2016 Chemistry H1 JC2 Meridian Junior College

Class Reg Number

Candidate’s Name: ___________________________
MERIDIAN JUNIOR COLLEGE

JC 2 Preliminary Examination
Higher 1
________________________________________________________________________
Chemistry 8872/01
23 September 2016
Paper 1 Multiple Choice
50 minutes
Additional Materials: OMR Sheet and Data Booklet
________________________________________________________________________
READ THESE INSTRUCTIONS FIRST
This booklet contains Section A of your paper.
Write your name, class and register number in the spaces provided at the top of this page.
There are thirty questions in this section. Answer all questions. For each question, there are four
possible answers labelled A, B, C and D. Choose the one you consider correct and record your
choice in soft pencil on the OMR answer sheet.
Read very carefully the instructions on the use of OMR answer sheet.
You are advised to fill in the OMR Answer Sheet as you go along; no additional time will be given for
the transfer of answers once the examination has ended.
Use of OMR Answer Sheet
Ensure you have written your name, class register number and class on the OMR Answer
Sheet.
Use a 2B pencil to shade your answers on the OMR sheet; erase any mistakes cleanly.
Multiple shaded answers to a question will not be accepted.
For shading of class register number on the OMR sheet, please follow the given examples:
If your register number is 1, then shade 01 in the index number column.
This document consists of 13 printed pages (including this cover page).
MJC Prelim 2016 1 © chemistry unit @ mjc

Section A
For each question there are four possible answers, A, B, C, and D. Choose the one
you consider to be correct.

1 The use of Data Booklet is relevant to this question.
Which of the following contains the most number of particles?
A Number of atoms in 9 dm3 of O2 gas at r.t.p.

B Number of ions in 600 cm3 of 0.5 mol dm–3 H2SO4 solution
C Number of electrons in 3.01 x 1022 Ca atoms
D Number of hydrogen atoms in 7 g of ammonia

2 20 cm3 of a hydrocarbon, CxHy, was burnt in 130 cm3 of excess oxygen.
After the combustion, the mixture was cooled to r.t.p and was found to occupy
a volume of 110 cm3. The remaining gases was passed through an excess of
aqueous alkali and the volume of gas is reduced to 30 cm3.
What is the molecular formula of this hydrocarbon?
A C4 H 4 B C4H6 C C4 H8 D C4H10

3 The red colouration in fireworks is caused by the reaction between
calcium nitrate and carbon. During a firework display, the reaction produces
calcium oxide and three gases; CO2, CO and nitrogen oxide, W.
An analysis of these gases revealed that the mole ratio of these 3 gases is
1: 2: 1 respectively.
What is gas W?
A N2O4 B N2O C NO D NO2


4 Sodium nitrate(V), NaNO3 decomposes on heating to form NaNOx and
oxygen.
8.50 g of NaNO3 was heated until a constant mass. The residue was dissolved
in water to prepare 1.00 dm3 of solution. 10.00 cm3 of this solution was reacted
against 30.00 cm3 of 0.0200 mol dm–3 of acidified potassium manganate(VII)
solution.
The excess potassium manganate(VII) solution required 10.00 cm3 of

0.0500 mol dm–3 ethanedioate solution for complete reaction as shown by the
equation below:
2MnO4– + 5(COO)22– + 16H+ 

 2Mn2+ + 10CO2 + 8H2O
What is the final oxidation state of nitrogen in NaNOx?
A +1 B +2 C +3 D +5
5 Chromium(III) oxide, Cr2O3, can undergo different reactions to give other

chromium–containing species as shown in the diagram below:
Al
Cr metal Cr2O3 CrO42– Cr2O72–
CrO3
CrO2
Which statement correctly describe these reactions?
A The formation of Cr2O72– from CrO42– is a redox reaction.

B Cr2O3 reacts with CrO3 in a disproportionation reaction to give CrO2.
C CrO3, CrO42–, Cr2O72– contains chromium in its highest oxidation state.
D Aluminium is acting as an oxidising agent.
6 Which species has two unpaired electrons?
A Cl+ B Mg C P D S2–

7 Use of the Data Booklet is relevant to this question.
What do these ions, 40Ca2+ and 31P3–, have in common?
A Both ions are isoelectronic.

B Both ions have more neutrons than protons.
C Both ions contain the same number of neutrons.
D Both ions have similar magnitudes of deflection in an electric field.
8 When one propanal molecule reacts with one hydrogen cyanide molecule by
addition reaction, how many bonds are broken and formed?
CH3CH2CHO + HCN 
 CH3CH2CH(CN)OH
number of  bonds number of  bonds number of  bonds

broken broken formed
A 0 1 3
B 2 0 3
C 2 1 1
D 2 1 3
9 In which substance must covalent bonds break on boiling?
A phosphorus (V) chloride

B caesium chloride
C silicon carbide
D magnesium
10 In which of the following pairs of compounds would the first compound have
a lower melting point than the second compound?
A CH3(CH2)2CH3 and CH3CH(CH3)CH3

B GaF3, GaCl3
C SiO2, SiCl4
D K2O, Na2O

.11 Which pair of molecules is polar?
A C2HCl3 and C2Cl4

B COS and COSe
C PCl3 and BCl3
D SO2 and XeF4
12 The kinetics of the redox reaction between mercury (II) chloride, HgCl2 and
oxalate ion, C2O42– was investigated and the following experimental results
were obtained.
2 HgCl2 (aq) + C2O42– (aq) 

 2Cl– (aq) + 2CO2 (g) + Hg2Cl2 (s)
Initial [HgCl2] / Initial [C2O42–] / Relative rate

experiment
mol dm–3 s mol dm–3 s / mol dm–3 s–1
1 0.20 0.10 1
2 0.20 0.30 9
3 0.40 0.30 18
Which statement is correct?
A The rate constant depends on the concentration of HgCl2 and C2O42–.

