PAPER 1

Section A
Four suggested answers labelled A, B, C
and D are given for each question. Choose
one correct answer.
1
The percentage of iron in a haemoglobin
molecule is 0.335%. If a haemoglobin
molecule consists of four iron(II) ions,
what is the relative molecular mass of
haemoglobin?
[Relative atomic mass of Fe is 55.8.]
A 6.66 ¡Ñ 102 C 1.67 ¡Ñ 104
B 4.16 ¡Ñ 103 D 6.66 ¡Ñ 104

2
Boron has two isotopes with relative
isotopic masses of 10 and 11. When

1.00 g of boron reacts completely with

hydrogen, 1.278 g of boron hidride,
B2H6, is produced. Which graph shows
the mass spectrum of boron?
A
Relative
intensity
4

3
2
1
0
m/e
8 9 10 1112
B
Relative
intensity
4

4
3
2
1
0
12 m/e
8 9 1011
Time: 1h 45 min
C
Relative
intensity
4
3
2
1
m/e
0
8 9 101112
D
Relative
intensity
4
3
2
1
m/e
0
8 9 101112
Which equation illustrates the first
ionisation energy of the given
element?
A C(g) ¡÷ C+(g) + e¡V
B Na(s) ¡÷ Na+(g) + e¡V
C Cl(g) + e¡V ¡÷ Cl¡V(g)
D O(g) + e¡V ¡÷ O¡V(g)
Vanadium has the electronic configuration
1s22s22p63s23p63d34s2. Which ion does
not exist?
A VO42¡V

¡V
B VO3
C VO2+
VO2+
D

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Actual 2008 STPM Chemistry Examination Paper
 5 The ionic radii of four ions are as
follows:
Ion Ionic radius/nm
P+ 0.095
Q2+ 0.031
R¡V 0.136
S¡V 0.126
Which ionic compound has bonding with
the greatest covalent character?
A PR C QR2
B PS D QS2

6
Which species has a trigonal planar
shape?
¡V
A BF3 C ClO3
B PCl3 D SO32¡V

7
Coordinate bonds do not exist in
A CO
B BeCl2
C PH4+
]3¡V
D
[Fe(CN)6
8
The graphs of initial rate versus
concentration of reactants for the reaction
X + Y ¡÷ Z are shown below.
Rate
[X]
Rate
[Y]
What is the order of the reaction with
respect to X and Y?
X Y
A 0 1
B 1 0
C 1 2
D 2 1
9
The thermochemical equation for the
reaction between nitrogen monoxide and
ozone is as follows:
NO(g) + O3(g) NO2(g) + O2(g);
£GH = ¡V200.0 kJ
If the activation energy of the reaction is
10.5 kJ mol¡V1, the activation energy of
the reverse reaction is
A 10.5 kJ mol¡V1
B 189.5 kJ mol¡V1
C 200.0 kJ mol¡V1
D 210.5 kJ mol¡V1
10
Which underlined molecule reacts as a
Lewis base?
A K2O + SO3 ¡÷ K2SO4
B
BF + NH¡÷ HN¡EBF
3333
¡V
C OH¡V + CO2 ¡÷ HCO3
D CH3Cl + FeCl3 ¡÷ CH3+ + FeCl4¡V

11
The equilibrium constant, K c, for a
reaction between ethanol and ethanoic
acid is 4.0 at 25 ¢XC. If 1.0 dm3 of an
aqueous solution containing 92.0 g
ethanol and 120.0 g ethanoic acid is
left to react until equilibrium is attained
at 25 ¢XC, 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
B 30.7 g D 73.6 g
12
In which reaction is the value of K
c
equals to the value of K p?
A N2O4(g) 2NO2(g)
B CO2(g) + C(s) 2CO(g)
C H2O(g) + C(s) H2(g) + CO(g)
D 3Fe(s) + 4H2O(g) Fe3O4(s) + 4H2(g)

13
An aqueous solution of a monobasic
acid has pH 3.5. A 25.00 cm3 volume
of an aqueous solution of the acid is
completely neutralised by 27.50 cm3
of a 0.10 mol dm¡V3 sodium hydroxide
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solution. The value of the dissociation
constant of the acid is
A 3.16 ¡Ñ 10¡V4 mol dm¡V3
B 3.48 ¡Ñ 10¡V5 mol dm¡V3
C 9.08 ¡Ñ 10¡V7 mol dm¡V3
D 9.99 ¡Ñ 10¡V8 mol dm¡V3
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 ¡V ¡X¡X¡V log ¡X¡X¡V¡X¡X¡X¡X¡X ,
n [reduced species]
E o
where 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¡V

