NANYANG JUNIOR COLLEGE

JC 2 PRELIMINARY EXAMINATION
Higher 2

CHEMISTRY

9647/01

Paper 1 Multiple Choice

27 September 2011
1 hour

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 name, CT and NRIC / FIN on the Answer Sheet in the spaces provided.

There are forty questions in this paper. Answer all questions. For each question there are
four possible answers A, B, C and D.
Choose the one you consider correct and record your choice in soft pencil on the separate
Answer Sheet.

Read the instructions on the Multiple Choice Answer Sheet 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.
You may use a calculator.

This document consists of 14 printed pages.

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Section A
For each question in this section, there are four possible answers, A, B, C, and D.
Choose the one you consider to be correct.
1.

A sample of 10 dm3 of polluted air is passed through limewater so that all the carbon
dioxide present is precipitated as calcium carbonate. The mass of calcium carbonate
formed is 0.05 g. What is the percentage, by volume, of carbon dioxide in the air
sample?
[Ar C, 12.0; O, 16.0; Ca, 40.1]
A

0.03 %

0.05 %

0.12 %

0.6%

CO2 + Ca(OH)2
CaCO3 + H2O

Amount of calcium carbonate = 0.05 / [40.1 + 12.0 + 3(16.0)] = 0.0004995 mol
Amount of carbon dioxide = 0.0004995 mol
Vol of carbon dioxide = 0.0004995 x 24 = 0.01199 dm3
Percentage by vol = 0.01199/10 x 100 = 0.12 %
2.

In an experiment, 100 cm3 of 0.020 mol dm3 acidified iron (II) sulphate solution is
quantitatively oxidized by 50 cm3 of a solution containing 0.020 mol dm3 of an
oxidizing agent, XO3. What is the final oxidation state of X?
A

+2

+3

Since its an MCQ question, you can immediately deduce that mole ratio
Fe2+ : XO3- = 2:1 as the volume of Fe2+ is twice the volume of XO3- while conc of both
solution is the same.
Fe2+ is oxidized to Fe3+, 1 mol Fe2+ gives out 1 mol e
=> 2 mol Fe2+ gives out 2 mol e
These 2 mol e is accepted by 1 mol XO3- (since Fe2+ : XO3- = 2:1)
O.S of X will decrease by 2
Original O.S = +5, new O.S = +5 2 = +3
3.

A vessel at standard pressure and temperature contains a mixture of 35Cl2 and 37Cl2.
The gaseous mixture occupies a volume of 5.6 dm3 and weighs 18 g, calculate the
percentage by mass of 35Cl2 in the mixture.
A

25 %

40 %

Amount of gas = 5.6/22.4 = 0.25 mol

Apparent Mr of gas = 18/0.25 = 72
Let fraction of 35Cl2 be x and 37Cl2 be (1-x)
70x + 74(1-x) = 72
x = 0.5

NYJC 2011 H2 Chemistry 9647/01 Prelim

50 %

75 %

4.

Equal masses of gaseous N2, NH3 and N2O are injected into an evacuated vessel to
produce a total pressure of 3 atm. How do the partial pressures of N2, NH3 and N2O
compare?
A

PN2 = PNH3 = PN2O

PN2 < PNH3 < PN2O

PNH3 < PN2 < PN2O

PN2O < PN2 < PNH3

For equal mass of N2, NH3 and N2O,

n(N2O) < n(N2) < n(NH3)
since partial pressure is proportional to the amount of gas,
PN2O < PN2 < PNH3
5.

Which of the following molecules/ions has the smallest bond angle?

A

AlH4

XeF2

SF2

H
H2

2-

..

Al
H

SO32

S
H

O
OH

F Xe F

O
OH
F

4 bp, 0 lp
Tetrahedral 109o
6.

3bp, 1lp
trigonal pyramidal 107o

2bp, 3lp
linear 180o

2bp, 2lp
bent 105o

Cyanamide, NH2CN, can form a product with boron trifluoride, BF3.

Which of the following structures represents the product?

Lone pair of electrons on N forms a dative bond to the B that has empty energetically
accessible orbitals to accept the electrons.

NYJC 2011 H2 Chemistry 9647/01 Prelim

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7.

The enthalpy change of solution of magnesium fluoride is negative (17.7 kJ mol1)

but the enthalpy change of solution of barium fluoride is positive (+3.8 kJ mol1).
What conclusion can be drawn from these data?
A

Magnesium fluoride is soluble in water, but barium fluoride is insoluble.

The hydration energy of the barium ion is numerically greater than that of the
magnesium ion.

The lattice energy of barium fluoride is numerically greater than that of the
magnesium fluoride.

The lattice energy of barium fluoride is numerically greater than the sum of the
hydration energies of the barium and fluoride ions.

A: We usually say that an insoluble salt has positive Hsol. BUT, this is not always true .
There are salts that have positive Hsol yet is soluble. This is because we have to also
consider S of the reaction.
B: Hhyd for barium ion is less exothermic (smaller magnitude) than magnesium ion as its
ionic radius is bigger.
C: FALSE. Mg2+ has a smaller ionic radius than Ba2+ hence, the LE of MgF2 is more
exothermic, i.e. the magnitude of LE is larger.
D: Hsol = Hhyd LE
LE and Hhyd are always negative.
|LE|> |Hhyd|, Hsol is positive.

NYJC 2011 H2 Chemistry 9647/01 Prelim

8.

Hydrogen peroxide decomposes in the presence of a catalyst according to the

equation below.
2H2O2 (aq) O2 (g) + 2H2O (l)
To determine the order of the reaction with respect to hydrogen peroxide, a student
performed an experiment using the method below.
The method is as follows:
Starting the reaction: the reactants H2O2 and catalyst are mixed and a stop-clock
started.
At measured time intervals, samples of the reaction mixture can be extracted.
Noting the time, the reaction is quenched by rapidly adding it to a large beaker of
cold water.
The concentration of the unreacted hydrogen peroxide remaining in each sample
can be found by titrating with standard potassium manganate(VII):
Which of the following statements is false?
A

The solution is quenched to reduce the rate of reaction.

The order of reaction with respect to hydrogen peroxide can be determined

from the graph of volume of potassium manganate(VII) against time, using the
half-life method.

The end-point of the titration is marked by the disappearance of the pink

colour.

Alternatively, the order of the reaction can be studied by measuring the

pressure of the system at measured time intervals.

The colour change should be from colourless to pink (due to excess KMnO4).
9.

The initial rates of the reaction between NO and O2 were obtained by changing the
pressures according to the table below.
Experiment
No.
1
2
3

Initial total pressure /

atm
5
8
10

Initial pressure of NO
/ atm
2
2
4

Initial rate /
atm s1
5.4
10.8
43.2

Which of the statements is true about the system above?

A

The order of the reaction with respect to NO is 1.

The overall order of the reaction is 3.

The rate constant k has units of s1.

The rate constant k increases as the initial total pressure increases.

NYJC 2011 H2 Chemistry 9647/01 Prelim

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Experiment
No.
1
2
3

Initial total
pressure / atm
5
8
10

Initial pressure
of NO / atm
2
2
4

Initial pressure
of O2
3
6
6

Initial rate /
atm s-1
5.4
10.8
43.2

Comparing expt 1 and 2,

When initial pressure of O2 doubles while NO remains constant, initial rate doubles. The
reaction is first order with respect to O2.
Comparing expt 2 and 3,
When initial pressure of NO doubles while initial pressure of O2 remains constant, intial rate
is 4 times faster. The reaction is second order with respect to NO.
Rate = k[NO]2[O2]
10.

From which of the following reactions can the bond energy of the OH bond be
determined by using only the standard enthalpy change of the reaction?
A

2 H (g) + O (g)
H2O (g)

H2O (l)
H (g) + O (g)

H2 (g) + O2 (g)
H2O (g)

H2O (l)
H2O (g)

NYJC 2011 H2 Chemistry 9647/01 Prelim

11.

The diagram below is a hydrogen-oxygen fuel cell.

Predict the changes in the pH of the solution around each of the electrode when a
current is flowing.
Porous electrode

O2

H2

1.00 mol dm-3 NaOH

Cathode

Anode

increase

decrease

decrease

decrease

decrease

increase

increase

increase

Cathode: Reduction of O2
O2 + 2H2O + 4e
4OH- (pH increases)
Anode: Oxidation of H2
H2 + 2OH-
2H2O + 2e (pH decreases)
12.

Given the following reaction:

A (g) + B (g) 2C (g) + 2D (g)

Kp = 2.10 x 102 atm2

An equimolar mixture of A and B is allowed to reach equilibrium at 700 K. Determine

the total pressure at equilibrium if the partial pressure of C at equilibrium was found to
be 2.00 atm.
A

1.28 atm

A (g) +
Initial P
Change P
Eqm P

x
-1
x1

4.00 atm

B (g)
x
-1
x -1

2C (g) +
0
+2
2

NYJC 2011 H2 Chemistry 9647/01 Prelim

4.28 atm

4.56 atm

2D (g)
0
+2
2
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2.10 102 =

(2)2 (2)2
( x 1)( x 1)

x = 1.28
Total P at eqm = 1.28 - 1 + 1.28 -1 + 2 + 2 = 4.56 atm

13.

The numerical value for the solubility product of calcium phosphate, Ca3(PO4)2, is
2.071033.
Determine the solubility of Ca3(PO4)2.

2.28 x 107 mol dm3

1.14 x 107 mol dm3

3.42 x 107 mol dm3

2.91 x 107 mol dm3

Ca3(PO4)2
3Ca2+ + 2PO433x

2x
Ksp = (3x)3(2x)2
2.071033 = 108x5
x = 1.14 x 107

14.

Which of the following solutions is unable to maintain a fairly constant pH when a

small amount of acid is added to it?

