Ans Key

1 C 2 D 3 C 4 A 5 B 6 B 7 B 8 A 9 C 10 A
11 D 12 C 13 C 14 C 15 A 16 D 17 C 18 C 19 B 20 D
21 A 22 C/D 23 A 24 C 25 B 26 B 27 A 28 D 29 B 30 D

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

What are the numbers of electrons and neutrons in the hydroxide (16O1H−) ion?

electrons neutrons
A 9 8
B 9 9
C 10 8
D 10 9

16
O has 8 neutrons and 8 electrons and 1H has 0 neutrons and 1 electron.
OH− has one extra electron due to the negative charge.
Thus, OH− will have (8+0)=8 neutrons and (8+1+1)=10 electrons.
Ans: C

2 The following graph shows the second ionisation energy of eight consecutive elements in
Period 2 and 3.

2nd IE

C
D

Atomic number

Which of the options A, B, C or D is silicon?

B+ has electronic configuration of noble gas since the subsequent species have the largest drop
in I.E. As such, B+ will have electronic config of 1s22s22p6. As such, B has electronic
configuration of 1s22s22p63s1, i.e. B is Na.
Thus, silicon will be D.

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3 The table identifies the shape and polarity of four molecules.

Which rows are correct?

molecule molecular shape polarity

1 NO2 bent polar
2 SO3 trigonal planar non-polar
3 CHI3 tetrahedral non-polar

A 1 only B 2 only C 1 and 2 only D 1, 2 and 3

✓1:NO2 has two bond pair and 1 lone electron, so the shape is bent and since dipole moment of
N-O bond cannot cancel each other, the molecule is polar.

✓2: SO3 has 3 bond pair and 0 lone pair, the shape is trigonal planar. The dipole moments of 3
S=O cancel each other, thus, the molecule is non-polar.

3: CHI3 has 4 bond pair and 0 lone pair, the shape is tetrahedral. The dipole moment of C-H
bonds cannot be cancelled by the resulting dipole of the other 3 C-I bonds, thus, the molecule
is polar.
Ans: C

4 Equimolar amounts of the liquids trichloromethane, CHCl3, and propanone, CH3COCH3, are
mixed together at 20 oC. The original intermolecular forces are disrupted and stronger
intermolecular forces (between CHCl3 and CH3COCH3) are made simultaneously.
The boiling point of trichloromethane is 61 oC. The boiling point of propanone is 56 oC.
Which row is correct?

initial temperature of mixture boiling point of mixture

A above 20 oC above 61 oC
B below 20 oC above 61 oC
C above 20 oC below 56 oC
D below 20 oC below 56 oC

Qn has mentioned that intermolecular forces formed between CHCl3 and CH3CO

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 4
5 A 25.0 cm3 sample of 0.20 mol dm−3 TlNO3 required 25.0 cm3 of 0.10 mol dm−3 acidified KMnO4
to oxidise it to Tl3+ in solution.

What is the oxidation state of the manganese in the reduced form?

A 2 B 3 C 4 D 7

Tl+ ⟶ Tl3+ + 2e-

Amt of Tl- = 0.20 x 25.0/1000 = 5.00 x 10-3 mol

Amt of electron lost = 5.00 x 10-3 x 2 = 1.00 x 10-2 mol

Amt of MnO4- = 0.10 x 25.0/1000 = 2.50 x 10-3 mol

Thus, MnO4- : e- = 2.50 x 10-3 : 1.00 x 10-2 = 1 : 4

Thus, the oxidation state of Mn = (+7) + 4(-1) = +3

Ans: B

6 A methane gas burner was incorrectly adjusted. When used, the methane reacted with
oxygen to form a mixture of carbon dioxide and carbon monoxide in a mole ratio of 9 : 1,
together with water vapour.

Which volume of oxygen was needed to burn 1 dm3 of methane in this burner?

A 0.95 dm3 B 1.95 dm3 C 3.90 dm3 D 19.5 dm3

Since the CO2 : CO = 9 : 1, the balanced equation for combustion of methane will be:
10CH4 + 19.5O2 ⟶ 9CO2 + 1CO + 20H2O

CH4 : O2 = 1 : 1.95.

