Institution 2020 9729/M/20 [Turn Over

A 2 and 3 only C 3 only

5 Which of the following mixtures will form a buffer solution?

A 1, 2 and 3 C 2 and 3 only

Which statements about this reaction are incorrect?

1 Homolytic fission occurs only in the initiation step.

A 1, 2 and 3 C 2 and 3 only

9 Which statements about benzene are correct?

1 Benzene undergoes substitution rather than addition reactions.

A 1, 2 and 3 C 2 and 3 only

10 Benzene is a cyclic aromatic hydrocarbon with 6 π electrons.

For a cyclic hydrocarbon to be aromatic, the molecule must

Which of the following hydrocarbons are aromatic?

A 1, 2 and 3 C 2 and 3 only

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

© Raffles Institution 2020 9729/M/20 [Turn Over

11 A reaction scheme involving a substituted alkane is given below.

12 A halogenoalkane, S, produces an amine when heated in a sealed tube with excess

2RI + 2Na  R–R + 2NaI

A 1, 2 and 3 C 2 and 3 only

© Raffles Institution 2020 9729/M/20 [Turn Over

14 Compound X was subjected to the following sequence of reactions.

Which of the following could be the structure of X?

15 Which of the following shows the compounds in order of increasing pKa?

A II < I < III < IV

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

© Raffles Institution 2020 9729/M/20 [Turn Over

For Examiner’s Use Only

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

© Raffles Institution 2020 9729/M/20 [Turn Over

lactic acid sodium lactate

on addition of OH− ………………………………………………………………………….……..[2]

© Raffles Institution 2020 9729/M/20 [Turn Over

(ii) Determine the acid dissociation constant, Ka, of lactic acid.

© Raffles Institution 2020 9729/M/20 [Turn Over

sample source effect on planepolarised light melting point / oC

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

© Raffles Institution 2020 9729/M/20 [Turn Over

(b) 1-bromobutane, CH3CH2CH2CH2Br, can react with ammonia to form 1-butanamine,

Suggest another role of ammonia in this reaction.

(ii) Ammonia is soluble in both water and ethanol.

© Raffles Institution 2020 9729/M/20 [Turn Over