20 cm3 of 0.1 mol dm3 NH3 with 10 cm3 of of 0.1 mol dm3 H2SO4

20 cm3 of 0.1 mol dm3 NaOH with 20 cm3 of of 0.2 mol dm3 CH3COOH

0.25 mol KHCO3 with 0.30 mol K2CO3

2-amino-2-methylethanoic acid

A :n(NH3) : n(H2SO4) = 2:1

Hence, there are only NH4Cl and excess H2SO4 left at the end of the reaction. This is not a
buffer.
B: reaction produces CH3COO-Na+ and the excess CH3COOH gives the acidic buffer
C: this is a mixture of a weak base CO32- and its conjugate acid, HCO3- , basic buffer
D: this is an amino acid with acidic and basic functional groups that can react with the small
amount of acid or base added to maintain the pH

NYJC 2011 H2 Chemistry 9647/01 Prelim

15.

The graph below shows the first ionisation energies of elements in the Periodic Table
plotted against increasing atomic number.
First I.E

A
B

C
D

Atomic number
What are the elements indicated by the letters A, B, C and D?

Group I metals

Group VII halogens

Noble gases

Transition elements

There is a drastic decrease in the 1st IE of elements immediately following

A/B/C/D. This is means that much less energy is required to remove the
outermost electron of these elements as the electron is from the next electron
shell that is further away from the nucleus. Hence, A/B/C/D are the last members
of the Period, i.e. Group VIII

NYJC 2011 H2 Chemistry 9647/01 Prelim

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16.

The highest oxides of the elements sodium to sulphur are separately added to water.
Which of the following diagrams best represents the pH of the solution produced?

pH

Na2O MgO

Al2O3

SiO2

Na2O MgO Al2O3 SiO2 P4O10 SO3

P4O10 SO3

pH

Na2O MgO

Al2O3

SiO2

pH

P4O10 SO3

pH

Na2O MgO

Al2O3

SiO2

P4O10 SO3

Basic oxides Na2O and MgO dissolves in water to give an alkaline solution.
Al2O3 and SiO2 are insoluble in water thus neutral solution obtained.
Acidic oxides P4O10 and SO3 dissolves in water to give acidic solutions.

17.

Which of the following property of Group II elements decreases from beryllium to

barium?

reactivity with water

stability of the carbonates

solubility of hydroxides

second ionisation energy

A: reactivity increases down the Grp as valence electrons are less attracted to the nucleus.
B: Polarising power of cation decreases and ionic bond strength increases down the grp.

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18.

Which of the following are the anions present when chlorine gas is passed through
hot concentrated potassium hydroxide.

ClO, ClO3

Cl, ClO4

Cl, ClO

Cl, ClO3

Chlorine will first form Cl and ClO first and further disproportionate to give Cl and ClO3

19.

What is the electronic configuration of the nickel cation which can form the complex
ion [Ni(CN)4]2?
( [Ar] 1s22s22p63s23p6 )

20.

[Ar] 3d84s0

[Ar] 3d64s0

[Ar] 3d44s2

[Ar] 3d64s2

A dilute solution of nickel (II) chloride is pale green at room temperature.

When a test tube containing nickel (II) chloride is immersed in liquid nitrogen
(temperature: 196 OC), the pale green solution solidifies and becomes colourless.
Which of the following statements best explains the observations above?

The chloride ion has been substituted by a stronger ligand.

The probability of d-d transitions was greatly reduced.

The solution does not contain any complex ions at -196 OC.

The oxidation state of nickel has changed from +2 to 0.

Lowered temperature means there is insufficient energy to excite the lower d-electrons to
higher energy levels

21.
H3C

How many stereoisomers does the above molecule have?

10

16

32

There are 4 stereocentres thus have 24 = 16 stereoisomers

H3C

22.

The compound C3H7Br undergoes a sequence of reactions as follows:

NYJC 2011 H2 Chemistry 9647/01 Prelim

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Tollens
reagent

acidified
K2Cr2O7

NaOH (aq)

C3H7Br

T + silver mirror

What could be the formulae for R, S and T?

CH3CH2CH2OH

CH3CH2CHO

CH3CO2

CH3CH2CH2OH

CH3CH2CHO

CH3CH2CO2

CH3CH2CH2OH

CH3CH2CO2H

CH3CH2CHO

CH3CH(OH)CH3

CH3COCH3

CH3CO2

Step 1: SN2 to form alcohol

Step 2: Alcohol gets oxidised to aldehyde
Step 3: Aldehyde gets oxidised to acid salt

23.

Which of the chloroalkanes, with formula C5H11Cl, gives the largest number of
isomeric products when heated with ethanolic potassium hydroxide?

CH3

CH3
CH3 CH2 CH CH2Cl

Cl
CH3 CH2 CH2 CH CH3

CH3 C

CH2Cl

CH3
CH3

CH3 CH2 C Cl
CH3

A: only 1 alkene structure possible CH3CH2C(CH3)=CH2

B: There is no H atom on neighbouring carbon for elimination to take place.
C: 2 cis-trans isomers CH3CH2CH=CHCH3 and 1 structural isomer CH3CH2CH2CH=CH2
obtained.
D: Elimination at C1-C2 gives CH3CH2C(CH3)=CH2. Elimination at C2-C3 gives
CH3CH=C(CH3)2

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24.

Compound E, C8H9ClO2, gives compound F, C8H7ClO2, on mild oxidation. F gives a

yellow precipitate on warming with alkaline iodine and reacts with 2 moles of aqueous
bromine.
Which one of the following is the correct structure for E?
Cl

Cl

CH3CH(OH)

OH

CH3CH(OH)

HO

25.

OH

Cl

CH3CH(Cl)

OH

OH

CH2(OH)CH2

Compound Y is boiled with aqueous sodium hydroxide and the resulting mixture
cooled and acidified with dilute sulphuric acid. The final products include a compound
C3H6O2 and an alcohol. The alcohol gives a positive iodoform test.
What is the formula for compound Y?

CH3CH2CO2CH3

CH3CH2 OCOCH3

CH3CH2CO2CH2CH3

HOCH2CH2 CO2CH2CH3

C: hydrolysed products are CH3CH3COO + CH3CH2OH

26.

What is the product of a nucleophilic substitution reaction between 2-iodobutane and

sodium ethoxide (CH3CH2O Na+)?

CH3CH=CHCH3

CH3CH2 CH(OCH3)CH2CH3

CH3CH2 CH(CH3)OCH2CH3

(CH3 )2CHCH2 OCH2CH3

C: O in ethoxide ion will substitute I atom in iodobutane

NYJC 2011 H2 Chemistry 9647/01 Prelim

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27.

When ethyl ethanoate undergoes hydrolysis with dilute sulphuric acid in the presence
of H218O, a mixture of two products is formed. Which of the following pairs correctly
gives the structures of the two products?

CH3CO18OH and CH3CH218OH

CH3COOH and CH3CH218OH

CH3C18OOH and CH3CH2OH

CH3CO18OH and CH3CH2OH

C: 18O atom in H218O will attack the ester carbon atom and displace the alcohol.

28.

Which of the following molecules has the lowest pKa?

Cl

COOH

H3C

COOH

CH2 COOH

COOH
CH3

A: Lowest pKa implies largest Ka. Thus the molecule must be most acidic. Benzene and
electron-withdrawing Cl atom helps to stabilize the negative charge on O in the conjugate
base of the acid.

29.

Which of the following statements explains why C6H5NH2 is a weaker base than
CH3NH2

The p orbital of nitrogen in C6H5NH2 is able to overlap with the orbital of

carbon in benzene ring.

The methyl group in CH3NH2 is electron withdrawing, hence stablising the ion
formed on dissociation.

The electron rich C6H5 group in C6H5NH2 is electron releasing.

C6H5NH2 is less volatile than CH3NH2.

D: interaction of p and p orbital means the lone pair on N can delocalize into benzene ring,
thus lone pair is less available to behave as a electron donor.

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30.

Partial hydrolysis of a decapeptide (containing 10 amino acid residues) using an

enzyme yielded the following tripeptide fragments:
HisTyrArg,

GlnThrAsp,

ArgHisTyr,

TyrArgThr,

AspArgHis,

ThrArgGln

Which of the following is the amino sequence of the decapeptide?

HisTyrArgThrAspArgGlnGlnThrArg

ThrArgGlnThrArgHisTyrThrAspArg

ThrAspArgGlnThrArgThr ArgHisTyr

ThrArgGlnThrAspArgHisTyrArgThr

Technique is to link up amino acids (AAs) that do not have other peptide arrangement e.g.
Gln, Asp, His. Then look for overlapping sequences between tripeptides.

NYJC 2011 H2 Chemistry 9647/01 Prelim

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Section B
For each questions in this section, one or more of the three numbered statements 1 to 3
may 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 can be used as a correct response.

31.

The electronic configuration of elements X, Y, and Z are as follows:

X: [Ar] 3d104s24p1
Y: [Ar] 3d104s24p4
Z: [Ar] 3d104s1
Which of the following statements are correct?

Compared to Y+ and Z2+, X3+ shows the greatest deflection towards the
negatively charged plate with constant electric field.

The ions, X2+, Y2+ and Z2+, each contains at least one unpaired electron.

Compounds X2Y3, ZY and XZ3 are likely to be formed.

1: true since the most highly charged ion will be deflected the most
2: X2+: [Ar] 3d104s1 (1 unpaired)
Y2+: [Ar] 3d104s24p2 (2 unpaired)
Z2+: [Ar] 3d9 (1 unpaired)
3: X: Ga, Y: Se VI, Z: Cu

32.

Which of the following substances contains at least two types of bonds?

KHF2

NH4Cl

Graphite

KHF2: ionic, covalent, hydrogen bond

NH4Cl: ionic, covalent
Graphite: covalent, vdw

33.

In which sequences are the molecules quoted in order of increasing boiling points?

