2022 Y6 Preliminary Examination

H2 Chemistry 9729 Paper 1

Suggested Solutions

Answer Key [PCl4]+

1 2 3 4 5 6 7 8 9 10 Cl
B A A B D D C B C D  3
P
Cl
Cl
11 12 13 14 15 16 17* 18 19 20* Cl
Bond angle 109.5
D C C B A A A C D B
SF6
21 22 23* 24 25* 26* 27 28 29 30
D C D B A A C B C D  4

Bond angle 90

1 B
Given:
4 B
angle of deflection  q H CH3
m
+1
+15○ = k( )  A
1
k = +15 H CH3
This hydrocarbon is a non-polar molecule
CH3
–5○ = +15( q )
m O
q = –1 CH3
3
m The C=O bond has a relatively large dipole
q=0  B moment (due to the large difference in the
m = 1+2 = 3 electronegativities of carbon and oxygen) and
 A 1
 q ≠– there are no other significantly polar bonds to
3
m offset the dipole moment of the C=O bond
q = +3−5 = −2 Thus, the molecule has the largest overall
m = 3+3 = 6 dipole moment among the four options.
 B 1
 q =–
3
m H3C Cl
q = +4−1 = +3
m = 4+5 = 9  C
 C 1 Cl CH3
 q ≠–
3
m C-Cl bond is polar but the dipole moments
q = +4−3 = +1 cancel out.
m = 4+5 = 9 Cl
 D 1
 q ≠–
3 O
m
Cl
 D C=O bond is more polar than C–Cl bond as O
2 A
is more electronegative than Cl but since both
Interpretation of the graph: C is likely to be in Group
1 since it has the lowest 1st IE. Since the four bonds are polar, there will be some degree of
elements are consecutive, B is in Group 18 and A is offset of dipole moments of the bonds, hence
in Group 17. this molecule does not have the largest overall
dipole moment among the four options.

3 A
O3 5 D
Both CO2 and Cl2 are non-polar molecules with
O weaker instantaneous dipole-induced dipole
 1
O O interactions (id-id) as compared to CH3OH and N2H4,
Bond angle <120 which have stronger intermolecular hydrogen
bonding. N2H4 has more extensive hydrogen bonds
PF5 (an average of 2 H-bonds per molecule) than CH3OH
(an average of 1 H-bond per molecule), hence N2H4
exhibit greatest deviation from ideal gas behaviour.
 2
Bond angles 90, 120

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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

8 B
Per H N N H Volatility is defined as the tendency of a substance to
molecule
H
CH
3C3 O H
H H vapourise. Since the halogens exist as non-polar
Total no. of simple covalent molecules, the volatility of the
H atoms halogens depends on the strength of the
bonded to 1 4 instantaneous dipole-induced dipole (id-id)
O/N interactions between molecules.
atom(s) Both bond length and bond strength are about
1 the covalent bond between the atoms in the
No. of lone 
pairs on halogen molecule. Thus, these factors do not
2 2 2 affect volatility.
O/N
atom(s) Each halogen molecule is comprised of two
Average identical elements from Group 17. Since the
no. of H elements present in each molecule is identical,
1 2  3 the resultant halogen molecule is non-polar.
bonds
possible Hence the electronegativity of the halogen
atom has no effect on the strength of the id-id
interactions.
6 D Strength of id-id interactions increases when
number of electrons in the molecule increases
Possible identities of X:  4
due to greater ease of distortion of the larger
P4O10(s) + 6H2O(l) → 4H3PO4(aq)
electron cloud. Hence, this statement is correct.
SO3(g) + H2O(l) → H2SO4(aq) 

Possible identities of Y:
Al2O3 is insoluble in water but is amphoteric, however 9 C
one mole of Al2O3 requires 6 moles of H+ for H2SO4 + 2NaOH → Na2SO4 + 2H2O
neutralisation, 30
Al2O3(s) + 6H+(aq) → 2Al3+(aq) + 3H2O(l) n(H2SO4) = × 0.1 = 0.003 mol
1000
hence, options A and B are incorrect as they do not
match the required mole ratio stated in the question 40
n(NaOH) = × 0.2 = 0.008 mol
with both given options for X. 1000

H2SO4 is the limiting reagent.

