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2019 JC2 H2 Chemistry Prelim Anderson Serangoon Junior College

1. The document is the first paper of multiple choice questions from the 2019 JC2 Preliminary Examinations in Chemistry held by Anderson Serangoon Junior College. It consists of 30 multiple choice questions to be answered in 1 hour. 2. The questions cover a range of chemistry topics including properties of elements, chemical bonding, gases, acid-base equilibria, redox reactions, and enthalpy changes. Data provided include successive ionization energies, standard enthalpy changes of reaction, and the ion product constant of water. 3. Students are instructed to choose the one correct answer for each question and record their choice on the provided answer sheet. Working should be done in the question paper. A

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0% found this document useful (0 votes)
438 views77 pages

2019 JC2 H2 Chemistry Prelim Anderson Serangoon Junior College

1. The document is the first paper of multiple choice questions from the 2019 JC2 Preliminary Examinations in Chemistry held by Anderson Serangoon Junior College. It consists of 30 multiple choice questions to be answered in 1 hour. 2. The questions cover a range of chemistry topics including properties of elements, chemical bonding, gases, acid-base equilibria, redox reactions, and enthalpy changes. Data provided include successive ionization energies, standard enthalpy changes of reaction, and the ion product constant of water. 3. Students are instructed to choose the one correct answer for each question and record their choice on the provided answer sheet. Working should be done in the question paper. A

Uploaded by

Padmalaya palo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 77

ANDERSON SERANGOON JUNIOR COLLEGE

2019 JC 2 PRELIMINARY EXAMINATIONS

CHEMISTRY 9729/01
Higher 2 19 September 2019
Paper 1 Multiple Choice 1 hour

Additional Materials: Multiple Choice Answer Sheet


Data Booklet

READ THESE INSTRUCTIONS FIRST

Write in soft pencil.


Do not use staples, paper clips, glue or correction fluid.
Write your name and class on the Answer Sheet in the spaces provided.

There are thirty questions on this paper. Answer all questions. 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 separate Answer
Sheet.

Read the instructions on the Answer 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 this booklet.
The use of an approved scientific calculator is expected, where appropriate.

This document consists of 18 printed pages and 2 blank pages.

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


2

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

The 68Ge isotope is medically useful because it undergoes a natural radioactive process to
give an isotope of a different element, 68Q, which can be used to detect tumours. This
transformation of 68Ge occurs when an electron enters the nucleus and changes a proton
into a neutron.
68
Which statement about the composition of an atom of Q is correct?

A It has 4 electrons in its outer p orbitals.


B It has 13 electrons in its outer shell.
C It has 37 neutrons.
D Its proton number is 32.

2 The successive ionisation energies (IE) of two elements X and Y are given in the table.

IE / kJ mol–1 1st 2nd 3rd 4th 5th 6th 7th 8th


X 786 1580 3230 4360 16000 20000 23600 29100
Y 1300 3380 5310 7460 8670 9330 22060 27070

What compound is most likely to be formed when X and Y are combined?

A ionic, with formula X2Y


B ionic, with formula XY2
C covalent, with formula XY2
D covalent, with formula X2Y

ASRJC JC2 PRELIMS 2019 9729/01/H2


3

3 Plants appear green due to the presence of chlorophyll. There are several closely related
chlorophylls and the diagram shows a simplified version of one. The various different
side–groups are all shown as R.

Note that the four N atoms and the Mg ion are planar.

Which of the descriptions of the bonds between Mg and the numbered N atoms is most likely
to be correct?

N atoms numbered
1 and 3 2 and 4

A co–ordinate ionic
B co–ordinate 
C ionic co–ordinate
D  co–ordinate

4 Which molecule has the largest dipole?

A B C D

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


4

5 Which graph best represents the behaviour of a fixed mass of an ideal gas under the
given conditions?

( is the density of the gas)

A B

p p
constant T constant V

0  0 T/K

C D

V
constant p constant T

0 T / °C 0 V

6 Which of the following, in aqueous solution, could be used to maintain the pH at about 5?

A ammonia and ammonium chloride


B ethanoic acid and sodium ethanoate
C sodium hydroxide and sodium ethanoate
D ethanoic acid only

ASRJC JC2 PRELIMS 2019 9729/01/H2


5

7 Values of the ionic product of water, Kw, at different temperatures are given in the table.

temperature / °C Kw / mol2 dm–6

15 4.50 x 10–15
30 1.47 x 10–14

What can be deduced from this information?

A The association of water molecules by hydrogen bonding increases as temperature


increases.
B Water is not a neutral liquid at 15 °C.
C The concentrations of both H+ and OH− increase as temperature increases.
D The ionic dissociation of water is an exothermic reaction.

8 Which property of the halogens increases on descending Group 17?

A volatility of the halogens


B bond energy of the halogen–halogen bond
C ease of oxidation of the halide ion
D thermal stability of the hydrogen halide

9 Trichloroisocyanuric acid is commonly used in swimming pools as a disinfectant. The


recommended concentration level of the acid is 1.50 mg per litre of water.

trichloroisocyanuric acid
Mr = 232.5

How many chlorine atoms are present in a 2.50 x 10 6 litre Olympic–sized swimming pool
filled with the recommended concentration level of trichloroisocyanuric acid?

A 2.91 x 1025
B 2.91 x 1028
C 9.71 x 1024
D 9.71 x 1027

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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10 When 720 cm3 of hydrogen sulfide gas, H2S, is passed through 40 cm3 of 0.500 mol dm–3
nitric acid, HNO3, a yellow solid of sulfur and a nitrogen–containing compound are formed.

The half–equation for oxidation of H2S is shown below.

H2S → S + 2H+ + 2e–

What could be the nitrogen–containing compound formed from the complete reaction?

[All volumes are measured at room temperature and pressure conditions under which H2S
is a gas.]

A N2
B NO
C NO2
D NH3

11 When m g of ethanol was burned under a container of water, it was found that the
temperature of 300 g of water rose by T °C.

thermometer

water

ethanol
(Mr = 46.0)

The enthalpy change of combustion of ethanol is –1371 kJ mol−1 and the specific heat
capacity of water is 4.2 J g−1 K−1.

Which expression below gives the percentage efficiency of this process?

m  4.2  T  46.0
A  100%
300  1371 1000

m  1371 1000
B  100%
300  4.2  T  46.0

300  4.2  (T + 273)  46.0


C  100%
m  1371 1000

300  4.2  T  46.0


D  100%
m  1371 1000

ASRJC JC2 PRELIMS 2019 9729/01/H2


7

12 The enthalpy change of the thermal decomposition of magnesium carbonate is given as


+117 kJ mol–1.

MgCO3(s) → MgO(s) + CO2(g)

What information, other than that given above, is required to calculate a value for the
enthalpy change of formation of MgCO 3(s)?

A enthalpy change of formation of magnesium oxide and enthalpy change of


combustion of carbon
B lattice energy of magnesium carbonate and of magnesium oxide
C first and second ionisation energies of magnesium
D bond energy of the C=O bonds in carbon dioxide

13 What will be the signs of the enthalpy and entropy changes when a liquid boils?

∆H ∆S
A + +
B – +
C – –
D + –

14 The alkaline hydrolysis of 2–chloro–2–methylpropane, (CH3)3CCl, with 0.2 mol dm–3 NaOH
produces 2–methylpropan–2–ol, (CH3)3COH.

(CH3)3CCl + OH– → (CH3)3COH + Cl–

20% of (CH3)3CCl in a solution of concentration 0.02 mol dm –3 hydrolyses in 5 minutes at


a certain temperature.

With reference to the overall order of this reaction, what percentage of (CH3)3CCl in a
solution of concentration 0.04 mol dm–3 would hydrolyse in 5 minutes at the same
temperature?

A 10% B 20% C 30% D 40%

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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15 The equation for the oxidation of nitrogen monoxide is shown below.

O2 + 2NO → 2NO2

The following rate equation was derived from initial rates experiments.

rate = k [O2] [NO]2

The results of the initial rates experiments are shown.

initial [O2] initial [NO] initial rate


/ mol dm–3 / mol dm–3 / mol dm–3 min–1
2.0 1.0 8.0
1.0 1.0 s
1.0 t 16.0
0.5 0.5 u

What are the missing values, s, t and u?

s t u

A 4.0 1.0 0.5


B 4.0 2.0 0.5
C 2.0 1.0 1.0
D 2.0 2.0 1.0

16 Which suggested mechanisms are consistent with the experimentally obtained rate
equation?

chemical equation rate equation suggested mechanism


1 H2O2 + 2H+ + 2I– → rate = k1 [H2O2] [I–] H2O2 + H+ → H2O + OH+ (fast)
2H2O + I2
OH+ + 2I– + H+ → H2O + I2 (slow)
2 CO + NO2 → CO2 + NO rate = k2 [NO2]2 NO2 + NO2 → N2O3 + O (slow)
N2O3 + CO → CO2 + 2NO (fast)
3 H2 + I2 → 2HI rate = k3 [H2] [I2] H2 → 2H (slow)
2H + I2 → 2HI (fast)

A 1, 2 and 3
B 1 and 2 only
C 2 and 3 only
D none

ASRJC JC2 PRELIMS 2019 9729/01/H2


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17 The graph shows how ∆Go changes with temperature for the reaction shown.