CH3CH2OH, (CH2OH)2, CH3CONHCH3

NH3, H2O, NH2OH

I2, HCl, HF
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CH3CH2OH, Hydrogen bond,

(CH2OH)2, hydrogen bond (more OH groups),
CH3COONHCH3, vdw (but large molecule with large no. of electrons, making the
vdw to be much stronger than the hydrogen bonding.
NH3, hydrogen bond, 1 hydrogen bond per molecule

H2O, hydrogen bond, 2 hydrogen bonds per molecule

NH2OH, hydrogen bond and largest molecule among the 3, largest no. of
electron, strongest vdw.
I2, vdw but larger molecule than HCl and HF. Hence vdw is strongest. (notice
that I2 is acutally a solid at standard conditions.

HCl, HF

34.

Given the following electrode potentials,

V2+ + 2e V
V3+ + e V2+
VO2+ + 2H+ + e V3+ + H2O
2H+ + 2e H2

E = 1.20 V
E = 0.26 V
E = + 0.34 V
E = 0.00 V

It can be inferred that the vanadium dissolves in 1 mol dm3 hydrochloric acid to form

H2

V3+

VO2+

V is oxidized to V2+ by H+:

Ecell = 0.00 (-1.20) > 0
V2+ is further oxidized to V3+ by H+:
Ecell = 0.00 (-0.26) > 0
V3+ can no longer be oxidized to VO2+ as Ecell < 0

35.

At 298 K, the dissociation constants for the carboxylic acids are given below:
RCOOH = 2.5 x 108
RCOOH = 3.0 x 1010
It can be inferred that

the pH of 1 mol dm3 RCOOH is greater than 1 mol dm3 RCOOH.

the Kb of RCOO is smaller than that of RCOO .

the electrical conductivity of a solution of RCOOH is greater than that of

RCOOH of the same concentration.

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1: RCOOH is a stronger acid due to the larger Ka. Hence its extent of dissociation is greater,
there is higher concentration of H+ ion, pH is lower.
2: Kb = Kw / Ka => Kb = 1.0 x 10-14 / Ka
3: greater extent of dissociation of RCOOH gives greater concentration of mobile ions to act
as charged carriers for conducting electricity.

36.

Copper(I) sulphate, Cu2SO4, can be made from copper(I) oxide under non aqueous
conditions. On adding this salt to water, it immediately undergoes disproportionation
reaction to form CuSO4 and Cu metal.
Which of the following statements are true?

A blue solution is formed upon adding Cu2SO4 to water.

The electronic configuration of Cu+ in this salt is 1s22s22p63s23p63d10

Cu2SO4 is a white solid.

Cu+ disproportionates to Cu2+ and Cu.

Cu2+ gives blue solution while Cu+ gives a colourless solid / white solid due to the filled 3d
subshell.

37.

38.

Which of the following particles are not formed in the steps indicated when ethane
reacts with chlorine gas in ultraviolet light?

Propagation Step

CH3CHCl2

Propagation Step

CH3CH2CHClCH3

Termination Step

HCl

Given the reaction below:

[Co(NH3)6]3+ (aq) + 3en (aq) [Co(en)3]3+ (aq) + 6NH3 (aq)
where en represents ethylenediammine, H2NCH2CH2NH2
Which of the following statements are true about this reaction?

The change in entropy is positive.

Both complexes are octahedral.

H is approximately 0 and the reaction is spontaneous at all temperatures.

1: There is an overall increase in the number of aq. molecules in the reaction, increasing the
disorder of the system.
2: Coordination number of Co3+ is 6 in both complexes.
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3: G is negative at all T since S>0 and H is approximately 0. H is approximately 0 as 3
Co N bonds are broken and formed in the reaction.

39.

40.

Which of the following reagents will have different reactions with the two alcohols,
(CH3)3CCH2OH and (CH3)2CHCH2CH2OH?

concentrated sulfuric acid

phosphorus pentachloride

acidified aqueous potassium manganate(VII)

Which of the following cannot be used to distinguish C6H5CHO from C6H5COCH3?

warm ammonical silver nitrate

Fehlings solution

2,4-DNPH

2:Fehlings solution does not react with benzaldehyde.

ERRATUM FOR PAPER 3 ANSWER

Q 1 b(ii) Isomer A:

Q 3 b(ii) rate constant= gradient = (any working) = 9 x 104 sec 1

Q 3 b (iii)
for slow step involving only 1 N2O5(g)
for sum of all steps adding to 2N2O5(g) 4NO2(g) + O2(g)
e.g.

I N2O5(g) NO2(g) + NO(g) + O2(g)slow

II N2O5(g) + NO(g) 3NO2(g)fast

NYJC 2011 H2 Chemistry 9647/01 Prelim

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1
NANYANG JUNIOR COLLEGE
JC 2 PRELIMINARY EXAMINATION
Higher 2
CANDIDATE
NAME

Answers with comments

TUTORS
NAME

CLASS

CHEMISTRY

9647/02

Paper 2 Structured Questions

19 September 2011
2 hours

Candidates answer on the Question Paper.

Additional Materials:

Data Booklet.

READ THESE INSTRUCTIONS FIRST

Write your name and class on all the work you hand in.
Write in dark blue or black pen on both sides of the paper.
You may use a soft pencil for any diagrams, graphs or rough working.
Do not use staples, paper clips, highlighters, glue or correction fluid.
Answer all questions.
A Data Booklet is provided.
At the end of the examination, fasten all your work securely together.
The number of marks is given in brackets [ ] at the end of each question or part question.
For Examiners
Use
1
2
3
4
5
Total

12
10
12
20
18
72

This document consists of 19 printed pages and 1 blank page.

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1

Planning (P)
There are four colourless solutions, labelled as A1, A2, B1 and B2. You are told that A1
and A2 could be 1.0 mol dm3 H2SO4 or 2.0 mol dm3 H2SO4. B1 and B2 are either
1.0 mol dm3 NaOH or 1.0 mol dm3 Ba(OH)2.
You are required to plan a simple experiment to identify A1, A2, B1 and B2.
You are provided with 200 cm3 of each solution,
a thermometer
polystyrene cup
common apparatus in the laboratory
No pH indicators are provided.
(a)

Suggest how we can first identify Ba(OH)2. Write an equation (with state symbols) to
explain your answer.
Add a few drops of A1 (or A2) to 2 cm3 of B1. Repeat this with B2. The solution
which gives a white precipitate is Ba(OH)2.
[1]
Ba(OH)2 (aq) + H2SO4 (aq) BaSO4 (s) + 2H2O (l)

[1]

There are only 4 solutions available in the question. There is no option to use
other reagents to identify Ba(OH)2.

Suggest how (to) identify should be instructions to manipulate the reagents

and unknowns B1 and B2 rather than to state Ba(OH)2 will give a white ppt with
H2SO4.

Ionic equations do not show spectator ions. However, many students thought H+
and OH- are spectator ions and left it out of the answer.
Incorrect: Ba2+ (aq) + SO42- (aq)
BaSO4 (s)
Correct : Ba2+ (aq) + 2OH- (aq) + 2H+ (aq) + SO42- (aq)
BaSO4 (s) + H2O (l)
In this case the full balanced equation is preferred over the ionic equation.
[2]

(b)

Write an equation for the reaction between sodium hydroxide and sulfuric acid.
2NaOH (aq) + H2SO4 (aq) Na2SO4 (aq) + 2H2O (l) [state symbols not necessary]

Usually such reaction would involve complete neutralization unless there is limited
NaOH. In this case, we can assume complete neutralization thus NaHSO4 is not
formed.
[1]

For
Examiners
Use

3
(c)

Outline the steps you will take to determine the identities of A1 and A2, using the
sodium hydroxide solution.
Step 1: Using a measuring cylinder, add 20 cm3 of A1 into the polystyrene cup
provided and record its initial temperature. Using another measuring
cylinder, measure 80 cm3 of NaOH and record its initial temperature.
[1]
Step 2: Add the 80 cm3 of NaOH into the polystyrene cup containing A1, stir
with the thermometer and record the highest temperature reached.
Rinse the cup.
[1]
Step 3: Repeat steps 1 and 2, this time replacing A1 with A2.

[1]

[Accept any specific volume suggested by student, but total volume of mixture
should be between 50-100 cm3.]

Titration / gravimetric methods are not feasible either because the reagents are
not provided or it is a tedious method for a simple question.
Part (a) and (b) would have given you the idea the type of practical to carry out i.e.
temperature measurements for neutralisation reactions.

Details of apparatus like volume, apparatus must be included in the plan.

Many used very small volumes of NaOH or very large vol of H2SO4 because they
forgot the stoichiometric ratio of H2SO4 : NaOH is 1 : 2.
Therefore, 2 times the volume (i.e. 40 cm3) of NaOH is required to neutralize 20
cm3 of 1.0 mol dm3 of H2SO4 while 4 times the vol (i.e. 80 cm3) of NaOH is
needed for 20 cm3 of 2.0 mol dm3 H2SO4.

Initial temp of NaOH AND H2SO4 need to be measured prior to mixing.

Pipette can be used for measuring the volumes but should not be used to
deliver the solutions during mixing because delivery is slow and would affect temp
measurement.

Neutralisation should take place in a polystyrene cup (placed in a beaker) and not
the other way around.

Noting highest temp reached after mixing is required; final temp or when temp
stabilize will not do.
[3]

(d)

Let T1 be the temperature change for the reaction between A1 and NaOH(aq) and
T2 be the temperature change for the reaction between A2 and NaOH(aq). Illustrate
how the identities of A1 and A2 can be deduced from the temperature changes
obtained in the procedure above.
2NaOH (aq) + H2SO4 (aq) Na2SO4 (aq) + 2H2O (l)
nNaOH used in both experiments = 1.0 x 80/1000 = 0.080 mol

For 1.0 mol dm3 H2SO4, nH2SO4 used = 1.0 x 20/1000 =0.020 mol
n(H2O) formed = 2 x nH2SO4 = 0.040 mol
For 2.0 mol dm3 H2SO4, nH2SO4 used = 2.0 x 20/1000 =0.040 mol

[1]

4
n(H2O) formed = nNaOH = 0.080 mol

[1]

Since number of moles of water formed in the two reactions are in the ratio of
1:2, temperature change for the two reactions is expected to be around 1:2.
If T2 = 2T1,
A2 is 2.0 mol dm3 H2SO4 and A1 is 1.0 mol dm3 H2SO4.

