2016 Chemistry H1 JC2 Victoria Junior College

VICTORIA JUNIOR COLLEGE
JC 2 PRELIMINARY EXAMINATIONS
Higher 1
CHEMISTRY 8872/01
Paper 1 Multiple Choice 22 September 2016
50 min
Additional Materials: Multiple Choice Answer Sheet

Data Booklet
READ THESE INSTRUCTIONS FIRST
Write in soft pencil.

Do not use staples, paper clips, highlighters, glue or correction fluid.
Write your NRIC/FIN number, name and CT group on the Answer Sheet.
There are thirty questions. 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 choices 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.
This document consists of 11 printed pages and 1 blank page.
 VJC 2016 8872/01/PRELIM/16 [Turn over

2
Section A
For each question there are four possible answers, A, B, C, and D. Choose the one you
consider to be correct.
1 In oxygen difluoride, OF2, fluorine has an oxidation number of –1. OF2 will react with
sulfur dioxide according to the following equation.
OF2 + SO2  SO3 + F2
What is oxidised and what is reduced in this reaction?
fluorine oxygen in OF2 sulfur

A reduced oxidised reduced
B reduced reduced oxidised
C oxidised oxidised reduced
D oxidised reduced oxidised
2 The shell of a chicken’s egg makes up 5% of the mass of an average egg. An average
egg has a mass of 50 g.
Assume the egg shell is pure calcium carbonate.
How many complete chicken’s egg shells would be needed to neutralise 50 cm3 of
2.0 mol dm–3 ethanoic acid?
A 1 B 2 C 3 D 4
3 Aluminium carbide, Al4C3, reacts readily with aqueous sodium hydroxide. The two
products of the reaction are NaAlO2 and a hydrocarbon. Water molecules are also
involved as reactants.
What is the formula of the hydrocarbon?
A CH4 B C2H6 C C3H8 D C6H12
4 Which statement about the ammonium ion, NH4+, is correct?
A All bond angles are 107o.

B Ammonium ions are formed when ammonia behaves as an acid.
C Ammonium ions are unreactive when heated with NaOH(aq).
D The bonds are all the same length.
 VJC 2016 8872/01/PRELIM/16

3
5 After the Fukushima nuclear disaster in 2011, a radioactive isotope of iodine, 131I, was
detected at water purification plants in Japan. Given that radioactive decay is a first
order reaction, and that the half–life of radioactive 131I is 8 days, how long will it take for
15 g of 131I to decay to 3.75 g?
A 8 days B 16 days C 24 days D 30 days
6 2–methylpropan–1–ol and butan–1–ol are structural isomers. 2–methylpropan–1–ol

has a lower boiling point.
Which statement explains why the boiling point of 2–methylpropan–1–ol is lower than
that of butan–1–ol?
A 2–methylpropan–1–ol cannot form hydrogen bonds.

B 2–methylpropan–1–ol has weaker covalent bonds than butan–1–ol.
C 2–methylpropan–1–ol has weaker dispersion forces than butan–1–ol.
D 2–methylpropan–1–ol molecules have more surface area than butan–1–ol
molecules.
7 Use of the Data Booklet is relevant to this question.
The most common ion–molecule reaction in gas clouds of the Universe is as shown.
H2(g) + H2+(g)  H(g) + H3+(g)
What could be the composition of an H3+ ion?
protons neutrons electrons

A 2 1 1
B 2 1 2
C 3 0 1
D 3 0 2
8 Which of the following equilibria will experience a shift in the position of equilibrium to
the right when the volume of the reaction vessel decreases at constant temperature?
A H2O(l) ⇌ H2O(g)
B 2NO(g) ⇌ N2(g) + O2(g)
C C2H4(g) + H2(g) ⇌ C2H6(g)
D H2O(g) + CH4(g) ⇌ CO(g) + 3H2(g)

4
9 The Haber Process is used to manufacture NH3(g) from N2(g) and H2(g) industrially,
using Fe solid as the catalyst. The process can be represented by the equilibrium
shown.
Which of the following statements regarding the Haber Process is correct?
A Fe lowers the activation energy of the forward reaction only.

B Fe increases the value of the equilibrium constant.
C Increasing the temperature increases the values of both k1 and k−1.
D Increasing the temperature increases the value of the equilibrium constant.
10 20 cm3 of 0.10 mol dm–3 sodium hydroxide solution is added to 25 cm3 of

0.15 mol dm–3 hydrochloric acid.
What is the approximate pH of the final solution?
A 1.4 B 2.8 C 4.5 D 7.0
11 X and Y are both monoprotic weak acids of equal concentration. X is a stronger acid
than Y.
Which statement about X and Y is correct?
A X is completely ionised in solution.

B The solution of X is less ionised than the solution of Y.
C The solution of X has a lower pH than the solution of Y.
D 1 mol of Y requires a smaller volume of 1 mol dm–3 aqueous NaOH for
neutralisation than 1 mol of X.
12 Which equation has a positive enthalpy change?
A I2(g)  I2(s)
B 2Cl(g)  Cl2(g)
C Ca(g)  Ca+(g) + e–
D C2H5OH(l) + 3O2(g)  2CO2(g) + 3H2O(l)
13 Calcium reacts with water to form calcium hydroxide and hydrogen.
Ca(s) + 2H2O(l)  Ca(OH)2(s) + H2(g)
Which of the following information is needed to calculate the standard enthalpy change
of formation of calcium hydroxide, Hof ?
I standard enthalpy change of formation of water

II standard enthalpy change of formation of hydrogen
III standard enthalpy change of reaction of calcium and water
A III only B I and II C I and III D II and III

 VJC 2016 8872/01/PRELIM/16
5
14 Acids react with Zn according to the following equation.
2H+(aq) + Zn(s)  Zn2+(aq) + H2(g)
The following graph is obtained when excess zinc is added to 1 dm3 of 0.010 mol dm–3
HCl.
volume of H2 / cm3
120
t/s
Which of the following represents the graph that will be obtained when excess zinc is
added to 1 dm3 of 0.010 mol dm–3 H2SO4?
volume of H2 / cm3
H2SO4
A 120
HCl
t/s
volume of H2 / cm3
HCl
B 120
H2SO4
t/s
volume of H2 / cm3
240 H2SO4
C 120 HCl
t/s
volume of H2 / cm3
120 HCl
D 60 H2SO4
t/s

6
15 X, Y and Z are elements in the same short period of the Periodic Table. The oxide of X
is amphoteric, the oxide of Y is basic and the oxide of Z is acidic. What is the order of
increasing ionic radius for these elements?
A X, Y, Z B X, Z, Y C Y, X, Z D Y, Z, X
16 The proton number of the element M is less than 20.
The aqueous chloride of M is acidic, and gives a white precipitate when reacted with
NaOH(aq). This precipitate dissolves on reacting either with NaOH(aq) or with
H2SO4(aq).
In which Group of the Periodic Table is M likely to be found?
A II B III C IV D V
17 The graph below shows how a property of the elements in the third period of the
Periodic Table varies with proton number.
proton number
What is the property?
A ionic radius
B melting point of the chloride
C pH of the oxide in water
D first ionisation energy
18 In 1869 Ladenburg suggested a structure for benzene, C6H6, in which one hydrogen
atom is attached to each carbon atom.
Ladenburg structure
A compound C6H4Br2 could be formed with the same carbon skeleton as the
Ladenburg structure.
How many structural isomers would this compound have?
A 2 B 3 C 5 D 6
 VJC 2016 8872/01/PRELIM/16
7
19 Compound G has the following structure.
How many geometric isomers does compound G have?
A 21 B 22 C 23 D 24
20 Which of the following compounds react with hot acidified KMnO4 to form products that
will give positive results for the 2,4–dinitrophenylhydrazine and the tri–iodoform tests?
A B C D
21 Which of the following statements about the compound below is correct?
A It will react with sodium hydroxide.

B It will react with Fehling’s solution.
C It will react with hydrogen cyanide in a substitution reaction.
D It can be oxidised by hot acidified potassium dichromate(VI) to a carboxylic acid.
22 The presence of a halogen in an organic compound may be detected by warming the

organic compound with aqueous silver nitrate.
Which compound would be the quickest to produce a precipitate?
A B C D

8
23 Which synthetic route will lead to the successful synthesis of the following product?
24 Nootkatone is one of the organic compounds found in grapefruit. Its structure is given
below.
Which statement about nootkatone is correct?
A It forms a yellow precipitate with alkaline I2(aq).