H2O(g) + CO(g) ⇌ H2(g) + CO2(g)

40

30
1 2 3 4
20

10

∆Go/ kJ mol–1 0

-10

-20

-30

-40
200 300 400 500 600 700 800 900 1000 1100 1200 1300
T/K

Equimolar amounts of H2O and CO were introduced into a sealed container and allowed to
reach equilibrium.

At which points on the graph above will the value of Kc be more than 1?

A 1 and 2 B 2 and 3 C 1, 2 and 3 D 1, 2, 3 and 4

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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18 Nitrosyl chloride, NOCl, is a yellow gas that can be formed between nitryl chloride, NO2Cl,
and nitric oxide, NO, in the following reaction.

NO2Cl(g) + NO(g) ⇌ NOCl(g) + NO2(g) ∆H < 0

NO2Cl and NO were initially allowed to react in a closed vessel at 800 K and equilibrium was
established.

The graph below shows how the pressure of NO 2Cl varied with time.

pressure of NO2Cl

0
time

What could be the changes made to the system at t1, t2 and t3?

t1 t2 t3

A NO2Cl was removed temperature was increased NO2Cl was added


temperature was
B NO2Cl was added NO2 was added
decreased
C NO2 was removed temperature was increased NO2Cl was added
temperature was
D NO2Cl was removed NO2Cl was added
decreased

ASRJC JC2 PRELIMS 2019 9729/01/H2


11

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

Consider the following reaction scheme starting from solution J.

Which of the following statements are correct?

1 The gas produced is able to reduce Fe 2+ to Fe.


2 The conversion from K to L involves a ligand exchange reaction.
3 The cation present in solution K reacts with Na2CO3 to produce a gas that
gives a white precipitate with Ca(OH)2(aq).

A 3 only
B 1 and 3
C 2 and 3
D none

20 Purine is a heterocyclic aromatic compound. The nitrogen atoms, labelled as Na and Nb, in
purine have different basicity. Na is basic whereas Nb is non–basic.

Na
Na

Na
Nb
H

Purine

Based on the above information, which bond is not present in purine?

A A  bond formed by 2sp2–2sp3 overlap


B A  bond formed by 1s–2sp2 overlap
C A π bond formed by 2p–2p overlap
D A  bond formed by 2sp2–2sp2 overlap

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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21 Which molecules are optically active?

Br
CH3

1
Br
CH3

2 Br CH3
CH3 Br

Br Br

CH3 CH3

A 1 and 2 only
B 1 and 3 only
C 2 and 3 only
D none

22 Which reactions would give the products stated?

Cl heat with NH3 in ethanol


1

Cl HCN with NaCN CN


2

Cl OH

3 heat with KOH(aq)

A 1 and 2 only
B 2 only
C 2 and 3 only
D none

ASRJC JC2 PRELIMS 2019 9729/01/H2


13

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

Which transformation can be readily achieved by only one substitution reaction?

COCH3 COCH3

Br

B (CH3)3CCH2F (CH3)3CCH2NH2
NO2 CH3

NO2
D CH3CH=CH2 CH3CH=CHCl

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


14

24 Compound Y has the following structure.

O
HO2CCH2CH2CCHCH CH2

CH2 NO2

When Y is treated with sodium borohydride, what is the final product obtained?

OH
HO2CCH2CH2CHCHCH CH2
A
CH2 NO2

OH
HOCH2CH2CH2CHCHCH2CH3
B
CH2 NO2

O
HOCH2CH2CH2CCHCH CH2
C
CH2 NO2

OH
HOCH2CH2CH2CHCHCH CH2
D
CH2 NH2

ASRJC JC2 PRELIMS 2019 9729/01/H2


15

25 Compound Z shows the following chemical properties.

 It does not give any observation with Fehling’s solution.


 1 mole of Z reacts with 2 moles of sodium metal.
 When PCl5(s) is added to Z, a sweet smelling product is obtained.

What could Z be?

A HO2CCH2CH2CH2CO2H
B HO2CCH2CH2CH2CHO
O

H C CH2CH2OH
C

OH
O

H C CH2CO2H
D

OH

26 Equal amounts of compounds P, Q, R and S are separately shaken with 100 cm3 of water.

The pH of each resultant solution is then measured.

CH3CH2CO2H CH3CH2COCl ClCH2CH2CO2H BrCH2CH2CO2H


P Q R S

Which sequence shows the correct order of decreasing pH of the solutions formed?

A P, R, S, Q
B P, S, R, Q
C Q, P, S, R
D Q, S, R, P

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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27 An amide, M, has the empirical formula C7H15ON. When M is hydrolysed by heating under reflux
with dilute hydrochloric acid, a carboxylic acid with empirical formula C 2H4O is obtained as one
of the products.

What could be the skeletal formula of M?

A 1, 2 and 3
B 2 and 3 only
C 1 only
D 3 only

ASRJC JC2 PRELIMS 2019 9729/01/H2


17

28 Lysine is an essential amino acid found in the body.

CO 2H

H2N H

(CH2)4NH 2

lysine

Lysine has pKa values of 2.2, 9.0 and 10.5.

When one mole of protonated lysine was titrated against hydroxide ions, the following
titration curve is obtained.

pH

moles of
hydroxide
added

Which statements are correct with respect to the curve above?

1 The –amino group has a pKa value of 10.5.


2 Equal amounts of H3N+CH(CO2H)(CH2)4NH3+ and H3N+CH(CO2H)(CH2)4NH2 are
present at point A.
3 The major species present at point C has no net charge.
4 The major species present at point B will migrate towards the cathode of an
electrolytic cell.

A 1 and 3 only
B 2 and 4 only
C 3 and 4 only
D 1, 2 and 4 only

ASRJC JC2 PRELIMS 2019 9729/01/H2 [Turn over


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

Quinone can be formed by oxidising quinol.

O O + 2H + + 2e ⇌ HO OH Eo = +0.70 V

quinone quinol

Which statements about this reaction are correct?

1 C bonded to O in quinone has an oxidation state of +2 while C bonded to O


in quinol has an oxidation state of +1.
2 Eocell for the reaction between quinol and acidified KMnO 4 is positive.
3 SO2 gas can be used to reduce quinone to quinol.

A 1, 2 and 3
B 1 and 3 only
C 2 and 3 only
D 1 only

30 Two separate electrolysis were performed as follows.

1. When aqueous sulfuric acid was electrolysed for 5 minutes, 0.01 mol of oxygen was
collected at the anode.

2. When molten aluminium oxide was electrolysed for 5 minutes, 0.01 mol of aluminium
was collected at the cathode.

If the current used in electrolysis 1 was I, what was the current used in electrolysis 2?

3 4
A I B I C I D 2I
4 3

ASRJC JC2 PRELIMS 2019 9729/01/H2


ANDERSON SERANGOON JUNIOR COLLEGE
2019 JC 2 PRELIMINARY EXAMINATIONS

NAME:_____________________________________ ( ) CLASS: 19 /____

CHEMISTRY 9729/02
Higher 2 4 September 2019
Paper 2 Structured Questions 2 hours
Candidates answer on the Question Paper.

Additional Materials: Data Booklet

READ THESE INSTRUCTIONS FIRST

Write your name, index number and class on all the work you hand in.
Write in dark blue or black pen.
You may use a pencil for any diagrams or graphs.
Do not use staples, paper clips, glue or correction fluid.

Answer all questions in the spaces provided on the Question Paper.


The use of an approved scientific calculator is expected, where appropriate.
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.

For Examiner’s Use

1 / 12

2 / 11

3 / 18
Paper 2

4 / 13

5 / 12

6 /9

Total / 75
This document consists of 26 printed pages and 2 blank pages.

ASRJC JC2 PRELIMS 2019 9729/02/H2 [Turn over


2

1 (a) Use the data from Table 1.1 to state and explain the relative reactivity of Group 2 elements as
reducing agents.

Table 1.1

Element Eo [M2+(aq)/M(s)] / V

Mg –2.38

Ca –2.87

Sr –2.89

Ba –2.90

……………………………………………………………………………………………………………

……………………………………………………………………………………………………………

……………………………………………………………………………………………………………

……………………………………………………………………………………………………..… [2]

(b) Table 1.2 gives data about some physical properties of calcium and copper.

Table 1.2

calcium copper

relative atomic mass 40.1 63.5

atomic radius (metallic) / nm 0.197 0.128

ionic radius (2+) / nm 0.099 0.069

electrical conductivity / 106 S cm1 0.298 0.596

density / g cm3 1.54 8.92

(i) Explain why the electrical conductivity of copper is higher than that of calcium.