[1]

[Other methods are acceptable.]

[3m; award according to the method used]

Many did not show the amt of water formed for each case and link it to the heat
T.

Cannot use H to identify A1 and A2 as it would be the same since it involves

neutralisation of strong acid and alkali. H is Q/n, the amt of heat evolved Q is
proportional to the amt of water produced.
[3]

(e)

Define the term enthalpy change of neutralisation.

The enthalpy change when one mole of water is formed during the
neutralisation of an acid and alkali under standard conditions.

enthalpy of neutralisation is an exothermic reaction therefore energy is not

required / needed.
[1]

(f)

Do you expect the enthalpy change of reaction per mole of acid to be more
exothermic, less exothermic or the same if
(i)

hydrochloric acid was used instead of sulfuric acid? Explain your answer.
Enthalpy change of reaction per mole of acid will be less exothermic
Reason: HCl is also a strong acid, and the amount of water formed per
mole of acid would be less.

(ii)

Give answers in terms of H of HCl and NOT H2SO4

Stating the word less or more alone is not enough since it could be
more / less endothermic or more / less exothermic, as some students have
given.

The key words in the question are per mole of acid. Many students wrongly
said H is the same because they based on per mole of water.

HCl and H2SO4 are both equally strong acids.

ethanedioic acid was used instead of sulfuric acid? Explain your answer.
Enthalpy change of reaction per mole of acid will be less exothermic
Reason: ethanedioic acid is a weak strong acid, and is only partially
dissociated. Part of the energy is used dissociate ethanedioic acid
completely before neutralisation occurs.

5
Many said the acid is a weak acid but did not explain why the H is lower
than that of a strong acid-base reaction.

Many also had the following misconceptions of why H is smaller:



Neutralisation reaction is not complete for a weak acid with a strong

base.

Amt of water formed for a weak acid would be less compared to a strong
acid.
[2]
[Total: 12]

Nitrobenzene may be made by reacting together concentrated nitric acid, concentrated

sulfuric acid and benzene.
Data about these three compounds and nitrobenzene are given in the table.

Compound

Boiling
point /oC

Density

Molar mass

Solubility in
water

/g cm-3

/ g mol-1

Nitrobenzene

210

1.20

123.0

insoluble

Benzene

80.1

0.88

78.0

insoluble

Concentrated nitric acid

120

1.36

63.0

soluble

Concentrated sulfuric acid

337

1.84

98.0

soluble

Preparation of nitrobenzene
1

Place 35 cm3 of concentrated nitric acid in a 500 cm3 round bottomed flask, and
add slowly 40 cm3 of concentrated sulfuric acid, keeping the mixture cool during
the addition by immersing the flask in cold water.

Place a thermometer in this nitrating mixture, and then add very slowly 29 cm3 of
benzene. This should be added about 3 cm3 at a time, and the contents of the
flask thoroughly mixed after each addition.

When all the benzene has been added, fit a reflux water condenser to the flask,
and place the latter in a water bath, which is then maintained at 55-60oC for 45
minutes.

6
(a)

(i)

What is the role of sulfuric acid in this reaction? Write a balanced equation
when the two acids are mixed.
Sulfuric acid acts as a catalyst that generates the stronger electrophile
NO2 + [1]
2H2SO4 + HNO3 NO2 + + 2HSO4 + H3O +
[1]
Many made the mistake of identifying NO + . Another common mistake is
2

not balancing the equation correctly; many students wrote H2O as the
product instead of H3O + .
(ii)

For safety reasons, it is important to keep the mixture cool in step 1. Explain
why the mixing of the acids is exothermic.
The hydration of the H+ released by the sulfuric acid gives out heat.
Stating that bonds formed gave out more energy than taken in when
bonds are broken is insufficient!
[3]

(b)

Suggest with reasoning, one more safety precaution you would take when carrying
out the experiment.
Any of the following:
 Concentrated sulfuric acid / Concentrated nitric acid is corrosive.
Wear gloves when handling it wear safety goggles or gloves when handling
it
 Nitrobenzene/benzene is carcinogenic or flammable, carry out the experiment
in a fume cupboard
[1]

(c)

Calculate the mass of nitrobenzene formed from benzene, assuming a 70% yield.
m
V
mass of benzene used = 29 0.88 = 25.52 g
25.52
nBenzene =
= 0.3272 mol,
78.0
35 x 1.36
nHNO3 =
= 0.7556 mol limiting reagent is Benzene.
63.0
70
assuming 70% yield, nnitrobenzenehence =
nbenzene [1]
100
70 25.52
mnitrobenzenehence =

123.0 = 28.17 = 28.2 g (ans) [1]

100 78.0
given density of benzene = 0.88 =

[2]

Very poor presentation of working by some students. No statements and units

by some students.

7
The preparation of organic compounds usually produces a mixture of the required
compound and other impurities. The purification of nitrobenzene is described below.
Purification of impure nitrobenzene
4

After completion of heating, pour the contents of the flask into a large excess of
cold water. Stir the mixture as vigorously as possible. Transfer the liquid to a
separating funnel and separate the aqueous layer from the nitrobenzene.

Return the nitrobenzene to the separating funnel, and wash with an equal
volume of dilute sodium carbonate solution, releasing the pressure as
necessary.

Transfer the nitrobenzene into a small conical flask, and add some anhydrous
granular potassium hydroxide. Shake until the liquid is completely clear.

Filter the nitrobenzene into a clean and dry distilling flask fitted with an air
condenser. Distil the nitrobenzene carefully, by boiling over a suitable range.

(d)

In step 4, the impure nitrobenzene is shaken with a large excess of cold water and the
two layers are allowed to separate.
(i)

Why is the mixture vigorously stirred with water?

The acids are more soluble in water, by vigorous stirring removes as
much of the acid from the nitrobenzene into the aqueous layer as
possible, hence purifying the nitrobenzene.
The highlight of the question is why use water, and not vigorous stirring; hence
many missed the main point of the question.

(ii)

Will the nitrobenzene be the upper or lower layer? Lower

Explain your answer.
Nitrobenzene has a higher density than water.
[2]

(e)

Suggest a reason for using potassium hydroxide as a drying agent, rather than the
more conventional calcium chloride or sodium sulfate.
The use of KOH would also eliminate any traces of acid in the nitrobenzene.
[1]

(f)

In step 7, distillation was carried out to purify the product. Suggest a suitable
temperature range for the collection of the fraction.
From 207oC to 211oC
To obtain a pure product, the distillation temperature range should be kept to
as small and as close to the boiling point as possible. Many students obviously
forgot their basic chemistry.
[1]

8
[Total : 10]

Nitrogen monoxide, NO, is a by-product of the combustion of hydrocarbon fuels in internal

combustion engines.
(a)

The compound nitrosyl fluoride, ONF, can be produced from nitrogen monoxide and
fluorine
2NO(g) + F2(g) 2ONF(g)

H = ()

The rate equation for this reaction is rate = k[NO][F2]

The mechanism has two steps. One of these steps produces ONF and the free
radical F in equimolar amounts.
(i)

Draw dot-and-cross electron diagrams for nitrogen monoxide, NO, and nitrosyl
fluoride, ONF.
NO

[1]

ONF

Comments: Just use x and (and no other symbols) for dot-&-cross diagrams.
(ii)

In the space below sketch the reaction pathway diagram for this reaction.

Potential
energy

Ea,1

Ea,2
ONF + F +NO

2NO + F2
H < 0

2NOF
Reaction pathway
 Labeling axis and diagrams correctly [1]
 Ea1 > Ea2 and exothermic reaction [1]

Many students did not realise that the reaction is a two-step reaction as
stated in the question.

From the information given, a possible mechanism for the reaction is :

F2 + NO ONF + F

(slow step, so as to agree with the rate equation)

NO + F ONF (fast)
Hence Ea1 > Ea2 since the first step is the rds.
[4]
(b)

One reaction which occurs in air polluted with nitrogen oxides is shown below.
2NO(g) + O2(g) 2NO2(g)
Five experiments were carried out to find the relationship between the initial
concentration of NO and of O2, and the initial rate of formation of NO2.
experiment

(i)

(ii)

initial concentrations / mol dm-3

initial rate of
formation of NO2

[NO]

[O2]

/ mol dm-3 s-1

0.001

0.001

7 x 10-6

0.001

0.002

14 x 10-6

0.001

0.003

21 x 10-6

0.002

0.003

84 x 10-6

0.003

0.003

189 x 10-6

What is the order of the reaction with respect to each of the reactants?
NO

Second order

O2

First order

[1]

Hence suggest an equation for the rate-determining step.

2NO(g) + O2(g) 2NO2(g)

[1]

Comment: Many students failed to score for this question as they

misread the question, and gave the rate equation instead of equation for
the rate-determining step.

10
(iii)

Comment on why this rate-determining step is unusual.

This reaction involves the collision of three particles at the correct
orientation and sufficient energy, which is statistically very highly
unlikely.
[1]
Comment: The main focus of the question is to comment on the ratedetermining step being unusual. Do not link it to the reaction being an
elementary reaction, which although is true, DOES NOT answer the
question.