B It reacts with Tollens’ reagent to give a silver mirror.
C It reacts with potassium cyanide in ethanol to form a nitrile.
D It reacts with hot acidified potassium manganate(VII) to form one organic
product.
 VJC 2016 8872/01/PRELIM/16

9
25 Compound R gives the following observations when reacted with the specific reagents.
 It forms orange precipitate with 2,4–dinitrophenylhydrazine.

 It liberates one mole of hydrogen gas with excess sodium.
Which of the following could be R?
A CH3CH(OH)CH2CHO
B HO2CCH2COCH2OH

10
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 that 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 1 and 2 2 and 3 1 only
are only are only are is
correct correct correct correct
No other combination of statements is used as a correct response.
26 A student wishes to study the kinetics of the following reaction.
He conducted four experiments using 0.100 mol dm–3 solutions of CH3CH2CHO, HCN,
and CN–. He summarised the results in the table below.
Volume of Volume Volume Volume

Temperature Initial rate /
Expt CH3CH2CHO of HCN / of CN– / of H2O /
/ oC mol dm–3 s–1
/ cm3 cm3 cm3 cm3
1 25 10 10 10 20 2.35 x 10–5
2 25 10 10 20 10 4.68 x 10–5
3 35 20 20 10 0 9.40 x 10–5
4 25 20 10 10 10 4.71 x 10–5
Given that the rate of reaction doubles for every 10 oC rise in temperature, which of the
following statements are correct?
1 The reaction is an addition reaction.

2 The rate equation is given by rate = k[CH3CH2CHO][CN–].
3 The units of the rate constant are mol–1 dm3 s–1.
 VJC 2016 8872/01/PRELIM/16

11
27 Urea is a product of animal metabolism. It can also be used as a fertiliser.
The diagram shows angle x in this molecule.
Which statements about the structure of urea are correct?
1 Angle x is approximately 120o.

2 The molecule has one  bond.
3 The molecule has only four lone pairs of electrons.
28 Which statements are correct about the chemical properties of the elements in the third
period of the Periodic Table?
1 Al2O3 is soluble in both KOH and HCl.

2 SiCl4 reacts with water to give H+ ions.
3 S reacts with water to give an acidic solution.
29 What would be the products formed when the following compound is boiled with
aqueous sodium hydroxide?
1 CH3CH2OH
2 CH3CH2O–Na+
3 ClCH2CH2CO2–Na+
30 Which of the following will show effervescence when heated with acidified potassium
manganate(VII)?
CH2

Victoria Junior College 6 C
2016 JC2 H1 Chemistry Prelim Paper 1
Suggested Answers
No. Ans No. Ans No. Ans

1 D 11 C 21 D
Option A: Both 2–methylpropan–1–ol and butan–
2 B 12 C 22 A
1–ol can form intermolecular hydrogen bonds due
3 A 13 C 23 D to the presence of –OH in the molecules.
4 D 14 C 24 D Option B: Both molecules have strong covalent
5 B 15 A 25 B bonds between their atoms.
6 C 16 B 26 A Options C and D: 2–methylpropan–1–ol has
weaker dispersion forces than butan–1–ol as 2–
7 D 17 C 27 A
methylpropan–1–ol is more spherical and has
8 C 18 B 28 B less (not more) surface area for electron
9 C 19 B 29 D interaction than butan–1–ol.
10 A 20 A 30 B
7 D
1 D In H3+,
OF2 is oxidised to F2 where the oxidation number p = 3, n = 0, e = 3 – 1 = 2 (one less e than p)
of F changes from –1 to 0.
OF2 is reduced to SO3 where the oxidation 8 C
number of O changes from +2 to –2. By Le Chatelier’s Principle, when the volume of
SO2 is oxidised to SO3 where the oxidation the reaction vessel decreases at constant
number of S changes from +4 to +6. temperature, the pressure of the system
increases. The position of equilibrium will shift in a
2 B direction to decrease the pressure, i.e. shift to the
Mass of CaCO3 in one chicken’s egg shell side of the equilibrium with fewer moles of
5 gaseous particles. Only option C has fewer moles
= 50 × = 2.5 g of gaseous particles on the right.
100
No. of moles of CaCO3 in one chicken’s egg shell Moles of gaseous Moles of gaseous
Option
= 2.5 ÷ 100.1 = 0.025 mol reactants products
No. of moles of ethanoic acid, CH3CO2H used A 0 1
= 2.0 × 50 × 10–3 = 0.10 mol B 2 2
2CH3CO2H + CaCO3  Ca2+(CH3CO2–)2 + H2O + CO2 C 2 1
No. of moles of CaCO3 needed D 2 4
= 0.10 ÷ 2 = 0.050 mol
No. of complete chicken’s egg shells needed 9 C
= 0.050 ÷ 0.025 = 2 Option A: Fe catalyst increases the rate of
reaction by lowering the activation energy of both
3 A the forward and backward reactions to the same
Equation: extent.
Al4C3 + 4NaOH + 4H2O  4NaAlO2 + 3CH4 Option B: Fe catalyst does not increase the value
Hydrocarbon is CH4. of equilibrium constant which is affected by
temperature changes only.
4 D Option C: Increasing the temperature increases
NH4+ is tetrahedral. The bond the values of both k1 and k−1. The value of k−1
angles are 109o and the bonds increases more than k1 since position of
are all of the same length. equilibrium shifts left as temperature increases to
NH4+ ions are formed when NH3 favour the backward endothermic reaction.
behaves as a base, i.e. a proton Option D: Increasing the temperature favours the
acceptor. backward endothermic reaction to remove excess
On heating, NH4+ + OH–  NH3 + H2O heat, leading to formation of more reactants and a
decrease in the value of equilibrium constant.
5 B
10 A
t1/2 t1/2
15 g  7.5 g  3.75 g (two half–lives) No. of moles of HCl used
Time taken = 2 × 8 = 16 days = 0.15 × 25 × 10−3 = 0.00375 mol
No. of moles of NaOH used
= 0.10 × 20 × 10−3 = 0.00200 mol (limiting reagent)
NaOH + HCl  NaCl + H2O
No. of moles of HCl left
= 0.00375 – 0.00200 = 0.00175 mol = nH+
[H+] in the final solution
1
= 0.00175 ÷ (45 × 10−3) = 0.0389 mol dm−3 16 B
pH = −lg(0.0389) = 1.4 The white precipitate is the hydroxide of M which
11 C is soluble in both NaOH(aq) and H2SO4(aq).
Option A: As X is a weak acid, it is only partially Hence M must be a Group III element with an
ionised in solution. amphoteric nature. M is therefore aluminium.
Option B: As X is a stronger acid than Y, X should AlCl3(aq) is acidic due to high charge density of
undergo ionisation to a larger extent than Y. Al3+.
Option C: For the same concentration, since X [Al(H2O)6]3+ + H2O ⇌ Al(H2O)5(OH)]2+ + H3O+
ionises to a larger extent than Y, [H+] is greater for Al3+(aq) + 3OH−(aq)  Al(OH)3(s)
X, giving it a lower pH. Al(OH)3(s) + NaOH(aq)  NaAl(OH)4(aq)
Opton D: For the same no. of moles of X and Y, 2Al(OH)3(s) + 3H2SO4(aq)  Al2(SO4)3(aq) + 6H2O(l)
they require the same volume of NaOH(aq) for
complete neutralisation. 17 C
Option A: Ionic radius of cation decreases across
12 C the period from Na+ to Si4+ due to increasing
Option A: Strength of dispersion forces increases effective nuclear charge as nuclear charge
when I2(g) is changed to I2(s) as the molecules increases across the isoelectronic series (10 e–).
are now closer together. This process is Ionic radius of anion decreases across the period
exothermic, i.e. it has a negative enthalpy change. from P3– to Cl– due to increasing effective nuclear
Option B: Formation of Cl–Cl covalent bond from charge as nuclear charge increases across the
Cl gaseous atoms (reverse of bond energy) is isoelectronic series (18 e–). Ionic radius of anion
exothermic, i.e. it has a negative enthalpy change. is larger than that of cation due to an additional
Option C: This process represents the first shell of electrons.
ionisation energy of Ca which is endothermic, i.e. Option B: Group I and Group II chlorides have
it has a positive enthalpy change. high melting points due to strong ionic bonds
Option D: This process represents the between oppositely charged ions which require a
combustion of ethanol which is exothermic, i.e. it lot of energy to overcome. Group III to Group VI
has a negative enthalpy change. chlorides have low melting points due to weak
intermolecular forces of attraction which require
13 C less energy to overcome.
Standard enthalpy change of reaction of calcium Option C: Na2O readily dissolves in water to form
and water, Hor NaOH which is strongly alkaline with a very high
= Hof (product) Hof (reactant) pH 13. MgO reacts slightly with water to form
=  Hof (Ca(OH)2)  2 Hof (water) (since the enthalpy Mg(OH)2 of pH 10. Al2O3 and SiO2 are insoluble
change of formation of Ca and H2 are both zero) in water giving pH 7. Non–metallic oxides form
Hence Hof (Ca(OH)2) = Hor + 2Hof (water) acids in water with low pH 2.
Option D: Generally, 1st IE increases across the
14 C period due to increasing effective nuclear charge.
The rate of reaction is faster (steeper gradient) Exceptions: 1st IE of Al < 1st IE of Mg and 1st IE of
with H2SO4 due to a higher concentration of H+ S < 1st IE of P.
ions. Since H2SO4 is a dibasic acid, using the
same volume and concentration of H2SO4 results 18 B
in twice the no. of moles of H+ present as 3 structural isomers are shown below.
compared to HCl. Since zinc is in excess, the
volume of H2 evolved at the end of the reaction
will be twice (240 cm3) that of the reaction with
HCl (120 cm3) since each molecule of H2SO4
releases two H+ ions.
15 A 19 B
From the acid–base nature of the oxides, it can G has two C=C
be deduced that X is in Group III, Y is in Group I bonds that can
or Group II, and Z is a non–metal. Since ionic exhibit geometric
radius of metal ion decreases across the period isomerism. The C=C
due to increasing nuclear charge, ion of X is bond in the ring does
smaller than ion of Y. Non–metal ion of the same not exhibit geometric
period has a larger ionic radius than a metal ion isomerism due to
as it gains electrons to form an additional shell of ring strain. The
electrons. Hence, ion of Z has the largest ionic terminal alkene does
radius. not exhibit geometric
isomerism due to two
identical H atoms on
one carbon atom of
the C=C bond.
2
No. of geometric isomers = 22 alcohol will be oxidised by hot K2Cr2O7 with
20 A H2SO4(aq) to form –CO2H.
Option A: The methyl ketone, RCOCH3 will give
positive results for the 2,4–dinitrophenylhydrazine 24 D
and the tri–iodoform tests. Option A: Nootkatone has no CH3CH(OH)– or
CH3CO– structural unit to form a yellow ppt with
alkaline I2(aq).
Option B: Nootkatone has no aldehyde group to
Option B: One of the products formed is a ketone react with Tollens’ reagent to give a Ag mirror.
which will give a positive result for the 2,4– Option C: Nootkatone does not contain C–X
dinitrophenylhydrazine test. However, none of the group to react with KCN(alc) to form a nitrile.
products has the RCOCH3 structure to give a Option D: Nootkatone reacts with hot acidified
positive result for the tri–iodoform test. KMnO4 to form only one organic product.
Option C: The product formed does not give