Zn(s) ¡V0.76
Ag+(aq) + e¡V
Ag(s) +0.80
What is the equilibrium constant, K c,
for the reaction 2Ag+(aq) + Zn(s) ¡÷
Zn2+(aq) + 2Ag(s) at 25 ¢XC?
A 1.31 ¡Ñ 10¡V53 dm3 mol¡V1
B 4.41 ¡Ñ 10¡V2 dm3 mol¡V1
C 2.76 ¡Ñ 1026 dm3 mol¡V1
D 7.61 ¡Ñ 1052 dm3 mol¡V1

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
¡V487 kJ mol¡V1, ¡V286 kJ mol¡V1 and
¡V278 kJ mol¡V1 respectively. The standard
enthalpy change, in kJ mol¡V1, for the
preparation is
A ¡V1051
B ¡V495
C ¡V209
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
acid
Standard enthalpy of
neutralisation/kJ mol¡V1
HF ¡V68.6
HCl ¡V57.6
HBr ¡V57.3
HI ¡V57.2
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
Periodic Table which is situated between
calcium and barium. Which statement is
true?
A The strontium ion has a higher charge
density than the calcium ion.
B Strontium sulphate is less soluble in
water than calcium sulphate.
C Strontium carbonate is more difficult
to decompose than barium carbonate
when heated.
D Strontium nitrate is more difficult to
decompose than barium nitrate when
heated.
21
Which property is true of the elements
in Group 14 of the Periodic Table on
descending the group?
A The electrical conductivity of the
elements decreases.
B The electronegativity of the elements
increases.
C The stability of the +4 oxidation state
of the elements increases.
D The catenation of the elements
decreases.
22
SiCl4 compound forms an acidic solution
with water while CCl4 compound does
not dissolve in water because
A silicon atom has empty 3d orbital
while carbon atom does not.
B the Si Cl covalent bond is weaker
than the C Cl covalent bond.
C the SiCl4 molecule is polar while the

CCl4 molecule is non-polar.

D
van der Waals forces between SiCl4
molecules are weaker than those
between CCl4 molecules.
23
At 500 ¢XC, nitrogen and hydrogen gases
react according to the equation
N2(g) + 3H2(g) ¡÷ 2NH3(g).
Which statement about the reaction is
true?
A The reaction is endothermic.
B The reaction occurs through three

steps.
C
The value of the equilibrium constant
is lower at a temperature more than
500 ¢XC.
D
The percentage yield of ammonia
increases when the pressure is
reduced.
24
Ammonia gas can be prepared in a
laboratory by heating an ammonium salt
with
A Devarda¡¦s alloy
B hydrochloric acid
C calcium hydroxide solution
D acidified solution of potassium
manganate(VII)
25
The reactivity of the halogens Cl2, Br2
and I2 decreases down Group 17 of the
Periodic Table. Which property does not
influence the trend in the reactivity of
the halogens?
A Atomic size
B Electron affinity
C Ionisation energy
D Bond energy
26
The oxidation states of several d-block
elements represented by letters which are
not the usual symbols for the elements
concerned in the Periodic Table are as
follows:
Element Oxidation state
X ¡V ¡V 3 ¡V ¡V ¡V ¡V
Y ¡V 2 3 4 ¡V ¡V ¡V
Z ¡V 2 3 4 5 6 7
Which statement is not true?
A X forms colourless hydrated ions.
B Y forms a compound with the
molecular formula K2YO4.
C Z2O is an oxidising agent.
D X, Y and Z form octahedral
complexes.
27
Zn2+ ions form a white precipitate,
Zn(OH)2, with an aqueous solution
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¡V .
C NH4
+ ions increase the solubility
product of Zn(OH)2.
D NH+ ions decrease the concentration
4
of OH¡V 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

OH

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

sodium hydroxide.
D It decolourises an acidified solution
of potassium manganate(VII).
29
Which compound reacts with chlorine
following the mechanisms for free
radicals and electrophilic substitution?
A CH3CH3
B CH2Cl2
C CH3CH=CH2
D C6H5CH3
30
Which compound is formed when
benzene reacts with 1-butene in the
presence of aluminium chloride?
A

CH2CH2CH2CH3
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

CH2Cl CHO
B

32
Each of the following compounds is put
into a test tube and an aqueous solution
of silver nitrate is added. The three test
tubes are then placed in a hot water
bath.