Since volume ratio = mole ratio for gases, 1dm3 of CH4 will required 1.95dm3 O2 gas for this
burner.
Ans: B

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7 At 298 K, bulb G contains 2 dm3 of argon gas at 2 kPa and bulb H contains 1 dm3 of neon
gas at 1 kPa.
Bulb G and H are connected by a 5 dm3 evacuated chamber, as shown below. The volume
of the connecting tubes can be assumed to be negligible.

evacuated
Ar chamber Ne

bulb G bulb H

The gases are mixed when the two taps are opened at constant temperature.

What is the final pressure of the system, in kPa?

3 5 5
A B C 1 D
8 8 3

Since the system is kept at constant temperature, p1V1 = p2V2

𝟒
For gas Ar, after opening the taps, pAr (2 + 1 + 5) = (2 kPa) (2 dm3) ⇒ pAr = 𝟖 kPa

𝟐
For as Ne, after opening the taps, pNe (2 + 1 + 5) = (1 kPa)(1 dm3) ⇒ pNe = 𝟖 kPa

𝟒 𝟐 𝟓
Final pressure of the system = + = kPa
𝟖 𝟖 𝟖
Ans: B

8 Which standard enthalpy change is represented by the correct equation?

A C(s) + O2(g) ⟶ CO2(g) ∆Hof (CO2 )

B Br2(l) ⟶ 2Br(g) BE(Br−Br)
C Ba(g) ⟶ Ba2+(g) + 2e− ∆Ho2nd IE (Ba)
D 2CO(g) + O2(g) ⟶ 2CO2(g) ∆Hocombustion (CO)

✓A: it is the correct equation

B: Bond energy is defined as breaking of gaseous covalent bond, state symbol for Br2 should
be (g) instead.

C: this is the sum of 1st and 2nd IE of Ba

D: this is two times of ∆Hocombustion (CO) since two moles of CO in the equation.
Ans: A

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 6
9 30 cm3 of 0.1 mol dm−3 sulfuric acid and 40 cm3 of 0.2 mol dm−3 sodium hydroxide were mixed
in a styrofoam cup.
Assume that the density and specific heat capacity of the final mixture are 1.0 g cm −3 and
4.2 J g−1 K−1 respectively.
Assume no heat loss to the surrounding, what is the temperature change of the solution given
that the standard enthalpy change of neutralisation is −57.3 kJ mol−1?

A −1.6 C B −1.2 C C +1.2 C D +1.6 C

½H2SO4 + NaOH ⟶ ½Na2SO4 + H2O

Amt of H2SO4 = 0.1 x 30/1000 = 3.00 x 10-3 mol

Amt of NaOH = 0.2 x 40/1000 = 8.00 x 10-3 mol

Since H2SO4 : NaOH = 1 : 2, H2SO4 is the limiting agent here.

∴ amt of H2O produced = 3.00 x 10-3 x 2 = 6.00 x 10-3 mol.

Heat released, q = -57.3 x 1000 / 6.00 x 10-3 = 343.8 J

q = mcT ⇒ 343.8 – ((30+40) x 1.0)(4.2)( T) ⇒ T = 1.2

Since the reaction is exothermic, the temperature of surrounding will increase.

Ans: C

10 Dinitrogen pentoxide, N2O5, decomposes when heated according to the following equation:

1
N2O5 ( g) ⎯⎯
→ 2NO2 ( g) + O2 ( g )
2

This reaction is first order with respect to N2O5 with a half-life of 25 min.

In one experiment, N2O5 at an initial pressure of 100 kPa was allowed to decompose at 400 K.
The partial pressure of O2 was measured at various times with the temperature kept constant.
What is the time taken for the partial pressure of O2 to reach 25 kPa?

A 25 min B 50 min C 75 min D 100 min

Mole ratio of N2O5 : O2 = 2 : 1.

Since p ∝ n, the max partial pressure of O2 produced will be 100/2 = 50 kPa. To produce 25 kPa
of O2, it will require one half time. Thus, the time taken needed will be just t½, i.e. 25 mins.
Ans: A

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11 In aqueous solution, an equilibrium is established between yellow CrO42− and orange Cr2O72− .