positive results for 2,4–dinitrophenylhydrazine
and tri–iodoform tests.
25 B
Orange ppt. with 2,4–dinitrophenylhydrazine
indicates presence of aldehyde and/or ketone.
1 mol of H2 gas liberated with excess Na indicates
presence of two –OH groups OR two –CO2H
Option D: The products formed do not give groups OR one –OH and one –CO2H groups.
positive results for 2,4–dinitrophenylhydrazine Option A: Aldehyde present to form orange ppt.
and tri–iodoform tests. with 2,4–dinitrophenylhydrazine. But only one
–OH group present to form 0.5 mol of H2 when
reacted with excess Na.
Option B: Ketone present to form orange ppt. with
2,4–dinitrophenylhydrazine. One –OH and one
21 D –CO2H groups present to form 1 mol of H2 when
Option A: Alcohol, aldehyde and ketone do not reacted with excess Na.
react with NaOH. Option C: No orange ppt. with 2,4–
Option B: Benzaldehyde does not react with dinitrophenylhydrazine as aldehyde or ketone is
Fehling’s solution. They only react with Tollens’ absent. One –OH and one –CO2H groups present
reagent. Only aliphatic aldehydes react with to form 1 mol of H2 when reacted with excess Na.
Fehling’s solution. Option D: Ketone present to form orange ppt. with
Option C: Aldehyde and ketone react with 2,4–dinitrophenylhydrazine. But only one –CO2H
hydrogen cyanide in an addition reaction. group present to form 0.5 mol of H2 when reacted
Option D: Aldehyde can be oxidised by hot with excess Na.
acidified K2Cr2O7 to a carboxylic acid while the
two secondary alcohol groups are oxidised to 26 A (1, 2 and 3 are correct)
ketones. Option 1: Correct
The reaction between a carbonyl compound and
22 A HCN involves the two reactant molecules
combining to form the cyanohydrin product.
Size of atom: F < Cl < Br < I
Hence it is an addition reaction.
Strength of bond: C–F > C–Cl > C–Br > C–I
Option 2: Correct
The larger the size of the halogen atom, the Comparing experiments 1 and 2, rate doubles
longer and weaker the C–X bond (where X = F, Cl,
when volume of CN– doubles in experiment 2.
Br, I) which is more easily broken. Hence C–I Hence reaction is first order wrt CN–.
bond is most easily broken and the I– ions formed Comparing experiments 1 and 4, rate doubles
will react with Ag+(aq) to form a yellow precipitate when volume of CH3CH2CHO doubles in
of AgI. experiment 4. Hence reaction is first order wrt
CH3CH2CHO.
23 D Comparing experiments 3 and 4, rate doubles
Options A and B: LiAlH4 in dry ether is unable to when temperature and volume of HCN doubles in
reduce alkene. experiment 3. Given that rate doubles for every
Option C: Hot KMnO4 with H2SO4(aq) will cause 10 oC rise in temperature, it can be deduced that
both –CH2OH and –CH2CH2CH3 side chains on reaction is zero order wrt HCN.
the benzene ring to be oxidised to –CO2H as both Hence, the rate equation is given by
side chains have a benzylic hydrogen. rate = k[CH3CHO][CN−]
Option D: Both aldehyde and alkene functional Option 3: Correct
groups will be reduced by H2, Pt. Only the primary This is an overall second order reaction.
3
Units of k = (mol dm−3 s−1) ÷ (mol dm−3)2
= mol−1 dm3 s−1
27 A (1, 2 and 3 are correct)

Option 1: Correct
There are three bond pairs and zero lone pair
around the C atom. Shape is trigonal planar
around the C atom and hence angle x =120o.
Option 2: Correct
The C=O bond is made up of one  bond and one
 bond while a single bond is made up of only one
 bond. Hence the molecule has only one  bond.
Option 3: Correct
There are two lone pairs of electrons on each O
atom and one lone pair of electrons on each N
atom. Hence the molecule has only four lone
pairs of electrons.
28 B (1 and 2 only are correct)

Option 1: Correct
Al2O3 is an amphoteric oxide which can react with
both KOH and HCl to form soluble compounds.
Al2O3(s) + 2KOH(aq) + 3H2O(l)  2K[Al(OH)4](aq)
Al2O3(s) + 6HCl(aq)  2AlCl3(aq) + 3H2O(l)
Option 2: Correct
SiCl4 undergoes hydrolysis in water as Si has
energetically accessible vacant 3d orbitals to
accept lone pairs of electrons from water to give
an acidic solution.
SiCl4 + 2H2O  SiO2 + 4HCl
Option 3: Incorrect
S does not react with water.
29 D (1 only is correct)
The chloroalkane will undergo substitution when

boiled with NaOH(aq) to form an alcohol. The
ester will undergo base hydrolysis to form
RCO2−Na+ and an alcohol.
30 B (1 and 2 only are correct)

Effervescence is observed due to formation of
CO2(g).
Option 1: Correct
Option 2: Correct
Option 3: Incorrect
4
Higher 1
CANDIDATE
NAME ……………………………………………….…………..
CT GROUP ……………………………..
CHEMISTRY 8872/02
Paper 2 13 September 2016
Candidates answer Section A on the Question Paper. 2 hours
Additional Materials: Answer Paper

Data Booklet
Write your name and CT group on all the work you hand in.
Write in dark blue or black pen on both sides of the paper.
You may use a soft pencil for any diagrams, graphs or rough working.
Section A
Answer all the questions.
Section B
Answer two questions on separate answer paper.
The number of marks is given in brackets [ ] at the end of each question or part question.
FOR EXAMINER’S USE
Section A Section B
A1 B4
A2 B5
A3 B6
Total / 80