Na2O(s) + H2O(l) → 2NaOH(aq) 
Since, one mol of H2SO4 is completely neutralised by
n(H2O) = 2 × n(H2SO4)
two mol of NaOH, oxide X is SO3 and oxide Y is
= 2 × 0.003
Na2O.
= 0.006 mol

Heat released from the reaction = n(H2O) × |∆Hneu|

7 C = 0.006 × 57.3 × 1000
Polarisability pertains to ease of distortion of = 343.8 J
the anion’s electron cloud and since the anion = heat absorbed by the solution
 A
is the same, i.e. CO32−, in both compounds, the
polarisability factor is the same in both. heat absorbed by the solution = mc|∆T|
Melting is not the same as thermal 343.8 = 70 × 1 × 4.2 × |∆T|
decomposition/ thermal stability. Melting point |∆T| = 1.2 °C
 B
involves change in states, not chemical
composition. Since heat is absorbed by the solution,
Since ionic radius of Ca2+ is smaller than that of ∆T = +1.2 °C.
Ba2+, the charge density of Ca2+ is higher.

q+ 10 D
charge density 
r+ H S G
− when temperature is
 A + + high enough such that
 C Ca2+ has a greater polarising power and distorts
|TS| > |H|
the electron cloud of CO32− anion to a greater
− at all temperatures not
extent. The C–O covalent bond within the CO32−  B − +
just at low T
anions in CaCO3 is weakened to a greater
extent as compared to that in BaCO3. − when temperature is
 C + + high enough such that
Hence CaCO3 decomposes at a lower |TS| > |H|
temperature.  D − + − at all temperatures
Lattice energy is a measure of the ionic bond
 D strength in metal carbonates and is not a
measure of their thermal stability.

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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

11 D Does not fulfil both criteria:

From the Data Booklet, • Only two NO molecules involved in the
E / V  A slow step, missing one H2 molecule.
H2O2 + 2H+ + 2e− ⇌ H2O +1.77 • Final products are N2O and H2O, not N2
O2 + 2H+ + 2e− ⇌ H2O2 +0.68 and H2O.
Does not fulfil criterion (1):
Ecell = +1.77 – (+0.68) • Only one NO molecule and one H2
= +1.09 V > 0  B
molecule involved in slow step, missing
 1 one NO molecule.
Overall equation:  C Fulfils both criteria.
2H2O2 → 2H2O + O2 Does not fulfil (2):
 D • Products of the reaction are N2 and H2O2,
H2O2 undergoes disproportionation where the not N2 and H2O.
oxidation state of O increases from −1 in H2O2
to 0 in O2 and decreases from −1 in H2O2 to −2
in H2O. 13 C
Both MnO4− and Fe3+ are oxidising agents and Let the orders of reaction with respect to K, L and M
will not react. be x, y and z respectively.
From the Data Booklet, both species are on rate = k[K]x[L]y[M]z
the left-hand side of the equation and show
 2
tendency to undergo reduction. Comparing experiments 1 and 2, keeping [L] and [M]
constant, when [K] is decreased by a factor of 2.5,
E / V relative rate decreases by a factor of 2.5. Hence,
MnO4− + 8H+ + 5e− ⇌ Mn2+ + 4H2O +1.52 reaction is 1st order with respect to K i.e. x = 1.
Fe3+ + e− ⇌ Fe2+ +0.77
From the Data Booklet, Comparing experiments 2 and 3, keeping [L]
E / V constant, when [K] is increased by a factor of 5 while
I2 + 2e− ⇌ 2I− +0.54 [M] is halved, relative rate increased by a net factor
S4O62−+ 2e− ⇌ S2O32− +0.09 of 1.25. Since the reaction is first order with respect
to K, relative rate should have increased by a factor
Ecell = +0.54 – (+0.09) of 5. Hence, halving [M] have resulted the relative
 3 = +0.45 V > 0 rate to decrease by a factor of 4 (i.e. 5 ÷ 1.25 = 4).
Reaction is second order with respect to M, i.e. z = 2.
Overall equation:
I2 + S2O32− → 2I− + S4O62− Mathematically,
rate2 k K expt2 L expt2 Mexpt2
x y z

