PAPER 1 Time: 1h 45 min

Section A

Four suggested answers labelled A, B, C C

and D are given for each question. Choose Relative
one correct answer. intensity
4
1 The percentage of iron in a haemoglobin
3
molecule is 0.335%. If a haemoglobin
molecule consists of four iron(II) ions, 2
what is the relative molecular mass of
haemoglobin? 1

[Relative atomic mass of Fe is 55.8.]

A 6.66 × 102 C 1.67 × 104 0
8 9 10 11 12
m/e

B 4.16 × 10 3
D 6.66 × 104
D
2 Boron has two isotopes with relative Relative
intensity
isotopic masses of 10 and 11. When 4
1.00 g of boron reacts completely with
hydrogen, 1.278 g of boron hidride, 3
B2H6, is produced. Which graph shows
2
the mass spectrum of boron?
A 1
Relative
intensity
4 0 m/e
8 9 10 11 12

3
3 Which equation illustrates the first
2 ionisation energy of the given
element?
1
A C(g) → C+(g) + e–
B Na(s) → Na+(g) + e–
0 m/e
8 9 10 11 12 C Cl(g) + e– → Cl–(g)
B D O(g) + e– → O–(g)
Relative
intensity
4
4 Vanadium has the electronic configuration
3 1s22s22p63s23p63d34s2. Which ion does
not exist?
2 A VO42–
1 B VO3–
C VO2+
0
8 9 10 11 12 m/e D VO2+
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 5 The ionic radii of four ions are as 9 The thermochemical equation for the
follows: reaction between nitrogen monoxide and
ozone is as follows:
Ion Ionic radius/nm
P +
0.095 NO(g) + O3(g) NO2(g) + O2(g);
Q2+ 0.031 ∆H = –200.0 kJ
R– 0.136
If the activation energy of the reaction is
S– 0.126
10.5 kJ mol–1, the activation energy of
Which ionic compound has bonding with the reverse reaction is
the greatest covalent character? A 10.5 kJ mol–1
A PR C QR2 B 189.5 kJ mol–1
B PS D QS2 C 200.0 kJ mol–1
D 210.5 kJ mol–1
6 Which species has a trigonal planar
shape? 10 Which underlined molecule reacts as a
A BF3 C ClO3– Lewis base?
B PCl3 D SO32– A K2O + SO3 → K2SO4
B BF3 + NH3 → H3N•BF3
7 Coordinate bonds do not exist in C OH– + CO2 → HCO3–
A CO D CH3Cl + FeCl3 → CH3+ + FeCl4–
B BeCl2
C PH4+
D [Fe(CN)6]3– 11 The equilibrium constant, Kc, for a
reaction between ethanol and ethanoic
8 The graphs of initial rate versus acid is 4.0 at 25 °C. If 1.0 dm3 of an
concentration of reactants for the reaction aqueous solution containing 92.0 g
X + Y → Z are shown below. ethanol and 120.0 g ethanoic acid is
left to react until equilibrium is attained
Rate
at 25 °C, what is the mass of ethanol
left?
[Relative molecular masses of ethanol
and ethanoic acid are 46.0 and 60.0
respectively.]
A 18.4 g C 61.3 g
[X]
B 30.7 g D 73.6 g
Rate
12 In which reaction is the value of Kc
equals to the value of Kp?
A N2O4(g) 2NO2(g)
B CO2(g) + C(s) 2CO(g)
[Y] C H2O(g) + C(s) H2(g) + CO(g)
What is the order of the reaction with D 3Fe(s) + 4H2O(g) Fe3O4(s) + 4H2(g)
respect to X and Y?
X Y 13 An aqueous solution of a monobasic
A 0 1 acid has pH 3.5. A 25.00 cm3 volume
B 1 0 of an aqueous solution of the acid is
C 1 2 completely neutralised by 27.50 cm3
D 2 1 of a 0.10 mol dm–3 sodium hydroxide