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

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

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

…………..…………………………………………………………………………………..… [2]

ASRJC JC2 PRELIMS 2019 9729/02/H2


3

(ii) Using relevant data from Table 1.2, explain why the density of copper is significantly
greater than that of calcium (no calculations are required).

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

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

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

…………………………………………………………………………………………………. [2]

(c) (i) Copper is a typical transition element and is used in alloys for aircraft engine parts.

Which of the following “electrons–in–boxes” diagrams best describes the valence


ground–state electronic configuration of a Cu+ ion? Explain your answer.

3s2 3p6 3d10


A ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂
3s2 3p6 3d10
B ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿⇂ ↿↿

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

….……………………………………………………………………………………………… [1]

(ii) Using the Cartesian axes shown in Fig. 1.1, draw fully–labelled diagrams of any two
d–orbitals of different shapes found in a Cu+ ion.

z z

y y

x x

Fig. 1.1
[2]

ASRJC JC2 PRELIMS 2019 9729/02/H2 [Turn over


4

(d) Silicon is the eighth most common element in the universe by mass. It very rarely occurs as
the pure element in the Earth's crust.

Table 1.3 shows the melting points of silica (SiO 2) and silicon.

Table 1.3

melting point / °C
silica 1710
silicon 1414

Silica and silicon each form a solid with the same type of structure.

(i) State the type of structure present in solid silica and silicon.

………………………………………………………………………………….……………... [1]

(ii) Using relevant data from the Data Booklet, suggest why the melting point of silica is
higher than that of silicon.

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

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

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

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

………………………………………………………………………………………………… [2]

[Total: 12]

ASRJC JC2 PRELIMS 2019 9729/02/H2


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2 (a) Alkene C, C7H10, on treatment with hot, concentrated potassium manganate(VII) forms an
optically inactive compound D, C5H8O3, and carbon dioxide gas.

D reacts with both Na2CO3 and alkaline aqueous iodine.

(i) Suggest two structural features that are present in D.

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

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

…………………………………………………………………………………………….… [2]

(ii) Hence, deduce the structures of C and D.

C D
[2]

ASRJC JC2 PRELIMS 2019 9729/02/H2


7

Ozone, O3, is an oxidising agent that causes carbon–to–carbon double bond cleavage.

When an alkene is treated with ozone, followed by zinc metal in acetic acid, two
carbonyl–containing products are obtained.

The following reactions illustrate two oxidations using ozone as the oxidising agent.

CH3 1. O3
C O + E
CH3 2. Zn, H3O+
C3H6O

1. O3
CHCH2CH3 O + F
2. Zn, H3O+
C3H6O

Both E and F react with 2,4–dinitrophenylhydrazine but only F reacts with Fehling’s solution.
E reacts with alkaline aqueous iodine but not F.

(iii) Suggest the identities of E and F.

E F
[2]

(iv) Use the above information and your answers to (a)(iii) to suggest the structure for
compound G in the following reaction.

1. O3
G CH3CHO + (CH3)2CHCHO
2. Zn, H3O+

G
[1]

ASRJC JC2 PRELIMS 2019 9729/02/H2 [Turn over


8

(b) (i) Limonene occurs in oil of lemons and is used to flavour some citrus drinks.

limonene

Draw the structural formula of the product, and describe what you might observe, when
limonene reacts with bromine in an inert solvent, until in excess.

observation …………………………………………………………………………………….

……………………………………………………………………………………………..... [2]

ASRJC JC2 PRELIMS 2019 9729/02/H2


9

Fig. 2.1 shows a reaction scheme involving an isomer of limonene, H.

excess HBr
a mixture of isomeric products
step 1 step 2
Cl Cl

Fig. 2.1

(ii) Suggest reagents and conditions for step 1.

………………………………………………………………………………………………. [1]

(iii) Draw the structure of the major product for step 2.

[1]

[Total: 11]

ASRJC JC2 PRELIMS 2019 9729/02/H2 [Turn over


10

3 Transition metals are building blocks for life and they make up the middle block of the Periodic
Table.

(a) Catalase is an important enzyme that reduces the damaging effects of hydrogen peroxide in
the biological system. It contains four iron–containing heme groups that allow the enzyme to
react with the hydrogen peroxide.

It catalyses the decomposition of hydrogen peroxide into water and molecular oxygen.

H2O2 → H2O + ½O2

(i) With the aid of a sketch of the Boltzmann distribution, explain why the addition of
catalase speeds up the decomposition of hydrogen peroxide.

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

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

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

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

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

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

…………………………………………………………………………………………….… [3]

ASRJC JC2 PRELIMS 2019 9729/02/H2


11

An investigation to study the rate of the catalysed decomposition of H2O2 can be conducted
as follows:

1 cm3 of catalase, extracted from a liver sample, was added to a 50 cm3 of 2 mol dm–3 H2O2
solution connected to a sealed glass pressure tube which measures the volume of O 2
collected. The time taken for 20 cm3 of O2 to produce was then measured.

(ii) Outline how you would determine the effect of changing the concentration of H 2O2 on
the rate of the catalysed decomposition of H2O2.

You are provided with the same solution used in the experiment described above.

State clearly the measurements you would take.

No details regarding use of specific glassware are required.

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

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

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

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

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

………………………………………………………………………………………………. [3]

(iii) Sketch a graph to show how, for a fixed concentration of catalase, the rate of
decomposition varies with the concentration of H 2O2 and explain the shape of the
graph.

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

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

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

………………………………………………………………………………………………. [2]

ASRJC JC2 PRELIMS 2019 9729/02/H2 [Turn over


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(b) Transition metal sulfides are generally insoluble in water.

Metal ions can be precipitated as metal sulfides by the following reaction.

M2+(aq) + S2−(aq) → MS(s)

Solution J containing 0.100 mol dm–3 of Fe2+ and 0.100 mol dm−3 of Mn2+ can be separated
easily by selective precipitation of the metal sulfides.

The Ksp values of two metal sulfides are shown in Table 3.1.

Table 3.1

Ksp / mol2 dm−6


FeS 3.7 x 10−19
MnS 3.7 x 10−13

(i) State which metal ion, Fe2+ or Mn2+, precipitates first when solid sodium sulfide is
slowly added to 100 cm3 of solution J.

………………………………………………………………………………………………. [1]

(ii) Hence, calculate the concentration, in mol dm –3, of sulfide ions when first trace of the
precipitate appears.

[1]

(iii) Determine the concentration, in mol dm–3, of the metal ion you have stated in (b)(i)
remaining in the solution when the other metal ion just starts to precipitate.

[1]

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(iv) An effective separation means that less than 1% of the metal ion should remain in the
solution when the other metal ion just starts to precipitate. Using your answer to (b)(iii),
deduce if the separation is effective.

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

……………………………………………………………………………………………..... [1]

One advantage of using sulfide ion as a precipitating reagent is that its concentration can be
controlled by regulating the pH of the solution.

Hydrogen sulfide behaves as a weak dibasic acid that dissociates in two steps:

Equilibrium (1) H2S ⇌ H+ + HS– Ka = 9.1 x 10–8

Equilibrium (2) HS– ⇌ H+ + S2– Ka = 1.0 x 10–15

(v) Using the above equilibria, explain how varying the pH of a mixture containing solution
J and sulfide ions can allow selective precipitation to take place.

You are not expected to perform any calculations.

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

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

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

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

………………………………………………………………………………………………. [2]

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(c) The most important ore of chromium is the mineral ferrous chromite, FeOCr2O3.

Fig. 3.1 shows a reaction scheme illustrating many of the characteristic properties of
transition metal compounds.

.
FeO Cr2O3

step I excess NaOH(aq)


with continuous flow of air

filter

filtrate residue
Na2CrO4(aq) Fe2O3(s)

H2SO4(aq) step IV HCl(aq)


step II heat
followed by H2O2

solution N FeCl3(aq)

step III excess step V NaCN(aq)


NaOH(aq)

dark green solution P solution Q

Fig. 3.1

(i) Construct a balanced equation for the reaction involving Cr 2O3 in step I, by using
changes in oxidation numbers, or otherwise. In this reaction, H 2O is a by–product.

……………………………………………………………………………………………..... [1]

(ii) State the series of colour changes that occurs in step II.

………………………………………………………………………………………………. [1]

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(iii) State the type of reaction that occurs in step III and give the formula of the complex
ion in solution P.

type of reaction ………………………………………………………………………………...

formula of complex ion ……………………………………………………………………. [1]

The oxidation number of iron in the iron–containing complex ion in solution Q and in FeCl3(aq)
is the same.

(iv) Suggest the formula of the compound in solution Q.

…………………………………………………………………………………………….… [1]

[Total: 18]

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4 Ethylamine, CH3CH2NH2, and phenylamine, C6H5NH2, are both weak bases, with pKb values of
3.35 and 4.63 respectively.

(a) Explain why the pKb value of ethylamine is lower than that of phenylamine.