Cl
CH3COCl
ClCH2COOH
I II III
Which sequence of the compounds
according to the ascending order of their
reactivity is correct?
A I, III, II
B II, I, III
C II, III, I
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 C5Cl, is converted to compound Z
H11
according to the following reaction scheme.
NaOH(aq) KMnO4/H+

C5H11Cl ....¡÷ Y ....¡÷ Z

£G£G
Z forms an orange precipitate with 2,4-dinitrophenylhydrazine and a yellow preci
pitate
with an alkaline solution of iodine. What are X, Y and Z?
X Y
Z
A CHCHCHCHCHCl CHCHCHCHCHOH CHCHCHCHCHO
32222322223222
B CHCHCH(Cl)CHCH CHCHCH(OH)CHCHCHCHCOCHCH
3
2233223 3223
C CHCH(Cl)CHCHCH CHCH(OH)CHCHCHCHCOCHCHCH
32233223 3223
D (CH)C(Cl)CHCH (CH)C(OH)CHCHCHCOCHCHCH
32233223 3223
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
dm¡V3 sodium hydroxide solution for
complete neutralisation. What is the
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
O
B HOOC¡XCOOH
C CH2=CHCOOH C CH3CH2OH
D HOOCCH=CHCOOH
OH
36
When a white solid P, with molecular
formula CHO, is refluxed with an
13102
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
true?
A The gas evolved forms white fumes
OH with hydrogen chloride.
B The gas evolved turns blue litmus
paper red.
C A liquid with a smell of vinegar is
formed.
A
OH
D
A layer of colourless oil is formed.
C ONa
ONa
O
B
CH2OH
C
OH
O
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38
What is the compound formed when
(CH3)2C=CHCN reacts with hydrogen
gas in the presence of platinum?
A (CH3)2CHCH2CN
B (CH3)2C=CHCH2NH2
C (CH)CHCHCHNH
32222
40
D
(CH3)2CHCH2NHCH3
39
GABA is a neuro-transmitter released
by red algae which encourages
shellfish larvae to settle on the
ocean bed. Its structural formula is
H2NCH2CH2CH2COOH. Which reagent
reacts only with the acidic group of
GABA?
Section B
For each question 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 as follows:
A B C D
1 only is 1 and 2 2 and 3 1, 2 and
correct. only are only are 3 are
correct. correct. correct.
42

41
The phase diagram of a mixture of two
liquids P and Q is as follows:
Vapour
pressure/
atm

1.0 Mole fraction 1.0

Q
P
What could P and Q be?
A HCl
B HNO2
C CH3CH2Cl
D CH3CH(OH)CH3
Ziegler-Natta catalyst is used in addition
polymerisation of ethene. Which
statement is not true of the process?
A It requires a low pressure.
B It requires a low temperature.
C It produces high density

poly(ethene).
D It is an example of free radical
polymerisation.
P
Q
1 Trichloromethane Propanone
2 Benzene Methylbenzene
3 Ethanol Water
The paper chromatogram of samples
W, X, Y and Z which is obtained
using ethanol as an eluent is shown
below.
Solvent
front
WXYZ
Which statement(s) is/are true of the
samples W, X, Y and Z?
1 W has a larger Rf value than Y.
2 X is a mixture of W and Y.
3 Z has the lowest solubility in
ethanol.
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43 Which property(ies) of the elements in 46 [Al(H2O)6]3+ ion is hydrolysed in a
queous
Period 2 and Period 3 of the Periodic solution according to the equation
Table change(s) periodically?
1 Electronegativity
2 Electrical conductivity
[Al(H2O)6]3+(aq) + H2O(l)
[Al(H2O)5(OH)]2+(aq) + H3O+(aq)
3 Enthalpy of vapourisation Which statement(s) about the reaction
is/are true?
44 The bond angles in methane, ammonia
and water molecules are shown
1 The [Al(H2O)5(OH)]2+ ion is not
stable with respect to hydrolysis.
below. 2 The reaction is a redox reaction.
3 The rate of reaction increases when

an acid is added.
H
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
107¢X of silver nitrate followed by an aqueous
109.5¢X
H
HH solution of ammonia. The reaction(s)
H
H
involved is/are
H
1 Ag+(aq) + I¡V(aq) ¡÷ AgI(s)
2 Ag+(aq) + Cl¡V(aq) ¡÷ AgCl(s)