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 solution. The value of the dissociation
constant of the acid is
A 3.16 × 10–4 mol dm–3
B 3.48 × 10–5 mol dm–3
C 9.08 × 10–7 mol dm–3
D 9.99 × 10–8 mol dm–3
14 When solid ammonium chloride is
added in excess to an aqueous solution
of ammonia containing phenolphthalein
as an indicator,
A a buffer solution is formed.
B hydrogen choride gas is evolved.
C the pink colour of the solution
remains unchanged.
D a solution with a pH less than 7 is
formed.
15 The partition coefficient of a liquid X
between ethoxyethane solvent and water
is 3.00. What is the mass of X extracted
from a 200 cm3 of an aqueous solution
containing 6.00 g of X, extracted twice
with 100 cm3 of ethoxyethane used in
each extraction?
A 3.60 g C 5.04 g
B 4.50 g D 5.63 g
16 The electrode potential, E, of a half-cell
is given by
0.059 [oxidised species]
E = E o – ——– log ——–————— ,
n [reduced species]
o
where E is the standard electrode
potential and n the number of electrons
transferred when the oxidised species
changes into the reduced species.
Given that E = 0.00 V at equilibrium
and
Half-cell reaction E o /V
Zn2+(aq) + 2e– Zn(s) –0.76
Ag+(aq) + e– Ag(s) +0.80
What is the equilibrium constant, Kc,
for the reaction 2Ag+(aq) + Zn(s) →
Zn2+(aq) + 2Ag(s) at 25 °C?
A 1.31 × 10–53 dm3 mol–1
B 4.41 × 10–2 dm3 mol–1
C 2.76 × 1026 dm3 mol–1
D 7.61 × 1052 dm3 mol–1
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17 In plating chromium onto plastic, the
cathode is a plastic object coated with
graphite. The graphite is used to
A enable oxidation to occur and
chromium to be deposited.
B form an alloy with chromium so as
to strengthen the coating.
C enable the plastic object to act as an
electrical conductor.
D make the surface of the plastic object
coarse so that chromium is adsorbed
on it.
18 In industry, ethanoic acid can be prepared
from the oxidation of ethanol with oxygen.
The standard enthalpies of formation
of ethanoic acid, water and ethanol are
–487 kJ mol–1, –286 kJ mol–1 and
–278 kJ mol–1 respectively. The standard
enthalpy change, in kJ mol–1, for the
preparation is
A –1051
B –495
C –209
D +495
19 The standard enthalpies of neutralisation
for the reactions between an aqueous
solution of sodium hydroxide and several
hydrohalic acids are given below.
Hydrohalic Standard enthalpy of
acid neutralisation/kJ mol–1
HF –68.6
HCl –57.6
HBr –57.3
HI –57.2
The standard enthalpy of neutralisation
of HF is the most negative because
A HF is the strongest acid.
B HF has the strongest covalent
bond.
C the fluorine atom has the highest
electronegativity.
D the fluorine ion has the most
exothermic enthalpy of hydration.
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 20 Strontium is an element in Group 2 of the C The value of the equilibrium constant
Periodic Table which is situated between is lower at a temperature more than
calcium and barium. Which statement is 500 °C.
true? D The percentage yield of ammonia
A The strontium ion has a higher charge increases when the pressure is
density than the calcium ion. reduced.
B Strontium sulphate is less soluble in
water than calcium sulphate. 24 Ammonia gas can be prepared in a
C Strontium carbonate is more difficult laboratory by heating an ammonium salt
to decompose than barium carbonate with
when heated. A Devarda’s alloy
D Strontium nitrate is more difficult to B hydrochloric acid
decompose than barium nitrate when C calcium hydroxide solution
heated. D acidified solution of potassium
manganate(VII)
21 Which property is true of the elements
in Group 14 of the Periodic Table on 25 The reactivity of the halogens Cl2, Br2
descending the group? and I2 decreases down Group 17 of the
A The electrical conductivity of the Periodic Table. Which property does not
elements decreases. influence the trend in the reactivity of
B The electronegativity of the elements the halogens?
increases. A Atomic size
C The stability of the +4 oxidation state B Electron affinity
of the elements increases. C Ionisation energy
D The catenation of the elements D Bond energy
decreases.
26 The oxidation states of several d-block
22 SiCl4 compound forms an acidic solution elements represented by letters which are
with water while CCl4 compound does not the usual symbols for the elements
not dissolve in water because concerned in the Periodic Table are as
A silicon atom has empty 3d orbital follows:
while carbon atom does not.
B the Si Cl covalent bond is weaker Element Oxidation state
than the C Cl covalent bond. X – – 3 – – – –
C the SiCl4 molecule is polar while the
CCl4 molecule is non-polar. Y – 2 3 4 – – –
D van der Waals forces between SiCl4 Z – 2 3 4 5 6 7
molecules are weaker than those
between CCl4 molecules. Which statement is not true?
A X forms colourless hydrated ions.
23 At 500 °C, nitrogen and hydrogen gases B Y forms a compound with the
react according to the equation molecular formula K2YO4.
N2(g) + 3H2(g) → 2NH3(g). C Z2O is an oxidising agent.
D X, Y and Z form octahedral
Which statement about the reaction is complexes.
true?
A The reaction is endothermic. 27 Zn2+ ions form a white precipitate,
B The reaction occurs through three Zn(OH)2, with an aqueous solution
steps. of ammonia. The white precipitate
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 dissolves when a NH4Cl solution is
added to it. Which statement explains
the observation?
A A soluble ZnCl2 compound is
formed.
B NH3 molecule is a stronger ligand
than OH–.
C NH4+ ions increase the solubility
product of Zn(OH)2.
D NH4+ ions decrease the concentration
of OH– ions in the solution.
28 Menthol is one of the substances added
into a cough mixture. The structure of
its molecule is as follows:
CH3
C
CH=CHCH2CH3
D
CH2CHCH2CH3
31 When a compound is heated with
an acidified solution of potassium
manganate(VII), a white precipitate is
formed and a gas which turns lime water
chalky is evolved. The possible structural
formula of the compound is
A CH2CH3 C CH2OH

OH
CH2Cl CHO
B D
CH(CH3)2
Which statement is true of menthol?
A It has two chiral centres.
B It has two functional groups.
C It reacts with an aqueous solution of 32 Each of the following compounds is put
sodium hydroxide. into a test tube and an aqueous solution
D It decolourises an acidified solution of silver nitrate is added. The three test
of potassium manganate(VII). tubes are then placed in a hot water
bath.
29 Which compound reacts with chlorine
following the mechanisms for free
radicals and electrophilic substitution? Cl
CH3COCl ClCH2COOH
A CH3CH3
B CH2Cl2 I II III
C CH3CH=CH2
D C6H5CH3 Which sequence of the compounds
according to the ascending order of their
30 Which compound is formed when reactivity is correct?
benzene reacts with 1-butene in the A I, III, II
presence of aluminium chloride? B II, I, III
A C II, III, I
CH2CH2CH2CH3 D III, II, I

B 33 Which pair of compounds corresponds

CH(CH3)CH2CH3 to the reagent used to differentiate the
two compounds?
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 Pair of compounds Reagent
A (CH3)3COH and (CH3)2CHCH2OH Sodium metal
B CH3CH2OH and C6H5OH Bromine water
C CH3CH2OH and CH3COOH Phosphorus(V) chloride
D C6H5OH and CH3COOH Aqueous solution of sodium hydroxide

34 An organic compound X, with molecular formula C5H11Cl, is converted to compound Z

according to the following reaction scheme.
NaOH(aq) KMnO4/H+
C5H11Cl ⎯⎯⎯⎯→ Y ⎯⎯⎯⎯→ Z
∆ ∆
Z forms an orange precipitate with 2,4-dinitrophenylhydrazine and a yellow precipitate
with an alkaline solution of iodine. What are X, Y and Z?
X Y Z
A CH3CH2CH2CH2CH2Cl CH3CH2CH2CH2CH2OH CH3CH2CH2CH2CHO
B CH3CH2CH(Cl)CH2CH3 CH3CH2CH(OH)CH2CH3 CH3CH2COCH2CH3
C CH3CH(Cl)CH2CH2CH3 CH3CH(OH)CH2CH2CH3 CH3COCH2CH2CH3
D (CH3)2C(Cl)CH2CH3 (CH3)2C(OH)CH2CH3 CH3COCH2CH2CH3