B The reaction is second order with respect to HgCl2.
C The rate of reaction is independent of C2O42–.
D The units for the rate constant are mol–2 dm6 s–1
13 Archaeologists used 14C, a radioactive isotope, in carbon dating. An artifact

is analysed and its 14C content is measured to be 20% of the typical initial
amount of 14C in trees.
Given that the radioactive decay of 14C has a half–life of 5500 years, what is
the approximate age of this artifact?
A 1.10 x 104 years B 1.28 x 104 years

C 1.38 x 104 years D 1.65 x 104 years

14 Experiments were carried out to investigate the rates of the decomposition
of 100 cm3 of 1.0 mol dm–3 hydrogen peroxide, catalysed by manganese(IV)
oxide.
H2O2 (aq) 
 H2O (l) + ½ O2 (g)
The volume of oxygen gas collected using a gas syringe was monitored. The
results are shown in the diagram below.
Volume of oxygen gas

/ dm3
Experiment 2
Experiment 1
Time
Which of the following alteration to the experimental conditions in

Experiment 1 would produce the curve observed in Experiment 2?
A Lowering the temperature

B Decreasing the amount of MnO2 used
C Diluting the hydrogen peroxide solution with water
D Adding some 0.1 mol dm-3 hydrogen peroxide

15 The standard enthalpy changes of combustion of carbon and hydrogen are
−394 kJ mol–1 and −286 kJ mol–1 respectively.
If the standard enthalpy change of combustion of propyne gas, C3H4,

is −1938 kJ mol–1, calculate the standard enthalpy change of formation of
propyne?
A +184 kJ mol–1 B –184 kJ mol–1

C +284 kJ mol–1 D −284 kJ mol–1


16 Which statements best defines the term bond energy for a diatomic molecule
HCl?
A Energy absorbed when one molecule of HCl is broken into its gaseous
atoms.
B Energy absorbed when one mole of HCl is broken into its gaseous
atoms.
C Energy released when one mole of HCl is formed from its gaseous
atoms.
D Energy released when one mole of HCl is formed from its gaseous
ions.

17 During the Contact process, sulfur dioxide is converted to sulfur trioxide as
shown by the equation below.
2SO2 (g) + O2 (g)

2SO3 (g) ∆H = −197 kJ mol–1
The following graph shows how the concentrations of the gases changed
when a series of changes was made.
Concentration /
mol dm–3
0.100
SO2
O2
0.050
SO3
0.000 Time / min

10 20 30 40
Which of the following statement does not agree with the above information?
A At 10 min, the value of the equilibrium constant, Kc, is 1.56.
B At 15 min, the temperature of the system was decreased.

C At 15 min, the pressure of the system was increased by reducing the
volume of the vessel.
D At 25 min, some sulfur dioxide gas was removed from the system.

18 The table below shows some data on two common acid–base indicators.
Approximate pH colour change

Indicator range of colour
change acid alkali
Methyl orange 3.2 – 4.4 red yellow
Bromothymol blue 6.0 – 7.6 yellow blue
What conclusion can be drawn about a solution which appears yellow with
both methyl orange and bromothymol blue?
A It is strongly acidic. B It is weakly acidic.

C It is neutral. D It is weakly alkaline.

19 What is the final pH of the resultant solution formed by mixing equal volumes
of Ba(OH)2 solutions, one with a concentration of 0.05 mol dm–3 and the
other with 0.01 mol dm–3?
A 12.3 B 12.5 C 12.8 D 13.1

20 The equilibrium constant, Kc, for this reaction represented by the equation
below is significantly greater than 1.0.
H2PO4 – + HCO3–
HPO42– + H2CO3
Which of the following states the correct relative strengths of the acid and
base in the reaction?
Acids Bases
A H2PO4 – > H2CO3 and HCO3– > HPO42–
B H2CO3 > H2PO4 – and HCO3– > HPO42–
C H2PO4 – > H2CO3 and HPO42– > HCO3–
D H2CO3 > H2PO4 – and HPO42– > HCO3–


21 The graph below shows the variation in the standard enthalpy change of
vaporisation, ∆H(vaporisation), for eight consecutive elements in the
Periodic Table, all with atomic number, Z  20.
 –1
∆H (vaporisation) / kJ mol
S V
R T
U
atomic number, Z
Which element forms an oxide which is amphoteric?
A Element P
B Element Q
C Element R
D Element V
22 4–oxobutanoic acid is used for metabolism in aerobic organisms. It can

undergo the following two-step reaction.
step 1 step 2
HO2CCH2CH2CHO   HO2CCH2CH2CH2OH   HO2CCH2CH2CH2I
What are the reagents and conditions required for step 1 and step 2?
step 1 step 2
A LiAlH4 in dry ether, r.t.p I2 with red phosphorus, heat
B LiAlH4 in dry ether, r.t.p I2, uv light
C NaBH4 in ethanol, r.t.p I2 with red phosphorus, heat
D NaBH4 in ethanol, r.t.p I2, uv light

23 Alcohol Q is treated with warm acidified potassium dichromate(VI) to form R.
R does not form a yellow precipitate with aqueous alkaline iodine nor produce
effervescence when sodium carbonate is added.
What is the identity of alcohol Q?
A propan–1–ol
B pentan–3–ol
C 3–ethylpentan–3–ol
D 3–methylbutan–2–ol
24 Bisdemethoxycurcumin is one of the active ingredients found in turmeric, a

spice commonly used in Asian cuisine.
O O
HO OH
bisdemethoxycurcumin
Which statement about bisdemethoxycurcumin is incorrect?
A It turns hot acidified potassium dichromate(VI) from orange to green.

B It decolorises hot acidified potassium manganate (VII).
C It has 4 geometrical isomers.
D It forms orange crystals when warmed with 2,4-DNPH.
25 Propyl ethanoate is heated with an aqueous solution of potassium hydroxide.
What are the products of this reaction?
A ethanol and propanoic acid

B ethanol and potassium propanoate
C propan–1–ol and ethanoic acid
D propan–1–ol and potassium ethanoate

Section B
For each of the questions in this section, one or more of the three numbered
statements 1 to 3 may be correct.
Decide whether each of the statements is or is not correct (you may find it helpful to
put a tick against the statements which you consider to be correct).
The responses A to D should be selected on the basis of
A B C D
1, 2 and 3 are 1 and 2 only are 2 and 3 only are 1 only is correct
correct correct correct
No other combination of statements is used as a correct response.

26 During the Haber process, ammonia is synthesised from elemental nitrogen
and hydrogen as shown in the equation below.
N2 (g) + 3H2 (g)

2NH3 (g) ∆H = −92 kJ mol–1
Which of the following statements is true?
1 To improve yield, the operating temperature of the system should be

kept low.
2 To improve yield, the operating pressure of the system should be kept
high.
3 When temperature is increased, the rate of the forward reaction
increases but the rate of the reverse reaction decreases.