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

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

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

……………………………………………………………………………………………………… [2]

(b) 20.0 cm3 of an aqueous solution of ethylamine was titrated against 0.20 mol dm3 hydrochloric
acid, HCl. It was found that the pH at the equivalence point was 5.91.

(i) Suggest an appropriate indicator for the titration, giving a reason for your choice.

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

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

…………………………………………………………………………………………….… [1]

(ii) Calculate the concentration of CH3CH2NH3+, in mol dm–3, at the equivalence point.

[1]

(iii) Hence, calculate the volume of hydrochloric acid needed to neutralise the ethylamine.

[1]

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(iv) Prove that the initial concentration of ethylamine is 0.102 mol dm–3.

[1]

(v) Hence, calculate the initial pH of ethylamine.

[1]

(vi) A total of 25.00 cm3 HCl was added in this titration. Calculate the final pH of the
resulting solution.

[1]

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(vii) Using the information given in the question and your answers to (b)(iii), (b)(v) and
(b)(vi), sketch the pH changes that occur during the titration when a total of
25.00 cm3 of HCl was added to 20.0 cm3 of an aqueous solution of ethylamine.

Label the following points on your sketch:

 pH and volume at maximum buffer capacity


 pH and volume at equivalence point
 final pH

pH

 volume of HCl
25.00 added / cm3
[2]

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(c) A buffer solution was prepared by mixing 200 cm3 of 0.15 mol dm–3 of phenylamine and
100 cm3 of 0.20 mol dm–3 of HCl.

(i) Calculate the pH of this buffer solution.

[2]

(ii) Write an equation to show how this solution can act as a buffer on the addition of an
alkali.

……………………………………………………………………………………………..... [1]

[Total: 13]

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5 Radical initiators are substances that can produce radicals under mild conditions and promote
radical reactions. These substances generally possess weak bonds. An example of a radical
reaction involving peroxide as the initiator is shown below :

H H
H H H
uv C C
C C + HBr
H peroxide Br
R R H

(a) Explain what is meant by the term radical and explain, with the aid of a diagram, how the
bond in the peroxide initiator, R–O–O–R, would break to produce radicals.

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

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

……………………………………………………………………………………………………… [2]

(b) The mechanism continues with the following steps.

Step 1: The radical produced from the peroxide initiator reacts with a HBr molecule
to generate a Br radical and an alcohol molecule.

Step 2: The Br radical formed approaches an alkene molecule, RCH=CH 2, to form a
stable alkyl radical.

Step 3: The alkyl radical reacts with another HBr molecule to form the organic product
and regenerates the Br radical.

Draw the displayed formula of the stable alkyl radical formed in Step 2 and the final organic
product formed when 2–methylbut–2–ene undergoes this radical reaction with HBr.

stable alkyl radical final organic product


[2]

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(c) Benzoic acid is often added to soft drinks as a preservative in the form of its salt,
e.g. sodium benzoate. However, it is reported that in the presence of ascorbic acid,
benzoic acid can undergo decarboxylation to form benzene, which is a known carcinogen.

The mechanism of this reaction is thought to involve four steps:

Step I: The hydroxyl radical, OH, is produced from the catalysed reduction
of oxygen by ascorbic acid.

Step II: The hydroxyl radical abstracts a proton from benzoic acid to form an
intermediate.

Step III: This intermediate then forms a phenyl radical and carbon dioxide gas.

Step IV: The phenyl radical abstracts a proton from water to produce benzene and
regenerates the hydroxyl radical.

Complete Fig. 5.1 to suggest the mechanism for Step III and Step IV. Show the structural
formulae of the intermediates, the movement of unpaired electron by using curly arrow
( ) and indicate any unpaired electron with a dot (●).

O
OH
H Step II
C
O + H OH

intermediate

Step III

O
HO H
+ OH + C
Step IV O

phenyl radical

Fig. 5.1

[3]

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(d) Fig. 5.2 shows the food label of a bottle of coffee.

Fig. 5.2

Table 5.1 shows the fuel values of some substances found in the bottle of coffee. The fuel
value is the amount of energy generated when one gram of a substance undergoes complete
combustion.

Table 5.1

substance fuel value / kJ g−1


carbohydrate 17
protein 17
fat 38

(i) Energy is provided by the carbohydrates, proteins and fats in the food and drinks
consumed.

If a student uses on average 7 kJ of energy per minute while studying, how many
minutes of this activity can be sustained by the energy obtained from one serving of
bottled coffee?

[2]

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23

Fats are metabolised into carbon dioxide and water when subjected to combustion in a bomb
calorimeter. The reaction of a typical unsaturated fat (triglyceride), C55H98O6, found in the
bottle of coffee is as follows:

153
C55H98O6 + O2 → 55CO2 + 49H2O ∆H = –x kJ mol−1
2

(ii) Using relevant data from Table 5.1, determine the value of x.

[1]

(e) Compounds R and S are structural isomers with the molecular formula of C 6H12O.

Table 5.2 shows results of the chemical tests carried out on R and S.

Table 5.2

observation
test reagent
R S
1 Tollens' reagent grey solid formed grey solid not formed
orange solution orange solution
2 aqueous bromine
remained remained

When R and S were separately subjected to chlorine in the presence of sunlight, both gave
only two monochlorinated products (not including stereoisomers).

Suggest a possible structure for R and S.

R S
[2]

[Total: 12]

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6 Nitrogenous bases such as guanine and thymine contribute to the structure of deoxyribonucleic
acid (DNA). If the compositions of these bases are altered significantly, it may lead to a change in
the DNA structure, which could cause cancer.

The structures of guanine and thymine are given below:

Studies have suggested that consumption of overcooked carbohydrates such as french fries may
lead to cancer. This is partly contributed by the Maillard reaction that takes place during cooking,
which typically occurs on the surface of the cooked food. This reaction occurs at temperatures
above 140 oC.

This question focuses on the Maillard reaction between asparagine and glucose, both of which are
found in potatoes. Fig 6.1 shows the structures of asparagine and glucose.

Fig 6.1

Nucleophilic attack by the amine group in asparagine on the electrophilic carbon of the aldehyde
group in glucose results in an imine, characterised by a carbon–nitrogen double bond. Water is
produced as a by–product.

If food containing this imine is consumed, gastric acid breaks down the imine to produce
acrylamide, a carcinogen. Acrylamide is then metabolised by an enzyme in the body, producing
glycidamide.

Glycidamide has a highly reactive epoxide group (a three–membered ring of two carbon atoms
and an oxygen atom). The lone pair of electrons on a nitrogen atom in guanine (one of the
nitrogenous bases) attacks one of the electrophilic carbon atoms of the epoxide group in
glycidamide. This eventually changes the DNA structure and causes cancer.

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(a) Table 6.1 shows the acrylamide content in some potato products.

Table 6.1

amount of acrylamide
potato product preparation method
(𝑢g / kg)
boiled potato cut into half, lengthwise 69
baked potato cut into half, lengthwise 1270
deep fried potato
cut into strips, lengthwise 4080
(french fries)

(i) Explain why boiled potato has the lowest amount of acrylamide.

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

……………………………………………………………………………………………… [1]

(ii) By considering the preparation method, suggest why deep fried potato has a higher
amount of acrylamide compared to baked potato.

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

……………………………………………………………………………………………… [1]

(b) Some recommendations have been proposed to reduce the production of acrylamide. Explain
why the following methods are effective.

(i) Soak the sliced potatoes in a weak acid, such as vinegar.

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

……………………………………………………………………………………………… [1]

(ii) Soak the sliced potatoes in a solution of amino acid, such as glycine.

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

……………………………………………………………………………………………… [1]

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(c) Using the structures of asparagine and glucose given in Fig 6.1, draw the structure of the
specific imine produced.

[1]

(d) (i) With reference to the structure of glycidamide below, explain why the circled carbon
atom in the epoxide group is more susceptible to nucleophilic attack by guanine.

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

……………………………………………………………………………………………… [1]

(ii) State why the reaction between guanine and glycidamide affects the DNA structure.

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

……………………………………………………………………………………………… [1]

(iii) Guanine reacts with glycidamide as described on page 24. Suggest why glycidamide
does not undergo the same nucleophilic attack by thymine.

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

……………………………………………………………………………………………… [1]

(iv) Phenylethene is a suspected carcinogen like acrylamide. Suggest an explanation for


this.

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

……………………………………………………………………………………………… [1]

[Total: 9]

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ANDERSON SERANGOON JUNIOR COLLEGE
2019 JC 2 PRELIMINARY EXAMINATIONS

CHEMISTRY 9729/03
Higher 2 18 September 2019
Paper 3 Free Response 2 hours
Candidates answer on separate Answer Booklet.

Additional Materials: Answer Booklet


Data Booklet

READ THESE INSTRUCTIONS FIRST

Write your name and class on all the work you hand in.
Write in dark blue or black pen.
You may use a pencil for any diagrams or graphs.
Do not use staples, paper clips, glue or correction fluid.

Section A
Answer all questions.

Section B
Answer one question.

A Data Booklet is provided.