35 An organic acid decolourises bromine C

water. 1.16 g of the acid in aqueous
solution requires 20.0 cm3 of a 1.0 mol O
dm–3 sodium hydroxide solution for C ONa
complete neutralisation. What is the ONa
possible structural formula of the acid?
[Relative atomic mass of H is 1.0, C is
12.0 and O is 16.0] D
A HCOOH
B HOOC—COOH O
C CH2=CHCOOH C CH3CH2OH
D HOOCCH=CHCOOH OH

36 When a white solid P, with molecular

formula C13H10O2, is refluxed with an
aqueous solution of sodium hydroxide
and then acidified with hydrochloric 37 A 2.0 cm3 volume of sodium hydroxide
acid, compounds Q and R are formed. solution is added to 0.1 g of ethanamide
What are Q and R? in a test tube and then heated. Which
Q R observation about the reaction is
A true?
A The gas evolved forms white fumes
CH2OH OH with hydrogen chloride.
B The gas evolved turns blue litmus
paper red.
B O C A liquid with a smell of vinegar is
C OH formed.
D A layer of colourless oil is formed.
OH

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 38 What is the compound formed when A HCl
(CH3)2C=CHCN reacts with hydrogen B HNO2
gas in the presence of platinum? C CH3CH2Cl
A (CH3)2CHCH2CN D CH3CH(OH)CH3
B (CH3)2C=CHCH2NH2
C (CH3)2CHCH2CH2NH2
40 Ziegler-Natta catalyst is used in addition
D (CH3)2CHCH2NHCH3
polymerisation of ethene. Which
39 GABA is a neuro-transmitter released statement is not true of the process?
by red algae which encourages A It requires a low pressure.
shellfish larvae to settle on the B It requires a low temperature.
ocean bed. Its structural formula is C It produces high density
H2NCH2CH2CH2COOH. Which reagent poly(ethene).
reacts only with the acidic group of D It is an example of free radical
GABA? polymerisation.

Section B

For each question in this section, one or P Q

more of the three numbered statements
1 Trichloromethane Propanone
1 to 3 may be correct. The responses A to
2 Benzene Methylbenzene
D should be selected as follows:
3 Ethanol Water

A B C D 42 The paper chromatogram of samples

1 only is 1 and 2 2 and 3 1, 2 and W, X, Y and Z which is obtained
correct. only are only are 3 are using ethanol as an eluent is shown
correct. correct. correct. below.

41 The phase diagram of a mixture of two Solvent

front
liquids P and Q is as follows:

Vapour
pressure/
atm

W X Y Z

Which statement(s) is/are true of the

samples W, X, Y and Z?
1.0 Mole fraction 1.0 1 W has a larger Rf value than Y.
Q P 2 X is a mixture of W and Y.
3 Z has the lowest solubility in
What could P and Q be? ethanol.

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 43 Which property(ies) of the elements in 46 [Al(H2O)6]3+ ion is hydrolysed in aqueous
Period 2 and Period 3 of the Periodic solution according to the equation
Table change(s) periodically?
[Al(H 2 O) 6 ] 3+ (aq) + H 2 O(l)
1 Electronegativity
[Al(H2O)5(OH)]2+(aq) + H3O+(aq)
2 Electrical conductivity
3 Enthalpy of vapourisation Which statement(s) about the reaction
is/are true?
44 The bond angles in methane, ammonia 1 The [Al(H2O)5(OH)]2+ ion is not
and water molecules are shown stable with respect to hydrolysis.
below. 2 The reaction is a redox reaction.
3 The rate of reaction increases when
H an acid is added.

47 A solution is prepared by dissolving a

small amount of sodium chloride and
N sodium iodide in water. The solution
C
formed is added with an aqueous solution
109.5°
107° of silver nitrate followed by an aqueous
H H H solution of ammonia. The reaction(s)
H
H H involved is/are
1 Ag+(aq) + I–(aq) → AgI(s)
2 Ag+(aq) + Cl–(aq) → AgCl(s)
3 AgCl(s) + 2NH3(aq) →
Ag(NH3)2+(aq) + Cl–(aq)

O 48 Which compound(s) and reagent(s)

with reaction condition(s) react to
104.5° form a compound with halogen atoms
H attached directly to its benzene ring?
H Compound Reagent/Reaction
condition
The difference in the bond angles in the
three molecules is due to 1 CH2CH3 Br2/Fe
1 the number of lone pair electrons in
the central atom.
2 the hybridisation of the central
atom.
3 the electronegativity of the central
atom. 2 CH2CH3 Cl2/Light

45 When a current of 0.8 A is passed

through a molten ionic compound for
1 hour, 1.00 × 10–2 mol of a metal is
deposited at the cathode. What could
the metal be? 3 CH(OH)CH3 I2/NaOH, ∆
[Faraday constant is 9.65 × 104 C mol–1.]
1 Fe
2 Cr
3 Pb
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 49 A breath analyser is used to determine
the alcohol content in a driver’s body.
Which statement(s) is/are true?
1 The alcohol to be determined is
ethanol.
2 The chemical substance used could
be acidified solution of potassium
dichromate(VI).
3 The chemical reaction involved is a
redox reaction.
© Majlis Peperiksaan Malaysia 2008
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50 Butyl lithium, with molecular formula
C4H9Li, is a very useful organometallic
compound in organic synthesis.
Which statement(s) is/are true of butyl
lithium?
1 It is more reactive than Grignard
reagents.
2 It is a starting substance in the
synthesis of silicone.
3 It can be used to prepare alcohols.
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 PAPER 2

Section A [40 marks]

Answer all questions in this section.

1 (a) “If two or more orbitals with equal energy are available, the orbitals are each filled
with one electron, with the electrons having parallel spins, before a second electron
of the opposite spin is added.”
(i) Name the above rule. [1 mark]
(ii) Draw a diagram showing valence shells filled with valence electrons for an atom
X with proton number 28. [1 mark]
(iii) State the number of unpaired electrons in atom X. [1 mark]
(iv) Why does the total energy of atom X decrease when there is a transfer of an
electron from one subshell to another? [1 mark]
(b) The decomposition of aqueous hydrogen peroxide can be accelerated by the addition
of a small amount of an acidic solution of sodium bromide. The catalysis steps are
as follows:
2Br– + H2O2 + 2H+ → Br2 + 2H2O
Br2 + H2O2 → 2Br– + 2H+ + O2
(i) Write an overall equation for the above exothermic reaction. [1 mark]
(ii) Sketch and label the energy profiles for the catalysed and uncatalysed reactions
on the axes below.