I2 oxidises S2O32− to give S4O62− while S2O32− =

rate3 k K x L y Mz
reduces I2 to give I−. expt3 expt3 expt3

0.20 k ( 0.0010 ) ( 0.08 ) ( 0.80 )

1 y z
Let the oxidation state of C in HC2O4− be x.
=
(+1) + 2x + 4(−2) = −1 0.25 k ( 0.0050 )1 ( 0.08 ) y ( 0.40 )z
⇒ x = +3
z
4 1  0.8 
=
Note: The oxidation state of both C atoms in 5 5  0.4 
HC2O4− can be determined by the calculation
4 = ( 2)
z
above since they are bonded to O atoms in the
same way. The oxidation state of each atom is z=2
 4 indicated below.
2 Comparing experiments 3 and 4, keeping [K]
O constant, when [L] is halved while [M] is doubled,
2 relative rate increased by a net factor of 2. Since
+1 O +3 C reaction is second order with respect to M, rate
-
H C +3 O should have increased by a factor of 4. Hence,
2 halving [L] have resulted the relative rate to decrease
O by a factor of 2 (i.e. 4 ÷ 2 = 2). Reaction is first order
2 with respect to L, i.e. y = 1.

12 C
The proposed reaction mechanism must fulfill two
criteria:

1. Given that rate = k[NO]2[H2], the slow step

should involve two NO molecules and one H2
molecule.
2. The overall equation should contain the products
N2 and H2O only, as given in the question.

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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

Mathematically,
rate3 k K expt3 L expt3 Mexpt3
x y z 16 A
= In order for end-point to be determined, the transition
rate 4 k K x L y Mz range of the indicator should fall within the region of
expt4 expt4 expt4
sharp pH change.
0.25 k ( 0.0050 ) ( 0.08 ) ( 0.40 )
1 y 2

=
0.50 k ( 0.0050 )1 ( 0.04 ) y ( 0.80 )2 For the first end-point, the sharp pH change occurs
y 2
between 5.33 and 9.73. Hence, a suitable indicator
1  0.08   0.40  would be bromothymol blue. Thymolphthalein will not
=
2  0.04   0.80  be suitable as its colour would have changed before
the first equivalence point is reached.
1 y  1
= ( 2)  
2 4 For the second end-point, the ethyl orange would be
2 = ( 2) a suitable indicator as its pH range is below 5.33.
1 y

Methyl red will not be suitable since its colour would

y =1 have changed before the second equivalence point
is reached.
∴ rate = k[K][L][M]2

17 A
14 B The colours of the silver halides and their solubilities
[NO]2 [O2 ] in concentrated aqueous ammonia are shown below.
Kc =
[NO]2
solubility in
AgX colour
concentrated NH3
2NO2(g) ⇌ 2NO(g) + O2(g)
AgCl white soluble
Initial n /
2.50 0 0 AgBr cream soluble
mol
AgI yellow insoluble
Change
−1.056 +1.056 +0.528
in n / mol
Hence, beaker 1 should be colourless. Yellow
Eqm n /
1.444 1.056 0.528 precipitates should be observed for beakers 2 and 3.
mol

2
 1.056   0.528  18 C
 0.8   0.8 
Kc =   
2
 Half (or fish-hook) arrows should be used to
 1.444   A represent homolytic fission and the movement
 0.8  of the lone electron in the chlorine radical.
 