27 Which oxides of Period 3 elements gives an acidic solution when dissolved in
water?
1 P4O10
2 Al2O3
3 SiO2


A B C D

28 Athletes taking part in the Olympics could be disqualified and have their medal
revoked for using banned performance–enhancing drugs.
DHEA, a steroid hormone, is illegally used as a performance–enhancing drug

as it has minimal side effects.
O
HO
DHEA
Which reagents would react with DHEA?
1 Thionyl chloride, SOCl2

2 Aqueous bromine
3 Cold alkaline KMnO4

29 2–methylpropanoic acid may be synthesised from propan–2–ol through a
series of reactions.
CH3CH(OH)CH3 
 CH3CH(CH3)COOH
Which sets of reagents would be suitable for this synthesis?
1 PBr3, ethanolic KCN, dilute H2SO4

2 Acidified KMnO4, HCN with NaCN catalyst, dilute H2SO4
3 Alkaline aqueous iodine, dilute H2SO4, HCN with NaCN catalyst


A B C D
30 Rosmarinic acid occurs in culinary herbs such as rosemary, sage and thyme.
OH
O OH OH
O
HO
OH
rosmarinic acid
Which products are obtained from the reaction of rosmarinic acid with
excess, hot concentrated acidic KMnO4?
OH
O OH OH
1
HO
OH
O
2
HO
OH
3 CO2
END OF PAPER

1
Class Reg Number

Candidate’s Name: ___________________________

JC 2 Preliminary Examination
Higher 1
________________________________________________________________________
Chemistry 8872/01
23 September 2016
Paper 1 Multiple Choice
50 minutes
Additional Materials: OMR Sheet and Data Booklet
________________________________________________________________________
This booklet contains Section A of your paper.
Write your name, class and register number in the spaces provided at the top of this page.
There are thirty questions in this section. Answer all questions. For each question, there are four
possible answers labelled A, B, C and D. Choose the one you consider correct and record your
choice in soft pencil on the OMR answer sheet.
Read very carefully the instructions on the use of OMR answer sheet.
You are advised to fill in the OMR Answer Sheet as you go along; no additional time will be given
for the transfer of answers once the examination has ended.
Use of OMR Answer Sheet
Ensure you have written your name, class register number and class on the OMR Answer
Sheet.
Use a 2B pencil to shade your answers on the OMR sheet; erase any mistakes cleanly.
Multiple shaded answers to a question will not be accepted.
For shading of class register number on the OMR sheet, please follow the given examples:
MJC Prelims 2016 1 © chemistry unit @ mjc

2
ANSWER SCHEME
Answer Answer Answer
Question Question Question
Key Key Key
1 D 11 B 21 A
2 A 12 D 22 C
3 B 13 B 23 B
4 C 14 D 24 A
5 C 15 A 25 D
6 A 16 B 26 B
7 A 17 B 27 D
8 D 18 B 28 A
9 C 19 C 29 D
10 D 20 A 30 C
MJC Prelims 2016 2 © chemistry unit @ mjc

Name: __________________________ Class: 15_______ Reg Number: _____

JC2 Preliminary Examination
Higher 1
________________________________________________________________________
Chemistry 8872/02
Paper 2 14 September 2016
2 hours
Additional Materials: Data Booklet
Writing Papers
________________________________________________________________________
Write your name, class and register number in the spaces at the top of this page.
This booklet contains Section A and Section B.
Section A: Pg 2 to 13
Answer all questions in Section A in the spaces provided on the question paper. You are advised to
spend about 1 h on Section A.
Examiner’s Use
Section B: Pg 14 to 21 Paper 1 MCQ / 30
Answer 2 out of 3 questions in Section B. You are / 33 %

advised to spend about 1 h on Section B.
Paper 2 Q1 / 10
Hand in Section B separately from Section A. Section A
Q2 / 10
Fasten your answers for Section B behind the given
Cover Page. Detach the Cover Page from the last Q3 / 11
page behind this booklet.
Q4 / 9
INFORMATION FOR CANDIDATES Paper 2

/ 40
Section B
The number of marks is given in brackets [ ] at the
end of each question or part question. Paper 2 / 80
Total / 67 %
Grand Total / 100 %
Grade
________________________________________________________________________
MJC Prelim 2016

Section A
Answer all the questions in this section in the spaces provided.
1 Vitamin C also known as ascorbic acid, is an essential nutrient for humans. Ascorbic
acid, C6H8O6 is a naturally–occurring organic compound with anti–oxidant properties.
It is very soluble in water to give weakly acidic solutions.
O
O
HO
OH
HO OH
ascorbic acid
Vitamin C supplements are commonly consumed for the purpose of supplementing the
diet and enhancing health. Vitamin C supplements are currently not subjected to
approvals, licensing or registration from Health Sciences Authority (HSA) in Singapore
before being sold in the local markets. However, health supplement dealers are
responsible for portraying accurate and truthful claims of their products. The label and
packaging material should also provide sufficient information to enable consumers to
make informed decisions when purchasing and consuming the products.
A Vitamin C tablet has the following information on its packaging.
SUPPLEMENT FACTS DOSAGE INSTRUCTIONS

Serving Size: 1 Tablet Adults and children over 12 years old:
Serving per Container: 20 Tablets Take 2 tablets per day with a glass of water,
Amount per % of Daily Value best taken first thing in the morning, can be
tablet used every day throughout the year.
Calories 9.16 Taking more than the recommended daily

intake may be harmful.
Total Carbohydrates 0.40 g 0%
Sugar 0g 0% Regular usage is recommended due to the
Vitamin C body inability to store Vitamin C.
1000 mg 1666 %
(Ascorbic acid) Food supplements should not be used as a
Sodium 225 mg 9% substitute for a varied diet or healthy lifestyle.
Amino Acid 3 mg –
STORAGE INSTRUCTIONS
Proprietary
Alanine, Lysine, Serine, Threonine, Tyrosine, Valine, Keep out of sight and reach of young children.
Arginine, Glutamic Acid, Aspartic Acid, Phenylalanine,
Keep the container closed and protect from
Glycine, Histidine, Isoleucine, Leucine
heat and moisture.
*Percent Daily Values are based on a
2000 Calories diet. Do not use after the best before end date.
*1.0 mg (milligram) = 1.0 x 10–3 g