Energy

Reaction coordinate
[3 marks]
(iii) State two observations for the catalysed reaction. [2 marks]

2 (a) Dmitri Mendeleyev is acknowledged by scientists as the founder of the modern

Periodic Table.
(i) What is the basis of Mendeleyev’s Periodic Table? [1 mark]
(ii) Based on his Periodic Table, Mendeleyev successfully predicted the properties
of some elements that had not been discovered. Name one of the elements.
[1 mark]
(b) A graph of first ionisation energy versus proton number for several elements in Period
3 of the Periodic Table is given below.
First
ionisation
energy
/kJ mol–1 Y

Proton number

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 (i) Identify the element labelled Y. [1 mark]
(ii) Why is the first ionisation energy of Y higher than that of the next element?
[1 mark]
(c) Cyclopropane decomposes into propene through the ring opening of cyclopropane
according to the equation

C3H6(g) → CH2=CHCH3(g)

The rate constant for the decomposition is 15.12 s–1 at 400 °C.
(i)Write the rate equation for the decomposition of cyclopropane. [1 mark]
(ii)Calculate the half-life of cyclopropane. [2 marks]
(iii)If 1.0 mol of cyclopropane is introduced into a 1 dm3 container, what is the
concentration of cyclopropane at 400 °C after two half-lives? [1 mark]
(iv) What is the relationship between cyclopropane and propene? [1 mark]
(v) Name a chemical compound, other than cyclopropane, that may be used to
produce propene. [1 mark]

3 (a) Silicon compounds are mainly used in making glass. The most common and cheapest
glass is soda glass which is manufactured by fusing sand, sodium carbonate and
limestone.
(i) State the components of soda glass, and write the equation for the reaction
involved. [2 marks]
(ii) State the main component of borosilicate glass and its property. [2 marks]
(b) Silicones are oils or rubber-like materials used commercially in a wide variety of
products. Commercial silicones have infinite O-Si-O chains with alkyl or aryl groups
attached to the silicon atoms.
(i) Draw the structure of chain silicone showing three repeating units with alkyl
groups. [2 marks]
(ii) State one property of silicone. [1 mark]
(iii) Explain why silicone is used in the manufacture of waterproof fabrics.
[3 marks]

4 (a) Phenylamine, C6H5NH2, reacts with nitric acid in the presence of concentrated
hydrochloric acid at a temperature of 0 °C to 5 °C to produce a salt used in dyeing
industry.
(i) Name this salt. [1 mark]
(ii) Write an equation to show the formation of this salt. [1 mark]
(iii) When an aqueous solution of this salt is heated to 70 °C, a vigorous reaction
occurs. Name the organic product formed. [1 mark]
(iv) When an aqueous solution of this salt is added to an alkaline solution of phenol,
a yellow precipitate is formed immediately. Name the chemical reaction which
occurs, and draw the structure of the yellow precipitate [2 marks]
(b) Insulin is a hormone which controls the concentration of glucose in the blood. It is
a globular protein which has two interlinked polypeptide chains.
(i) Draw the structural formula of the basic unit in a polypeptide. [1 mark]
(ii) What is meant by a polypeptide? [1 mark]
(iii) Explain why insulin is easily denatured under a strong alkaline or acidic
condition. [2 marks]
(iv) Name one type of bonding which can contribute to the rigidity of the structure
of the insulin molecules. [1 mark]

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 Section B [60 marks]

Answer any four questions in this section.

5 A methane molecule dissociates homolytically in the presence of a chlorine free radical

to form a methyl free radical.
(a) Using the valence-shell electron pair repulsion theory, compare the shape of a methyl
free radical to that of a methane molecule. [6 marks]
(b) The standard enthalpies of atomisation of several species are given in the following
table.

Species Standard enthalpy of atomisation/kJ mo1–1

CH4 + 1740
•CH3 + 1305
HC1 + 431

(i) Calculate the standard enthalpy of reaction for the homolytic dissociation of
methane by a chlorine free radical. [6 marks]
(ii) Sketch the enthalpy diagram for the reaction. [3 marks]

6 (a) Ammonia is a nitrogen fertiliser which is very soluble in water. It is prepared

commercially by the Haber process. 1.0 mol of nitrogen gas and 1.0 mol of hydrogen
gas are introduced into a 2.0 dm3 volumetric flask at 450 °C. The amount of hydrogen
gas is 0.40 mol at equilibrium.
Calculate the equilibrium constant for the reaction involved at this temperature.
[7 marks]
(b) A colourless gas X is an oxide of nitrogen. It changes to a brown gas Y when heated
and forms X again when cooled. Identify gases X and Y, and explain the
observations. [4 marks]
(c) Gases X and Y are allowed to react in a closed container until equilibrium is
reached.
(i) State and explain what would be observed when the pressure of the container is
increased at constant temperature. [2 marks]
(ii) Explain the equilibrium position when a small amount of argon gas is added to
the equilibrium mixture at constant volume. [2 marks]

7 (a) The table below shows the formulae of ions with proton numbers 7 to 13 except
proton number 10.

Proton number 7 8 9 11 12 13
Formula of ion N3– 02– F– Na+ Mg2+ A13+

(i) Sketch a graph of the ionic radius against proton number. [2 marks]
(ii) Explain your graph. [3 marks]
(b) In industry, one of the stages in nitrogen extraction is the liquefaction of air by applying
high pressure and low temperature. The liquefied air contains mainly nitrogen, oxygen
and argon.

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 (i) Why is carbon dioxide not found in the liquefied air? [1 mark]
(ii) Explain how pure nitrogen is obtained from the liquefied air, and state one of
the uses of liquid nitrogen. [3 marks]
(iii) Give a reason for the inertness of nitrogen, and explain a natural phenomenon
which produces nitrogen oxides. [3 marks]
(c) The relative molecular mass of aluminium chloride calculated from its vapour density
at different temperatures are shown in the table below.