The use of an approved scientific calculator is expected, where appropriate.

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 15 printed pages and 1 blank page.

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Section A
Answer all the questions from this section.

1 (a) Iron(III) cation complexes with a thiocyanate anion (SCN–) to form the iron(III) thiocyanate
complex, [Fe(SCN)]2+ at 298 K, according to the following equation.

Fe3+(aq) + SCN–(aq) ⇌ [Fe(SCN)]2+(aq) H < 0


yellow colourless blood red

(i) Write an expression for Kc for this reaction, stating its units. [2]

(ii) The Kc value of this reaction is 4.99 x 10 2. Calculate the percentage of [Fe(SCN)]2+ in a
Fe3+–[Fe(SCN)]2+ mixture when [SCN–] = 5.00 x 10–3 mol dm–3. [2]

(iii) State and explain the difference in observations when the reaction is carried out at
500 K. [2]

(b) Describe the variations in melting points of the elements sodium to chlorine and explain these
variations in terms of their structures and bonding. [5]

(c) Compounds B, C, D and E are oxides or chlorides of Period 3 elements.

B and C have high melting points while D and E have low melting points.

B is insoluble in water but soluble in hot concentrated sodium hydroxide.

When water was added separately to 0.100 mol each of C, D and E, a neutral solution was
obtained for C while an acidic solution was obtained for D and E. The resulting solution of D
required 0.500 mol of silver nitrate for complete precipitation.

1 mol of E requires 2 mol of aqueous sodium hydroxide for complete neutralisation.

Identify compounds B to E, and write equations for the reactions described above. [6]

[Total: 17]

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2 (a) Helium is used to fill party balloons.

A 60.0 dm3 industrial tank of helium gas at 27 °C and 125 atm was used to fill up some balloons.
After some balloons were filled, the pressure in the tank was reduced to 50 atm.

(i) How many moles of helium was used to fill the balloons? [2]

(ii) Assuming each filled balloon is a sphere with a radius, r, of 0.15 m and has an internal
pressure of 1.2 atm, what is the maximum number of balloons that can be filled with the
remaining gas in the tank at the same temperature?

3
4r
(volume of sphere = )
3
[2]

(iii) State and explain if helium gas behaves more ideally in the tank, or when present in
balloons. [2]

(b) (i) Using the thermochemical data shown in Table 2.1, draw a fully labelled energy cycle to
calculate the standard enthalpy change of combustion of liquid propan–2–ol.

Table 2.1

Standard enthalpy change of formation of liquid propan–2–ol –318 kJ mol–1


Standard enthalpy change of combustion of carbon –394 kJ mol–1
Standard enthalpy change of formation of water –286 kJ mol–1
Standard enthalpy change of vapourisation of water +41 kJ mol–1
[2]

(ii) By using your answer to (b)(i), and relevant data from the Data Booklet and Table 2.1,
calculate the standard enthalpy change of vapourisation of propan–2–ol. [2]

(iii) Hence, explain why combustion of liquid propan–2–ol takes place at all temperatures.
[2]

(c) (i) State and explain how the acidities of 2–methylpropan–2–ol,


2–chloro–2–methylpropanoic acid and 2,2–dimethylpropanoic acid might compare with
each other.

(CH3)3COH (CH3)3CCO2H
2–methylpropan–2–ol 2,2–dimethylpropanoic acid

(CH3)2CClCO2H
2–chloro–2–methylpropanoic acid
[3]

(ii) Outline how 2,2–dimethylpropanoic acid may be produced from


2–chloro–2–methylpropane, (CH3)3CCl. Include the structure of the intermediate
compound in your answer. [3]

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5

(iii) Grignard reagents, with different alkyl or aryl groups (R’–MgBr), react with carbonyl
compounds to yield alcohols.

O OH
R'-MgBr
C C + Mg(OH)Br
R'' R (or H) + R' R''
followed by H3O R (or H)

Use the above information to suggest a synthesis of 2–methylpropan–2–ol from


2–chloropropane according to the scheme in Fig. 2.1. Include reagents and conditions for
all steps, and the structures of the intermediate organic compounds, G and H, in your
answer.

Step 1 Step 2 Step 3


(CH3)2CHCl G H (CH3)3COH
2–chloropropane 2–methylpropan–2–ol

Fig. 2.1
[5]

[Total: 23]

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3 (a) Nitrate, NO3–, and phosphate, PO43–, are oxoanions of nitrogen and phosphorous
respectively.

(i) Draw dot–and–cross diagrams to show the bonding in NO 3– and PO43–. Hence, suggest
the shape of each of these ions. [3]

(ii) The 2s and 2p orbitals of nitrogen atoms can hybridise in the same way as the 2s and
2p orbitals of carbon atoms.

Suggest the hybridisation state of nitrogen in NO3–. [1]

(iii) Table 3.1 shows the bond lengths of two nitrogen–oxygen bonds.

Table 3.1

Bond N–O N=O

Bond length (pm) 136 115

The experimental bond length of each nitrogen–oxygen bond in the nitrate ion, NO3–,
is 128 pm.

By reference to your answers to (a)(i) and (a)(ii), explain this observed bond length in
NO3–. [1]

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(b) Fig. 3.1 shows the synthesis of compound K from phenylamine.

O O

step 1 step 2 step 3

NH2 NHCOCH3
NHCOCH3 NH2

NaNO2
step 4 HCl

CH3CH2ONa
O
followed by
O O
N
Cl H 2O

O step 6 step 5
OH N N
N
K

Fig. 3.1

(i) Suggest the reagents and conditions in steps 1 and 2. [2]

(ii) Explain why step 1 needs to be carried out before step 2. [1]

(iii) Explain why step 6 would not occur in the absence of sodium ethoxide, CH3CH2ONa.
[1]

The reaction in step 6 is carried out in a suitable solvent and is found to be bimolecular.

(iv) Describe the mechanism for this reaction. In your answer, you should show all charges,
lone pairs and the movement of electrons using curly arrows.

You may use R to represent any part of the molecule that does not take part in the
reaction. [3]

(v) Predict the effect on the rate of the reaction in step 6 if the volume of solvent used is
doubled. [1]

(vi) Explain whether compound K or phenol undergoes electrophilic substitution more


readily. [2]

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(c) Both acetanilide and 4–aminoacetophenone are solids at room temperature and pressure.

NHCOCH3 H2N COCH3

acetanilide 4-aminoacetophenone

(i) Suggest and explain, with the aid of equations, the solubility of each of the compounds
in HCl(aq). [3]

(ii) Using your answer to (c)(i), outline how these two compounds could be separated from
each other in a mixture and recovered in their original solid forms using chemicals
normally found in the laboratory. [2]

[Total: 20]

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Section B
Answer one question from this section.

4 (a) Alkenes have many diverse industrial applications. They are used as starting materials for
many chemicals.

One of the reactions of alkenes involves the addition of hydrogen to form alkanes. This
process of hydrogenation of alkenes at room temperature requires the use of a catalyst. The
Wilkinson’s catalyst precursor, RhCl(PPh)3 (where Ph represents a phenyl group), is one of
them.

When the Wilkinson’s catalyst precursor was added to propene dissolved in benzene with
hydrogen gas being passed through the solution, the following dissociation took place:

Fig. 4.1 shows the proposed mechanism for the hydrogenation of propene.

Fig. 4.1

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11

(i) Triphenylphosphine, PPh3, is a ligand in the Wilkinson’s catalyst precursor,


RhCl(PPh3)3.

Explain what is meant by the term ligand. [1]

(ii) Determine the oxidation state of rhodium in RhCl(PPh3)3. [1]

(iii) The species in the equations shown in Fig. 4.1 have various roles. They can be
reactants, products, catalysts or intermediates.

Suggest, with a reason in each case, the roles of the species M and N. [2]

(iv) Rhodium can also form octahedral complexes with bidentate ligands like
ethane–1,2–diamine, en.

Copy and complete the diagram below to suggest the structure for this complex.

(You may use to represent en.) [1]

(b) Scientists have recently made vanadium into a useful catalyst for hydrogenation.

Vanadium was named after Vanadis, the Scandinavian goddess of beauty, because of the
wide range of colours it exhibits in its complexes.

(i) Explain why a solution of [V(H2O)6]2+ is violet whereas a solution of [V(H2O)6]3+ is green.
[1]

(ii) Nitric acid is an oxidising agent.

NO3– + 4H+ + 3e– ⇌ NO + 2H2O Eo = +0.96 V

Predict the products of, and write an equation for the reaction that occurs when nitric
acid is added to a solution containing V2+(aq) ions. [2]

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(c) Alkenes can be hydrated to form alcohols using various reagents. One such reagent is
concentrated sulfuric acid.

Alkenes react with concentrated sulfuric acid in the cold to produce alkyl hydrogensulfates.
Addition of water with heating then produces the alcohol product.

(i) Suggest a mechanism for the reaction of propene with concentrated sulfuric acid to
produce the alkyl hydrogensulfate as shown.