2
Section A
Answer all questions in the space provided.
1 A 2.00 g salt contains a mixture of potassium iodate, KIO3, and potassium iodide, KI.
Dissolving this mixture in the presence of acid will lead to formation of iodine in a redox
reaction as shown:
IO3– + 5I– + 6H+  3I2 + 3H2O
(a) (i) Identify the oxidising and reducing agent in this reaction and state its change in
oxidation number.
Oxidising agent: Change in oxidation number:
Reducing agent: Change in oxidation number:
[2]
(ii) 2.00 g of this mixture was dissolved in a 250 cm3 solution containing excess
acidified potassium iodide solution. The iodine produced in this reaction reacts
with sodium thiosulfate, Na2S2O3 as shown below.
2S2O32– + I2  S4O62– + 2I–
10.0 cm3 of the resultant solution requires 22.35 cm3 of 2.50 x 10–2 mol dm–3
thiosulfate to completely react with the iodine formed. Determine the percentage
composition by mass of potassium iodide and potassium iodate in the mixture.
[3]
When a colourless solution containing KIO3 and starch is mixed with acidified sodium
hydrogensulfite, NaHSO3, the resultant mixture is initially colourless but turned to blue–black
after some time. The blue–black colouration is only formed when the concentration of iodine
in the solution is sufficiently high.
(b) (i) When iodate ions are first mixed with hydrogensulfite ions, iodide and sulfate(VI)
ions are formed. Write two half–equations and hence a balanced equation for
this redox reaction.
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………[2]
 VJC 2016 8872/02/PRELIM/16

3
(ii) The iodate in excess will oxidise the iodide generated above to form iodine.
However, the iodine is reduced immediately back to iodide by hydrogensulfite.
Write two half–equations and hence a balanced equation for the reaction
between iodine and hydrogensulfite.
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………[2]
(iii) With reference to the reaction between iodide and iodate as well as your
answers to (b)(i) and (b)(ii), explain why a blue–black colouration is formed after
some time when a colourless solution containing KIO3 and starch is mixed with
acidified sodium hydrogensulfite, NaHSO3.
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………[2]
(c) 20 cm3 of a gaseous mixture containing gaseous ethanol, carbon monoxide and
excess oxygen was burned completely. There was a contraction of 1 cm3. When the
product mixture was passed through sodium hydroxide, there was a further contraction
of 6 cm3. All gas volumes are measured at 400 K and 1 atm.
Determine the molar composition of the ethanol and carbon monoxide in this gaseous
mixture.
[3]
[Total: 14]

4
2 Ibuprofen is one of the most commonly used nonsteroidal anti-inflammatory drugs and can
be made from the following process:
(a) State the type of reaction for the conversion of A to B.
…………………………………………………………………………………………….........[1]
(b) Describe a simple chemical test to distinguish between A and B, giving the reagents
and conditions, observations, and balanced equation for the positive test.
[2]
(c) Suggest reagents and conditions that can be used to convert compound C to
Ibuprofen in one step in the laboratory.
…………………………………………………………………………………………….........[1]
(d) A student commented that ibuprofen can be produced via a 3-step synthesis in the
laboratory starting from compound D, as shown below.
 VJC 2016 8872/02/PRELIM/16

5
State the reagents and conditions for steps 1, 2 and 3. Give the structures of the
intermediates X and Y.
X: Y:
Step 1: ………………………………………………………………………………………..
Step 2:
………………………………………………………………………………………..
Step 3:
……………………………………………………………………………………. [4]
(e) Ibuprofen can be also synthesised when compound D reacts with carbon monoxide
over palladium catalyst.
Use the concept of activation energy, together with an appropriate sketch of the
Boltzmann distribution, to explain why the addition of a suitable catalyst speeds up a
chemical reaction.
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….........[3]

6
(f) Young children can find it difficult to swallow tablets or pills. As a result, ibuprofen is
supplied as an “infant formula” emulsion, which is a homogeneous mixture of two or
more liquids (e.g. oil and water) that are immiscible.
To prevent the liquids from separating, an emulsifier is used and one such emulsifier is
polysorbate 80. Its structure is given below.
O
CH2 C H
CH3 CH2 6 O C OCH2CH2OH
7
H
O OCH2CH2OH
OCH2CH2OH
polysorbate 80
Explain why this molecule acts as an emulsifier.
…………………………………………………………………………………………….............
…………………………………………………………………………………………….............
…………………………………………………………………………………………….........[1]
(g) The decomposition of ibuprofen follows a first order kinetics with a half-life of 1.5 hours.
Calculate the mass of the drug that remains in the blood for a dosage of 400 mg after
6 hours.
[1]
[Total: 13]
 VJC 2016 8872/02/PRELIM/16

7
3 (a) Substances R, S and T react according to the following equation:
R(aq) + 2S(aq) + T(aq)  2U(aq) + V(aq)
To find the rate equation for the above reaction, separate experiments were performed.
The results are shown below.
(i) By showing your working clearly on the graph above, prove that the order of
reaction with respect to T is first order.
[1]
(ii) Deduce the order of reaction with respect to R and S.
[2]

8
(iii) Write the rate equation for the reaction. Hence, calculate a value for the rate
constant, giving its units.
[2]
(b) Piperidine is a monoacidic base and is widely used building block and chemical
reagent in the synthesis of organic compounds.
N
H
piperidine
(i) The pH of an aqueous solution of piperidine is 10.1. Calculate the concentration

of hydroxide ions in the solution.
[1]
(ii) In a titration, 25 cm3 of the aqueous solution of piperidine in (b)(i) was found to
react completely with 30 cm3 of 0.15 mol dm-3 of HCl (aq). Calculate the
concentration of piperidine solution.
[1]
(iii) With reference to your answers to (b)(i) and (b)(ii), explain why piperidine is a
weak base.
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………[1]
(iv) Which of the indicators from the table below could you use for this titration in
(b)(ii)? Explain your answer.
Indicator Working range Low pH color High pH color
Tetrabromophenol blue 3.0 – 4.6 yellow blue
Thymolphthalein 9.3 – 10.5 colorless blue
……………………………………………………………………………………………...
…………………………………………………………………………………………...[1]
 VJC 2016 8872/02/PRELIM/16

9
(c) When 1 mole of X is mixed with 1 mole of Y, the results were as shown:
X(g) + Y(g) Z(g) + E(l)
(i) Experiments were carried out on the above equilibrium with changes in the
conditions. Plot and indicate on the graph (using dotted lines) the variation of X
with time for each experiment.
(I) Experiment 1: Lower pressure
[1]
(II) Experiment 2: More X used initially
[1]
(ii) Explain the shape of the graph obtained for experiment 1 in (c)(i).
……………………………………………………………………………………………...
……………………………………………………………………………………………...
……………………………………………………………………………………………[2]
[Total: 13]

10
Section B
Answer two questions from this section on separate answer paper.

4
(a) Describe the bonding in benzene in terms of orbital overlap. You may draw a diagram
to illustrate your answer. [3]
(b) The successive ionisation energies in kJ mol–1 of the elements, X and Y, are given
below.
1st 2nd 3rd 4th 5th 6th 7th 8th
X 580 1817 2745 11577 14842 19379 23326 27465
Y 1000 2252 3357 4556 7004 8496 27107 31719
(i) Deduce the group that element X and Y belongs to. [2]
(ii) Hence, give the formula of the compound formed between X and Y. [1]
(c) Beta-methylstyrene undergoes the reactions shown below:
(i) State the reagents and conditions required for reactions I to III. [3]
(ii) Beta-methylstyrene exists naturally as a pair of geometric isomers. Draw the

structures of the isomers, clearly labelling each isomer. [2]
(d) I2 is not very soluble in water. However when I2 reacts with KI(aq), it forms highly
soluble KI3.
Draw the dot and cross diagram of the I3− ion (including all lone pairs of electrons), and
deduce its shape and bond angle. [2]
 VJC 2016 8872/02/PRELIM/16

11
(e) The standard enthalpy change of vapourisation (∆Hovap), is defined as the energy
required to convert 1 mol of a compound into the gaseous state.
The table below shows the ∆Hovap of NH3 and NI3.
Compound Standard enthalpy change of vapourisation,
∆Hovap / kJ mol-1
NH3 +23.35
NI3 + 28.29
(i) Explain why the ∆Hovap of NI3 is more endothermic than NH3. [2]
AlI3 has a simple molecular structure. In the gas phase, it dimerises readily to
form the dimer Al2I6. The two species are related by equilibrium (I) shown below:
Al2I6(g) ⇌ 2AlI3(g) ------ (I) ∆H > 0
(ii) A 10.0 g sample of Al2I6 was allowed to vapourise in a 2 dm3 vessel at 400 oC.
Given that the degree of dissociation (α) of Al2I6 was 0.35, find the Kc value for
equilibrium (I) at 400 oC. [3]
(iii) Explain what happens to the position of equilibrium (I) for each of the changes
below.
( I) The reaction was carried out at 500 oC.