2CrO42−(aq) + 2H+(aq) ⇌ Cr2O72−(aq) + H2O(l)

Which statement regarding the ions and the equilibrium is correct?

A It is a redox reaction.

B Adding more water to the mixture turns the solution orange.

[Cr2O7 2 − ][H2O]
C The Kc expression for the equilibrium is Kc = .
[CrO 4 2− ]2 [H+ ]2

D Increasing the pH turns the solution yellow.

A: the oxidation state of Cr in CrO42- and Cr2O72- are both 6. Thus, there is no change in
oxidation state, thus, it is not a redox reaction.

B: add more water will shift the POE to the left. Since the left hand side of the equation has
greater number of concentration terms, add more water will dilute the concentration to the
greater extend, result in the leftward shift of POE. Thus, solution will turn yellow.

C: H2O is the solvent in this equation, and the concentration of water is kept constant in
aqueous medium, thus, H2O will not be included in the Kc expression.

✓D: increase pH value indicating the solution will become more basic with more OH-. The OH-
will remove H+ from the equation, based on LCP, the POE will shift to the left to replenish some
of the H+ reacted, thus, solution will turn yellow.
Ans: D

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12 The graph shows how ΔGꝊ changes with temperature for the reaction shown.

H2O(g) + CO(g) ⇌ H2(g) + CO2(g)

50

40

30
4 3 2 1
20
GꝊ / kJ mol−1
10

-10

-20

-30
200 300 400 500 600 700 800 900 1000 1100 1200 1300
T/K

Equimolar amounts of H2O and CO were introduced into a sealed container and allowed to
reach equilibrium.

At which points will the concentration of H2 be greater than the concentration of H2O at
equilibrium?

A 1 only B 1 and 2 only C 3 and 4 only D 2 , 3 and 4

H2O(g) + CO(g) ⇌ H2(g) + CO2(g)

initial a a 0 0
change −c −c +c +c
final a−c a−c c c

c×c
Kc =
(a - c) ×(a - c)

When [H+] > [H2O] at equilibrium, c > (a – c) ⇒ Kc > 1 at equilibrium

When Kc > 1 ⇒ G < 0, implies point 3 and 4.

Ans: C

© Jurong Pioneer Junior College 9729/01/J2 MID YEAR EXAM/2023

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13 The variation of the ionic product of water, Kw, with temperature is given in the table.

Temperature / oC Kw / mol2 dm−6

25 1.00 x 10−14
50 5.50 x 10−14
62 1.00 x 10−13

What can be deduced from this information?

A The ionisation of water is an exothermic process.

B [H+] is more than [OH−] as temperature increases.
C pH of water at 25 oC is higher than at 62 oC.
D The equilibrium position lies furthest to the right at 25 oC.

A: ionisation of water is a bond breaking process, which is endothermic

B: as temperature increases, Kw value increases. However, the [H+] = [OH-].

✓C: at 25oC, [H+] = 7.00 x 10-7 ⇒ pH = 7. At 62oC, [H+] = 3.16 x 10-7 ⇒ pH = 6.5. Thus, pH of water at
25oC is higher than that at 62oC.

D: at 25oC, Kw is the smallest which implies the [H+] and [OH-] is the smallest at 25oC. Thus,
the POE lies furthest to the left.
Ans: C

14 What is the pH value of the final solution when V cm3 of dilute nitric acid of pH 2.0 is mixed
with V cm3 of dilute nitric acid of pH 4.0 followed by the addition of 2V cm3 of water?

A 1.5 B 2.3 C 2.6 D 3.0

[H+] of HNO3 of pH 2.0 = 10−2 = 0.01 moldm−3 ∴amt of H+HNO3 of pH 2.0 = 0.01V mol

[H+] of HNO3 of pH 4.0 = 10−4 = 0.0001 moldm−3 ∴amt of H+HNO3 of pH 4.0 = 0.0001V mol

Amt of H+total = 0.01V + 0.0001V = 0.0101V mol

Total volume of final solution = V + V + 2V = 4V dm−3

∴ [H+]final solution = 0.0101V / 4V = 0.002525 moldm−3

∴ pH = -lg [H+] = -lg (0.002525) = 2.60
Ans: C

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 10
15 Which solution will solid silver phosphate, Ag3PO4, be the least soluble in, at 25 oC?
(The numerical value of Ksp(Ag3PO4) is 8.89 x 10−17)