(a) (i) On the structure below, circle and name fully three functional groups present
in ascorbic acid. You need not consider the alkenol part of the molecule in
your answer.
[2]
O
O
HO
OH
HO OH
alkenol
(ii) Draw a labelled diagram to explain why ascorbic acid is very soluble in
water.
[1]
(iii) The packaging says “Keep the container closed and protect from heat and
moisture.” By considering your answer in (a)(i), suggest why the Vitamin C
tablets should be stored under such conditions.
[1]

(b) Iodometric titration can be used to determine the amount of ascorbic acid in
samples of Vitamin C supplements. During this reaction, the iodine is rapidly
reduced to iodide ions, while ascorbic acid, C6H8O6, is oxidised to produce
dehydroascorbic acid, C6H6O6.
(i) Use the above information to construct a balanced equation between

ascorbic acid and iodine.
[1]
To validate the amount of ascorbic acid as claimed on the packaging, one

Vitamin C tablet was dissolved completely. The volume was made up to 500 cm3
with deionised water.
25.0 cm3 of this solution required 17.40 cm3 of 0.015 mol dm–3 of iodine solution
for complete reaction, using starch as an indicator.
(ii) Calculate the amount of ascorbic acid that has reacted with iodine.
[1]

(iii) Determine the mass (in mg) of ascorbic acid present in one Vitamin C tablet.
Hence, state if the information on the packaging is accurate.
[2]
(iv) The structure of dehydroascorbic acid, the oxidised form of ascorbic acid is
shown below.
O
O
HO
O
HO O
dehydroascorbic acid
Suggest a simple chemical test to distinguish between ascorbic acid and

dehydroascorbic acid. State only the positive observation you would make.
[2]
[Total: 10]

2 With dwindling supplies of fossil fuels, renewable sources of fuels such as biofuels
have been touted as a sustainable alternative to meet the world’s growing energy need.
Bio–methanol, CH3OH is a potential fuel for ground transportation, as it could be easily
adapted for conventional gasoline internal combustion engines with minimum
modification. The combustion of methanol is as follows:
2CH3OH (l) + 3O2 (g) 

 2CO2 (g) + 4H2O (l)
(a) Define the term standard enthalpy change of combustion of methanol.

[1]
(b) Using relevant data in the Data Booklet, calculate the standard enthalpy change
of combustion of methanol.
[2]
(c) The widely accepted value for the standard enthalpy change of combustion of
methanol is –715.0 kJ mol–1.
Suggest why there is a discrepancy between your answer in (b) and this widely
accepted value.
[1]

(d) Methanol was combusted completely under a beaker of water, as shown in the
diagram.
thermometer
beaker
water
spirit burner
methanol
The experimental results obtained are shown below.
Mass of water in beaker = 800 g

Initial temperature of water = 25.8 C
Initial mass of burner and methanol = 356.8 g
Final mass of burner and methanol = 350.9 g
The specific heat capacity of water is 4.18 J g–1 K–1.
Given that this process is 60% efficient, and using the value of standard enthalpy
change of combustion of methanol in (c), calculate the final temperature of the
water in the beaker.
[2]

Bio–methanol, CH3OH is also currently studied as a potential green fuel which reduces
the pollution to the environment. One of the common pollutants due to the combustion
of fossil fuels is sulfur dioxide, SO2. In the presence of excess oxygen, sulfur dioxide
can be catalytically oxidised to from sulfur trioxide, SO3.
(e) Draw the dot–and–cross diagram of SO2. Suggest a value for the bond angle in
the SO2 molecule and explain in detail how this angle arises.
[3]
(f) Suggest why SO3 exists but CO3 does not.

[1]
[Total: 10]

3 The elements found between Group II and Group III of the Periodic Table are called
d–block elements, which exhibit very different properties from the other elements in
the Periodic Table. Copper is an example of a d–block element, and it forms
compounds that have chemical properties that differ from compounds of Period 3
elements.
(a) When a soluble copper(II) salt is dissolved in water, the aqueous ion [Cu(H2O)6]2+
is formed. When concentrated HCl is added to the solution, [Cu(H2O)6]2+ is
converted to [CuCl4]2– according to the following equilibrium.
[Cu(H2O)6]2+ (aq) + 4Cl– (aq)

[CuCl4]2– (aq) + 6H2O (l)
blue yellow
(i) Write the expression for the equilibrium constant, Kc, for this reaction.
[1]
(ii) A solution is prepared in which the initial concentration of [Cu(H2O)6]2+ and

Cl– ions are 1.00 mol dm–3 and 4.00 mol dm–3 respectively. After equilibrium
is established, the concentration of [Cu(H2O)6]2+ is 0.075 mol dm–3.
Calculate the value of Kc for this equilibrium and state its units.
[2]

(iii) Describe and explain what you would observe when water is added to a
solution of [CuCl4]2– (aq) ions.
[2]
(b) When heated in chlorine, Period 3 elements form chlorides.

(i) Complete the sketch for chlorides of Period 3 to show how the pH for
1 mol dm3 aqueous solutions changes along the period.
[2]
pH
NaCl MgCl2 AlCl3 SiCl4 PCl5

(ii) Account for the pH of the aluminium chloride solution, writing equations
where appropriate.
[2]
(iii) Using structure and bonding, account for the relative melting points of MgCl2
and SiCl4.
[2]
[Total: 11]

4 Benzene is a natural constituent of crude oil and is used as a precursor to the
manufacture of other derivatives with more complex structures.
(a) Describe the bonding in benzene in terms of orbital overlap.