(II) A sample of Ar(g) was introduced into a 1 dm3 vessel containing AlI3(g) and
Al2I6(g) at 400 oC. [2]
[Total: 20]

12
5 (a) Describe the carbon atom, 12C, as fully as you can, including the nature and location of
the sub-atomic particles, and sketch the shapes of the filled valence orbitals. [3]
(b) Predict, with reasons, how the radius of carbon atom would compare with
(i) C– ion; [1]
(ii) C+ ion [1]
(c) Esters of carboxylic acids are often used as components of synthetic fruit flavours.
Ethyl butanoate, P, CH3CH2CH2CO2CH2CH3, is a major component of strawberry
flavourings.
(i) Name the reagents and state conditions needed to synthesise P from butanoic
acid. [1]
(ii) Write an equation for the formation of P from butanoic acid. [1]
(d) CH3CH2CH(NH2)CH3 can be synthesized from CH3CH2CH2CH2OH through a 3-step

reaction route.
Suggest reagents and conditions for each step, showing the structural formulae of the
intemediates produced. [4]
(e) Compound A, C4H10O2, reacts with sodium metal but is insoluble in aqueous sodium
hydroxide, and does not form pale yellow precipitate with alkaline aqueous iodine. On
treatment with hot acidified sodium manganate(VII), A gives B, C4H8O3, which is
soluble in aqueous sodium hydroxide. On treatment of B with phosphorus
pentachloride, a compound C, C4H6OCl2 is obtained. On warming B with concentrated
sulfuric acid, D, C8H12O4 is obtained.
(i) From the observations provided above, suggest the identity of the compounds, A
to D, giving your reasons and explain the reactions. [8]
(ii) Compound E, an isomer of compound A, can also react with sodium metal but
forms a pale yellow precipitate with alkaline aqueous iodine. Suggest a structure
for compound E. [1]
[Total: 20]
 VJC 2016 8872/02/PRELIM/16

13
6 (a) Magnesium, silicon and phosphorus are elements in the third period of the Periodic
Table. Arrange the elements in order of increasing melting point. Explain your answer
in terms of structure and bonding. [4]
(b) There is said to be a ‘diagonal relationship’ between beryllium and aluminium as they
show similar chemical behaviour due to their similarities in electronegativity and
charge density.
(i) When a few drops of water are added to solid beryllium chloride, steamy white
fumes are evolved and a white solid remains, which is insoluble in water.
Write a balanced equation for this reaction. [1]
(ii) When a large amount of water is added to solid beryllium chloride, a clear,
weakly acidic solution is obtained. Explain. [1]
(iii) At 750 oC, the relative molecular mass of gaseous beryllium chloride
corresponds to the formula BeCl2. At 550 oC, gaseous beryllium chloride exists
as a mixture of BeCl2 and Y (relative molecular mass of Y is 160).
Determine the molar composition of gaseous beryllium chloride at 550 oC which

has a relative molecular mass of 100. Draw a diagram to illustrate the nature of
the bonding in Y and indicate the value of the bond angle about Be. [2]
(c) A solid mixture contains two oxides of Period 3 elements. To separate the oxides,
water was added to the mixture, followed by filtration. Effervescence was observed
when sodium carbonate was added to the filtrate. The residue does not react with
dilute acid and dilute alkali.
(i) Identify the two oxides present in the mixture. [1]
(ii) Hence, write an equation for the oxide that reacts with water. [1]
(d) (i) Write an equation, with state symbols, to define the Cl–F bond energy in ClF3. [1]
(ii) The following reaction occurs in the gas phase.
3F2(g) + Cl2(g)  2ClF3(g), Hor = –328 kJ mol–1
Use these and other data from the Data Booklet to calculate the average bond
energy of the Cl–F bond in ClF3. [2]
(e) An experiment is conducted to determine the enthalpy change of neutralisation

between methanoic acid (HCO2H) and aqueous sodium hydroxide. Some methanoic
acid is added to excess sodium hydroxide solution. The changes in temperature and
amount of reagents mixed are recorded as follows.
Initial temperature / oC 24.0

o
Final temperature / C 34.0
Mass of HCO2H added / g 1.84
–3 3
Volume of 1 mol dm NaOH(aq) used / cm 50.0
(i) Define standard enthalpy change of neutralisation with respect to methanoic acid
and aqueous sodium hydroxide. [1]

14
(ii) Use the above data to calculate the enthalpy change of neutralisation, assuming
that 4.2 J is required to raise the temperature of 1 cm3 solution by 1°C. [2]
(iii) The magnitude of enthalpy change of neutralisation between aqueous nitric acid
and aqueous sodium hydroxide is found to be larger than the value calculated in
(e)(ii). Explain why this is so. [1]
(f) Propanone, CH3COCH3, an important industrial solvent, can be converted into another
industrially important solvent, MIBK, by the following sequence.
(i) When F is formed in step I, no other compound is produced. Suggest a

structural formula for F, which contains one –OH group. [1]
(ii) Name the types of reaction occurring in steps I and III. [1]
(iii) G is formed from F in step II. Suggest the reagent and condition for step II. [1]
[Total: 20]
 VJC 2016 8872/02/PRELIM/16

Higher 1
CANDIDATE
NAME ……………………………………………….…………..
CT GROUP ……………………………..
CHEMISTRY 8872/02
Paper 2 13 September 2016
Candidates answer Section A on the Question Paper. 2 hours
Additional Materials: Answer Paper

Graph Paper
Data Booklet
Write your name and CT group on all the work you hand in.
Write in dark blue or black pen on both sides of the paper.
You may use a soft pencil for any diagrams, graphs or rough working.
Section A
Answer all the questions.
Section B
Answer two questions on separate answer paper.
The number of marks is given in brackets [ ] at the end of each question or part question.
FOR EXAMINER’S USE
Section A Section B
A1 B4
A2 B5
A3 B6
Total / 80

2
1 A 2.00 g salt contains a mixture of potassium iodate, KIO3, and potassium iodide, KI.
Dissolving this mixture in the presence of acid will lead to formation of iodine in a redox
reaction as shown:
IO3– + 5I– + 6H+  3I2 + 3H2O
(a) (i) Identify the oxidising and reducing agent in this reaction and state its change in
oxidation number.
Oxidising agent: IO3– Change in oxidation number: +5 to 0
Reducing agent: I– Change in oxidation number: –1 to 0
Identifying correct oxidising agent and reducing agent

Correct change in the oxidation number for OA and RA. [2]
(ii) 2.00 g of this mixture was dissolved in a 250 cm3 solution containing excess
acidified potassium iodide solution. The iodine produced in this reaction reacts
with sodium thiosulfate, Na2S2O3 as shown below.
2S2O32– + I2  S4O62– + 2I–
10.0 cm3 of the resultant solution requires 22.35 cm3 of 2.50 x 10–2 mol dm–3
thiosulfate to completely react with the iodine formed. Determine the percentage
composition by mass of potassium iodide and potassium iodate in the mixture.
.
No of moles of I2 in 10.0 cm3 solution = 2.50 x 10–2 x x½
= 2.79 x 10–4 mol
No of moles of I 2 in 250 cm3 solution = 2.79 x 10–4 x

.
= 6.98 x 10–3 mol
No of moles of IO3– in 2.00 g = x 6.98 x 10–3

= 2.33 x 10–3 mol
Mass of potassium iodate in 2.00 g = 2.33 x 10–3 x (39.1+127+48.0)

= 0.500 g
Percentage of potassium iodate by mass = (0.500 / 2.00) x 100%

= 25%
Percentage of potassium iodide by mass = 100 – 25

= 75% [3]
When a colourless solution containing KIO3 and starch is mixed with acidified sodium
hydrogensulfite, NaHSO3, the resultant mixture is initially colourless but turned to blue–black
after some time. The blue–black colouration is only formed when the concentration of iodine
in the solution is sufficiently high.
 VJC 2016 8872/02/PRELIM/16

3
(b) (i) When iodate ions are first mixed with hydrogensulfite ions, iodide and sulfate(VI)
ions are formed. Write two half–equations and hence a balanced equation for
this redox reaction.
Reduction half-equation: IO3– + 6H+ + 6e–  I– + 3H2O