A 2.0 mol dm−3 AgNO3(aq)

B 2.0 mol dm−3 K3PO4(aq)
C 2.0 mol dm−3 NH3(aq)
D pure water

✓A: presence of common ion, Ag+, will shift POE to the left, decrease the solubility
Let s be the solubility of Ag3PO4(s) in the solution
Ag3PO4(s) ⇌ 3Ag+(aq) + PO43−(aq)
Initial - 2.0 0
Change - s s
equilibrium - 2.0 + s ≈ 2.0 s

Ksp = (2.0)3(s) = 8.89 x 10−17 ∴ s = 1.11 x 10−17

B: presence of common ion, PO43-, will shift POE to the left, decrease the solubility
Ag3PO4(s) ⇌ 3Ag+(aq) + PO43−(aq)
Initial - 0 2.0
Change - s s
equilibrium - s 2.0 + s ≈ 2.0

Ksp = (2.0)(s)3 = 8.89 x 10−17 ∴ s = 6.67 x 10−9

C: NH3 will form complex with Ag+ ion, which will decrease [Ag+]. POE will shift right to dissolve
more Ag3PO4(s), thus, increase solubility.

D: pure water will neither increase nor decrease the solubility of Ag3PO4
Ans: A

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16 The structure of 1,3,5-Triazine resembles that of benzene.

1,3,5-Triazine

Which statement about 1,3,5-triazine is correct?

A Its empirical formula is CN.

B A molecule of 1,3,5-triazine has six  bonds.
C The six C–N  bonds are formed by 2sp2–2sp2 overlap.
D All the carbon-nitrogen bonds are of the same length.

A: there is one H attach to each C in the molecule, so the empirical formula is CHN.

B: there are a total of 6 C-N  bonds, however, there are 3 more C-H  bonds.

C:  bond is always formed by side-way overlap of unhybridised p orbitals. 2sp2-2sp2 overlap
results in the C-N  bonds.

✓D: there is delocalisation of electrons across the 3 C and 3 N atoms, resulting in the equal
bond length of the C-N bonds, similar to benzene.
Ans: D

17 Allyl alcohol, CH2=CHCH2OH, can be converted into propanal, CH3CH2CHO by using a catalyst
containing a ruthenium complex.

Which type of reaction is the overall process?

A addition B oxidation C isomerisation D Reduction

CH2=CHCH2OH ⟶ CH3CH2CHO

Both compounds have the same molecular formula of C3H6O, thus, they are isomers to each
other.

Addition, oxidation and reduction will always result in the change of molecular formulae of
compounds. Thus, the overall process will be isomerisation.
Ans: C

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 12
18 Androstenolone is a steroid secreted by the adrenal cortex.

Androstenolone, Mr = 288

When it is treated with cold KMnO4, it gives a compound Z, the Mr of Z is 322.

How many chiral centres does Z have?

A 6 B 7 C 8 D 9

*
* *
*
*
* *
*

The -OH group highlighted in red will not be oxidised due to the Mr of Z given.
∴ there are a total of 8 chiral centres as marked in the diagram
Ans: C

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19 Pulegone is an oily liquid with a pleasant odour similar to peppermint.

pulegone

Which product is formed from an electrophilic addition reaction with pulegone?

A B

C D

A: it is formed through reduction with H2, Ni catalyst and heat.

✓B: it is formed through electrophilic addition of dry HBr(g).

C: it is formed through mild oxidation with cold alkaline KMnO4(aq).

D:
Ans: B

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 14
20 Methylbenzene can undergo the following reaction.

Which statement about the mechanism of this reaction is correct?

A The hybridisation states of the carbon atoms in benzene do not change during the
reaction.
B The  electron cloud of benzene will attack the O atom in ClSO3H.
C The mechanism of this reaction is electrophilic addition.
The bond broken in ClSO3H is the S−O bond.
D

A: during electrophilic substitution reaction, the hybridisation state of the C atom will change
from sp2 to sp3 (arenium ion intermediate) and then back to sp2.