A full arrow should be used to represent the
= 0.35296 bond formation between OH− and electrophilic
= 0.353 mol dm −3 carbon atom. Similarly, the heterolytic fission of
 B
C–Br bond should be represented by a full
arrow to indicate the transfer of an electron pair
15 A to Br.
Electron movement is represented correctly
 C
2SO2(g) + O2(g) ⇌ 2SO3(g) using half arrows.
[SO3 ]2 Electron move from regions of high electron
Kc = density to low electron density. The full arrow
[SO2 ]2 [O2 ]
should point from the lone pair of electrons on
OH− to the electrophilic carbon.
 1 If the stoichiometric coefficients are halved,
1
SO2(g) + O2(g) ⇌ SO3(g)  D
2 The transfer of electrons to electrophilic C from
heterolytic fission of C–Br bond is incorrect as
[SO3 ] 1 1 a bromide ion, Br−, is formed. This is indicative
Kc ' = = Kc 2 ≠ K
1 2 c that the electron pair of the C–Br bond was
[SO2 ][O2 ]2 transferred to Br.
At dynamic equilibrium, the rates of the forward
 2
and backward reactions are equal but not zero. 19 D
By Le Chatelier’s Principle, when pressure
A racemic mixture contains equal proportions of
increases, the position of equilibrium shifts to
each enantiomer. They cancel out each other’s
 3 the right to produce less moles of gas, favouring  A rotation of plane-polarised light and hence
the forward reaction. Hence, more moles of there is no overall effect. It is therefore optically
SO3 will be produced.
inactive.
By Le Chatelier’s Principle, when temperature
Enantiomers have identical physical properties
is reduced, position of equilibrium shifts to the except that in the way they rotate plane-
right to favour the forward exothermic reaction  B
polarised light. Hence, they have the same
 4 to produce heat. Rates of the forward and
melting points.
backward reaction will decrease but the rate of
Enantiomers have different biological
the forward reaction is decreased to a smaller  C
behaviour in the human body.
extent.
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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

Enantiomers have identical physical properties 21 D

except that they rotate plane polarised light in
 D slow -
opposite directions. Hence, they have the same Br Br Br + Br
solubility in the same solvent.
H
+
H O
20 B Br H2O Br
The hydrogen atoms can be classified based on the
carbon atom i.e. whether it is primary, secondary or H2O H
+
tertiary. H O OH
+
H Br Br + H3O

(secondary) H H
Two molecules are involved in the slow step.
H H (primary)  1
Overall order of reaction is 2.
H H See step 2. Water is a nucleophile as it donates
H
H  2 its lone pair of electrons on O to the positively
charged C atom of the carbocation.
(primary) H See step 1. The intermediate formed is a
 3
trigonal planar carbocation.
H H H H
See step 1 which forms the more stable
(secondary) (tertiary) secondary carbocation as compared to the
primary carbocation shown below:
There are two distinct groups of secondary Br
hydrogen atoms as the secondary carbon  4
atoms are bonded to different groups. The
monosubstituted chloroalkanes formed by free Also, water is in excess as compared to the Br–
radical substitution are isomers. formed in step 1. As such, water participates in
step 2 to generate the major product, not Br–.