Oxidation half-equation: HSO3– + H2O  3H+ + SO42– +2e–
Redox equation: IO3– + 3HSO3–  I– + 3H+ + 3SO42– [2]
(ii) The iodate in excess will oxidise the iodide generated above to form iodine.
However, the iodine is reduced immediately back to iodide by hydrogensulfite.
Write two half–equations and hence a balanced equation for the reaction
between iodine and hydrogensulfite.
I2 +2e–  2I–
HSO3– + H2O  3H+ + SO42– +2e–
I2 + HSO3– + H2O  2I – + SO42– + 3H+ [2]
(iii) With reference to the reaction between iodide and iodate as well as your
answers to (b)(i) and (b)(ii), explain why a blue–black colouration is formed after
some time when a colourless solution containing KIO3 and starch is mixed with
acidified sodium hydrogensulfite, NaHSO3.
The iodine formed from iodide and iodate reacts with hydrogensulfite.
Thus its concentration remains low and no blue–black colouration is
observed.
After some time, when all the hydrogensulfite ions have been consumed,
iodine concentration increases significantly and thus a blue–black
colouration is observed. [2]
(c) 20 cm3 of a gaseous mixture containing gaseous ethanol, carbon monoxide and
excess oxygen was burned completely. There was a contraction of 1 cm3. When the
product mixture was passed through sodium hydroxide, there was a further contraction
of 6 cm3. All gas volumes are measured at 400 K and 1 atm.
Determine the molar composition of the ethanol and carbon monoxide in this gaseous
mixture.
Let the volume of C2H5OH and CO be x cm3 and y cm3 measured at 400 K and 1
atm respectively.
C2H5OH(g) + 3O2(g)  2CO2(g) + 3H2O(g)

Change /cm3 –x –3x +2x +3x
Total change in volume = 2x + 3x – x – 3x = x
2CO(g) + O2(g)  2CO2(g)

Change /cm3 –y –1/2y +y
Total change in volume = y – y – ½ y = – ½y
Hence x – ½ y = –1 ----eqn (1)
The further contraction is due to the removal of CO2 by NaOH.

Hence, 2x + y = 6 ----eqn(2)
Solving the two simultaneous equations gives x = 1 and y = 4

4
Molar composition of ethanol = (1/20) x 100% = 5%

Molar composition of CO = (4/20) x 100% = 20% [3]
[Total: 14]
2 Ibuprofen is one of the most commonly used nonsteroidal anti-inflammatory drugs and can
be made from the following process:
(a) State the type of reaction for the conversion of A to B.
Substitution [1]
(b) Describe a simple chemical test to distinguish between A and B, giving the reagents
and conditions, observations, and balanced equation for the positive test.
2,4-dinitrophenylhydrazine, room temperature
Orange ppt observed for B. No orange ppt for A.
Alternative answer:
I2(aq), NaOH, warm
Yellow ppt observed for B. No yellow ppt for A.
[2]
(c) Suggest reagents and conditions that can be used to convert compound C to
Ibuprofen in one step in the laboratory.
K2Cr2O7, H2SO4(aq), heat. (KMnO4 not accepted – may oxidise side chain) [1]
 VJC 2016 8872/02/PRELIM/16

5
(d) A student commented that ibuprofen can be produced via a 3-step synthesis in the
laboratory starting from compound D, as shown below.
State the reagents and conditions for steps 1, 2 and 3. Give the structures of the
intermediates X and Y.
X:
Y:
Step 1:
Reagent: PCl5,
Condition: Room temperature
Step 2:
Reagent: Alcoholic KCN
Condition: Reflux
Step 3:
Reagent: H2SO4(aq)
Condition: Heat [4]

6
(e) Ibuprofen can be also synthesised when compound D reacts with carbon monoxide
over palladium catalyst.
Use the concept of activation energy, together with an appropriate sketch of the
Boltzmann distribution, to explain why the addition of a suitable catalyst speeds up a
chemical reaction.
number of
molecules with T1
a given energy
Ea’ Ea energy
where
Ea = activation energy for uncatalysed reaction
Ea’ = activation energy for catalysed reaction
A catalyst works by providing an alternative pathway with lower activation

energy, Ea,’
so that there are more molecules with energy  Ea’.
Hence frequency of effective collisions increases leading to a higher rate. [3]
(f) Young children can find it difficult to swallow tablets or pills. As a result, ibuprofen is
supplied as an “infant formula” emulsion, which is a homogeneous mixture of two or
more liquids (e.g. oil and water) that are immiscible.
To prevent the liquids from separating, an emulsifier is used and one such emulsifier is
polysorbate 80. Its structure is given below.
O
CH2 C H
CH3 CH2 6 O C OCH2CH2OH
7
H
O OCH2CH2OH
OCH2CH2OH
polysorbate 80
Explain why this molecule acts as an emulsifier.
Presence of OH groups that render the molecule to be soluble in water.

Presence of non-polar hydrocarbon groups that render the molecule to be
soluble in oil / non-polar liquids.
[1]
(g) The decomposition of ibuprofen follows a first order kinetics with a half-life of 1.5 hours.
Calculate the mass of the drug that remains in the blood for a dosage of 400 mg after
6 hours.
 VJC 2016 8872/02/PRELIM/16

7
For a first order reaction, half-life is constant.

6 hours  4 half-lives
Final mass of ibuprofen = (1/2)4 x 400
= 25 mg [1]
[Total: 13]
3 (a) Substances R, S and T react according to the following equation:
R(aq) + 2S(aq) + T(aq)  2U(aq) + V(aq)
To find the rate equation for the above reaction, separate experiments were performed.
The results are shown below.
(i) By showing your working clearly on the graph above, prove that the order of
reaction with respect to T is first order.
Shows 3 constant t1/2 on graph of [T] against time.

Graph shows constant t12= 2 min
Reaction is first order with respect to T. [1]

8
(ii) Deduce the order of reaction with respect to R and S.
Graph of [R] against time is a straight line with constant gradient.

Rate of reaction is constant at different concentrations of R.
Reaction is zero order with respect to R.
When concentration of S increases by 2 times, the gradient increases by 2
times.
Reaction is first order with respect to S. [2]
(iii) Write the rate equation for the reaction. Hence, calculate a value for the rate
constant, giving its units.
Rate = k[S][T] (ecf)

k = (0.100)/ (4)(2)
= 0.0125 mol-1 dm3 min-1
[2]
(b) Piperidine is a monoacidic base and is widely used building block and chemical
reagent in the synthesis of organic compounds.
N
H
piperidine
(i) The pH of an aqueous solution of piperidine is 10.1. Calculate the concentration

of hydroxide ions in the solution.
pOH = 14-10.1
= 3.9
[OH−] = 10−3.9
= 1.26 x 10−4 mol dm−3 [1]
(ii) In a titration, 25 cm3 of the aqueous solution of piperidine in (b)(i) was found to
react completely with 30 cm3 of 0.15 mol dm-3 of HCl (aq). Calculate the
concentration of piperidine solution.
CpiperidineVpiperidine = CHCl VHCl

Cpiperidine(25/1000) = (30/1000) (0.15)
Cpiperidine= 0.180 mol dm−3 [1]
(iii) With reference to your answers to (b)(i) and (b)(ii), explain why piperidine is a
weak base.
[OH−] is much lower than piperidine concentration

Piperidine did not undergo complete dissociation to give OH−. Thus it is a
weak base. [1]
 VJC 2016 8872/02/PRELIM/16

9
(iv) Which of the indicators from the table below could you use for this titration in
(b)(ii)? Explain your answer.
Indicator Working range Low pH color High pH color
Tetrabromophenol blue 3.0 – 4.6 yellow blue
Thymolphthalein 9.3 –10.5 colorless blue
Tetrabromophenol blue.
It is a strong acid-weak base titration.
Alternative reason (not too important vs type of acid-base titration):

The working range of the indicator should fall within the range of rapid pH
change of the titration curve. [1]
(c) When 1 mole of X is mixed with 1 mole of Y, the results were as shown:
X(g) + Y(g) Z(g) + E(l)
(i) Experiments were carried out on the above equilibrium with changes in the
conditions. Plot and indicate on the graph (using dotted lines) the variation of X
with time for each experiment.
(I) Experiment 1: Lower pressure
[1]
(II) Experiment 2: More X used initially
[1]

10
(ii) Explain the shape of the graph obtained for experiment 1 in (c)(i).
When there is lower pressure, molecules are less crowded together.