B: the electron deficient atom is S in the electrophile, +SO2Cl. Thus, the p electron cloud of
benzene will attack the S atom in electrophile +SO2Cl.

C: the mechanism is electrophilic substitution

✓D: S-O bond will be broken during the reaction.

Ans: D

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21 Which reagent can be used to distinguish between the two compounds below?

CH3CH(OH)CH(OH)CH3 HOCH2CH2OCOCH3

A alkaline I2(aq), heat B acidified K2Cr2O7(aq), heat

Fehling’s solution
C 2,4-DNPH D

✓A: First compound contains -CH(OH)CH3 fragment which will give yellow ppt of CHI3 with
iodoform test whereas second compound (which contains a primary alcohol and ester) will not
give yellow ppt with iodoform test since it does not have −CH(OH)CH3 or −COCH3 in aldehyde
or ketone functional group.

B: The primary alcohol group in both compound will be oxidised with hot acidified K2Cr2O7(aq),
giving a colour change from orange to green.

C: Both compounds give a negative test with 2,4-DNPH since both do not have aldehyde nor
ketone functional groups.

D: Both compounds give a negative test with Fehling’s solution since both do not have aliphatic
aldehyde functional group.
Ans: A

22 Which reaction will not produce a mixture of two enantiomers?

A B

C D

A: The reaction is nucleophilic addition. There is equal probability for CN− nucleophile to
attack either side of the trigonal planar C=O of the ketone, producing a racemic mixture.

B: The reaction is electrophilic addition. In the 2nd step of the mechanism, there is equal
probability for Br− ion to attack either side of the trigonal planar C+ of the carbocation,
producing a racemic mixture.

✓C: C atom of C-Cl is not chiral due to 2 identical -CH2CH3 groups attached to it. So the
product alcohol won’t be chiral and thus this reaction will NOT produce a mixture of two
enantiomers.

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✓D: the reaction is Sn2 and will result in pure enantiomers with inversed configuration.
Ans: C/D

23 Which molecules rotate plane polarised light?

1 2 3 4

A 1 and 4 only B 2 and 4 only C 1, 2 and 4 only D 1, 3 and 4 only

Compound 3 contains internal plane of symmetry, thus, it is a meso compound and cannot
rotate plane-polarised light, whereas compound 4 has no internal plane of symmetry.

Compound 2 contains internal plane of symmetry, thus, it is a meso compound and cannot
rotate plane-polarised light, whereas compound 1 has no internal plane of symmetry.

Ans: A

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24 Compound E has the following structure.

OH

Which statements are correct about the organic product formed after compound E has
reacted with hot acidified KMnO4?

1 It contains 6 carbon atoms.

2 It can react with 3 moles of PCl5.
3 It gives a yellow ppt with alkaline aqueous iodine.
4 It can react with 2 moles of aqueous NaOH.

A 1 and 2
B 1 and 3
C 2 and 4
D 3 and 4

1: the organic product only contains 4 carbons.

✓2: there are 3 −OH group in the product, which will react with 3 moles of PCl5.

3: there are no fragments in the product could give positive iodoform test.

✓4: there are two -COOH groups in the product, which will react with 2 moles of NaOH.
Ans: C

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 18

25 The pKa values of benzoic acid and the hydroxybenzoic acids are shown.

Why is 2-hydroxybenzoic acid so much more acidic than 4-hydroxybenzoic acid?

A A pair of its molecules are hydrogen-bonded to each other.

B Its conjugated base is stabilised by internal hydrogen bonding.
C Its hydroxy group has electron-withdrawing properties.
D The negative charge of its conjugated base is spread over two oxygen atoms.

Acid strength depends on the stability of the anion.

A: hydrogen bonding between molecules affects the boiling point of the compound, not the
acidity of the compound.

✓B: the intra-molecular hydrogen bonding formed will stabilise the anion to a greater extend
for 2-hydroxybenzoic acid whereas for 4-hydroxybenzoic acid, the OH group is too far away
from the -COO- group to form intra-molecular hydrogen bonding.

C: -OH attached to the benzene is strongly ring activating as delocalisation of lone pair of
electrons on O into benzene ring due to p-p orbital overlap will intensify the negative charge
and destabilise the anion.