OSO3H

isopropyl hydrogensulfate

Show the displayed structure of the electrophile, the structure of the intermediate and
the movement of electron pairs by using curly arrows. [3]

(ii) Explain why is preferentially produced instead of .


OSO3H
[1]

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(d) Chromium(VI) is an important high oxidation state chromium and it occurs in two well–known
anions, chromate(VI), CrO42–, and dichromate(VI), Cr2O72–.

Acidified potassium dichromate(VI) is a common oxidising agent that can be used to oxidise
sulfur dioxide.

(i) Construct a balanced equation for the reaction between acidified potassium
dichromate(VI) and sulfur dioxide. [1]

(ii) Calculate the Eocell and hence, the standard Gibbs free energy change for this reaction.
[2]

(iii) Both potassium dichromate(VI) and potassium manganate(VII) are useful oxidising
agents in organic chemistry.

The scheme shown in Fig. 4.2 shows the different products formed when compound P
is oxidised by potassium dichromate(VI) and potassium manganate(VII).

Q
hot acidified (C9H6O6)
KMnO4
P
(C12H14O3)
HBr(g)
hot acidified S
K2Cr2O7

Fig. 4.2

Compound P does not react with an acid or a base at room temperature.

Suggest the structures of compounds P, Q and S. [3]

(iv) Compound R can also be converted to compound T which contains an acyl chloride
and an alkyl chloride functional groups.

COCl

COCl
2
Cl
1

Explain the different reactivities of the two chlorine atoms, Cl 1 and Cl 2, in T. [2]

[Total: 20]

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5 Metals like cobalt and nickel have been widely used since ancient times.

(a) In the presence of ligands, the d–orbitals in a transition metal ion are split into two levels.

Fig. 5.1 shows how the d–orbitals are split in an octahedral environment.

energy gap

degenerate d–orbitals
in an isolated gaseous d–orbitals in an
atom octahedral
environment

Fig. 5.1

In a ‘high spin’ state, the electrons occupy all the d–orbitals singly, before starting to pair up
in the lower energy d–orbitals.

In a ‘low spin’ state, the lower energy d–orbitals are filled in first, by pairing up if necessary,
before the higher energy d–orbitals are used.

(i) Use diagrams like the one above to show the electronic distribution of the cobalt(II) ion
in a high spin state, and in a low spin state. Label your diagrams. [2]

(ii) Transition elements with unpaired 3d electrons are paramagnetic. In the presence of
a magnetic field, these unpaired electrons align themselves in such a way that they
are attracted to the field. The strength of paramagnetism shown in transition metal
complexes depends on the total number of unpaired 3d electrons.

Using your answer from (a)(i), explain which spin state of the cobalt(II) ion is relatively
more paramagnetic. [1]

When air is bubbled through an aqueous solution containing CoCl2, NH4Cl and NH3, and the
resulting solution evaporated, crystals of a salt can be isolated. , which contains an
octahedral cation, has the following composition by mass:

Co, 25.2%; N, 24.1%; H, 5.1%; Cl, 45.6%

(iii) Calculate the empirical formula of . [1]

(iv) On adding an excess of AgNO 3(aq) to an aqueous solution containing 0.01 mol of ,
1.43 g of AgCl(s) is precipitated.

The cation in  can exist as two isomers. One of the isomers of the cation in  has no
net dipole moment. Draw the structure of this cation. Show clearly the arrangement of
the ligands and the oxidation number of the central metal ion in your diagram. [2]

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15

(b) The nickel–cadmium (Ni–Cd) battery is a common rechargeable battery used in portable
power tools and emergency lightings. It is made up of a cadmium electrode, Cd, and nickel
oxyhydroxide electrode, NiO(OH), immersed in sodium hydroxide.

During discharge, cadmium hydroxide, Cd(OH)2, is deposited at the cadmium electrode.

Cd(s) + 2OH–(aq)  Cd(OH)2(s) + 2e–

Nickel(II) hydroxide, Ni(OH)2, is formed at the nickel oxyhydroxide electrode.

(i) Construct a half–equation for the reaction that occurs at the cathode during discharge
and hence, write the equation for the overall reaction during discharge. [2]

(ii) When a Ni–Cd battery is recharged, Cd(OH)2 is converted back to Cd. Given that the
charging process is 86% efficient, how many hours does it take to restore 5.5 g of Cd
metal using a current of 2.0 A? [3]

(c) Reduction reactions involving organic compounds are commonly carried out using reducing
agents like hydrogen gas with nickel metal catalyst and lithium aluminium hydride, LiAlH4.

Compound F is reacted with both as shown in Fig. 5.2.

LiAlH4 I

O H O
HO C CH CH C C NH2
CN
H2 , Ni
F J

Fig. 5.2

Draw the structures of products I and J. [2]

(d) Compound W, C9H9NO4, rotates plane–polarised light. W reacts with tin and concentrated
hydrochloric acid, followed by careful neutralisation to give compound X, C9H11NO2.

X liberates carbon dioxide with sodium hydrogencarbonate and decolourises


aqueous bromine to give Y, C9H9NO2Br2. When X reacts with PCl5, compound Z, C9H9NO,
is formed.

Deduce the structures of W, X, Y and Z, stating clearly your reasoning. [7]

[Total: 20]

ASRJC JC2 PRELIMS 2019 9729/03/H2 [Turn over


ANDERSON SERANGOON JUNIOR COLLEGE
2019 JC 2 PRELIMINARY EXAMINATIONS

NAME:______________________________ ( ) CLASS: 19 /____

CHEMISTRY 9729/04
Paper 4 Practical 27 August 2019
2 hours 30 minutes

Candidates answer on the Question Paper.


Additional Materials: As listed in the Confidential Instructions

READ THESE INSTRUCTIONS FIRST

Write your name, class and index number on all the work you hand in.
Give details of the practical shift and laboratory where appropriate, in the boxes provided.
Write in dark blue or black pen.
You may use a pencil for any diagrams, graphs or rough working.
Do not use staples, paper clips, glue or correction fluid.

Answer all questions in the spaces provided on the Question Paper.

The use of an approved scientific calculator is expected, where appropriate.


You may lose marks if you do not show your working or if you do not use appropriate units.
Quantitative Analysis Notes are printed on pages 22 and 23.

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.

Shift For Examiner’s Use

Laboratory 2

Total

This document consists of 23 printed pages.

ASRJC JC2 PRELIMS 2019 9729/04/H2 [Turn over


2

Answer all the questions in the spaces provided.

1 To determine the order of reaction with respect to the concentration of iodine in the
iodination of propanone reaction

FA 1 is 1.00 mol dm–3 propanone, CH3COCH3


FA 2 is 1.00 mol dm–3 sulfuric acid, H2SO4
FA 3 is an aqueous solution of iodine, I2
FA 4 is 0.0100 mol dm–3 sodium thiosulfate, Na2S2O3
FA 5 is 0.50 mol dm–3 sodium hydrogencarbonate, NaHCO 3

You are also provided with a starch indicator.

The iodination of propanone, to form iodopropanone, proceeds as shown in the equation below.

Reaction 1: CH3COCH3(aq) + I2(aq) → CH3COCH2I(aq) + HI(aq)

This reaction is first order with respect to both CH3COCH3 and H+ ions.

You are to investigate the order of reaction with respect to I2.

A reaction mixture containing FA 1, FA 2, and FA 3 is first prepared. At different chosen times,


aliquots (fixed volumes) of this reaction mixture is removed and quenched using excess FA 5.

The remaining amount of I2 at different times can then be determined by titration against FA 4.
Each titration can only be performed once.

Reaction 2: 2S2O32–(aq) + I2(aq) → 2I–(aq) + S4O62–(aq)

The required order of reaction can be obtained by the graphical analysis of your results.

The first aliquot should be removed approximately 4 minutes after the reagents were mixed. You
will then remove four further aliquots, at time intervals of your choice, up to a maximum time of
20 minutes.

Prepare a table in the space provided on page 4 in which to record, to an appropriate level of
precision, your chosen time, the actual time and your titration results for each of your aliquots. All
values of actual time should be converted to decimal value, t, in minutes and recorded to one
decimal place.

For example if actual time = 4 min 33 s then t = 4 min + 33/60 min = 4.6 min

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3

Experiment

Safety: Propanone is flammable. Transfer your titrated solutions into the waste bottle for later
disposal. Keep this bottle stoppered when not in use.

Keep the conical flask (reaction mixture) stoppered except when removing aliquots.

Preparing the boiling tubes

1. Label each of the boiling tubes with one of your chosen times.
2. Add approximately 10 cm3 of FA 5 to each of these boiling tubes.

Preparing the reaction mixture

3. Using a pipette, transfer 25.0 cm3 of FA 1 into the 100 cm3 beaker.
4. Using a different pipette, transfer 25.0 cm3 of FA 2 into the same 100 cm3 beaker.
5. Using a burette, transfer 50.00 cm3 of FA 3 into the 250 cm3 conical flask, labelled reaction
mixture.
6. Pour the contents of the 100 cm3 beaker into this 250 cm3 conical flask. Start the stopwatch,
insert the stopper and swirl the mixture thoroughly. Once you have started the stopwatch,
allow it to continue running for the duration of the experiment. You must not stop the
stopwatch until you have collected all of your aliquots.