Temperature /°C 200 600 800

Relative molecular mass 269 163 133

Explain why the relative molecular mass of aluminium chloride shows different values
at the different temperatures. [3 marks]

8 (a) What is meant by a transition element? [1 mark]

(i) State and explain what would be observed when an aqueous solution of potassium
thiocyanate is added to an aqueous solution of iron(III) ions. [4 marks]
2+ –
(ii) A Fe ion reacts with CN ions to form the complex ion hexacyanoferrate(II).
Draw the shape of this complex ion. State the number of 3d suborbitals which
are not filled with electrons, and give reasons for your answer. [4 marks]
(b) The stability constants, expressed as their logarithms, of the complex ions [CuC14]2– and
[Cu(NH3)4]2+ are 5.6 and 13.2 respectively.
(i) Explain what happens when an aqueous solution of ammonia is added to an
aqueous solution of [CuCl4]2–. [4 marks]
(ii) Predict the stability constants, expressed as their logarithms, of the complex ion
[Cu(EDTA)]2–, and give a reason for your answer. [2 marks]

9 Compound A, with the molecular formula C5H12O, which has a straight chain structure
is an optically active alcohol. When A is heated with alumina, compounds B and C
are formed. B shows geometrical isomerism but C does not. When C is heated with an
acidified potassium manganate(VII) solution, compound D is formed and a gas which turns
lime water chalky is evolved. When D is heated with an aqueous solution of ammonia,
compound E is formed which reacts with lithium tetrahydridoaluminate(III) to form
compound F.
(i) Write the structural formulae of compounds A, B, C, D, E and F. Justify your
answers. [10 marks]
(ii) Write the structural formulae of the cis and trans isomers of compound B. [1 mark]
(iii) Write the equations for all the reactions above. [4 marks]

10 (a) Propene polymerises in the presence of benzoyl peroxide, C6H5COO-OOCC6H5, to

form polypropene. Explain, with chemical equations, the reactions which occur in
the polymerisation of propene. [7 marks]
(b) An optically active compound Z, with molecular formula C4H9C1, reacts with
ethanolic potassium hydroxide solution to form three isomers of unsaturated organic
compounds.
(i) Write the structural formula of Z, and explain its reaction with ethanolic potassium
hydroxide solution. [5 marks]
(ii) Determine the isomer of Z which reacts with ethanolic potassium hydroxide
solution to form only one organic compound. Give a reason for your answer.
[3 marks]

© Majlis Peperiksaan Malaysia 2008 Actual 2008 STPM Chemistry Examination Paper 13

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 SUGGESTED ANSWERS

PAPER 1
Section A Energy
+10.5 kJ
+10.5kJ +(10.5 + 200) kJ
1. D Let relative molecular mass of haemoglobin NO + O3
molecule, HbFe4 = Mr.
4 × 55.8
% Fe = ———— × 100 = 0.335% –200 kJ
Mr NO2 + O2
Mr = 6.66 × 104
2. A 2B + 3H2 → B2H6 Reaction coordinate
1.00 g boron forms 1.278 g B2H6
∴ Mass of H = 0.278 g 10. B A Lewis base is an electron-pair donor. NH3
mol B 2 has a lone pair that is donated to the empty
——— = — orbital in BF3.
mol H 6
92.0
1.00 11. B [C2H5OH] = ——– = 2 mol dm–3
—— 46
Ar 1
⇒ ——— = — ⇒ Ar = 10.8 120.0
0.278 3 [CH3COOH] = ——— = 2 mol dm–3
——– 60
1
C2H5OH + CH3COOH CH3COOC2H5 +
Let % abundance of 10B : 11B = x% : (100 – x)% H2O
10x + 11(100 – x) Let x = number of moles of ethanol that has
∴ ————–——— = 10.8
100 reacted
⇒ x = 20% x2
—————— = 4.0
∴ 10B : 11B = 1 : 4 (2 – x)(2 – x)
3. A First ionisation energy is the amount of energy ⇒ x = 1.333
required to remove one mole of electrons ∴ Mass of C2H5OH left = (2 – 1.333) × 46
from one mole of gaseous atoms to form one = 30.7 g
mole of unipositive ions. 12. D For Kc = Kp, number of moles of gases on
4. A Valence electronic configuration of 3d3 4s2 right-hand side = left-hand side.
indicates that vanadium can have oxidation 13. C pH = 3.5 ⇒ [H+] = 3.16 × 10–4
states of +1 to +5. Let concentration of monobasic acid
The oxidation states of V in VO42– is +6, = c mol dm–3
in VO3– is +5, in VO2+ is +5 and in VO2+ is ∴ 25.00 × c = 27.50 × 0.10
+4. ⇒ c = 0.11 mol dm–3
5. C Fajan’s rule for a compound to exhibit high [H ] = Ka × c
+
covalent character: Ka = 9.08 × 10–7 mol dm–3
(i) Small cation 14. A A weak base and its salt forms an alkaline
(ii) Large anion buffer solution.
(iii) High ionic charge 15. C Let x = mass of X extracted in the first
6. A PCl3, ClO3– and SO32– are trigonal pyramidal extraction
in shape.
7. B x
——
100
————— = 3.00 ⇒ x = 3.60 g
3- 6.00 – x
+ CN ————
H 200
NC CN
C O H—P—H Fe ∴ Mass of X remaining in aqueous solution
H NC CN = 6.00 – 3.60 = 2.40 g
CN
Let y = mass of X extracted in the second
extraction
8. C The first graph shows the relationship: y
——
Rate = k[X] ⇒ 1st order 100
————— = 3.00 ⇒ y = 1.44 g
The second graph shows the relationship: 2.40 – y
Rate = k[Y]2 ⇒ 2nd order ————
200
9. D Total mass of X extracted = 3.60 + 1.44
= 5.04 g