[2]
(b) Benzene is used to synthesise phenylpropenes. Phenylpropenes have been

used as starting materials for a variety of effective insecticides.
The following depicts a 3–step synthesis route to produce compound R from

3-phenyl-1-propene.
Br
HBr (g)
step I step II
Br
3-phenyl-1-propene Compound P
Compound Q
step III
Br
Compound R

(i) Draw the structure of compound P in the box provided.
[1]
(ii) State the type of reaction and the required reagents and conditions for
steps II and III.
[2]
Type of reaction Reagents and conditions
Step II
Step III
(c) Benzene can be converted to compound S, C6H3Br3, under appropriate

conditions.
(i) Suggest two possible structures for compound S and state the name of
each structure you have drawn.
[2]
(ii) Hot acidified KMnO4 can be used to distinguish between compound S and
ethylbenzene. State the expected observations when hot acidified KMnO4
is added separately to compound S and ethylbenzene. Write a balanced
equation to account for the observation taking place.
[2]
[Total: 9]
END OF SECTION A

Section B
Answer any two questions from this section on separate answer paper.
Begin each question on a fresh sheet of writing paper.
5 Both 2–chloro–1–phenylethanone, C6H5COCH2Cl and sodium hydroxide are caustic

in nature.
2–chloro–1–phenylethanone has been used as a component for some tear gases. Its
irritant properties is a result of its reaction with water in body tissues to produce
hydrochloric acid. Articles contaminated with 2–chloro–1–phenylethanone can be
washed with hot aqueous sodium hydroxide.
(a) Write a balanced equation of the reaction between C6H5COCH2Cl and NaOH (aq).
[1]
(b) The following graphs were obtained from two experiments on such hydrolysis. In
each experiment, the overall [NaOH(aq)] remained virtually constant at the value
given.
[C6H5COCH2Cl]
/ 102 mol dm3
2.00
1.80
1.60
1.40
1.20
1.00
0.80
0.60
0.40
[NaOH] = 0.10 mol dm3
0.20
[NaOH] = 0.20 mol dm3

0.00
0 20 40 60 80 100 120 140 160 180
time / min

(i) Use the graphs to calculate the order of reaction with respect to
C6H5COCH2Cl and NaOH. Show all relevant working.
[3]
(ii) Hence, write the rate equation for this reaction.

[1]
(iii) In a different experiment, when [C6H5COCH2Cl] = 0.200 mol dm−3 and

[NaOH] = 0.200 mol dm−3, the initial rate is 4.64 x 10–3 mol dm−3 min−1.
Determine the rate constant for this reaction and state its units.
[2]
(c) The addition of a catalyst increases the rate of reaction between C6H5COCH2Cl
and NaOH.
With the aid of the Boltzmann distribution curve, state and explain the effect of a
catalyst on the rate of reaction.
[3]
(d) Same amounts of 2–chloro–1–phenylethanone and 2–bromo–1–phenylethanone

were treated separately with hot aqueous sodium hydroxide followed by
treatment with acidified silver nitrate solution. The following results were
obtained:
observations upon adding acidified

compound
AgNO3 solution
2–chloro–1–phenylethanone ppt forms slowly after 10 minutes
2–bromo–1–phenylethanone ppt forms after 2 minutes
Account for the above observations fully. In your answer, you should clearly
explain for the relative rates and state the identity and colour of the ppt formed.
[3]

(e) Halogen derivatives react with sodium hydroxide differently under different
conditions.
A reaction scheme involving 4–chloro–3–methylbutan–2–one is shown below.
X
step I step II
O Cl C5H8O
OH
4-chloro-3-methylbutan-2-one 3-methylbutan-2-ol
(i) Suggest reagents and conditions for steps I and II.

[2]
(ii) Suggest the structure of compound X.

[1]
(iii) The table below gives the boiling points of two organic compounds.
Mr boiling point / C
4–chloro–3–methylbutan–2–one 120 154
3–methylbutan–2–ol 88.0 110
Account for the observed boiling points. In your answer, you should state
the predominant type of interactions present in the two compounds.
[2]
(iv) Explain why solid NaOH is able to dissolve in 3–methylbutan–2–ol.

[1]
(f) Sodium hydroxide reacts with hydrofluoric acid and hydrochloric acid to form
sodium fluoride and sodium chloride respectively.
Quoting appropriate data from the Data Booklet, explain why the melting point of
the sodium fluoride is higher than that of sodium chloride.
[1]
[Total: 20]

6 Cinnamic acid is an organic acid that is obtained from the oil of cinnamon. It is also
possible to synthesise cinnamic acid from 3–oxo–3–phenylpropanoic acid.
The synthetic pathways below show reactions using 3–oxo–3–phenylpropanoic acid

as a starting material.
O O OH O
2,4-DNPH, heat OH
two steps
A OH
COOH
3-oxo-3-phenylpropanoic acid C
II
OH O O
IIII
dilute KOH (aq) OH OH
B
cinnamic acid
(a) State the reagents, conditions and the type of reaction for each of the reactions I
and II.
[3]
(b) Draw the structural formulae of the compounds A and B.

[2]
(c) Suggest a two–step reaction sequence with appropriate intermediate, reagents

and conditions for the synthesis of C from 3–oxo–3–phenypropanoic acid.
O O OH O
OH OH
COOH
3-oxo-3-phenylpropanoic acid
C

[2]

(d) Compounds D and E are isomers of cinnamic acid.
OH
HO
H O
compound D compound E
(i) Describe a chemical test that would show a positive result with D and a
negative test with E.
[2]
(ii) Write a balanced equation to account for the positive observation for the
chemical test you have described in (d)(i).
[1]
(e) Cinnamic acid, C8H7COOH, is a monobasic acid with an acid dissociation

constant of 3.63 x 10–5 mol dm–3.
C8H7COOH (aq))
C8H7COO– (aq) + H+ (aq)
The following titration curve is obtained when 25.0 cm3 of a solution of cinnamic
acid is titrated against a solution of 0.015 mol dm–3 of sodium hydroxide.
pH
Volume of NaOH(aq) / cm3

0 20.50
(i) Write the Ka expression for cinnamic acid.

[1]
(ii) Use data from the graph to calculate the concentration of the cinnamic acid
used.
[1]

(iii) Using your answers in (e)(i) and (e)(ii), determine the initial pH (represented
by x on the graph) of the cinnamic acid solution.
[2]
(iv) Deduce if the standard enthalpy change of neutralisation of sodium

hydroxide with hydrochloric acid would be more or less exothermic as
compared with cinnamic acid. Explain your answer.
[2]
(f) A 1.00 dm3 buffer solution at pH 4.3 was prepared by mixing sodium cinnamate,
C8H7COONa and cinnamic acid.
(i) What do you understand by the term buffer solution?

[1]
(ii) Write an equation to illustrate how this solution acts as a buffer when a small
amount of sodium hydroxide is added.
[1]
(iii) The pH of an acidic buffer can be calculated by using this formula.