By Le Chatelier’s principle, position of equilibrium shifts left for
X(g) + Y(g) Z(g) + E(l)
to increase the number of moles of gas.
Hence, more X is present at equilibrium.
When there is lower pressure, rate decreases hence a gentler gradient is
observed. [2]
[Total: 13]
Section B
Answer two questions from this section on separate answer paper.

4
(a) Describe the bonding in benzene in terms of orbital overlap. You may draw a diagram
to illustrate your answer.
atomic
The sigma bond formed between carbon–carbon is formed by

the head–on overlap of the orbital of carbon atoms.
The sigma bond formed between carbon–hydrogen is formed by
the head–on overlap of the atomic orbital of carbon and the s orbital of hydrogen
atom.
The pi bond formed between carbon atoms is formed by the
sideways overlap of the p orbital of carbon atoms.
These pi bonds are formed above and below the ring of carbon atoms.
[3]
(b) The successive ionisation energies in kJ mol–1 of the elements, X and Y, are given
below.
1st 2nd 3rd 4th 5th 6th 7th 8th
X 580 1817 2745 11577 14842 19379 23326 27465
Y 1000 2252 3357 4556 7004 8496 27107 31719
 VJC 2016 8872/02/PRELIM/16

11
(i) Deduce the group that element X and Y belongs to.
There is a big jump between the 3rd and 4th ionisation energy of X, hence
there are 3 valence electrons.
X: Group III
There is a big jump between the 6th and 7th ionisation energy of Y, hence
there are 6 valence electrons.
Y: Group VI [2]
(ii) Hence, give the formula of the compound formed between X and Y.
X2Y3 [1]
(c) Beta-methylstyrene undergoes the reactions shown below:
(i) State the reagents and conditions required for reactions I to III.
I: HI(g), room temperature

II: NaOH(aq), heat
III: I2, NaOH(aq), warm [3]
(ii) Beta-methylstyrene exists naturally as a pair of geometric isomers. Draw the

structures of the isomers, clearly labelling each isomer.
[2]
(d) I2 is not very soluble in water. However when I2 reacts with KI(aq), it forms highly
soluble KI3.
Draw the dot and cross diagram of the I3− ion (including all lone pairs of electrons), and
deduce its shape and bond angle.
Shape: Linear
Bond angle: 180o
[2]

12
(e) The standard enthalpy change of vapourisation (∆Hovap), is defined as the energy
required to convert 1 mol of a compound into the gaseous state.
The table below shows the ∆Hovap of NH3 and NI3.
Compound Standard enthalpy change of vapourisation,
∆Hovap / kJ mol-1
NH3 +23.35
NI3 + 28.29
(i) Explain why the ∆Hovap of NI3 is more endothermic than NH3. [2]
Although NH3 molecules are held by hydrogen bonding,

NI3 has a much greater number of electrons than NH3.
Hence more energy is needed to overcome
the stronger dispersion forces in NI3. [2]
AlI3 has a simple molecular structure. In the gas phase, it dimerises readily to
form the dimer Al2I6. The two species are related by equilibrium (I) shown below:
Al2I6(g) ⇌ 2AlI3(g) ------ (I) ∆H > 0
(ii) A 10.0 g sample of Al2I6 was allowed to vapourise in a 2 dm3 vessel at 400 oC.
Given that the degree of dissociation (α) of Al2I6 was 0.35, find the Kc value for
equilibrium (I) at 400 oC.
Concentration of Al2I6 = 10.0 / 2

= 5.00 g dm−3
[Al2I6] = 5.00 / 816
= 0.00613 mol dm−3
[Al2I6] (after dissociation) = 0.65 x 0.00613
= 0.00398 mol dm−3
[AlI3] = 2 x 0.35 x 0.00613
= 0.00429 mol dm−3
2
[AlI3 ]
Kc =
[Al2 I6 ]
0.004292
=
0.00398
= 0.00462 mol dm−3
[3]
(iii) Explain what happens to the position of equilibrium (I) for each of the changes
below.
( I) The reaction was carried out at 500 oC.

(II) A sample of Ar(g) was introduced into a 1 dm3 vessel containing AlI3(g) and
Al2I6(g) at a 400 oC.
 VJC 2016 8872/02/PRELIM/16

13
For (A), when the temperature is increased, the endothermic reaction is

favoured or to remove the excess heat.
Hence, the position of equilibrium (I) will shift to the right.
For (B), the concentration of AlI3(g) and Al2I6(g) remains the same
and there is no shift in the position of equilibrium (I). [2]
[Total: 20]
5 (a) Describe the carbon atom, 12C, as fully as you can, including the nature and location of
the sub-atomic particles, and sketch the shapes of the filled valence orbitals.
12
C has 6 neutral neutrons and 6 positively charged protons located at the centre
of the atom.
It has 6 negatively charged electrons moving around the nucleus of the atom.
Correct sketch of 2s and any two 2p orbitals
2s orbital 2p orbitals [3]
(b) Predict, with reasons, how the radius of carbon atom would compare with
(i) C– ion;
C– ion has (slightly) larger radius than C atom as it has the same nuclear
charge but there is extra electrostatic repulsion produced by the incoming
electron(s) in the valence shell. So C– ion experiences a smaller effective
nuclear charge leading to weaker pull of electrons by nucleus. [1]
(ii) C+ ion
C+ ion has (slightly) smaller radius than C atom as it has the same nuclear
charge but an electron is lost from the valence shell. So C+ ion experiences
a greater effective nuclear charge leading to stronger pull of electrons by
nucleus. [1]
(c) Esters of carboxylic acids are often used as components of synthetic fruit flavours.
Ethyl butanoate, P, CH3CH2CH2CO2CH2CH3, is a major component of strawberry
flavourings.
(i) Name the reagents and state conditions needed to synthesise P from butanoic
acid.
Ethanol and concentrated sulfuric acid, heat [1]
(ii) Write an equation for the formation of P from butanoic acid.
CH3CH2CH2CO2H + CH3CH2OH  CH3CH2CH2CO2CH2CH3 + H2O [1]

14
(d) CH3CH2CH(NH2)CH3 can be synthesized from CH3CH2CH2CH2OH through a 3-step

reaction route.
Suggest reagents and conditions for each step, showing the structural formulae of the
intemediates, X and Y produced.
X: CH3CH2CH=CH2
Y: CH3CH2CH(Cl)CH3
Step 1:
Reagent: Excess conc H2SO4
Condition: 170 OC
Step 2:
Reagent: HCl(g)
Condition: room temperature
Step 3:
Reagent: Excess conc NH3(alcoholic)
Condition: Heat in sealed tube [4]
(e) Compound A, C4H10O2, reacts with sodium metal but is insoluble in aqueous sodium
hydroxide, and does not form pale yellow precipitate with alkaline aqueous iodine. On
treatment with hot acidified sodium manganate(VII), A gives B, C4H8O3, which is
soluble in aqueous sodium hydroxide. On treatment of B with phosphorus
pentachloride, a compound C, C4H6OCl2 is obtained. On warming B with concentrated
sulfuric acid, D, C8H12O4 is obtained.
(i) From the observations provided above, suggest the identity of the compounds, A
to D, giving your reasons and explain the reactions.
A: (CH3)2C(OH)CH2OH
B: (CH3)2C(OH)CO2H
C: (CH3)2CClCOCl
D:
A has –OH / -CO2H groups as it can react with Na metal via redox / acid-
metal reaction.
A does not have CO2H group as it cannot dissolve in NaOH & does not
have CH3CH(OH)- group (no oxidative cleavage) as it does not give pale
yellow precipiate (CHI3) with alkaline I2(aq).
A is a primary or secondary alcohol which can be oxidised by NaMnO4.
 VJC 2016 8872/02/PRELIM/16

15
B has –CO2H group as it can undergo neutralisation with NaOH to give an

ionic salt, which is soluble in water.
B undergoes substitution with PCl5 to give C  B has –OH / -CO2H groups.
In the presence of H2SO4 which acts a a catalyst, B undergoes
condensation on its own to form ester. [8]
(ii) Compound E, an isomer of compound A, can also react with sodium metal but
forms a pale yellow precipitate with alkaline aqueous iodine. Suggest a structure
for compound E.
CH3CH(OH)CH2CH2OH or CH3CH(OH)CH(OH)CH3 [1]
[Total: 20]
6 (a) Magnesium, silicon and phosphorus are elements in the third period of the Periodic
Table. Arrange the elements in order of increasing melting point. Explain your answer
in terms of structure and bonding.
Phosphorus, magnesium, silicon