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 16. D E o cell = +0.80 – (–0.76) = +1.56 V 29. D The aromatic nucleus undergoes electrophilic
At equilibrium substitution while the methyl side chain can
0.059 undergo free radical substitution.
⇒ 0 = E o cell – ——— log Kc 30. B
2
⇒ Kc = 7.61 × 1052 dm3 mol–1 CH3CH2CH=CH2 + CH3CH2CHCH3
17. C Plastic is a non-conductor while graphite is a
conductor.
18. B C2H5OH + O2 → CH3COOH + H2O
∆H = Σ ∆Hf (products) – Σ ∆Hf (reactants) 31. A
= [–487 + (–286)] – [(–278) + 0] CH2CH3 COOH
= –495 kJ mol–1 + 6[O] + CO2 + 2H2O
19. D The small F – ion has a very exothermic
enthalpy of hydration. white precipitate
20. B Descending Group 2:
32. C Ease of hydrolysis : RCOCl > RCl > C6H5Cl
• Ionic size increases, thus charge density
33. B C6H5OH (phenol) forms a white precipitate
decreases
with bromine water but ethanol does not.
• Solubility of sulphates decreases
34. C Z forms an orange precipitate with
• Thermal stability of carbonates and nitrates
2,4-dinitrophenylhydrazine and a yellow
increases
precipitate with I2/OH– indicates that Z is
21. D Descending Group 14:
a ketone with CH3C=O group. Thus, Y
• Conductivity increases as metallic character
is a secondary alcohol with CH3CH(OH)-
increases
group, and X is a haloalkane with
• Electronegativity decreases
CH3CHCl- group.
• Stability of +4 oxidation state decreases
35. D Decolourises bromine water ⇒ alkene
• Carbon can undergo catenation but not
Number of moles of NaOH = 0.02
other elements
22. A Si is in Period 3. It has empty 3d orbitals 1.16
Number of moles of acid = ——–
to accept lone pairs of electrons from water Mr
molecules. 0.02
If acid is monobasic ⇒ ——– = 1
23. C Reaction between N2 and H2 is exothermic. 1.16
——
Thus when temperature increases, the value Mr
of Kc decreases. ⇒ Mr = 58 ≠ Mr of (C)
24. C When an NH4+ compound is heated with a 0.02
base, NH3 gas will be liberated. If acid is dibasic = ——– = 2
1.16
25. C Ionisation energy involves the formation of ——
Mr
positive ions.
⇒ Mr = 116 = Mr of (D)
26. B & C
36. B
X has one oxidation state only (Sc). Hence,
it will form colourless hydrated ions.
NaOH(aq)
Y has an oxidation state of +6 in K2YO4. But the C O +
C O– Na + Na –O
+

oxidation states of Y are +2, +3 and +4 only.

O O
Z2O means Z has oxidation state of +1 but Z (P) HCl(aq)
does not have oxidation state of +1.
27. D The presence of NH4+ ions cause a common C OH + HO
ion effect which decreases the concentration O (R)
of OH– ions. This causes the ionic product of (Q)
[Zn2+][OH–]2 < Ksp of Zn(OH)2.
28. D There are three chiral centres. 37. A When ethanamide is heated with NaOH,
There is only one functional group (–OH). NH3 gas is liberated and sodium ethanoate is
The –OH group does not react with NaOH. formed.
It is a secondary alcohol that can be NH3 gas forms white fumes with HCl gas.
oxidised. 38. C ( C H 3 ) 2 C = C H C ≡ N + 3H2 →
CH3
(CH3)2CHCH2CH2NH2
39. D –COOH is the acidic group. It can react with
*
an alcohol.
* 40. D Ziegler-Natta catalyst produces HDPE at low
* OH temperature and pressure via coordination
CH(CH3)2 polymerisation.

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 Section B atom X increases (not decrease as in
41. A The mixture shows negative deviation. Thus, the question).
intermolecular forces between molecules in (b) (i) 2H2O2 → 2H2O + O2
the mixture are stronger than those between (ii)
molecules in the pure liquids. CHCl3 and energy
propanone molecules are held together by E2
hydrogen bonds which are stronger than
the van der Waals forces between CHCl3
molecules or propanone molecules.
42. No answer E1
W has a smaller Rf value than Y.
2H2O2
X is not a mixture of W and Y.
Z and W seem to have the same (lowest) ∆H
solubility in ethanol. 2H2O + O2
43. D Electronegativity, electrical conductivity
and enthalpy of vapourisation are periodic reaction coordinate
functions of the elements across a period. E2 = activation energy without catalyst
E1 = activation energy with catalyst
44. A The difference in the bond angles is due to ∆H = enthalpy change
the number of lone pairs in the molecules.
According to VSEPR theory, lone pair- (iii) The solution turns reddish-brown at
lone pair repulsion > lone pair-bond pair the beginning (due to formation of
repulsion > bond pair-bond pair repulsion Br2) then becomes colourless (Br2 is
45. B Quantity of electricity reduced to Br–).
=I×t
= (0.8 × 1 × 60 × 60)/ 9.65 × 104 2. (a) (i) Properties of elements are periodic
= 2.98 × 10–2 F functions of atomic mass.
To deposit 1 mol of the metal, quantity of (ii) Germanium
2.98 × 10–2 (b) (i) Phosphorus
electricity required = ————— =3F (ii) P has a stable half-filled p subshell.
1.00 × 10–2
The metal ion has a charge of +3. (c) (i) Rate = k [C3H6]
46. A [Al(H2O)5(OH)]2+ can be hydrolysed to (This is a first order reaction because
Al(OH)3 under basic conditions. the unit for the rate constant k is s–1.)
47. D Ag+ ions form precipitates with Cl– and I– ln 2
(ii) t 1 = ——
ions. AgCl dissolves in ammonia to form —
2 k
[Ag(NH3)2]+ complex ions. 0.693
= ———
48. A The reaction is an electrophilic substitution 15.12
reaction of the aromatic nucleus. = 0.0458 s
49. D Ethanol can be consumed. (iii) 0.25 mol dm–3 (1.0 → 0.5 → 0.25)
K2Cr2O7 oxidises ethanol to ethanoic acid and (iv) Both have the same molecular formula.
is itself reduced to Cr3+ ions. They are structural isomers.
50. D Organolithium compounds are more reactive (v) Propanol (dehydration of propanol
than Grignard reagents and they can be used forms propene)
to prepare alcohols. Silicones are also prepared
from chlorosilanes. 3. (a) (i) Soda glass consists of SiO2, Na2O,
CaO.
PAPER 2 SiO2 + Na2CO3 → Na2SiO3 + CO2
Section A (ii) Main component is B2O3 and SiO2.
1. (a) (i) Hund’s rule Has low expansion coefficient, can
(ii) withstand temperature/heat change
3d 8 4s 2 without cracking.
(b) (i) R R R