[salt]
pH  pK a  lg
[acid]
[salt]
Calculate the ratio of in this buffer solution.
[acid]
[2]
[Total: 20]

7 This question involves the various elements in third period (sodium to argon).
(a) Describe and explain briefly the variation in the atomic radius of the elements for
the third period.
[2]
(b) Describe the variation in melting point of the elements for the third period.
[2]
(c) Aluminium reacts with chlorine and oxygen to form aluminium trichloride, AlCl3,
and aluminium oxide, Al2O3, respectively.
Solid AlCl3 sublimes into a gas at 180 C while Al2O3 melts at 2072 C.
Suggest the type of structure and bonding present in gaseous AlCl3 and solid
Al2O3.
[3]
(d) Describe what would be observed when sodium and sulfur are separately burned
in oxygen. Write balanced equations for any reactions that occur.
[2]
(e) Figure 1 shows the variation in second ionisation energy (IE) of the elements in
the third period and Figure 2 shows the successive ionisation energy of element
G in the third period.
Second IE / kJmol-1
log10 IE / kJmol-1
Na Mg Al Si P S Cl Ar 1st 2nd 3rd 4th 5th 6th 7th 8th
Figure 1 Figure 2
(i) Explain why the second ionisation energy of sulfur is higher than that of
either of the elements immediately preceding or following it.
[2]
(ii) Explain why the second ionisation energy of silicon is lower than that of
aluminium.
[1]
(iii) State the group to which element G is likely to belong.

[1]

(f) Chlorine exists in various oxidation states in different compounds. It undergoes
disproportionation with hot sodium hydroxide according to the equation below.
3Cl2 (g) + 6NaOH (aq) 

 5NaCl (aq) + NaClO3 (aq) + 3H2O (l)
(i) Explain what is meant by the term disproportionation, using the reaction of
chlorine with hot sodium hydroxide as an example.
[1]

(ii) Draw a dot-and-cross diagram to illustrate the bonding in ClO3 , showing
the outermost shell electrons only. Suggest the shape of the ion.
[2]
(iii) Define the term enthalpy change of formation of aqueous NaClO3.

[1]
(g) Ethyne, C2H2, undergoes addition reaction with limited chlorine to form C2H2Cl2.
C2H2 (g) + Cl2 (g) 

 C2H2Cl2 (g)
(i) Two possible products are formed at the end of the addition reaction.
Draw the structures of the two products. Indicate which product is polar and
explain briefly your choice.
[2]
(ii) Midway into the reaction, a sample of reaction mixture was passed through
an ioniser which ionises the molecules into ions. These ions are subjected
to an electric field which causes the ions to be deflected and then detected.
The identity of the ions and their masses are given in the table below.
ion mass
+ 71
(Cl2)
(C2H2Cl2)+ 97
(C2H2Cl2)2+ 97
Suggest with a reason, the ion which would be most easily deflected.
[1]
[Total: 20]
END OF SECTION B

MJC Prelim 2016 22 [Turn Over
2016 MJC H1 Chemistry Prelim P2 Suggested Answers
1(a) (i)
O ester
secondary alcohol O
HO
OH
HO OH alkenol
primary alcohol
(ii) 
 O
H H

O

O
HO
OH

HO O 
H
hydrogen bond
 O
 H H
(iii) Ester functional group in ascorbic acid undergoes hydrolysis.
(b) (i) C6H8O6 + I2 

 C6H6O6 + 2 H+ + 2 I–
17.40
(ii) No. of moles of iodine that has reacted = × 0.015 = 2.61 x 10–4
1000
No. of moles of ascorbic acid that has reacted = 2.61 x 10–4
(iii) No. of moles of ascorbic acid present in 500 cm3 (in one tablet)
500
= × 2.61 × 104 = 5.22 x 10–3 mol
25
Mass of ascorbic acid present in 500 cm3 (in one tablet)

= 5.22 × 103 × 176 = 0.919 g = 919 mg
The information on the packaging is not accurate.

(iv) Add aqueous Br2 to each compound separately in the dark.
Observation:
 For ascorbic acid, decolourisation of reddish–brown Br2 will be
observed.
Alternative viable chemical test also accepted
2 (a) It is the energy evolved when one mole of methanol is completely burnt in
excess oxygen under standard conditions (or 298 K and 1 atm).
3
CH3OH (l) + O2 (g) 
 CO2 (g) + 2 H2O (l)
2
(b) Hco(CH3OH) = (2794) – (3320) = 526 kJ mol–1
(c) The bond energy values given in the Data Booklet are average values.
(d) Mass of methanol combusted = 356.8 – 350.9 = 5.9 g

5.9
No. of moles of methanol combusted = = 0.1844
32.0
Quantity of heat released = 0.1844 x 715.0 = 131.8 kJ

60
Quantity of heat absorbed = 131.8 x = 79.10 kJ
100
Quantity of heat absorbed = m c T
79.10 x 1000 = 800 x 4.18 x (Tf – 25.8)
Tf = 49.5C
xx xx
(e) x
x O x
x S x
x O xx
There are 2 bond pair and 1 lone pair around central atom. To minimise repulsion
(and maximise stability), the 3 electron pairs are directed to the corners of an
equilateral triangle.
Since lone pair–bond pair repulsion is stronger than bond pair–bond pair
repulsion, SO2 has a bent shape and the bond angle is 119.
(f) S is a Period 3 element and can expand octet structure due to the availability of
vacant and energetically accessible d orbitals.
[CuCl4 2  ]
3 (a) (i) Kc =
[ [Cu(H2O)6 ]2+ ] ] [Cl  ]4

(ii)
[Cu(H2O)6]2+ + 4Cl–
[CuCl4]2– + 6H2O
Initial [ ] 1.00 4.00 0 –
Change in [ ] –0.925 –3.70 +0.925 –
Equilibrium [ ] 0.0750 0.300 0.925 –
0.925
Kc  = 1520 mol–4 dm12
(0.0750)(0.300)4
(iii) Yellow solution turns blue/ green.