Removing aliquots of reaction mixture

7. At approximately 4 minutes, using a 10.0 cm3 pipette, remove a 10.0 cm3 aliquot of the
reaction mixture. Immediately transfer this aliquot into the boiling tube labelled 4 minutes
and swirl the mixture. Note the actual time when half of the reaction mixture has emptied
from the pipette. Replace the stopper in the flask.
8. At each of your chosen times, repeat step 7 but transfer each aliquot to its appropriately
labelled boiling tube.

Titrations

9. Pour the whole of the contents of a boiling tube into a clean 250 cm3 conical flask. Wash
out the boiling tube and add the washings to the conical flask.
10. Titrate the iodine in this solution with FA 4. Add about 1 cm3 of starch indicator when the
colour of the solution turns pale yellow. The solution will turn blue–black. The end–point is
reached when the dark blue–black colour just disappears. Record your results.
11. Empty the contents of this conical flask into the waste bottle. Wash this conical flask
thoroughly with water.
12. Repeat steps 9 to 11 for each of your boiling tubes.

ASRJC JC2 PRELIMS 2019 9729/04/H2 [Turn over


5

(b) (i) On Fig 1.1, plot a graph of volume of sodium thiosulfate, FA 4, on the y–axis, against
time, t, on the x–axis. Start the x–axis at t = 0. You should choose a scale which will
allow you to extrapolate your graph back to t = 0.

Draw the most appropriate best–fit line taking into account all of your plotted points.

Fig 1.1
[2]

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6

(ii) Deduce the order of reaction with respect to the I2 in reaction 1. Explain your answer.

order................................................................................................................................

explanation......................................................................................................................

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

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

(c) (i) Write the rate equation for the iodination of propanone.

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

(ii) Calculate the gradient of the line you have drawn in Fig 1.1, showing clearly how you
did this.

gradient = ........................................
[1]

(iii) Use your answer from (c)(ii) to determine the rate of change of amount of S 2O32– ions
required in mol min–1.

rate of change of amount of S2O32– ions required = ............................ mol min–1


[1]

(iv) Hence, deduce the rate of disappearance of I2 in mol min–1.

rate of disappearance of I2 = ............................ mol min–1


[1]

ASRJC JC2 PRELIMS 2019 9729/04/H2


7

(v) Use your answer from (c)(iv) to calculate the rate of change of [I2] in the reaction
mixture.

rate of change of [I2] in the reaction mixture = ............................................


[1]

(vi) Hence, calculate the value of the rate constant for this reaction.

rate constant = ............................................


[1]

(d) Step 7 requires you to mix each aliquot immediately with an excess of sodium
hydrogencarbonate solution, FA 5. Suggest a clear explanation for this requirement.

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

…………………………………………………………………………………………………….... [1]

(e) Explain why the concentration of iodine in FA 3 is very much lower than the concentrations
of propanone in FA 1 and of H+ ions in FA 2.

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

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

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

…………………………………………………………………………………………………….... [1]

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8

(f) Planning

The Finkelstein reaction can be used to synthesise 1–iodopropane, a colourless liquid, from
1–bromopropane and sodium iodide. The reaction is carried out using dry propanone as a
solvent.

CH3CH2CH2Br + NaI ⇌ CH3CH2CH2I + NaBr

(i) What type of reaction is the Finkelstein reaction?

……………………………………...……………………………………………………….. [1]

(ii) Explain why it is important for dry propanone to be used as a solvent for this reaction.

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

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

(iii) Table 1.1 shows the solubilities of sodium bromide and sodium iodide in propanone.

Table 1.1

solubility at 25 °C
compound
in g / 100 g of propanone

sodium bromide 0.00841

sodium iodide 39.9

Use this information to explain why, although the reaction between CH 3CH2CH2Br and
NaI is reversible, the reaction produces a very high yield of CH3CH2CH2I.

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

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

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

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

ASRJC JC2 PRELIMS 2019 9729/04/H2


9

Sodium iodide is a white crystalline solid.


1–bromopropane is a colourless liquid which has a density of 1.35 g cm–3.

Table 1.2 gives the boiling points of 1–bromopropane, 1–iodopropane and propanone.

Table 1.2

compound boiling point / oC

1–bromopropane 71.0

1–iodopropane 102.6

propanone 56.0

A 100% yield of pure 1–iodopropane is assumed to be obtained using the procedure


described below:

1–bromopropane, an excess of sodium iodide and propanone solvent are mixed and then
heated under reflux conditions for around thirty minutes.

The crude 1–iodopropane product is distilled to produce the pure 1–iodopropane.

[Ar: C, 12.0; H, 1.0; O, 16.0; Br, 79.9; I, 126.9; Na, 23.0]

(iv) Calculate the minimum volume of 1–bromopropane you would use to prepare 10 g of
pure 1–iodopropane, showing your working.

[1]

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10

(v) Write a plan for the preparation of about 10 g of pure 1–iodopropane.

In your plan you should:

 give a full description of the procedures you would use to prepare the crude
1–iodopropane;
 draw a labelled diagram of the assembled apparatus you would use to obtain
the pure 1–iodopropane.

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

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

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

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

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

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

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

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

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

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

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

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

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12

2 Investigation of the dissolution of potassium iodide and lithium chloride in water

Both KI and LiCl can dissolve in water to give aqueous solutions.

KI(s) → K+(aq) + I(aq) H > 0

LiCl(s) → Li+(aq) + Cl(aq) H < 0

The temperature change when a mixture containing KI and LiCl dissolves in water is due to the
summation of the temperature change when KI and LiCl dissolve separately in water.

FA 6 is a mixture containing equal masses of potassium iodide, KI, and lithium chloride, LiCl.

The T per gram of LiCl dissolved in water may be found by first determining the relationship between
mass of KI dissolved in water and the change in temperature of the water due to its dissolution. The
temperature change when FA 6 dissolves completely in water is then determined.

(a) Determination of the value of the decrease in temperature, TKI, for the dissolution of KI
in water

(i) You will follow the instructions to perform the following experiment.

1. Weigh accurately about 2.0 g of KI using a weighing bottle.


2. Using a measuring cylinder, transfer 25 cm3 of deionised water into a Styrofoam cup.
Place the cup inside a second Styrofoam cup, which is placed in a 250 cm 3 beaker.
3. Stir and measure the initial temperature of the water in the Styrofoam cup.
4. Add the KI in the weighing bottle into the water in the Styrofoam cup.
5. Stir the mixture continuously until it reaches its minimum temperature. Record this
temperature.
6. Reweigh the weighing bottle.
7. In an appropriate format in the space below, record all measurements of mass and
temperature.
8. Calculate the value of the decrease in temperature, TKI, for this experiment.

Results

[4]

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13

(ii) Using the mass of KI and TKI obtained in (a)(i), together with the data in Table 2.1, plot
a graph of TKI against the mass of KI used on the grid in Fig 2.1.
Draw the most appropriate line, taking into account all of the plotted points.

Table 2.1

decrease in temperature,
mass of KI / g
TKI / C
4.00 4.1
6.00 6.2

TKI / C 8.00 7.8

12

10

0
0 1 2 3 4 5 6 7 8
mass of KI / g

Fig 2.1
[1]

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14

(b) Determination of the maximum temperature change, Tm, for the dissolution of FA 6 in
water

The maximum temperature change, Tm, when FA 6 dissolves completely in water was
determined by measuring the temperature at timed intervals. The mass of FA 6 used in the
experiment was 6.020 g.

The results from this experiment are plotted on the grid in Fig 2.2 on Page 16.

Draw two best–fit lines, the first taking into account the points before the FA 6 was added and
the second taking into account the points after the reaction had finished.

Extrapolate both lines to four minutes.

Determine a value for the maximum temperature change, Tm, at t = 4.0 min using the graph.

Tm = ……………………………..C
[2]

(c) (i) Using the graph in (a)(ii), determine the change in temperature due to the dissolution of
potassium iodide in FA 6.

TKI = ………………………C
[1]

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15

(ii) Using your results in (b) and (c)(i), determine the change in temperature due to the
dissolution of lithium chloride in FA 6.

TLiCl= ………………………C
[1]

(iii) Hence, show clearly how the T per gram of LiCl dissolved in water can be determined.

T per gram of LiCl = …………………………….C g1


[3]

ASRJC JC2 PRELIMS 2019 9729/04/H2 [Turn over


16

52.0

50.0

48.0

46.0

44.0

42.0

T / C 40.0

38.0

36.0

34.0

32.0

30.0

28.0
0.0 2.0 4.0 6.0 8.0 10.0 12.0 14.0 16.0 18.0 20.0 22.0 24.0 t / min

Fig 2.2

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17

(d) Planning

When solid hydrated barium chloride, BaCl2.xH2O, dissolves in water, Ba2+(aq) and Cl–(aq)
ions are formed.