 1 22 C
Cl A Lewis acid catalyst is required to generate a
3-chloro-2-methylpentane stronger electrophile. For example,

Cl FeBr3 + Br2 → FeBr4– + Br+

The electrophile Br+ reacts with the nucleophilic

aromatic ring to form 5 atoms with sp2 hybridisation
2-chloro-4-methylpentane (with five p orbitals overlapping) and 1 atom with sp3
hybridisation (which contains 4  bonds including the
Since there exists only one tertiary hydrogen
newly formed  bond with the Br). Hence, the “U-
 2 atom, the relative proportion of tertiary shape” should have its opening pointing to the sp3
monochloroalkane will be the smallest. hybridised atom.
There are three isomeric primary
monochloroalkane products. Their structures
are shown below. 23 D
OH F

F OH
Cl
1-chloro-4-methylpentane
 3
Compound X Compound Y
Add Br2 in CCl4
Cl Compound X: No decolourisation of Br2
*  A
Compound Y: Decolourisation of orange–red
Br2 (due to presence of phenol)
1-chloro-2-methylpentane
Add neutral FeCl3(aq)
(Molecule is chiral and exists as a pair of Compound X: No violet complex formed
enantiomers.)  B
Compound Y: Violet complex formed
H• radicals are not formed during free radical (due to presence of phenol)
 4 substitution. Only Cl• and alkyl radicals are Warm with K2Cr2O7(aq) and H2SO4(aq)
formed in the propagation step. Compound X: orange solution turns green
(due to oxidation of primary alcohol)
 C
Compound Y: orange solution remains
(phenols and alkyl side chains do not undergo
oxidation with K2Cr2O7)

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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

Warm with KOH(aq), then add excess Note: the ester functional group will react with
HNO3(aq), followed by AgNO3(aq) NaOH(aq) via alkaline hydrolysis if heating is
C–F bonds are considered inert (due to their involved.
 D
high bond strength) and hence the F atoms in Only the 2 phenolic groups and the 3 alcohol
both compounds do not get substituted by the groups will undergo condensation with ethanoyl
 D
OH– ions in KOH. chloride. Hence, 1 mol of chlorogenic acid only
reacts with 5 mol of ethanoyl chloride.

24 B
No reddish–brown ppt with Fehling’s solution:
No aliphatic aldehyde
Pale yellow ppt with hot alkaline aq. I2:
O OH
contains or H3C C
C O
H3C
H Cl
The C=O belongs to the ester functional group
and will not give a positive iodoform test. In the
presence of hot alkali, the hydrolysis of the
 A
ester can occur. This forms a carboxylate ion
and an alcohol. Both do not give a positive
iodoform test too.
Structure does not contain an aliphatic
aldehyde. The secondary alcohol has the
 B
appropriate structure which will give a positive
iodoform test.
Aliphatic aldehyde is present. A reddish–brown
 C
ppt will be formed with Fehling’s solution.
Benzaldehyde. Gives no reddish–brown ppt
 D with Fehling’s solution but will also not give a
positive iodoform test.
26 A
The diagrams below show the isolated part of starting
reagent that needs to react for the synthesis of
chlorogenic acid to happen. For the synthesis to be
feasible, the other parts of the molecule need to
remain unreacted.
OH HO
OH
Two steps are required: nucleophilic
substitution of the Cl atom, and oxidation of the
primary alcohol to the carboxylic acid.
 1
These two steps are problematic as both
involve heating with a base or an acid. This will
result in the hydrolysis of the ester group as
well. In addition, the oxidation process will also
oxidise the secondary alcohol groups on the
six-membered carbon ring.
O
O HO
OH

Two steps are required: nucleophilic addition

25 A (adding HCN to the ketone), and acid
 2
carboxylic acid hydrolysis to convert the nitrile to the carboxylic
acid.
O
tertiary
alcohol HO Step 2 is problematic as it involves heating with
OH
ester an acid, resulting in the hydrolysis of the ester
O as well.