3
AgCl(s) + 2NH3(aq) ¡÷
Ag(NH3)2+(aq) + Cl¡V(aq)
O 48 Which compound(s) and reagent(s)
with reaction condition(s) react to
form a compound with halogen atoms
104.5¢X
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 ¡Ñ 10¡V2 mol of a metal is
deposited at the cathode. What could
the metal be? 3
CH(OH)CH3 I2/NaOH, £G
[Faraday constant is 9.65 ¡Ñ 104 C mol¡V1.]
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.
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.
c Majlis Peperiksaan Malaysia 2008 Actual 2008 STPM Chemistry Examination Paper
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 e
ach filled
with one electron, with the electrons having parallel spins, before a second ele
ctron
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 add
ition
of a small amount of an acidic solution of sodium bromide. The catalysis steps a
re
as follows:
2Br¡V + H2O2 + 2H+ ¡÷ Br2 + 2H2O
Br2 + H2O2 ¡÷ 2Br¡V + 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 reac
tions
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 mode
rn
Periodic Table.
(i) What is the basis of Mendeleyev¡¦s Periodic Table? [1 mark]
(ii) Based on his Periodic Table, Mendeleyev successfully predicted the properti
es
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.
YFirst
ionisation
energy
/kJ mol¡V1
Proton number
10 Actual 2008 STPM Chemistry Examination Paper c Majlis Peperiksaan Malaysia 20
08
(i) Identify the element labelled Y.
[1 mark]
(ii) Why is the first ionisation energy of Y higher than that of the next elemen
t?
[1 mark]
(c) Cyclopropane decomposes into propene through the ring opening of cyclopropan
e
according to the equation
C3H6(g) ¡÷ CH2=CHCH3(g)
The rate constant for the decomposition is 15.12 s¡V1 at 400 ¢XC.
(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 t
he
concentration of cyclopropane at 400 ¢XC 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 che
apest
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 vari
ety of
products. Commercial silicones have infinite O-Si-O chains with alkyl or aryl gr
oups
attached to the silicon atoms.
(i) Draw the structure of chain silicone showing three repeating units with alky
l
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 ¢XC to 5 ¢XC to produce a salt used in dyein
g
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 ¢XC, a vigorous reacti
on
occurs. Name the organic product formed. [1 mark]
(iv) When an aqueous solution of this salt is added to an alkaline solution of p
henol,
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 bloo
d. 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 struct
ure
of the insulin molecules. [1 mark]
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Actual 2008 STPM Chemistry Examination Paper 11
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 f
ollowing
table.
Species Standard enthalpy of atomisation/kJ mo1¡V1
CH4 + 1740
¡ECH3 + 1305
HC1 + 431
(i) Calculate the standard enthalpy of reaction for the homolytic dissociation o
f
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 pre
pared
commercially by the Haber process. 1.0 mol of nitrogen gas and 1.0 mol of hydrog
en
gas are introduced into a 2.0 dm3 volumetric flask at 450 ¢XC. The amount of hydro
gen
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 exc
ept
proton number 10.
Proton number 7 8 9 11 12 13
Formula of ion N3¡V 02¡V F¡V 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, o
xygen
and argon.
12 Actual 2008 STPM Chemistry Examination Paper
c Majlis Peperiksaan Malaysia 2008
(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 phenome
non
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 /¢XC 200 600 800
Relative molecular mass 269 163 133
Explain why the relative molecular mass of aluminium chloride shows different va
lues
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 potassi
um
thiocyanate is added to an aqueous solution of iron(III) ions. [4 marks]
(ii) A Fe2+ ion reacts with CN¡V 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¡V 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
]2¡V
aqueous solution of [CuCl4.
[4 marks]
(ii) Predict the stability constants, expressed as their logarithms, of the comp
lex ion
[Cu(EDTA)]2¡V, and give a reason for your answer. [2 marks]
9
Compound A, with the molecular formula C5O, which has a straight chain structure
H12
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 whic
h turns
lime water chalky is evolved. When D is heated with an aqueous solution of ammon
ia,
compound E is formed which reacts with lithium tetrahydridoaluminate(III) to for
m
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 orga
nic
compounds.
(i) Write the structural formula of Z, and explain its reaction with ethanolic p
otassium
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]
c Majlis Peperiksaan Malaysia 2008
Actual 2008 STPM Chemistry Examination Paper 13
SUGGESTED ANSWERS SUGGESTED ANSWERS
NO + O3
1+10.5 kJ +(10.5 + 200) kJ
¡V200 kJ
NO2 + O2
Reaction coordinate
PAPER 1
Section A
Energy
1.
D Let relative molecular mass of haemoglobin
molecule, HbFe4 = M r.
4 ¡Ñ 55.8
% Fe = ¡X¡X¡X¡X ¡Ñ 100 = 0.335%
M
r
M = 6.66 ¡Ñ 104
r
2. A 2B + 3H2 ¡÷ B2H6
1.00 g boron forms 1.278 g B2H6
¡ï Mass of H = 0.278 g 10. B A Lewis base is an electron-pair donor. NH3
has a lone pair that is donated to the empty
mol B 2
¡X¡X¡X = ¡X
orbital in BF3.
mol H 6
92.0
1.00
11. B [C2H5OH] = ¡X¡X¡V = 2 mol dm¡V3
¡X¡X
46
A 1
r
. ¡X¡X¡X = ¡X . A = 10.8
r
120.0
0.278 3
[CHCOOH] = ¡X¡X¡X = 2 mol dm¡V3
¡X¡X¡V
3
60
1
C2H5OH + CH3COOH