[Cu(H2O)6]2+ (aq) + 4Cl– (aq)
[CuCl4]2– (aq) + 6H2O(l) --- (1)
Position of equilibrium in (1) shifts left to increase [[Cu(H2O)6]2+] and [Cl–].
Concentration of [Cu(H2O)6]2+ (blue) increases.
(b) (i)
pH
7
6.5
3
2
1
NaCl MgCl2 AlCl3 SiCl4 PCl5
(ii) AlCl3 undergoes both hydration and hydrolysis to form

a slightly acidic solution with pH = 3.0
Hydration of AlCl3
AlCl3 (s) + 6H2O (l)  [Al(H2O)6]3+ (aq) + 3Cl– (aq)
Hydrolysis of AlCl3
[Al(H2O)6]3+(aq) + +
[Al(H2O)5(OH)] (aq) + H (aq)

The high charge density of the Al3+ polarizes the electron cloud of one of its
surrounding water molecules, weakening and breaking the O-H bond which
results in the release of a proton.
(iii) MgCl2 has giant ionic lattice structure. Large amount of energy is required
to overcome strong electrostatic force of attraction between oppositely
charged ions.
SiCl4 has simple molecular structure. Small amount of energy is required to

overcome weak intermolecular van der Waals’ attraction between
molecules.
[Total: 11]

4 (a) Benzene is a planar molecule containing a hexagonal ring of six carbon atoms,
each with a hydrogen atom attached. Each carbon in the benzene ring forms two
σ bonds with 2 other carbon atoms and one σ bond with a hydrogen atom. This
involves the head-on overlap of orbitals.
The remaining electron is in a 2p orbital perpendicular to the plane of C atoms.

Each 2p orbital overlaps sideway equally with the 2p orbital of its neighbours so
that the six unbonded p electrons are completely delocalised in the  electron
cloud above and below the plane of the ring.
Br
(b) (i)
Compound P
(ii)
Type of reaction Reagents and conditions
Step II Substitution Br2 with FeBr3, in the dark
Step III Elimination Ethanolic KOH, heat
(c) (i)
Br Br
Br Br
Br Br
Br Br
Br
1,2,3–tribromobenzene 1,2,4–tribromobenzene 1,3,5–tribromobenzene
Any 2 of the 3 structures.
(ii) Compound S: No decolourisation of purple KMnO4.
Ethylbenzene: Decolourisation of purple KMnO4 with (effervescence of
colourless CO2 gas which forms white ppt with Ca(OH)2).
CH2CH3 COOH
KMnO4 / H+
+ 6 [O]
+ CO2 + 2 H2O
heat
benzoic acid
[Total: 9]
END OF SECTION A

5 (a) C6H5COCH2Cl + NaOH 
 C6H5COCH2OH + NaCl
(b)
[C6H5COCH2Cl] /
102 mol dm3
2.00
1.80
1.60
1.40
1.20
1.00
0.80
0.60
[NaOH] = 0.10 mol dm-3

0.40
0.20
[NaOH] = 0.20 mol dm-3
t½ t½
0.00
0 20 40 60 80 100 120 140 160 180
time / min
(i) From graph of [NaOH] = 0.10 / 0.20 mol dm−3,
t½ is constant at 60 / 30 min.
Hence order of reaction w.r.t C6H5COCH2Cl = 1
From graph of [NaOH] = 0.10 mol dm−3,

(2.00  0.00)  102
Rate =  2.27  10 4 mol dm−3 min−1
0  88
From graph of [NaOH] = 0.20 mol dm−3,
(2.00  0.00) 102
Rate =  4.55 104 mol dm−3 min−1
0  44
When [NaOH] doubles, rate is approximately doubled.
Hence order of reaction w.r.t NaOH = 1
(ii) Rate = k [C6H5COCH2Cl] [NaOH]
4.64 × 10-3
(iii) k = = 0.116 mol−1 dm3 min−1
0.200  0.200
(c)
Number of particles
No. of particles with E > Ea for

with given energy
catalysed reaction
No. of particles with E > Ea for

uncatalysed reaction
Ea, cat Ea, uncat Kinetic Energy
 The catalyst increases the rate of reaction by providing an alternative reaction

pathway of lower activation energy.
 Number of reactant particles with E ≥ Ea increases,
 Frequency of effective collisions increases.
 Since rate of reaction is proportional to the frequency of effective collisions,
rate of reaction increases.
(d)
Compound Precipitate
2–chloro–1–phenylethanone White AgCl ppt
2–bromo–1–phenylethanone Cream AgBr ppt
 Strength of C–X bond hence ease of breaking: C–Cl > C–Br

 Order of reactivity of R-X: R-Cl < R-Br
(e) (i)
Steps Reagents and conditions
I ethanolic NaOH , heat
II H2(g), Pd or Pt, r.t.p
(ii) O

(iii) Both compounds have simple molecular structures.
4–chloro–3–methylbutan–2–one has a higher boiling point than
3–methylbutan–2–ol. The extensive van der Waals forces of attraction
between 4–chloro–3–methylbutan–2–one molecules is stronger than the
hydrogen bonding between 3–methylbutan–2–ol molecules. (due to
difference in the size of the electron cloud)
(iv) The formation of ion–dipole results in the release of energy that causes the
detachment of ions from the lattice for solvation.
(f)
 Cationic radius: Cl– (0.181 nm) > F– (0.136 nm)
 Lattice energy of NaF is more exothermic than NaCl
 Since lattice energy is a measure of ionic bond strength, melting point of NaF
is higher than NaCl
[Total: 20]

6 (a)
Reaction I Reagents and Conditions: NaBH4 in ethanol, r.t.p.
Type of Reaction: Reduction
Reaction II Reagents and Conditions: Excess conc H2SO4, 170oC
Type of Reaction: Elimination
(b)
O O 2N NO 2 OH O
HO N O -K+
N
H
A B
(c)
O O OH O
OH OH
COOH
HCN, trace amount of NaCN/ NaOH

10 °C - 20 °C
dilute HCl (aq) / H2SO4 (aq)
OH O heat
OH
CN
(d) (i) Test: Tollens’ reagent,heat.
Observation: Silver mirror obtained for D but not for E.
(ii)
OH OH
O
+ 2 [Ag(NH3)2] + 3 OH O
-
H O
+ 2 Ag + 4 NH3 + 2 H2O