(iv)

The actual mechanism for the reaction between NO and O2 is actually

bimolecular. By considering the relative stabilities of the reactant molecules
involved, suggest a more plausible mechanism for the reaction.
fast
2NO(g)

N2O2(g)

N2O2(g) + O2(g)
2NO2

[1]
[4]

(c)

At 700 oC, nitrogen monoxide and hydrogen react as follows:

2NO(g) + 2H2(g) N2(g) + 2H2O(g)
(i)

Explain briefly why the initial reaction rate would be expected to increase by
increasing each of the following:
the pressure,
When pressure is increased, the particles are brought closer together and
hence frequency of collision of molecules increases. The frequency of
effective collision also increases.
[1]
Comments: This is not a reversible reaction, do not discussed in terms of
LCP and POE for both parts.
the temperature.
When temperature increases, the number of particles with energy greater
than activation energy increases. The frequency of effective collision
therefore increases.
[1]

(ii)

Suggest, with reasons, whether you would expect the reaction between
nitrogen monoxide and hydrogen to be endothermic or exothermic.
Exothermic.

[1]

The reaction involves forming of highly stable N2 and H2O molecules from
highly unstable NO molecule.
[1]
[4]
[Total:12]

11
4

Iron is the fourth most common element in the Earth's crust. It has more than one oxidation
state and many of its compounds are coloured.
(a)

What do you understand by the terms transition element, ligand and complex ion?
A transition
element:

is a dblock element which forms at least one stable ion with a

partially filled d orbital.

A complex ion:

is a species that contains a central metal atom/ion surrounded

by molecules or anions (known as ligands) which forms
coordinate bonds to the metal centre.

A ligand:

is a molecule or anion with at least one lone pair of electrons

that it can use to form a coordination bond to the central metal
atom/ion in a complex ion.
[3]

(b)

Explain why so many transition element complexes are coloured.

In the complexes, the ligands cause the 3d orbitals to split into two energy

levels.
d-electrons in the lower energy level absorb energy in the visible spectrum

and becomes excited to a vacant and higher energy d-orbital.

The unabsorbed complementary wavelengths are emitted.
Such d-d electron transitions are responsible for the colour of the
compounds. [1/2 m each point underlined]

[2]

12
(c)

Blueprints, the detailed plans for architectural or engineering projects, were made in
the 19th century by forming the insoluble complex Prussian Blue on sensitised paper.
Prussian Blue is the name given to the deep blue precipitate formed by adding a
solution of Fe3+(aq) to a solution of [Fe(CN)6]4-(aq).
The following diagram shows the reactions of iron and its compounds.
Step I
Cl2

Yellow solution
of A

Green solution of
Fe2+

Na2CO3

Reddish-brown
precipitate, B

NH3 (aq)

Colourless and
odourless gas, C

Ca(OH)2

Reddish-brown
precipitate
remains
(i)

White
precipitate

[Fe(CN)6]4- (aq)

Fe3+

Deep Blue
precipitate, D

A reddish-brown precipitate is seen when sodium carbonate is added to the

aqueous solution of A. This precipitate is insoluble upon the addition of
aqueous ammonia. Suggest the identity of the cation in A.
A:

[Fe(H2O)6]3+

[1]

Water ligands must be shown explicitly since question mentioned solution

A is yellow.
(ii)

Identify B, C and D
B:

Fe(OH)3

C:

CO2

D:

Fe4[Fe(CN)6]3 or Fe3[Fe(CN)6]2

Simply

[3]

give the formula. Theres no need to name the compounds.

Note

for B: the precipitate formed is the hydroxide ppt. and not the carbonate
ppt. Revise your QA notes again: acidic cations form hydroxide ppt. since the
carbonate would have reacted to form CO2 (see part (iii)); remaining (nonacidic) cations form carbonate ppt. e.g. CuCO3, ZnCO3 etc.

wasnt well done. A precipitate should be a neutral compound so all that

was required was to give the formula of the neutral compound formed
between Fe3+ and [Fe(CN)6]4-. The better students who observed that

13
reduction of Fe and oxidation of [Fe(CN)6]4- is a feasible process (check E
values in DB) will get Fe3[Fe(CN)6]2.
3+

(iii)

With the use of relevant equations, explain why gas C is formed when Na2CO3
is added to solution A.
Fe3+ has high charge density due to its high charge. It is able to polarize
the O-H bond in the water ligand, causing hydrogen ion to be released.
2+
+





[Fe(H2O)6]3+(aq) + H2O(l) 



[Fe(H2O)5 (OH)] (aq) + H3O (aq)

CO32- + 2H3O+ CO2 + 3H2O

This question tested students understanding of acidic cations and it was not
well done. Many attempted to write an equation between Fe3+ and Na2CO3 and
failed to do so. Suppose if this were a more direct question asking for an
explanation for the pH of AlCl3 solution, we expected many could have done
better. You must learn to bridge this gap and relate your (indirect) exam
questions to content we have learnt in the syllabus.
(iv)

By quoting and using relevant E values from the Data Booklet, explain why in
Step I when chlorine gas is bubbled into the solution containing Fe2+(aq), the
solution turned from green to yellow. When the experiment was repeated using
iodine, no such observation was seen.
Cl2 + 2e

2Cl

Eo = +1.36 V

I2 + 2e

2I

Eo = +0.54 V

Fe3+ + e

Fe2+

Eo = +0.77 V

E values for chlorine is more positive, indicating chlorine is a stronger

oxidising agent than iodine hence its able to oxidise green Fe2+ to yellow
Fe3+
[1]
Reaction between Cl2 and Fe2+;
Eocell = +1.36 0.77 = +0.59 V > 0 reaction is feasible

[1]

There is no reaction between I2 and Fe2+;

Eocell = +0.54 0.77 = 0.23V < 0 reaction is not feasible

[1]

This question was generally well done. Some students who merely calculated
the two Ecells and made no attempt to explain the reactions/observation further
lost marks because this was not a simple predict if the reaction occurs type of
question. Read the question carefully and leave no gaps in your explanation so
the examiner cannot penalize you.
Learn to quote Eo values accurately (keep them as reduction equations and
with signs, as in the data booklet)
[9]

14
(d)

Iron is essential in almost all organisms. An important biological complex containing

iron is haemoglobin. The diagram below shows the structure of a haemoglobin
molecule.

(i)

What is the role of haemoglobin in the body?

Oxygen carrier
Only a simple answer required. Explanation not required.

(ii)

State the type of hybridisation for the nitrogen atom labelled, N1 in the diagram
given.

(iii) State the type of bond that the nitrogen atom labelled, N1 forms with the Fe ion
in the diagram given.
(ii) sp2, (iii) dative/co-ordinate bond
The 2 in the notation sp2 is a superscript.
Spelling of names must be correct

(iv) Name one other poison that can affect haemoglobin in the same way as carbon
monoxide.
NaCN / KCN) / HCN
The general term cyanide is not acceptable.

[4]
(e)

A nail of mass 1.50 g was dissolved in an excess of dilute sulfuric acid to form 100
cm3 of solution. A 25 cm3 sample of the solution required 8.0 x 10-4 mol of manganate
(VII) for complete oxidation.
By assuming that, in dissolving in sulfuric acid, the iron in the nail was converted
entirely into Fe2+ (aq), calculate

15
MnO4 + 8H+ + 5Fe2+ Mn2+ + 5Fe3+ + 4H2O
(i)

the number of moles of Fe2+ produced from the nail.

n(Fe2 + ) from nail = 8.0 x 104 x 5 x

(ii)

100
= 0.016 mol
25

the percentage of iron in the nail.

% by mass of iron in nail =

0.016 x 55.8
x 100% = 59.5%
1.50
[2]
[Total: 20]

Comments

Working should be CONCISE ( avoid evaluating intermediate answers).

Working should be PRECISE ( ALL working must be clearly shown).

e.g.

writing x100/25 instead of x 4 ;

writing 8.0 x 10-4 x 5 instead of 4 x 10-3 )

It is incorrect to calculate the amount of nail, i.e. the expression 1.50 / 55.8 shows
gross misunderstanding of the system present.
There should not be any error in rounding up the answers.

Values of the base dissociation constants, pKb for some weak bases are given below.
Compound

Phenylamine,
C6H5NH2

Pyridine,
C5H5N

Ethylamine,
CH3CH2NH2

Piperidine,
C5H10NH

Formula
NH2
N
H

N
NH2

pKb
(iii)
Structural
formula of
ions formed
after
reaction
with HCl
(aq)

9.42

8.75

3.19

2.89

NH3

N+

NH3

16
(a)

(i)

Which is the weakest base? Phenylamine

(ii)

Explain in terms of molecular structures, why piperidine and phenylamine

have significantly different pKb values.

Piperidine is a stronger base than phenylamine.

In piperidine,

an electron donating alkyl group increases the electron density on the

nitrogen atom
In phenylamine,
the lone pair of electrons on the nitrogen atom is delocalised over the
benzene ring.
The lone pair of electrons of nitrogen in piperidine is more available for
bonding with a proton compared to that of phenylamine
OR The lone pair of electrons of nitrogen in phenylamine is less available for
bonding with a proton compared to that of piperidine.

Generally Well-done.
Common mistakes will be stating the benzene ring is electronwithdrawing. Electron-withdrawing/electron-donating would refer to the
substituents attached to the benzene.
(iii)

Draw the structures of the ions formed when each of the bases are reacted
with aqueous hydrochloric acid in the table above.

(iv)

Calculate the pH of 0.100 moldm-3 of phenylamine.

OH =

K bc = ( 10 9.42 ) x 0.10

pOH = lg OH = 5.21

pH = 14 pOH = 8.79 = 8.8

Generally well-done. A few were careless in their computation.
[8]

(b) Phenylamine can be synthesised from nitrobenzene in a two-step process shown.

(i)

Write the formula of the intermediate P in the blank.

17

Step 1
NO2

Step 2

Sn, conc HCl

NaOH (aq)

+
NH3

NH2

(ii)

State the bases (pyridine, ethylamine and piperidine) that could be used in
place of sodium hydroxide in step 2. Explain your answer.

All of the bases are stronger bases than phenylamine, and hence they
will all be able displace phenylamine from its salt.
[2]

In the redox reaction in step 1, tin reacts with hydrochloric acid to generate tin (II) ions
which acts as a reducing agent. In reducing nitrobenzene, tin (II) ions are oxidized to
tin (IV) ions.