CH3COOC2H5 +
Let % abundance of 10B : 11B = x% : (100 ¡V x)%
H2O
10x + 11(100 ¡V x) Let x = number of moles of ethanol that has
¡ï ¡X¡X¡X¡X¡V¡X¡X¡X = 10.8
100
reacted
.
x = 20% x2
¡X¡X¡X¡X¡X¡X = 4.0
¡ï 10B : 11B = 1 : 4
(2 ¡V x)(2 ¡V x)
3. A First ionisation energy is the amount of energy
. x = 1.333
required to remove one mole of electrons
¡ï Mass of CHOH left = (2 ¡V 1.333) ¡Ñ 46
from one mole of gaseous atoms to form one 25= 30.7 g
mole of unipositive ions.
12. D For K c = K p, 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 ¡Ñ 10¡V4
states of +1 to +5.
Let concentration of monobasic acid
The oxidation states of V in VO42¡V is +6,
= c mol dm¡V3
in VO¡V is +5, in VO+ is +5and in VO2+ is
32 ¡ï 25.00 ¡Ñ c = 27.50 ¡Ñ 0.10
+4.
. c = 0.11 mol dm¡V3
5. C Fajan¡¦s rule for a compound to exhibit high
[H+] =
K ¡Ñ c
a
covalent character:
K = 9.08 ¡Ñ 10¡V7 mol dm¡V3
(i) Small cation
a
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
¡V
6. A PCl, ClO and SO2¡V are trigonal pyramidal
33 3
extraction
in shape.
x
7.
B ¡X¡X
100
¡X¡X¡X¡X¡X = 3.00 . x = 3.60 g
3-6.00 ¡V x
+ CN
¡X¡X¡X¡X
H
200
NC
CN
C

O H¡XP¡XH Fe ¡ï Mass of X remaining in aqueous solution

H
NC CN = 6.00 ¡V 3.60 = 2.40 gCN Let y = mass of X extracted in the second
extraction
8. C The first graph shows the relationship:
y
¡X¡X
Rate = k[X] . 1st order
100
¡X¡X¡X¡X¡X = 3.00 . y = 1.44 g
The second graph shows the relationship:
2.40 ¡V y
¡X¡X¡X¡X
Rate = k[Y]2 . 2nd order
200
9. D
Total mass of X extracted = 3.60 + 1.44
= 5.04 g
14 Actual 2008 STPM Chemistry Examination Paper
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
16. D
17. C
18. B
19. D
20. B
21. D
22. A
23. C
24. C
25. C
E o
cell = +0.80 ¡V (¡V0.76) = +1.56 V
At equilibrium
0.059
. 0 = E o ¡V ¡X¡X¡X log K
cellc
2
. K = 7.61 ¡Ñ 1052 dm3 mol¡V1
c
Plastic is a non-conductor while graphite is a
conductor.
CHOH + O¡÷ CHCOOH + HO
25232
£GH = £U £GHf(products) ¡V £U£GHf(reactants)
= [¡V487 + (¡V286)] ¡V [(¡V278) + 0]
= ¡V495 kJ mol¡V1
The small F¡V ion has a very exothermic
enthalpy of hydration.
Descending Group 2:

¡E
Ionic size increases, thus charge density
decreases
¡E
Solubility of sulphates decreases
¡E
Thermal stability of carbonates and nitrates
increases
Descending Group 14:
¡E
Conductivity increases as metallic character
increases
¡E
Electronegativity decreases
¡E
Stability of +4 oxidation state decreases
¡E
Carbon can undergo catenation but not
other elements
Si is in Period 3. It has empty 3d orbitals
to accept lone pairs of electrons from water
molecules.
Reaction between N2 and H2 is exothermic.
Thus when temperature increases, the value
of K decreases.
c
When an NH4+ compound is heated with a
base, NH3 gas will be liberated.
Ionisation energy involves the formation of
positive ions.

29. D
30. B
31. A
32. C
33. B
34. C
35. D
36. B
26.
B & C
X has one oxidation state only (Sc). Hence,
it will form colourless hydrated ions.
Y has an oxidation state of +6 in K2YO4. But the
oxidation states of Y are +2, +3 and +4 only.
Z2O means Z has oxidation state of +1 but Z
does not have oxidation state of +1.
27.
D The presence of NH4+ ions cause a common
ion effect which decreases the concentration
of OH¡V ions. This causes the ionic product of
[Zn2+][OH¡V]2 < K sp of Zn(OH)2.
28.
D There are three chiral centres.
There is only one functional group (¡VOH).
The ¡VOH group does not react with NaOH.
It is a secondary alcohol that can be
oxidised.
CH3
CO
CO¡VNa+ + Na+¡VO