O Si O Si O Si
(iii) 2
(iv) When an electron is transferred from R R R
one subshell to another, the electron where R = alkyl group
gains energy and is promoted to a (ii) High viscosity liquid / stable towards
higher subshell. The total energy of heat / chemically inert

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 (iii) When applied to fabric, the O atoms pyramidal shape with smaller bond angle
of silicone form hydrogen bonds with of < 109.5°.
molecules on the surface of fabrics. c
The hydrophobic organic groups act H
H
as barrier on the surface of fabrics H
and repel water. Silicone fluid shows
spreading properties due to low surface (b) (i) Enthalpy of atomisation is the heat
tension, forming a film on the fibre that energy required to convert one mole
water cannot wet. The hydrophilic –OH of a covalent compound (or species)
group is replaced by the hydrophobic into its free gaseous atoms.
organic group (–CH3) that repels water. ∆H
Thus, water falling on the fabric roll CH4(g) + Cl•(g) ⎯→ •CH3(g) + HCl(g)
off instead of penetrating through and
wetting it. +1740 kJ +1305 kJ +431kJ

4. (a) (i) Benzene diazonium chloride C(g) + 4H(g) + Cl(g)

(ii) C6H5NH2 + HNO2 + HCl → Enthalpy of reaction,
C6H5N2+ Cl– + 2H2O ∆H = +1740 – (+1305) – (+431)
(iii) Phenol = + 4 kJ mol–1
(iv) Coupling reaction (ii)
– energy
-N=N- -O

(b) (i) H

H2N C COOH •CH3(g) + HCl(g)

R ∆H = +4 kJ mol–1
The basic unit in polypeptide is amino CH4(g) + Cl•(g)

acid.
reaction coordinate
(ii) Long chain of amino acids bonded by
peptide linkages 6. (a) N2(g) + 3H2(g) ↔ 2NH3(g)
(iii) Hydrogen bonds are disrupted and Initial: 1 mol 1 mol 0 mol
hydrolysis occurs on the –CONH- At equilibrium: 0.8 mol 0.4 mol 0.4 mol
group.
0.8 0.4 0.4
(iv) Hydrogen bond between C=O group of ≡ [ ] in 2 dm3 —— mol —— mol —— mol
2 2 2
an insulin molecule with N–H group of
another insulin molecule. [NH3]2
Kc = ————–
[N2] [H2]3
Section B
0.4 2
5. (a) VSEPR (valence-shell electron-pair repulsion) 冢——
2 冣
theory states that the geometry of a molecule = ——————
0.8 0.4 3
is determined by the repulsion among the
electron-pairs associated with a central atom.
冢
—— ——
2 冣冢2 冣
The electron-pairs arrange themselves as far = 12.5 mol–2 dm6
apart as possible to minimise the repulsion. (b) Gas X is N2O4.
Repulsion between electron-pairs increases Gas Y is NO2.
in the order: Decomposition of N2O4 to NO2 is an
bond pair – bond pair < bond pair – lone endothermic process.
pair < lone pair – lone pair N2O4(g) 2NO2(g) ; ∆H = +ve
CH4: Has four bonding electron-pairs and When heated, the equilibrium position shifts
no lone pair. Hence, tetrahedral shape with to the right, colourless N2O4 decomposes to
bond angle of 109.5°. the brown NO2.
H When cooled, the equilibrium position shifts
to the left, colourless N2O4 is formed.
(c) N2O4(g) 2NO2(g)
H C H (i) When pressure is increased, the
H mixture turns light brown / pale
•CH3: Has three bonding electron-pairs yellow as more N2O4 is formed. The
and one lone electron. Hence, trigonal equilibrium position shifts to the left