(iii)

Write an equation to show the reaction between tin and hydrochloric acid.

Sn + 2HCl Sn2+ + 2Cl- + H2

[1]

The reaction is just a metal + acid reaction.

Read the question carefully. It tells you that Sn is being oxidized to Sn2+.
Then something must be reduced! H+ is reduced to H2.
(iv)

By means of balanced half-equations, write an equation to show the redox

reaction for step 1.
reduction half-equation :

+ 7H+ + 6e

2 H2O

+
NH3+

NO2

oxidation half-equation : Sn2+ Sn4+ + 2e

[1] for both half-equations correct
Overall equation:
+ 3Sn2+ + 7H+
NO2

2 H2O

+ 3Sn4+

+
NH3+
+

[1]
[3]

18
Badly done.

(c)

Question wants the redox reaction for STEP 1, not the equation for the reaction
of acid with Sn! Pls read question carefully.

Do you remember how to balance a redox half-equation?

o

Balance the non H and O atoms

Balance O with H2O

Balance H with H+

Balance the charges with electrons

For alkaline medium, add OH-, same number as H+ to both sides of the
equations

Phenylamine undergoes the following reaction scheme.

Br

Step 1
NH2

Step 2
NHCOCH3
Q

(i)

Br2, under
suitable
conditions

NHCOCH3
R

Suggest the reagents and conditions for step 1.

CH3COCl, room temperature
[1]

All students must know by now that acyl chlorides and amines undergo
condensation to give amides at room temperature.
A few indicated heating which is unnecessary.
Some used carboxylic acid that is not feasible. Note that we only look at
carboxylic acid reacting with amine to give peptide bonds when we are
talking about amino acids reactions.
(ii)

Another possible product besides R is formed. Suggest its structual formula.

Br
NHCOCH3 [1]
This part tests on the knowledge on directing effects of groups on
benzene ring. N atom that is attached to the benzene ring has no
multiple bonds directly bonded to it, so it is 2,4 directing.
[1]

19
(iii)

Intermediate Q has three other isomers, X, Y and Z. Identify the other isomers
given the following information:

Isomer X gives ammonia on reaction with hot aqueous sodium hydroxide.

On reaction with hot acidified potassium manganate (VII), 1,4-dibenzoic
acid is formed.

Isomer Y gives methanoic acid on reaction with hot aqueous hydrochloric

acid.

Isomer Y can be used to form the following polymer:

O

O
N

CH3

CH3

CH3

Both X and Y do not react with aquoeus bromine, but reacts with bromine
in the presence of iron (III) bromide.

Isomer Z does not give methanoic acid nor ammonia on hydrolysis.

1 mol of Z reacts with 3 mol of aqueous bromine to give a substituted

product.

Suggest structures for X, Y and Z.

NH2

O
C

NH2

HN

CH3

CH3
CH3

[1]

[1]

[1]
[3]

Must know the reactions well and at the same time, structural isomerism.
Note that all 3 structures must be isomers of Q with molecular formula: C8H9NO
And while drawing the structures, be mindful that C has 4 bonds and N has 3 bonds.
Isomer X:
Give ammonia on heating with aq NaOH: amide bond CONH2 is hydrolysed to give
ammonia.
Gives 1,4-dibenzoic acid means that the 2 substituents must be at 1,4 positions.

20
Isomer Y:
Gives methanoic acid on reaction with HCl: hydrolysis of amide group, NHCOH
Y can form the given polymer: the 2 substituents are at 1,3 positions
Isomer Z:
No methanoic acid nor ammonia on hydrolysis means that there is no amide bonds
with NHCOH or CONH2 groups.
1 mole of Z reacts with 3 moles of aq Br2: a phenol or phenylamine is present! But it
cannot be phenol as the structure would not fit into the molecular formula.
Other possible answers:
NH2

H3C

NH2

O
O

[Total : 18]

-------End of Paper-------

2011 NYJC Prelim H2 Chemistry 9647/03 Answers with comments

General Comments: DO NOT use pencil to draw organic molecules when
presenting your answers.
1 (a) (i)

I.

(CN)2 + H+ + e
HCN
E= +0.37 V
Cl2 + 2e
2Cl
E = +1.36V
Ecell = +1.36 (+0.37) = +0.99V
Overall Equation: Cl2 + 2HCN
(CN)2 + 2H+ + 2Cl[2]

II.

(CN)2 + H+ + e
HCN
E = +0.37 V
22S4O6 + 2e
2S2O3
E = +0.09 V
Ecell = +0.37 (+0.09) = +0.28 V
Overall Equation: (CN)2 + 2H+ + S2O32-
2 HCN + S4O62- [2]

III.

(CN)2 + H+ + e
HCN
E = +0.37 V
Cr2O72- + 14H+ + 6e 2Cr3+ + 7H2O
E = +1.33 V
Both are oxidising agents. Hence reaction cannot proceed.
[2]

Comments: Students are required to make use of the Data Booklet by calculation
of Ecell values to show the feasibility of the reactions. Many students wasted time
in describing the reaction and observations which were NOT required in the
question.

Cx C

x x x

x
xN

x x x

(ii)
N

[1] correct dot-cross diagram [1] linear

Comments: Many students were careless in drawing in the dot-and-cross
diagram and did not use alternating dots and crosses to represent the electrons
of N and C, and drew the following WRONG diagram.

x x x

C C

x x x

x
xN

Nxx

Diagram is wrong as each C should have 4 outer electrons

represented by dots or crosses, and NOT by dots alone.
(b) (i) This is because the reaction proceeds with an inversion of configuration.
[1]

CH3

H3C
-

NC

Cl

NC

Cl

H
(CH2)4CH3

(CH2)4CH3

[1] To illustrate the inversion in structural formula (3D wedge diagram)

Comments: Many students could not articulate the inversion of configuration
caused by the SN2 mechanism. An equation showing 3D molecules for this
inversion is essential.
(ii)

Isomer A:

2011 NYJC Prelim H2 Chemistry 9647/03 Answers

1 (a) (i)

I.

(CN)2 + H+ + e
HCN
E= +0.37 V
Cl2 + 2e
2Cl
E = +1.36V

E cell = +1.36 (+0.37) = +0.99V

Overall Equation: Cl2 + 2HCN
(CN)2 + 2H+ + 2Cl-

II.

(CN)2 + H+ + e
HCN
E = +0.37 V
S4O62- + 2e
2S2O32E = +0.09 V

E cell = +0.37 (+0.09) = +0.28 V

Overall Equation: (CN)2 + 2H+ + S2O32-
2 HCN + S4O62-

III.

(CN)2 + H+ + e
HCN
E = +0.37 V
Cr2O72- + 14H+ + 6e 2Cr3+ + 7H2O
E = +1.33 V
Both are oxidising agents. Hence reaction cannot proceed.

x x x

x
xN

Cx C

x x x

(ii)
N

linear

(b) (i) This is because the reaction proceeds with an inversion of configuration.
CH3

H3C
-

NC

Cl

NC

Cl

(CH2)4CH3

(CH2)4CH3

To illustrate the inversion in structural formula (3D wedge diagram)

(ii)
CH2CH3
H3C

Isomer A:

Cl

(CH2)3CH3
2

Comments: Students had problems deducing the structural formula of A.

Since the question states that compound A loses its optical activity after reaction
with ethanolic NaCN, Compound A must be an optically active compound (hence
contain *C) and be a 3o RX so that it undergoes SN1 mechanism (hence forming
an optically inactive racemic mixture).
Type of reaction: SN1

[1]

CH2CH3

CH2CH3

slow

+
H3C

H3C

Cl

(CH2)3CH3

(CH2)3CH3

CH2CH3
H3C

(CH2) 3CH3

Cl

[1] Slow step

[1] dipoles and
curly arrows

CH2CH3
CN

H3C

CN

(CH2) 3CH3

(iii)
Reaction b(i) OR SN2 mechanism is faster. [1]
The rate determining step in b(i) involves NaCN.
OR rate = k[NaCN][RX] [1]
Comments: To explain the effect on rate, always relate to the slow step in the
mechanism.

(c)

B
OH

K2Cr2O7 ,
H2SO4 (aq)

OH

HCN
NaCN

OH

Na in
ethanol

OH
OH

OH
OH

Heat under
reflux

CN

CH2NH2

H3C

heat with
concentrated
H2SO4

H3C

CH2NH3

D
(does not give
CO2(g) with
Na2CO3)

[1] each for B, C and D [1] for reagents and conditions for stage I
Comments:
Reagents and conditions for stage I : The oxidizing reagent used must be
K2Cr2O7 and not KMnO4 as we do not want the alkene group to undergo
oxidation.
For the reduction of B
B contains three functional groups, nitrile, alkene and carboxylic acid.
When NaBH4 is used, the best answer is the reduction of the nitrile group,
since carboxylic acids are very hard to reduce (only reduced by LiAlH4) and
alkenes are only reduced by hydrogenation.
Note: In general, nitriles are NOT reduced by NaBH4. The usual reducing
agents that can reduce nitriles are LiAlH4, Na in ethanol and H2 with Pt.

2(a)(i) (There is a plane of symmetry in the molecule or both chiral centres

contain the same groups attached to it), the two chiral centres rotate the plane
of polarised light to the same extent but in the opposite direction hence
cancelling out the optical activity.[1]

Pls note the correct phrasing underlined above. Quite a number of students
wrote polarization of light which is a WRONG usage in this case.
CH3

(ii)

Compound A: H3C

CH2

CH

CH2

CH2

CH2

CH3

CH3 CH3
H3C

CH

CH2

CH3

CH3

Compound C:

CH3 CH3
H3C

Compound D:

CH3

CH3 CH3

Many wrote formulae like C4H9 and C3H7. STUDENTS ARE REMINDED NOT TO
USE SUCH FORMULAE DURING EXAM AS THEY ARE AMBIGUOUS AND DO
NOT GIVE US HOW THE ATOMS ARE CONNECTED TO EACH OTHER.
There is also NO NEED TO USE CONDENSED FORMULE. A formula like
H2ClC- is generally not preferred. Please write out to show how the atoms are
attached.
(iii)

Isomers A to D are simple molecular compounds with weak van der Waals
forces between molecules.[1] However, as we move down the table from
A to D, the molecules become increasingly branched[1], hence they have
less surface area of contact with their neighbouring molecules resulting in
weaker vdw forces between molecules.[1] Hence less energy is required
to break the vdw bonds, resulting in lower b.p. down the table.