O
(P)
37. A
38. C
39. D
40. D
The aromatic nucleus undergoes electrophilic
substitution while the methyl side chain can
undergo free radical substitution.
CH3CH2CH=CH2 + CH3CH2CHCH3
CH2CH3 COOH
+ 6[O] + CO2 + 2H2O
white precipitate
Ease of hydrolysis : RCOCl > RCl > C6H5Cl
C6H5OH (phenol) forms a white precipitate
with bromine water but ethanol does not.
Z forms an orange precipitate with
2,4-dinitrophenylhydrazine and a yellow
precipitate with I2/OH¡V indicates that Z is
a ketone with CH3C=O group. Thus, Y
is a secondary alcohol with CH3CH(OH)group,
and X is a haloalkane with
CH3CHCl- group.
Decolourises bromine water . alkene
Number of moles of NaOH = 0.02
1.16
Number of moles of acid = ¡X¡X¡V
M
r
0.02
If acid is monobasic . ¡X¡X¡V = 1
1.16
¡X¡X
M
r
. M r = 58 ¡Ú M r of (C)
0.02
If acid is dibasic = ¡X¡X¡V = 2
1.16
¡X¡X
M
r
. M r = 116 = M r of (D)
NaOH(aq)
O
HCl(aq)
C OH + HO
(R)
O
(Q)
When ethanamide is heated with NaOH,
NH3 gas is liberated and sodium ethanoate is
formed.
NH3 gas forms white fumes with HCl gas.
(CH) C=CHC¡ÝN + 3H¡÷

32
2
(CH3)2CHCH2CH2NH2
¡VCOOH is the acidic group. It can react with
an alcohol.
Ziegler-Natta catalyst produces HDPE at low
temperature and pressure via coordination
polymerisation.

OH
CH(CH3)2
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
Actual 2008 STPM Chemistry Examination Paper 15
Section B
41.
A The mixture shows negative deviation. Thus,
intermolecular forces between molecules in
the mixture are stronger than those between
molecules in the pure liquids. CHCl3 and
propanone molecules are held together by
hydrogen bonds which are stronger than
the van der Waals forces between CHCl3
molecules or propanone molecules.
42.
No answer
W has a smaller Rf value than Y.
X is not a mixture of W and Y.
Z and W seem to have the same (lowest)
solubility in ethanol.
43. D
Electronegativity, electrical conductivity
and enthalpy of vapourisation are periodic
functions of the elements across a period.
44.
A The difference in the bond angles is due to
the number of lone pairs in the molecules.
According to VSEPR theory, lone pair-
lone pair repulsion > lone pair-bond pair
repulsion > bond pair-bond pair repulsion
45.
B Quantity of electricity
= I ¡Ñ t
= (0.8 ¡Ñ 1 ¡Ñ 60 ¡Ñ 60)/ 9.65 ¡Ñ 104
= 2.98 ¡Ñ 10¡V2 F
To deposit 1 mol of the metal, quantity of
2.98 ¡Ñ 10¡V2
electricity required = ¡X¡X¡X¡X¡X = 3 F
1.00 ¡Ñ 10¡V2
The metal ion has a charge of +3.
46. A
[Al(H2O)5(OH)]2+ can be hydrolysed to
Al(OH)3 under basic conditions.
47. D
Ag+ ions form precipitates with Cl¡V and I¡V
ions. AgCl dissolves in ammonia to form
[Ag(NH3)2]+ complex ions.
48.
A The reaction is an electrophilic substitution
reaction of the aromatic nucleus.
49.
D Ethanol can be consumed.
K2Cr2O7 oxidises ethanol to ethanoic acid and
is itself reduced to Cr3+ ions.
50.
D Organolithium compounds are more reactive
than Grignard reagents and they can be used
to prepare alcohols. Silicones are also prepared
from chlorosilanes.
PAPER 2
Section A
 1. (a) (i) Hund¡¦s rule
(ii)
3d8
4s2