HO O HO
O
phenol
OH O OH
OH
secondary One step required: reduction of ketones to
alcohol OH
secondary alcohols
chlorogenic acid  3
The use of LiAlH4 is problematic as it will result
Heating in the presence of a dilute acid will in the reduction of the carboxylic acid (and the
result in acid hydrolysis of the ester to give two ester). However, we can use NaBH4 in this
organic products. synthesis. It will allow for the selective reduction
 A of the ketones only, as it is not strong enough
Note: in addition to acid hydrolysis, there will be to reduce the carboxylic acid (and the ester).
oxidation of the secondary alcohol groups on
the organic product with the cyclohexane ring.
Only 1 mol of carboxylic acid functional group 27 C
is present, per mol of chlorogenic acid. Only The amine containing N1 is a tertiary amine. It
0.5 mol of CO2 is produced.  A cannot undergo condensation with ethanoyl
 B chloride.
RCOOH + ½Na2CO3 → RCOO–Na+ + ½CO2 + N2 belongs to an amide functional group.
½H2O  B Amides are neutral due to the unavailability of
Only the 2 phenolic groups and the carboxylic the lone pair of electrons for donation.
acid will undergo neutralisation with NaOH. The Heating with aq. H2SO4 involves two reactions:
alcohols remain unreacted. Hence, 1 mol of acid hydrolysis of the amide group and
 C  C
chlorogenic acid only reacts with 3 mol of 6eutralization of any basic groups
NaOH(aq) at room temperature. Both products are cationic:

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Dunman High School 2022 Y6 Preliminary Examination – H2 Chemistry 9729/01 Solutions

o
O Since ECu2+ /Cu is the most positive, Cu2+ will be
 1
COOH preferentially reduced at the cathode.
OH o
H
+
Since EZn2+ /Zn is the most negative, Zn will be
R + H
N  2 preferentially oxidised at the anode, followed by
N
H Cu.
H and COOH The cell voltage must be adjusted such that Ag
Both carboxylic acid groups and the amide does not get oxidised i.e. only copper and
 3 o
group will be reduced by LiAlH4. There will be a metals with less positive Eo than ECu2+ /Cu are
loss of 3 oxygen atoms from methotrexate. preferentially oxidised.
O COOH

30 D
N + 12[H]
Electronic configuration of Fe3+: [Ar]3d5
R H
N COOH
 A
 D Arrangement of electrons in 3d orbitals:

Electronic configuration of Cu2+: [Ar]3d9

OH
 B
Arrangement of electrons in 3d orbitals:
N
+ 3H2O
R H OH
N Electronic configuration of Cr3+: [Ar]3d3
 C
Arrangement of electrons in 3d orbitals:

28 B
Before the addition of NaCN(s) Electronic configuration of Ni2+: [Ar]3d8
o
EAg+ /Ag = +0.80 V  D
o Arrangement of electrons in 3d orbitals:
EFe3+ /Fe2+ = +0.77 V

o o
Since EAg+ /Ag is more positive than EFe3+ /Fe2+ ,
reduction happens in half–cell 1 and oxidation
happens in half–cell 2.

Eocell = +0.80 – (+0.77) = +0.03 V

Electrons flow from half–cell 2 to half–cell 1. The

cathode increases in mass as Ag+(aq) is reduced to
Ag(s) and is deposited onto the cathode.

After the addition of excess NaCN(s)

o
EAg+ /Ag = +0.80 V
o
EFe(CN) 3-
/Fe(CN)6 4-
= +0.36 V
6

o o
Since EAg+ /Ag is more positive than EFe(CN) 3-
/Fe(CN)6 4-
,
6
reduction still happens in half–cell 1 and oxidation still
happens in half–cell 2 (i.e. no change in polarity of
electrodes).

Eocell = +0.80 – (+0.36) = +0.44 V

(cell potential becomes more positive)

Electrons still flows from half–cell 2 to half–cell 1. The

cathode continues to increase in mass as Ag+(aq) is
reduced to Ag(s) and is deposited onto the cathode.

29 C
At the anode: At the cathode:
o o
EZn2+ /Zn = –0.76 V ECu2+ /Cu = +0.34 V
o o
ECu2+ /Cu = +0.34 V EZn2+ /Zn = –0.76 V
o
EAg+ /Ag = +0.80 V EoH2 O/H2 = –0.83 V

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