Comments: Always start this kind of answer by identifying the structure and
bonding. That scores mark for the first point.
Comments: Quite a number of students wrote more branching leads to more
surface area of contact which is WRONG
Comments: Many students like to use the term branch out. Students should just
use the terms unbranched or highly branched. Students should avoid using
the terms linear as well.
Comments: Many did not relate explanation to the molecules A, B, C, D
themselves but discussed generally.
7

Comments: Many answered the question with respect to A and D instead of A

to D
(iv)

4 molecules + ratio [ + + + + 1]
Structural formula

mole ratio
6
3

CH3 CH3
Cl

CH2 CH2 CH CH
Cl
CH3 CH3

H3C

CH

H3C

CH2

CH2

CH CH
CH3 CH3

CH2

CH2

CH

CH3

CH3
CH3

Cl
Cl
CH2 CH3
H3C

CH2

CH

CH

CH2

CH3

Comments: Many did not get the ration right, they should understand or see tutor
quickly. This question on ratio of isomers may appear in Paper 1 as well as
Paper 2 and 3.
(v)
CH3 CH3

CH3 CH3
H3C

CH2

CH

CH2

H3C

CH2

CH

CH2 CH3

CH3

CH3 CH3

H3C

CH2

CH

CH

H3C

CH2

CH

CH HC

CH

CH3
CH3

CH3 CH3

OR

[1st one preferred, because more branched.][1]

CH3 CH3
H3C
H3C

CH2
CH2

CH
CH

CH

CH2

CH

CH3 CH3
(but not
produces less than 6 branches.)

CH2

CH2 CH2

or any other combination that

(b)

pH = 7.4;
pOH = 14-7.4 = 6.6;
[OH-] = 10-6.6 = 2.512 10-7 moldm-3 [1]
Ksp of Pb(OH)2 = [Pb2+(aq)][OH-(aq)]2 = 1.43 10-20;
[Pb2+(aq)]total = (1.43 10-20) / (2.512 10-7)2 = 2.26 x 10-7 moldm-3
Comments: Many made the mistake of doing
[Pb2+(aq)]total = (1.43 10-20) / (2 2.512 10-7)2; It is important to know
when to 2 when not to 2, pls see your tutor.
Ksp of PbSO4 = [Pb2+(aq)][SO42-(aq)] = 2.53 10-8;
[SO42-(aq)]total = 2.53 10-8/ 2.26 x 10-7 = 0.1116 moldm-3
Ksp of BaSO4 = [Ba2+(aq)][SO42-(aq)] = 1.0810-10;
[Ba2+(aq)]total = 1.0810-10/0.1116 = 9.67 10-10 moldm-3
Therefore the barium ion concentration is within safety limits
since [Ba2+] is < 1.45 10-5 moldm-3 [2]
Comments: Overall, many are still using the wrong method. They are
using the Let x be the solubility method. In this question, we cannot do
that because there is common ion effect, therefore the method is different.

(c)(i) Down the group, the Increase in screening effect and atomic radius
outweigh the increase in nuclear charge. Hence, net attraction of
outermost electron decreases. Less energy required to remove the
valence electron. [2]
Comment: We should always mention both reasons of radius and
screening effect to account for ionization energy or related concepts like
reactivity of metals.
Comments: Many said that nuclear charge remains the same. In this
context, the term nuclear charge will refer to the number of protons in the
nucleus. Hence it should increase as we go down the group because of
the increasing number of protons down the group.
Comments: Many students introduce the term polarizing power in this
question. There is no such occurrence in this question. Students should
see their tutors to understand fully the usage of the term polarizing.
Please do not take it for granted.
(ii)

Lithium and sodium metals have high boiling points due to their stronger
metallic bonding hence can be obtained via electrolysis and (isolated)
even in a high temperature environment. [1] Potassium, rubidium and

caesium having larger atomic radius, have weaker metallic bonding and
vaporises in the high temperature environment. [1]
(iii)

Lithium ion behaves like Mg2+. (diagonal relationship). It has a high charge
density and is able to polarise the oxygen molecule breaking the O=O
double bond[1]. As we come down the group, the other group one ions
have larger ionic radii and hence have a lower charge density is unable to
polarise the molecule completely, hence giving O22- and O2- ions. [1]

3(a)

10

Hrxn

N2O3(g) + N 2O 5(s)

2N 2O 4(g)

-54.1
-57.2(2)
N 2O3(g) + N 2O5(g)
4NO 2(g)

-112.5
NO(g) + NO 2(g) + O 2(g) + N 2O3(g)

-114.2
-39.8
2NO(g) + 2NO 2(g) +O 2(g)

Hrxn = ( 39.8) ( 54.1) + 2x( 57.2) (112.5) + ( 114.2)

= 22.2 kJ
Comment: Elements must balance on either side of each arrow!
(b)(i) [1] graph is a straight line (passing through zero)

Rate of Reaction / Pa s-1

1.2
1.0
0.8
0.6
0.4
0.2
0.0
0

200

400

600

800

1000

1200

1400

Pressure of N2O5(g) remaining /Pa

[1] explanation ; since rate is directly proportional to

pressure/concentration of N2O5(g),
the reaction is first order wrt N2O5(g)
Comment: Label axes of all graphs.
Inspection method is not accepted. Must use graph to explain why reaction is first
order wrt to N2O5, i.e. gradient.
(ii)

[1 for gradient] rate constant= gradient = (any working) = 9 x 104 sec 1

11

[1 for correct unit]

Comment: Again, make use of the graph to find k. Finding k by substitution of
one set of experimental data is not acceptable here.
(iii)

[1] for slow step involving only 1 N2O5(g) (no ecf)

[1] for sum of all steps adding to 2N2O5(g) 4NO2(g) + O2(g)
e.g. I
N2O5(g) NO2(g) + NO(g) + O2(g)
slow
II
N2O5(g) +NO(g) 3NO2(g)
fast

Comment: Poorly done. Start with slow step that contains 1 molecule of N2O5
since rate equation only has N2O5, and its first order. (Recall the relation between
rate equation and the slow step of the mechanism.) Add further steps such that
the sum of the steps add up to the overall balanced equation as given in the
question.
Probably it is because it is a first order reaction, so many proposed the
mechanism to be SN1, a type of nucleophilic substitution reaction for organic
reactions that does not make any sense here!
(c)

[]

LiF

Size of atoms decreases across a Period. Smallest ionisable atom is F largest

ionisable atom is Li in Period 2
[]

CsS

Period 3 noble gas is Ar with 18 electrons. Ca2+ and S2- are isoelectronic (same
no. of electrons) with Ar.
[]

ZnF

Outermost electronic configuration for Zn: 3d104s2 Zn2+ is the smallest +2

charged ion with filled d subshells, ions with +2 charge and filled d subshells are
below Zn.
[]

SrBr2

Chemically unreactive Period 4 element is Kr (noble gas)

(d)

(i)

CO2

[1/2]

12

C
D

CaCO3
Ca(HCO3)2

[1/2]
[1]

The white ppt that CO2 forms with limewater (Ca(OH)2) is CaCO3. Further
bubbling of CO2 forms soluble Ca(HCO3)2
Ca(OH)2 (aq) +CO2 (g) CaCO3 (s) + H2O (l)
CaCO3 + H2O + CO2 --> Ca(HCO3)2

(ii)

MO + H2O
M(OH)2 +

M(OH)2

2 HCl

MCl2 + 2H2O

nHCl for 25.0 cm3 aliquots = 0.0985 x 20.30/1000 = 0.0020 mol [1]
nHCl reacting with E = 0.0020 x 250/25 =
nMO = nM(OH)2

x 0.020 =

0.020 mol

0.010 mol [1]

MA = 1.9735 / 0.010 = 197.35 197.4 [1]

[3]*** can be awarded if students use a one step method i.e. no
intermediate answers. BUT ALL WORKING MUST BE SHOWN.,

(iii)

A is likely to be a carbonate (since CO2 is evolved on heating)

Hence formula will be MCO3
Hence Ar of M will be 197.35 12.0 3(16.0) = 137.35 [1]
M is likely to be Barium. [1]

Comment:
Most are know that the no. of moles of A or E is required so that Mr can be
obtained by taking mass/no. of moles.
Common mistakes:
Taking the wrong mole ratio. Note that from balanced equation, it should be
MO:HCl = 1:2!
Not reading the question carefully and found the Mr of E (MO) instead of A
(MCO3)
Poor presentation of answers was penalised.
SHOW ALL WORKINGS!
Giving units for Mr (Mr has NO UNITS!)