(iii) 2
(iv) When an electron is transferred from
one subshell to another, the electron
gains energy and is promoted to a
higher subshell. The total energy of
atom X increases (not decrease as in
the question).
(b) (i) 2H2O2 ¡÷ 2H2O + O2
(ii)
energy
2H2O2
E1
E2
£GH2H2O + O2
reaction coordinate
E2 = activation energy without catalyst
E1 = activation energy with catalyst
£GH = enthalpy change
(iii) The solution turns reddish-brown at
the beginning (due to formation of
Br2) then becomes colourless (Br2 is
reduced to Br¡V).
2. (a) (i) Properties of elements are periodic
functions of atomic mass.
(b)
(c)
(ii) Germanium(i) Phosphorus
(ii) P has a stable half-filled p subshell.
(i) Rate = k [C3H6]
(This is a first order reaction because
the unit for the rate constant k is s¡V1.)
ln 2 (ii) t 1 = ¡X¡X
¡X k2
0.693 = ¡X¡X¡X
15.12
= 0.0458 s
(iii) 0.25 mol dm¡V3 (1.0 ¡÷ 0.5 ¡÷ 0.25)
(iv) Both have the same molecular formula.
They are structural isomers.
(v) Propanol (dehydration of propanol
forms propene)
3. (a)
(b)
(i) Soda glass consists of SiO2, Na2O,
CaO.
SiO2 + Na2CO3 ¡÷ Na2SiO3 + CO2
(ii) Main component is B2O3 and SiO2.
Has low expansion coefficient, can
withstand temperature/heat change
without cracking.
(i) R R R
O Si O Si O Si
R R R
where R = alkyl group
(ii) High viscosity liquid / stable towards
heat / chemically inert
16 Actual 2008 STPM Chemistry Examination Paper
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
(iii) When applied to fabric, the O atoms
of silicone form hydrogen bonds with
molecules on the surface of fabrics.
The hydrophobic organic groups act
as barrier on the surface of fabrics
and repel water. Silicone fluid shows
spreading properties due to low surface
tension, forming a film on the fibre that
water cannot wet. The hydrophilic ¡VOH
group is replaced by the hydrophobic
organic group (¡VCH3) that repels water.
Thus, water falling on the fabric roll
off instead of penetrating through and
wetting it.
4. (a)
(i) Benzene diazonium chloride
(ii)
C6H5NH2 + HNO2 + HCl ¡÷
C6H5N2+ Cl¡V + 2H2O
(iii) Phenol
(iv) Coupling reaction
-N=N--O¡V
(b)
(i) H
H2N C COOH
R
The basic unit in polypeptide is amino
acid.
(ii) Long chain of amino acids bonded by
peptide linkages
(iii) Hydrogen bonds are disrupted and
hydrolysis occurs on the ¡VCONHgroup.
(iv) Hydrogen bond between C=O group of
an insulin molecule with N¡VH group of
another insulin molecule.
Section B
5.
(a) VSEPR (valence-shell electron-pair repulsion)
theory states that the geometry of a molecule
is determined by the repulsion among the
electron-pairs associated with a central atom.
The electron-pairs arrange themselves as far
apart as possible to minimise the repulsion.
Repulsion between electron-pairs increases
in the order:
bond pair ¡V bond pair < bond pair ¡V lone
pair < lone pair ¡V lone pair
CH4: Has four bonding electron-pairs and
no lone pair. Hence, tetrahedral shape with
bond angle of 109.5¢X.
H
H
C
H
H
¡ECH3: Has three bonding electron-pairs
and one lone electron. Hence, trigonal
pyramidal shape with smaller bond angle
of < 109.5¢X.

c
H

H
H
(b)
(i) Enthalpy of atomisation is the heat
energy required to convert one mole
of a covalent compound (or species)
into its free gaseous atoms.
£GH
CH4(g) + Cl¡E(g) .¡÷ ¡ECH3(g) + HCl(g)
+1740 kJ +1305 kJ +431kJ
C(g) + 4H(g) + Cl(g)
Enthalpy of reaction,
£GH = +1740 ¡V (+1305) ¡V (+431)
= + 4 kJ mol¡V1
(ii)
energy
CH4(g) + Cl¡E(g)
¡ECH3(g) + HCl(g)
£GH = +4 kJ mol¡V1
reaction coordinate

6.
(a) N2(g) + 3H2(g) . 2NH3(g)
Initial: 1 mol 1 mol 0 mol
At equilibrium: 0.8 mol 0.4 mol 0.4 mol
0.8 0.4 0.4
¡Ý [ ] in 2 dm3 ¡X¡X mol ¡X¡X mol ¡X¡X mol
222
[NH3]2
K = ¡X¡X¡X¡X¡V
c[N2] [H2]3

¡X¡X0.4 2
2
= ¡X¡X¡X¡X¡X¡X
0.8 0.4
¡X¡X¡X¡X3
2 2
= 12.5 mol¡V2 dm6
(b)
Gas X is N2O4.
Gas Y is NO2.
Decomposition of N2O4 to NO2 is an
endothermic process.
N2O4(g)
2NO2(g) ; £GH = +ve
When heated, the equilibrium position shifts
to the right, colourless N2O4 decomposes to
the brown NO2.
When cooled, the equilibrium position shifts
to the left, colourless N2is formed.
O4
(c) N2O4(g)
2NO2(g)
(i)
When pressure is increased, the
mixture turns light brown / pale
yellow as more N2O4 is formed. The
equilibrium position shifts to the left
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
Actual 2008 STPM Chemistry Examination Paper 17
as the reaction to the left is Dissociation of dimer Al2Cl6 occurs between
accompanied by a reduction in the 400 ¡V 800 ¢XC.
number of moles of the gases.
ionic radius
(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¡V
O2¡V
F¡V