[C8H7COO ][H+ ]
(e) (i) Ka 
[C8H7COOH]
20.50
(ii) No. of moles of NaOH = × 0.015 = 3.075 x 10–4
1000
3.075 104
[cinnamic acid] = = 0.0123 mol dm–3
25
1000
(iii) [H+]= 0.0123 × 3.63 × 10 5 = 6.682 x 10–4 mol dm–3
x = –lg (6.682 x 10–4) = 3.18
(iv) Some of the energy evolved from the neutralisation process is used to
further dissociate the weak acid, cinnamic acid completely.
Thus the enthalpy change of neutralisation between sodium hydroxide and

hydrochloric acid will be more exothermic than that between sodium
hydroxide and cinnamic acid.
(f) (i) A buffer solution is one which is capable of maintaining a fairly constant pH
when small amounts of acid or base are added to it.
(ii) C8H7COOH + OH– 

 C8H7COO– + H2O
[salt]
(iii) 4.3 = –lg (3.63 x 10–5) + lg
[acid]
[salt]
= 0.724
[acid]
[Total: 20]

7 (a) Atomic radius decreases from sodium to agron across the period as effective
nuclear charge increases.
(b) Melting point generally increases from sodium to aluminium (through the metals)
until a maximum / highest at silicon (giant molecular) and then decreases from
phosphorus to argon (simple molecular).
(c) Gaseous AlCl3 has a simple molecular structure, with weak van der Waals’ forces
of attraction between molecules and covalent bonds between atoms.
Solid Al2O3 has a giant ionic lattice structure, with strong electrostatic forces of
attraction between oppositely charged ions.
(d) Sodium burns very vigorously with a bright yellow flame to form white solid.
4Na + O2   2Na2O
Sulfur burns slowly with blue flame.

S + O2   SO2
(e) (i) Sulfur has a larger nuclear charge than phosphorus but shielding effect is
relatively constant since the inner quantum shell of electrons remain the
same. Sulfur has a larger effective nuclear charge. There is stronger
electrostatic attraction between the nucleus and the valence electrons. More
energy is required to remove the valence electron.
Inter-electron repulsion is present in the doubly-filled 3p orbital of Cl+ .

Hence less energy is required.
(ii) 2nd IE of Si involves removal of 3p valence electron which is further away

from the nucleus hence 3p electron experience weaker electrostatic
attraction with the nucleus and thus less energy is required.
(iii) Group VII
(f) (i) Disproportionation is a redox reaction in which atoms of an element in a

-
single substance (i.e. Cl2) undergoes oxidation (from 0 in Cl2 to +5 in ClO3 )
and reduction (from 0 in Cl2 to -1 in Cl-) simultaneously.
(ii)
-
There are 3 bond pairs and 1 lone pair around central Cl atom in ClO3 .
-
Hence ClO3 is trigonal pyramidal.
(iii) Enthalpy change of formation of NaClO3 (aq) is the energy change when
one mole of NaClO3 (aq) is formed from its constituent elements (Na, Cl2
and O2).
(g) (i)
Cis isomeric product is polar as the dipole moments do not cancel out in the
molecule.
(ii) (C2H2Cl2)2+ due to the largest charge-to-mass ratio
[Total: 20]
END OF SECTION B

2016 Chemistry H1 JC2 Meridian Junior College

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MERIDIAN JUNIOR COLLEGE

READ THESE INSTRUCTIONS FIRST

This booklet contains Section A of your paper.

Use of OMR Answer Sheet

This document consists of 13 printed pages (including this cover page).

MJC Prelim 2016 1 © chemistry unit @ mjc

Which of the following contains the most number of particles?

A Number of atoms in 9 dm3 of O2 gas at r.t.p.

What is the molecular formula of this hydrocarbon?

A N2O4 B N2O C NO D NO2

MJC Prelim 2016 2 © chemistry unit @ mjc

The excess potassium manganate(VII) solution required 10.00 cm3 of

2MnO4– + 5(COO)22– + 16H+ 

What is the final oxidation state of nitrogen in NaNOx?

5 Chromium(III) oxide, Cr2O3, can undergo different reactions to give other

Which statement correctly describe these reactions?

A The formation of Cr2O72– from CrO42– is a redox reaction.

6 Which species has two unpaired electrons?

MJC Prelim 2016 3 © chemistry unit @ mjc

What do these ions, 40Ca2+ and 31P3–, have in common?

A Both ions are isoelectronic.

number of  bonds number of  bonds number of  bonds

9 In which substance must covalent bonds break on boiling?

A phosphorus (V) chloride

A CH3(CH2)2CH3 and CH3CH(CH3)CH3

MJC Prelim 2016 4 © chemistry unit @ mjc

A C2HCl3 and C2Cl4

2 HgCl2 (aq) + C2O42– (aq) 

Initial [HgCl2] / Initial [C2O42–] / Relative rate

Which statement is correct?

A The rate constant depends on the concentration of HgCl2 and C2O42–.

13 Archaeologists used 14C, a radioactive isotope, in carbon dating. An artifact

A 1.10 x 104 years B 1.28 x 104 years

MJC Prelim 2016 5 © chemistry unit @ mjc

Volume of oxygen gas

Which of the following alteration to the experimental conditions in

A Lowering the temperature

If the standard enthalpy change of combustion of propyne gas, C3H4,

A +184 kJ mol–1 B –184 kJ mol–1

MJC Prelim 2016 6 © chemistry unit @ mjc

2SO2 (g) + O2 (g)

0.000 Time / min

A At 10 min, the value of the equilibrium constant, Kc, is 1.56.

B At 15 min, the temperature of the system was decreased.

MJC Prelim 2016 7 © chemistry unit @ mjc

Approximate pH colour change

A It is strongly acidic. B It is weakly acidic.

A 12.3 B 12.5 C 12.8 D 13.1

MJC Prelim 2016 8 © chemistry unit @ mjc

Which element forms an oxide which is amphoteric?

22 4–oxobutanoic acid is used for metabolism in aerobic organisms. It can

MJC Prelim 2016 9 © chemistry unit @ mjc

What is the identity of alcohol Q?

24 Bisdemethoxycurcumin is one of the active ingredients found in turmeric, a

Which statement about bisdemethoxycurcumin is incorrect?

A It turns hot acidified potassium dichromate(VI) from orange to green.

25 Propyl ethanoate is heated with an aqueous solution of potassium hydroxide.

What are the products of this reaction?

A ethanol and propanoic acid

MJC Prelim 2016 10 © chemistry unit @ mjc

The responses A to D should be selected on the basis of

No other combination of statements is used as a correct response.

N2 (g) + 3H2 (g)