13

4(a)

Down the group, thermal stability of HX decreases [1]

as the H-X bond length increases and it becomes easier to break the H-X
bond. [1]

Most students could do this question well. Students who have lost marks is due
to the careless choice of words. Be very careful. There are no ions present in HX. It makes it hard for the examiner to give you full credit if you show a poor
understanding in basic bonding.
Some of you may have gotten full marks but your answers were too long and
some parts were repetitive. Focus on the main points/key words and make sure
you have enough time to do the rest of the question. As a guide, you should have
spent no more than 3mins on this 2m question.
There is a small number who confused the explanation of thermal stability for Gp
VII (H-X bond length) with Gp II compounds (polarization) OR bp/volatility
discussion (in terms of IMF), please clarify it with your tutors ASAP!
(b)

The Si-F bond formed is very strong hence the reaction is very
exothermic/very stable products are formed. [1]

This question, being a new part (b) and not a(ii), is NOT related to part (a)
thermal stability. Think about what you write. Common (illogical) mistakes are:
The H-F bond is very strong and hence gives out a lot of energy to break the
strong covalent bonds in SiO2. (Bond breaking takes in, not give out, energy.)
H-F is a strong oxidising/reducing agent. (Theres no change is oxidation
state for both F and Si so this cannot be a redox reagent.)
(c)(i)
V/T

V [1]
This question was very disappointing. We have seen a lot of different graphs of
Ideal gases in MCQs last term but many students cannot do this question well.
Please make sure you understand how to deduce the shape of a graph by
transforming the ideal gas equation to make V/T (the y) the subject and fitting
the relationship between y and x to one of the following 3 possibilities: (1) a
constant graph, (2) a directly proportional graph (y=mx) and (3) an inversely
proportional graph (y = m/x). Consult your tutor to clear up your doubts.

14

(ii)

Gas X is HF while Gas Y is HCl [1]

Work out V/T values.
Experiment
Gas X
No.
T/K
V / dm3
V /T
dm3K-1
1
200
20 000
100
2
300
22 500
75
3
600
24 000
40

Gas Y
V / dm3
V /T
dm3K-1
16 500
82.5
20 000
66.7
23 500
39.1

The V/T values of Gas X deviates more from a constant value than Gas Y.
Hence Gas X behaves less like an ideal gas than Gas Y. [1]
Gas X is HF which has stronger hydrogen bonds between molecules while
HCl has weaker permanent dipole-permanent dipole interactions. [1]
This being part (ii) is related to (i) but few students managed to see the
connection. Its an ideal gas question and your answer should focus on how the
ideal gas assumptions (in particular the intermolecular forces) relate to the
difference in deviation of HF and HCl from ideal gas behaviour. Common
mistakes are:
Failure to recognize theres hydrogen bonding in HF.
Leaving gaps in your answers such as . Gas X is less ideal hence theres
strong intermolecular force in X hence Gas X is HF. Give a complete
explanation where possible. Make sure you write every single thought that
went through your mind ON paper otherwise the examiner cant give you
credit for it.
Learn to showcase your understanding. Identify the exact strong IMF in
HF (as H-bond) since you are able to so the examiner can give you credit for
it.
(d)(i) ICl prefers to form stronger permanent dipole-permanent dipole
interactions between its polar molecules rather than weak Van der Waals
forces with non-polar solvent molecules. [1]
A good solubility explanation should look at the formation of intermolecular forces
between the solvent and solute molecules.

15

(ii)
[1]

[NB: Since dimer is planar, iodine should

have 4bp and 2lp - square planar]

The dot-cross diagram was disappointing. There should only be dots and crosses
and no arrows for dative bonds (think of your AlCl3 dimer: to show a dative bond,
simply show a pair of dots (or crosses) between the atoms). Many students also
carelessly missed out remaining lone pairs on chlorine and iodine. Be very
careful! You cannot afford to lose marks like that in ALevels.
(iii)

2 BrF3 [BrF2]+ + [BrF4]- or BrF3 [BrF2]+ + F- [1]

BrF3 ionizes/forms ions. The mobile ions (in molten state) are able to act
as charge carriers.

Few students could do this question. A very common answer is BrF3 Br3+ + 3Fwhich is unacceptable as we have never seen bromine in a +3 state on its own.
Another common answer is BrF3 Br- + 3F- which is unacceptable as well as
the charges are not balanced: a neutral molecule cannot break up to form 4 units
of negative charge.
(e)(i)

OH
C CH2CH3
Intermediate X CH2

[1]

Step I: HCN, trace amount of NaOH/NaCN, 10-20oC

Step III: LiAlH4 in dry ether
Most students could get the intermediate X. Those who did not possibly
overlooked clues from the molecular formula of X (given in the question) and step
V where X was further reacted.
Make sure you study your organic reagents and conditions well! You should
score for this question but those who were haphazard didnt. Some common
mistakes observed:
The reaction between HCN and carbonyl is a cold reaction (10-20oC). There
are only 2 cold reactions in the syllabus. Whats the other one?
Recall your mechanism: NaOH/NaCN is catalyst for the N.A. (thats why its
trace amount). HCN is the reagent. Some students confuse the 2 and wrote
trace amount HCN.
LiAlH4 is the only RA that can reduce acid (to alcohol). Its used at room
temperature. (Not all reactions are heat under reflux.)

16

(ii)

Step IV. [1]

There are 5 isomeric products in all. [1]
For reference (not required in ans)
H
H
OH

C CH CH3

C CH2CH3

C CH2CH3

CH2OH

CHOH

CH2

(has cis- trans isomers) (has cis- trans isomers)

Step I is not the correct answer as although theres a racemic mixture formed in
the step, the effect is not lasting as the chiral centre will be removed in step IV
upon forming the alkene.
(iii)

(CH3)2CHMgBr [1]

Most students managed to do this question. A handful was careless and missed
out/had too many hydrogens on their carbon. To avoid this, you can always draw
out the answer. Theres no need to give it as a condensed formula like this
answer (unless the question states so).
(iv)

NB: 6 in total but award a maximum of 5

Structures [1 each]

O O
Z

H 3C C C

CH3

O
Y

H3C C OH
HO

H 3C C C C
X

CH3

CH3

Reasoning (3 in all. each)

17

OH
H
[] Reaction of CH3MgBr with Aldehdye: Product X contains
(deduce from Grignard reaction)

CH
CH3

[] Reaction with Na: X contains 1 alcohol group (do not accept phenol or
carboxylic acid as these are not possible in C6H12O)

OH
H
[] Reaction with alkaline aq I2: X contains
methyl carbonyl)

CH
CH3 (do not accept

[] Reaction with concentrated acidified KMnO4: X contains an alkene that

underwent oxidative cleavage to form 2 products.
[] Reaction with Na: Y contains 1 carboxylic acid group (do not accept
phenol or alcohol as Y is an oxidised product unless student stated tertiary
alcohol)

O
[] Reaction with alkaline aq I2: Z contains 2 H3C CH (do not accept
methyl alcohol as Z is an oxidised product)
For deductive questions, students must learn to
APPLY your theoretical understanding to the context of the question to make
smart and helpful deductions, e.g. for a reaction with Na, DO NOT merely list
down it could contain an alcohol, phenol or acid but THINK in this case, are
there any functional groups that can be eliminated. Look for other clues like
molecular formula or reactions that have happened to form the compound etc.
Dont be blinded by the reaction you think is happening. Look around the
molecule for any other fuctional group that may have also reacted. In this
case, it wasnt simply the alkene being oxidised to form Y and Z but the 2o
alcohol should have also been oxidised to a ketone.
A significant number of students managed to get all structures of X, Y and Z
right but somehow did not manage to get the full marks for their deductions.
This shouldnt be the case. Learn to write your deductions according to your
structures derived (see attached sample).

18

19

5(a)(i) Ester [1]

Comments: Almost all students recognised the ester functional group. Common
mistakes include ketone, carbonyl and even alkane 
(ii)
O

*
O
O

[1 for both correct]

10 electrons [1]
Comments: Every bond consists of two electrons. Benzene itself would have
another 6 electrons.
(iii)
CH3

COOH
KMnO4, dil H 2SO4
heat under reflux
COOH

CH3

PCl 5, room temp

COCl

room temperature
O

HO

COCl

O
O

[1 for each correct step: correct reagents and conditions and intermediate]
Comments: A significant number of students had difficulty getting the third step
correct. Many were not able to identify alcohol needed for the conversion.

20

(iv)

Test: KMnO4, dilute H2SO4, heat [1]

Observation with DEHP: Purple KMnO4 decolorised
Observation with Compound A: Purple KMnO4 remains unchanged
[1 for both observations correct]

Comments: Please follow the template above when answering questions on

distinguishing tests (Test, Observation with , Observation with ), this is so
that you do not missed out any points. And remember this: please do not write
No reaction and No Observation for compounds with negative test.
(b)
Boltzmann Distribution Curve:
Key:
Number of
molecules

T1

Temperature T2 > T1
No of molecules with energy Ea at T1

T2

No of molecules with energy Ea at T2

Ea

Kinetic energy

Both curves sketched correctly, including labeled axes and key [1]
As temperature increases, molecules possess greater kinetic energy.
Hence, the number of molecules with energy greater or equal to activation
energy is larger [1] as shown by the two shaded areas in the diagram above.
This results in higher frequency of effective collisions and hence higher rate
of reaction. [1]
Comments: Majority of students answered this part correctly.

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(c)(i)
H3N+

COO

HN

[1]
strong ionic bonds between zwitterions [1]
a lot of energy required to overcome the strong bonds [1]
(ii)
NH2-CH(CH2CH2COOH)-COOH + H+ +NH3-CH(CH2CH2COOH)-COOH
[1]
NH2-CH(CH2CH2COOH)-COOH + OH- NH2-CH(CH2CH2COOH)-COO- + H2O
[1]
Comments: The majority of students gave correct equations. Those who did not
score two full marks started with NH2-CH(CH2CH2COO-)-COO-,
+
NH3-CH(CH2CH2COO-)-COO- and +NH3-CH(CH2CH2COOH)-COOH.
Remember: do not use reversible arrows!
(iii) [1 for either of the following correct]

OR

Comments: Many students missed out showing bonds between O and H atoms
for OH groups.
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Mr of dipeptide = 303 [1]

Comments: A significant number of students failed to calculate the Mr of the
dipeptide correctly. Remember
(iv)
It refers to the three dimensional conformation of a protein results from further
folding, cross-linkings and coiling of the amino acid chains caused by interactions
between the R-groups of the amino acids. [1]
[1 for any of the following correct]
Hydrogen bonding between R-groups of glutamine
van der Waals forces between R-groups of theanine
van der Waals forces between R-groups of theanine and glutamine

23