Na+
Mg2+
Al3+
7 8 9 10 11 12 13 proton number
(ii) All the ions are isoelectronic (having
the same number of electrons, 10 e¡V),
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¡V, O2¡V, F¡V, 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 ¡Ñ 35.5)
= 133.5
At 200 ¢XC, aluminium chloride exists as
a dimer Al2Cl6 as its rmm is twice that of
AlCl3.
At 800 ¢XC, aluminium chloride exists as
monomer AlCl3 as its rmm is 133.
At 600 ¢XC, both monomer AlCl3 and
dimer Al2Cl6 exist in equilibrium as its rmm
is >133 but < 269.
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¡V(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¡V is a stronger ligand
than H2O. Hence, SCN¡V displaces a
H2O ligand, forming the complex
ion [Fe(H2O)5SCN]2+ which is red in
colour.
]4¡V
(ii) [Fe(CN)6
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¡V ions.
orbitals hybridised to
accept electrons from CN¡V ions

Fe2+
3d
4s
4p
(b)
(i) Yellow solution turns a deep blue
colour.
[CuCl4]2¡V(aq) + 4NH3(aq) ¡÷
yellow solution
[Cu(NH3)4]2+(aq) + 4Cl¡V(aq)
deep blue solution
]2+
[Cu(NH3)4has a higher stability
]2¡V
constant than [CuCl4 which implies
]2+
that the complex ion [Cu(NH3)4 is
more stable. Cl¡V is a weaker ligand
and is displaced by the stronger NH3
ligand.
(ii) The stability constant of [Cu(EDTA)]2¡V
complex, expressed in logarithm, is
higher than 13.2.
[EDTA]4¡V is a stronger ligand than Cl¡V
and NH3 because it is a polydentate /
chelating ligand that is attached to the
metal ion by several bonds.
18 Actual 2008 STPM Chemistry Examination Paper
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
 9. (i)A is an optically active alcohol
H H H OH H
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

C*

C*
H H H
H
HO
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
one end. Under strong oxidation (when
H H H H H
heated with KMnO4), the C=C double
C 1-pentene
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 OHWhen carboxylic acid D is heated with
H H H
ammonia, an amide E is formed.
D butanoic acid
Amide E with LiAlH is reduced to an
amine F.
H C C C C N H(ii)
CH3 C2H5 CH3 H
H H H
C C C C
H H H O H 4
E butanamide

H H H CH
H H H H H 25
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
H H H H H H H H H H H H H H H
ABC
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
H H H H H H H H
CD
H H H O H H H O H
H C C C C OH+ NH3

H C C C C N H+H2O
H H H H H H
DE
c Oxford Fajar Sdn. Bhd. (008974-T) 2008 Actual 2008 STPM Chemistry Examination
Paper 19
 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¡VOOCC6H5 acts as initiator, undergoes photochemical/ther
mal
decomposition to form free radicals
C6H5COO OOCC6H5 ¡÷ 2C6H5COO¡E ¡÷ 2C6H5¡E + 2CO2
CH¡E+ CHCH = CH¡÷ CHCHCH¡E
6532652
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.
C6CHCH2¡E + CH ¡÷ CHCH2CHCH2¡E
H5CH2 C6H5
CH3 CH3 CH3 CH3
CH3
C6H5CHCH2CHCH2¡E + CH CH2 ¡÷ C6H5CHCH2 CH CH2 CH CH2¡E ¡÷ ¡÷ C6H5CHCH2 CH CH2 CH CH2¡E
n
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3
(iii) Termination step:
Two free radicals combine to form a molecule.
CHCHCH¡E + CHCHCH¡E ¡÷ CHCHCHCHCHCH
65265 265 2265
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 fou
r 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 grou
ps on the unsaturated
carbon atom.
20 Actual 2008 STPM Chemistry Examination Paper
c Oxford Fajar Sdn. Bhd. (008974-T) 2008
3 33
C C C C
3 33
C C C C
H H CHCH CHHH C C C C H
Hence the three isomers areH H H H , H H and H CH3
(ii) There are three possible isomers of Z that give only one organic compound w
ith ethanolic KOH.
CH3
CH3
CH3CH2CH2CH2Cl / CH3 CCH3
/ CH3 CH CH2Cl.
Cl
Reaction with ethanolic KOH:
ethanolic
CH3CH2CH2CH2Cl

CH3CH2CH=CH2 + KCl + H2O

KOH
1-butene
CH3

CH3 CH3
ethanolic
CH3 CH CH2Cl
CHCCH
CHC=CH + KCl + HO
3 3KOH 322methylpropene
Cl
The products formed do not have geometrical isomers because they have the same g
roup on the
unsaturated carbon atoms.
c Oxford Fajar Sdn. Bhd. (008974-T) 2008 Actual 2008 STPM Chemistry Examination
Paper 21