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 as the reaction to the left is
accompanied by a reduction in the
number of moles of the gases.
(ii) When argon gas is added to the
equilibrium mixture at constant volume,
the equilibrium position is unaffected
because the partial pressure of each
component gas remains unchanged.
7. (a) (i)
N3–
ionic radius
O2–
F–
Na+
Mg2+ 3+
Al
7 8 9 10 11 12 13 proton number
(ii) All the ions are isoelectronic (having
the same number of electrons, 10 e–),
hence almost similar shielding effect
but the nuclear charge increases with
increasing proton number. Hence, the
effective nuclear charge increases.
Therefore, the ionic size decreases in the
order: N3–, O2–, F–, Na+, Mg2+, Al3+.
(b) (i) Under very low temperatures, CO2 is
in solid form and is filtered off.
(ii) Pure nitrogen is obtained by fractional
distillation of liquefied air. N2 is more
volatile and is distilled out while O2 is
left in the residual liquid air.
Liquid nitrogen is used as refrigerant
to freeze food rapidly / as biological
preservation.
(iii) Nitrogen is inert due to the strong triple
covalent bond in N2 molecule that has
a high bond energy and requires a lot
of energy to break.
Nitrogen oxides are produced during
thunderstorms. Lightning provides very
high energy to break the strong covalent
bonds in N2 and O2, thus enabling
nitrogen and oxygen gases to react to
form nitrogen oxides.
N2(g) + O2(g) → 2NO(g)
Further oxidation:
2NO(g) + O2(g) → 2NO2(g)
(c) RMM of AlCl3 = 27.0 + (3 × 35.5)
= 133.5
At 200 °C, aluminium chloride exists as
a dimer Al2Cl6 as its rmm is twice that of
AlCl3.
At 800 °C, aluminium chloride exists as
monomer AlCl3 as its rmm is 133.
At 600 °C, both monomer AlCl3 and
dimer Al2Cl6 exist in equilibrium as its rmm
is >133 but < 269.
18 Actual 2008 STPM Chemistry Examination Paper
Ace Ahead STPM Chem Vol 2 08 Q&A 4th.indd 18
Dissociation of dimer Al2Cl6 occurs between
400 – 800 °C.
8. (a) Transition element is an element that forms
at least a stable simple ion with partially
filled d orbitals.
(i) [Fe(H2O)6]3+(aq) + SCN–(aq) →
[Fe(H2O)5SCN]2+(aq) + H2O(l)
Yellow solution becomes blood-red.
An aqueous solution of iron(III) contains
[Fe(H2O)6]3+. SCN– is a stronger ligand
than H2O. Hence, SCN– displaces a
H2O ligand, forming the complex
ion [Fe(H2O)5SCN]2+ which is red in
colour.
(ii) [Fe(CN)6]4–
4-
CN
NC CN
Fe Octahedral shape
NC CN
CN
Two of the 3d orbitals are not filled
with electrons.
There are six electrons in Fe2+. The
electrons in the 3d subshells rearrange
to form vacant orbitals in order to
accept lone pair electrons from the
CN– ions.
orbitals hybridised to
accept electrons from CN– ions
Fe2+
3d 4s 4p
(b) (i) Yellow solution turns a deep blue
colour.
[CuCl4]2–(aq) + 4NH3(aq) →
yellow solution
[Cu(NH3)4]2+(aq) + 4Cl–(aq)
deep blue solution
[Cu(NH3)4]2+ has a higher stability
constant than [CuCl4]2– which implies
that the complex ion [Cu(NH3)4]2+ is
more stable. Cl– is a weaker ligand
and is displaced by the stronger NH3
ligand.
(ii) The stability constant of [Cu(EDTA)]2–
complex, expressed in logarithm, is
higher than 13.2.
[EDTA]4– is a stronger ligand than Cl–
and NH3 because it is a polydentate /
chelating ligand that is attached to the
metal ion by several bonds.
© Oxford Fajar Sdn. Bhd. (008974-T) 2008
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 9. (i) H H H OH H A is an optically active alcohol
implies that A has a chiral carbon
H C C C C C H atom that is attached to four different
groups.
H H H H H
C3H7 C3H7
A 2-pentanol
H H H C* C*
HO H H OH
H C C C C C H CH3 CH3

H H H H H
B 2-pentene
When heated with alumina, A undergoes
H H H elimination to alkenes B and C.
H C C C C C H
C is an alkene with C=C double bond at
H H H H H one end. Under strong oxidation (when
C 1-pentene heated with KMnO4), the C=C double
bond breaks and carboxylic acid D is
H H H O formed and CO2 gas that turns lime
water chalky is evolved.
H C C C C OH
When carboxylic acid D is heated with
H H H
ammonia, an amide E is formed.
D butanoic acid

H H H O H Amide E with LiAlH4 is reduced to an

amine F.
H C C C C N H (ii)
CH3 C2H5 CH3 H
H H H
E butanamide C C C C

H H H H H H H H C2H5
cis-2-pentene trans-2-pentene
H C C C C N H

H H H H
F butanamine

(iii)

H H H OH H H H H H H H
Al2O3
2H C C C C C H H C C C C C H + H C C C C C H + 2H2O
䉭
H H H H H H H H H H H H H H H
A B C

H H H H H H O
KMnO4
H C C C C C H + 5[O] H C C C C OH + CO2 + H2O
䉭
H H H H H H H H
C D

H H H O H H H O H

H C C C C OH + NH3 H C C C C N H + H2O
䉭
H H H H H H
D E

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 H H H O H H H H H H
LiAlH4
H C C C C N H + 4[H] H C C C C N H + H2O

H H H H H H H
E F
10. (a) Free radical addition polymerisation.
(i) Initiation step:
Benzoyl peroxide, C6H5COO–OOCC6H5 acts as initiator, undergoes photochemical/thermal
decomposition to form free radicals
C6H5COO OOCC6H5 → 2C6H5COO• → 2C6H5• + 2CO2
C6H5• + CH3CH = CH2 → C6H5CHCH2•
CH3
(ii) Propagation steps:
The free radical reacts with propene monomer to form another free radical.
The chain propagates as successive monomers add on until a long polymeric chain is formed.
C6H5CHCH2• + CH CH2 → C6H5 CHCH2CHCH2•

CH3 CH3 CH3 CH3

CH3

C6H5CHCH2CHCH2• + CH CH2 → C6H5CHCH2 CH CH2 CH CH2• → → C6H5CHCH2 CH CH2

冢 冣nCH CH2•

CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

(iii) Termination step:

Two free radicals combine to form a molecule.

C6H5CHCH2• + C6H5 CHCH2• → C6H5 CHCH2CH2CHC6H5

CH3 CH3 CH3 CH3

(b) (i) Z is

H H H H

H C C C C H

H H Cl H
Z is optically active implies that Z has a chiral carbon that is attached to four different groups.

C2H5 C2H5

C* C*
Cl H H Cl
CH3 CH3

Z undergoes elimination reaction with ethanolic potassium hydroxide solution to form two
different alkenes (unsaturated organic compounds): 1-butene, CH3CH2CH=CH2 and 2-butene,
CH3CH=CHCH3.
CH3CH2CH(Cl)CH3 + KOH → CH3CH2CH=CH2 + KCl + H2O
CH3CH2CH(Cl)CH3 + KOH → CH3CH=CHCH3 + KCl + H2O
2-butene forms two geometrical (cis-trans) isomers because it has different groups on the unsaturated
carbon atom.

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 H H CH3 CH3 CH3 H

H C C C C H C C C C

Hence the three isomers are H H H H , H H and H CH3

(ii) There are three possible isomers of Z that give only one organic compound with ethanolic KOH.

CH3 CH3

CH3CH2CH2CH2Cl / CH3 C CH3 / CH3 CH CH2Cl.

Cl

Reaction with ethanolic KOH:

ethanolic
CH3CH2CH2CH2Cl CH3CH2CH=CH2 + KCl + H2O
KOH 1-butene

CH3 CH3 CH3

ethanolic
CH3 CH CH2Cl CH3 C CH3 CH3 C=CH2 + KCl + H2O
KOH methylpropene
Cl

The products formed do not have geometrical isomers because they have the same group on the
unsaturated carbon atoms.

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