Si has the highest melting point as it has a giant covalent structure, and strong
covalent bonds between atoms.
Mg has a giant metallic lattice with metallic bonds / electrostatic attraction
between the delocalised electrons and cations.
P exists as simple covalent molecules with weak dispersion forces between the
molecules.
More energy is required to overcome the covalent bonds between Si atoms than
the metallic bonds of Mg, while least energy is required for the dispersion forces
between P molecules. [4]
(b) There is said to be a ‘diagonal relationship’ between beryllium and aluminium as they
show similar chemical behaviour due to their similarities in electronegativity and
charge density.
(i) When a few drops of water are added to solid beryllium chloride, steamy white
fumes are evolved and a white solid remains, which is insoluble in water.
Write a balanced equation for this reaction.
BeCl2(s) + H2O(l)  BeO(s) + 2HCl(g)

[OR BeCl2(s) + 2H2O(l)  Be(OH)2(s) + 2HCl(g)] [1]
(ii) When a large amount of water is added to solid beryllium chloride, a clear,
weakly acidic solution is obtained. Explain.
Due to the high charge density of Be2+, BeCl2 undergoes hydration and
hydrolysis / Be2+(aq) pulls electrons away from one of the surrounding
water molecules, hence weakening the O–H bond which results in the
release of a proton and give rise to an acidic solution. [1]
(iii) At 750 oC, the relative molecular mass of gaseous beryllium chloride
corresponds to the formula BeCl2. At 550 oC, gaseous beryllium chloride exists
as a mixture of BeCl2 and Y (relative molecular mass of Y is 160).
Determine the molar composition of gaseous beryllium chloride at 550 oC which

has a relative molecular mass of 100. Draw a diagram to illustrate the nature of
the bonding in Y and indicate the value of the bond angle about Be.

16
100 = 80x + 160(1 – x)

x = 0.75 and 1 – x = 0.25
Composition is 75% BeCl2 and 25% Y.
Trigonal planar with respect to Be, hence bond angle is 120o. [2]
(c) A solid mixture contains two oxides of Period 3 elements. To separate the oxides,
water was added to the mixture, followed by filtration. Effervescence was observed
when sodium carbonate was added to the filtrate. The residue does not react with
dilute acid and dilute alkali.
(i) Identify the two oxides present in the mixture.
P4O6 / P4O10 and SiO2 [1]
(ii) Hence, write an equation for the oxide that reacts with water.
P4O6 + 6H2O  4H3PO3

[OR P4O10 + 6H2O  4H3PO4] [1]
(d) (i) Write an equation, with state symbols, to define the Cl–F bond energy in ClF3.
1 1
ClF3(g)  Cl(g) + F(g)
3 3
[1]
(ii) The following reaction occurs in the gas phase.
3F2(g) + Cl2(g)  2ClF3(g), Hor = –328 kJ mol–1
Use these and other data from the Data Booklet to calculate the average bond
energy of the Cl–F bond in ClF3.
Hor = BE(reactants) – BE(products)

–328 = 3BE(F–F) + BE(Cl–Cl) – 6BE(Cl–F)
–328 = 3(158) + 244 – 6BE(Cl–F)
BE(Cl–F) = 174 kJ mol–1 [2]
(e) An experiment is conducted to determine the enthalpy change of neutralisation

between methanoic acid (HCO2H) and aqueous sodium hydroxide. Some methanoic
acid is added to excess sodium hydroxide solution. The changes in temperature and
amount of reagents mixed are recorded as follows.
Initial temperature / oC 24.0

Final temperature / oC 34.0
Mass of HCO2H added / g 1.84
Volume of 1 mol dm–3 NaOH(aq) used / cm3 50.0
 VJC 2016 8872/02/PRELIM/16

17
(i) Define standard enthalpy change of neutralisation with respect to methanoic acid
and aqueous sodium hydroxide.
The enthalpy change when 1 mole of water is formed when methanoic acid
neutralises sodium hydroxide and is carried out in an infinitely dilute
aqueous solution under standard conditions of 298K and 1 atm. [1]
(ii) Use the above data to calculate the enthalpy change of neutralisation, assuming
that 4.2 J is required to raise the temperature of 1 cm3 solution by 1°C.
Heat evolved
= 50.0 × 4.2 × (34.0 – 24.0)
= 2100 J
No. of moles of water formed

= 1.84 ÷ 46.0
= 0.0400 mol
∆Hneut
= –2100 ÷ 0.0400
= –52500 J mol–1
[OR –52.5 kJ mol–1] [2]
(iii) The magnitude of enthalpy change of neutralisation between aqueous nitric acid
and aqueous sodium hydroxide is found to be larger than the value calculated in
(e)(ii). Explain why this is so.
Nitric acid is a strong acid which dissociates completely in solution while

methanoic acid is a weak acid which dissociates partially in solution.
Some energy released during neutralisation is used to ionise the weak acid.
[1]
(f) Propanone, CH3COCH3, an important industrial solvent, can be converted into another
industrially important solvent, MIBK, by the following sequence.
(i) When F is formed in step I, no other compound is produced. Suggest a

structural formula for F, which contains one –OH group.
[1]

18
(ii) Name the types of reaction occurring in steps I and III.
Step I: addition
Step III: reduction [1]
(iii) G is formed from F in step II. Suggest the reagent and condition for step II.
Excess concentrated H2SO4, 170 oC [1]
[Total: 20]
 VJC 2016 8872/02/PRELIM/16

2016 Chemistry H1 JC2 Victoria Junior College

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VICTORIA JUNIOR COLLEGE

Additional Materials: Multiple Choice Answer Sheet

READ THESE INSTRUCTIONS FIRST

Write in soft pencil.

Read the instructions on the Answer Sheet very carefully.

This document consists of 11 printed pages and 1 blank page.

 VJC 2016 8872/01/PRELIM/16 [Turn over

OF2 + SO2  SO3 + F2

What is oxidised and what is reduced in this reaction?

fluorine oxygen in OF2 sulfur

Assume the egg shell is pure calcium carbonate.

What is the formula of the hydrocarbon?

A CH4 B C2H6 C C3H8 D C6H12

4 Which statement about the ammonium ion, NH4+, is correct?

A All bond angles are 107o.

 VJC 2016 8872/01/PRELIM/16

A 8 days B 16 days C 24 days D 30 days

6 2–methylpropan–1–ol and butan–1–ol are structural isomers. 2–methylpropan–1–ol

A 2–methylpropan–1–ol cannot form hydrogen bonds.

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

H2(g) + H2+(g)  H(g) + H3+(g)

What could be the composition of an H3+ ion?

protons neutrons electrons

 VJC 2016 8872/01/PRELIM/16 [Turn over

Which of the following statements regarding the Haber Process is correct?

A Fe lowers the activation energy of the forward reaction only.

10 20 cm3 of 0.10 mol dm–3 sodium hydroxide solution is added to 25 cm3 of

What is the approximate pH of the final solution?

A 1.4 B 2.8 C 4.5 D 7.0

Which statement about X and Y is correct?

A X is completely ionised in solution.

12 Which equation has a positive enthalpy change?

13 Calcium reacts with water to form calcium hydroxide and hydrogen.

Ca(s) + 2H2O(l)  Ca(OH)2(s) + H2(g)

I standard enthalpy change of formation of water

A III only B I and II C I and III D II and III

14 Acids react with Zn according to the following equation.

2H+(aq) + Zn(s)  Zn2+(aq) + H2(g)

 VJC 2016 8872/01/PRELIM/16 [Turn over

16 The proton number of the element M is less than 20.

In which Group of the Periodic Table is M likely to be found?

What is the property?

How many structural isomers would this compound have?

19 Compound G has the following structure.

How many geometric isomers does compound G have?

21 Which of the following statements about the compound below is correct?

A It will react with sodium hydroxide.

22 The presence of a halogen in an organic compound may be detected by warming the

Which compound would be the quickest to produce a precipitate?

 VJC 2016 8872/01/PRELIM/16 [Turn over

Which statement about nootkatone is correct?

A It forms a yellow precipitate with alkaline I2(aq).

 VJC 2016 8872/01/PRELIM/16

 It forms orange precipitate with 2,4–dinitrophenylhydrazine.

Which of the following could be R?

 VJC 2016 8872/01/PRELIM/16 [Turn over

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

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

26 A student wishes to study the kinetics of the following reaction.

Volume of Volume Volume Volume

1 The reaction is an addition reaction.

 VJC 2016 8872/01/PRELIM/16

27 Urea is a product of animal metabolism. It can also be used as a fertiliser.

The diagram shows angle x in this molecule.