D: this factor applies to all three different benzoic acid, thus, it cannot explain the much
higher acidity of 2-hydroxybenzoic acid than 4-hydroxybenzoic acid.
Ans: B

© Jurong Pioneer Junior College 9729/01/J2 MID YEAR EXAM/2023

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26 When mixed with aqueous Br2, 1 mole of X reacts with 2 moles of Br2.
What could X be?

A B

C D

Br2(aq) will react with phenol and alkene functional groups. 1 mole of Br2(aq) will be substituted
to position 2, 4, 6 wrt to −OH group in phenol. 1 mole of Br2(aq) will be reacted with 1 mole of
C=C bond.

A: it will react with 3 moles of Br2(aq)

✓B: it will react with 2 moles of Br2(aq)

C: it will react with 4 moles of Br2(aq)

D: it will react with 3 moles of Br2(aq)

Ans: B

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 20

27 Compound R can be formed from 1-bromopropane using a nucleophilic substitution reaction

followed by an oxidation reaction.

What is the identity of R?

A propanoic acid
B Propanone
C Propylamine
D propyl ethanoate

Ans: A

28 Consider the following four compounds.

1 CH3COOH
2 CH3COCl
3 C6H5OH
4 CH3OCOCH3

What is the relative order of increasing acidity of these compounds in water?

least acidic most acidic

A 2 3 1 4
B 2 4 3 1
C 4 2 3 1
D 4 3 1 2

CH3COCl will hydrolyse in water to form strong acid, HCl, thus, it will be the strongest acid
among all the compounds.

CH3OCOCH3 is an ester, which is neutral in nature. Thus, it is the least acidic.

CH3COOH is a stronger acid compared to C6H5OH, as the negative charge is dispersed over
two highly electronegative O atom, which stabilise the anion, make it a stronger acid compared
to phenol.

Thus, the increasing acidity is 4 < 3 < 1 < 2.

Ans: D

© Jurong Pioneer Junior College 9729/01/J2 MID YEAR EXAM/2023

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29 A small peptide X is hydrolysed according to the following reaction.

What is the Mr of X?

A 359 B 377 C 431 D 449

When an amide linkage undergoes hydrolysis, one more of H2O is added to the fragments,
increasing the Mr by 18.

When X undergoes hydrolysis, it forms a total of 5 fragments ∴a possible structure looks like
below:

When X undergoes hydrolysis, a total of 4 moles of H2O will be used to break the 4 peptide
bonds.

Thus, the Mr of X is 75 x 2 + 89 + 105 x 2 - 18 x 4 = 377

Ans: B

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 22

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

The diagram of a galvanic cell setup is shown below.

high-resistance
voltmeter
V
salt bridge
Pt electrode O2(g) at 1 bar

1 mol dm–3 H+(aq)

1 mol dm–3 Fe2+(aq)
1 mol dm–3 Fe3+(aq) Pt
electrode
half-cell S half-cell T

Which of the following changes will result in an increase in the cell potential?

1 Adding water to half-cell S.

2 Adding solid NaOH to half-cell S.
3 Adding water to half-cell T.

A 1, 2 and 3 B 1 and 2 only C 2 and 3 only D 2 only

From Data Booklet:

Fe3+(aq) + e− ⇌ Fe2+(aq) EꝊ = + 0.77V -- [O]
O2(g) + 4H+(aq) + 4e− ⇌ 2H2O(l) EꝊ = + 1.23V -- [R]
EꝊcell = (+ 1.23V) – (+ 0.77V) = + 0.46V

1. When water is added to half-cell S, [Fe3+] and [Fe2+] decrease to the same extend, POE
remains the same ∴ cell potential remains the same

✓2. When solid NaOH is added to half-cell S, the half-cell changes to

Fe(OH)3 + e- ⇌ Fe(OH)2 + OH− with EꝊ = − 0.56V
The EꝊcell = (+ 1.23V) − (− 0.56V) = + 1.79V ∴cell potential increases

3. When water is added to half-cell T, [H+] decreases, POE shift to the left, making the EꝊ
value less positive ∴ cell potential decreases
Ans: D

© Jurong Pioneer Junior College 9729/01/J2 MID YEAR EXAM/2023