The concentration of dissolved chloride ions in a solution can be determined by titration with
aqueous silver nitrate of known concentration.

Ag+(aq) + Cl–(aq) → AgCl(s)

Potassium chromate(VI), K2CrO4(aq), can be used as the indicator for the reaction. At the
end–point of the titration, it forms a red precipitate in the presence of excess silver ions.

The solubilities, in mol dm–3, of the various ionic solids at 20 C are given in Table 2.2.

Table 2.2

anion
cation Cl– CrO42– SO42–
Ag+ 1.32 x 10–5 6.63 x 10–5 0.940
Ba2+ 1.72 1.10 x 10–5 1.05 x 10–5

E.g. the solubility of AgCl at 20 C = 1.32 x 10–5 mol dm–3

Sulfuric acid must be added to the solution to prevent the Ba 2+(aq) ions from interfering with
the action of the potassium chromate(VI) indicator.

(i) How would Ba2+(aq) ions interfere with the action of this indicator?

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

……………………………………………………………………………………………...… [1]

(ii) How does the addition of sulfuric acid prevent Ba 2+(aq) ions from interfering with the
action of this indicator?

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

……………………………………………………………………………………………...… [1]

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18

(iii) In an initial rough titration, excess silver nitrate solution is added so that the end–point
is exceeded.

Draw a sketch graph to show how the mass of silver chloride varies with the volume of
silver nitrate added.

mass of AgCl

0
volume of AgNO3
[1]

You are provided with the apparatus normally used in a school laboratory and the following
materials:

3.00 g of hydrated barium chloride, BaCl2.xH2O


0.050 mol dm–3 aqueous silver nitrate
1.0 mol dm–3 potassium chromate(VI) solution
1.0 mol dm–3 sulfuric acid

(iv) Describe how you would prepare a solution of barium chloride that is suitable for use in
your titration. You should give details of any apparatus used.

……………………………………………………………………………………………………

……………………………………………………………………………………………………

……………………………………………………………………………………………………

……………………………………………………………………………………………………

……………………………………………………………………………………………...… [2]

(v) A known volume of the barium chloride solution you have prepared in (d)(iv) is
transferred to a conical flask.

In what order should the other three solutions then be added to the flask?

first….……………………………………………………………………………………….……

second……………………………………………………………………………………………

third………………………………………………………………………………………….……
[1]

[Total: 18]

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19

3 (a) Carry out the following tests on FA 7 which contains two cations and one anion from the
following list: NH4+, Mg2+, Al3+, Ca2+, Cr3+, Mn2+, Fe2+, Fe3+, Cu2+, Zn2+, CO32–, NO3–, NO2–,
SO32–, SO42–, Cl–, Br –, I–.

Carefully record your observations in the space provided in Table 3.1.

Unless otherwise stated, the volumes given below are approximate and should be estimated
rather than measured. Test and identify any gases evolved.

Table 3.1

test observations
1. Add 1 cm depth of FA 7 to a
test–tube.

Add aqueous ammonia slowly, with


shaking, until no further change is
seen.

Filter the mixture and add dilute nitric


acid drop–wise to the filtrate, until no
further change is seen.

(You may continue with test 2, while


waiting for the filtration process to
complete.)

2. Add 1 cm depth of FA 7 to a
test–tube.

Add aqueous barium nitrate,

followed by dilute nitric acid.

[3]

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20

Summary

Identify the ions present in FA 7. Use evidence from your observations in Table 3.1 to support
your deductions on the identification of the cations in FA 7.

FA 7 contains the cations …………………………… and ……………………………

evidence ……………………………………………………………………………………...………..

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

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

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

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

FA 7 contains the anion …………………………… [2]

FA 8 is an aqueous solution of FeCl3.

(b) (i) Perform the tests described in Table 3.2, and record your observations in the table.

Test and identify any gases evolved. If there is no observable change, write no
observable change.

Table 3.2

test observations
1. Add 1 cm depth of FA 8 to a
test–tube.

Add FA 4 slowly, with shaking,


until no further change is seen.

Leave it to stand.

2. Add 1 cm depth of FA 8 to a
test–tube.

Add 1 cm depth of FA 5, with


shaking, until no further change is
seen.

3. Add 1 cm depth of FA 8 to a
test–tube.

Add 1 cm depth of aqueous


potassium iodide, with shaking,
until no further change is seen.

[2]

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21

(ii) Explain your observation(s), in test 2 in Table 3.2, in terms of the chemistry involved.

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

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

………………………………………………………...…………………………………….. [2]

Table 3.3 gives some standard electrode potential values.

Table 3.3

electrode reaction Eo / V
Fe3+ + e– ⇌ Fe2+ +0.77
[Fe(CN)6]3– + e– ⇌ [Fe(CN)6]4– +0.36
I2 + 2e– ⇌ 2I– +0.54

(iii) Explain the observation(s), in test 3 in Table 3.2, in terms of the chemistry involved.

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

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

………………………………………………………...…………………………………….. [2]

(iv) Consider your observation(s) when aqueous potassium iodide was added to FeCl3
solution in test 3 in Table 3.2. No such colour change was observed when aqueous
potassium iodide was added to a solution containing [Fe(CN)6]3– ions.

Use data from Table 3.3 to explain the observations and comment on the difference in
observations in terms of the stability of the [Fe(CN)6]3– ion and the iron–containing
complex ion in FeCl3.

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

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

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

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

………………………………………………………...…………………………………….. [2]

(v) State what you would expect to observe when an equal volume of hexane is added to
the mixture you have obtained in test 3 in Table 3.2.

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

………………………………………………………...…………………………………..… [1]

[Total: 14]

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22

Qualitative Analysis Notes


[ppt. = precipitate]

(a) Reactions of aqueous cations

reaction with
cation
NaOH(aq) NH3(aq)
aluminium, white ppt. white ppt.
Al3+(aq) soluble in excess insoluble in excess
ammonium,
ammonia produced on heating –
NH4+(aq)
barium,
no ppt. (if reagents are pure) no ppt.
Ba2+(aq)
calcium,
white ppt. with high [Ca2+(aq)] no ppt.
Ca2+(aq)
grey–green ppt.
chromium(III), grey–green ppt.
soluble in excess
Cr3+(aq) insoluble in excess
giving dark green solution
blue ppt.
copper(II), pale blue ppt.
soluble in excess
Cu2+(aq) insoluble in excess
giving dark blue solution
green ppt. turning brown on contact green ppt. turning brown on contact
iron(II),
with air with air
Fe2+(aq)
insoluble in excess insoluble in excess
iron(III), red–brown ppt. red–brown ppt.
Fe3+(aq) insoluble in excess insoluble in excess
magnesium, white ppt. white ppt.
Mg2+(aq) insoluble in excess insoluble in excess
off–white ppt. rapidly turning brown off–white ppt. rapidly turning brown
manganese(II),
on contact with air on contact with air
Mn2+(aq)
insoluble in excess insoluble in excess
zinc, white ppt. white ppt.
Zn2+(aq) soluble in excess soluble in excess

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23

(b) Reactions of anions

ion reaction
carbonate,
CO2 liberated by dilute acids
CO32–
chloride,
gives white ppt. with Ag+(aq) (soluble in NH3(aq))
Cl–(aq)
bromide,
gives pale cream ppt. with Ag+(aq) (partially soluble in NH3(aq))
Br–(aq)
iodide,
gives yellow ppt. with Ag+(aq) (insoluble in NH3(aq))
I–(aq)
nitrate,
NH3 liberated on heating with OH–(aq) and Al foil
NO3–(aq)
NH3 liberated on heating with OH–(aq) and Al foil
nitrite,
NO liberated by dilute acids
NO2–(aq)
(colourless NO  (pale) brown NO2 in air)
sulfate,
gives white ppt. with Ba2+(aq) (insoluble in excess dilute strong acids)
SO42–(aq)
sulfite, SO2 liberated on warming with dilute acids;
SO32–(aq) gives white ppt. with Ba2+(aq) (soluble in dilute strong acids)

(c) Tests for gases

gas test and test result


ammonia, NH3 turns damp red litmus paper blue
carbon dioxide, CO2 gives a white ppt. with limewater
(ppt. dissolves with excess CO2)
chlorine, Cl2 bleaches damp litmus paper
hydrogen, H2 “pops” with a lighted splint
oxygen, O2 relights a glowing splint
sulfur dioxide, SO2 turns aqueous acidified potassium manganate(VII) from purple to colourless

(d) Colour of halogens

halogen colour of element colour in aqueous solution colour in hexane


chlorine, Cl2 greenish yellow gas pale yellow pale yellow
bromine, Br2 reddish brown gas / liquid orange orange–red
iodine, I2 black solid / purple gas brown purple

ASRJC JC2 PRELIMS 2019 9729/04/H2

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