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2024 Prelims NJC H2 Chem P3 (QP)

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1

NATIONAL JUNIOR COLLEGE

SH2 PRELIMINARY EXAMINATION
Higher 2

CANDIDATE
NAME

SUBJECT REGISTRATION
CLASS NUMBER

CHEMISTRY 9729/03
Paper 3 Free Response 17 September 2024
2 hours
Candidates answer on Question Paper.
Additional Materials: Data Booklet

READ THE INSTRUCTIONS FIRST

Write your subject class, registration number and name on all For Examiner’s Use
the work you hand in.
Write in dark blue or black pen. Section A
You may use a soft pencil for any diagrams or graphs.
Do not use staples, paper clips, glue or correction fluid.
1 /20
Section A
Answer all questions. 2 /20
Section B
Answer one question. 3 /20

A Data Booklet is provided. Section B

The use of an approved scientific calculator is expected, (*circle the question you
where appropriate. attempted)

4 /20
The number of marks is given in brackets [ ] at the end of
each question or part question.
5 /20

Paper 3
/80
Total

This document consists of 32 printed pages.

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

Section A
Answer all the questions in this section.

1 (a) Chlorinated phenols have seen growing applications as fungicides, herbicides,

insecticides, and as starting materials in the production of various pesticides since the
1930s.

It can be readily produced from compound A using chlorine in water.

compound A

(i) Write a balanced equation for the reaction between compound A and excess
aqueous chlorine. [1]

(ii) Compound A undergoes a series of reactions shown in the reaction scheme below.

State the reagent and condition for Reaction I and II, and hence draw the structures
of B and E. [4]

(iii) Write a balanced equation for reaction III. [1]

………………………………………………………………………………..………………

NJC/H2 Chem Preliminary Examination/03/2024

………………………………………………………………………………..………………

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) Vanadium is a transition element that exhibits variable oxidation states.

(i) Explain why vanadium can form stable ions with varying oxidation states. [1]

(ii) Write the full electronic configuration for V3+ . [1]

(iii) Draw a fully labelled diagram of the experimental set-up used to measure the
standard electrode potential of the VO2+ (aq)/V3+(aq) half-cell. [3]

A Latimer diagram below summarises the standard electrode potential data of vanadium
complexes in acidic medium.

VO3− +1.00 V VO2+

+0.34 V
V3+

The standard electrode potential x for converting VO3− to V3+, is not the sum of
+1.00 V and +0.34 V. Instead, it can be calculated from Gꝋ.

(iv) Write the half-equation for the conversion of VO3− to V3+. [1]

(v) Calculate the standard electrode potential x, given that Gꝋ for the conversion of
VO3− to V3+ is −129 kJ mol-1. [1]

…..……………………………………………………………………………………………

NJC/H2 Chem Preliminary Examination/03/2024

…..……………………………………………………………………………………………

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

The diagram below illustrates the configuration of a cell in a vanadium redox battery. The
reactants are dissolved in an acidic solution, stored in large tanks, and circulated through
the cell. A polymer membrane facilitates the movement of specific ions.

When discharging, the battery supplies electricity to the power grid on demand through
a control switch. During charging, the battery uses electricity from the wind turbines to
reverse the chemical reaction.

(i) State the polarity of electrode A when the cell is discharging. Explain your answer.
[2]

(ii) Write an equation for the reaction that occurs when the cell is being charged. [1]

…………………………………………………..……………………………………………

NJC/H2 Chem Preliminary Examination/03/2024

…………………………………………………..……………………………………………

(d) The exhaust from heavy-duty diesel engines emits considerable particulate matter (PM)
and pollutant gases like nitrogen oxides. A Continuous Regenerating Trap (CRT) is a
device intended for use in the exhaust systems of diesel-powered buses and trucks to
eliminate PM and pollutant gases.

(i) Explain, with the aid of an equation, why oxides of nitrogen are present in the engine
exhaust. [1]

(ii) State one harmful effect of nitrogen oxides. [1]

(iii) Identify one other pollutant gas present in engine exhaust. Provide a chemical
equation to illustrate its removal in the catalytic chamber of a CRT. [2]

………………………………………………………………………………………………..

[Total: 20]

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

2 (a) 4-nitrobenzoyl chloride can be synthesized from benzene in four steps as shown in
Fig 2.1.

Fig 2.1

(i) Suggest the structures for compounds P, Q and R. [3]

(ii) Suggest reagents and conditions for each of the steps 1, 2, 3 and 4. [2]

………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024

(b) Procainamide is used for treating heart ventricular issues. Procainamide can be
synthesized from 4-nitrobenzoyl chloride in 2 steps as shown in Fig 2.2.
H H
O Cl O N O N
C C N C N

step I step II

NO2 NO2 NH2

Procainamide
Fig 2.2

(i) State the reagents and conditions needed for step I and II. [2]

(ii) An alternative synthesis pathway for procainamide is shown in Fig 2.3.

H
O Cl O Cl O N
C C C N

step I step II

NO2 NH2 NH2

Procainamide
Fig 2.3

Suggest why the yield of procainamide obtained from Fig 2.3 would be lower
compared to that from Fig 2.2. [1]

………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(c) Nitrogen atoms in organic compounds are potential Brønsted-Lowry base.

The 3 nitrogen atoms on procainamide have different basicity.

Rank the three nitrogen atoms in order of increasing basicity. Explain your answer.
[3]

……………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024

(d) Ethyl ethanoate can undergo the following hydrolysis.

(i) The standard entropy change in a chemical reaction can be defined as shown in
Equation 2.1.

Equation 2.1 : ∆Soreaction = ∑ Sꝋ (products) – ∑ Sꝋ (reactants)

Table 2.1

Standard enthalpy change Standard Molar Entropy

Species
of formation / kJ mol–1 (Sꝋ) / J K–1mol–1
CH3COOCH2CH3 – 479 258
CH3COOH – 484 160
CH3CH2OH – 287 161
H2O – 286 70

Use the data in Table 2.1 and Equation 2.1, calculate the standard Gibb’s free
energy change for the hydrolysis of ethyl ethanoate. [2]

(ii) With reference to the Data Booklet, calculate the enthalpy change of reaction for
the hydrolysis of Ethyl ethanoate. Explain why this value is different from the answer
in (i). [2]

………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(e) Gibbs free energy under non-standard conditions (∆G) is related to the standard Gibbs
free energy (∆Gꝋ), gas constant (R), temperature (T) and the reaction quotient (Q).

∆G = ∆Gꝋ + RT ln Q

Reaction quotient is the relative amounts of products and reactants present during a
reaction at a particular instance and has the same expression as the equilibrium
constant, K.

(i) Prove that ∆Gꝋ = – RT ln K, when reaction is at equilibrium. [1]

An aqueous solution at 30 C is known to have the following composition.

compound concentration / mol dm–3

ethanol 2.20
ethanoic acid 3.10
ethyl ethanoate 0.82
water 55.3

(ii) Write an expression for the reaction quotient, Q, for the reaction above and use the
data to calculate ∆G at this particular instance. [2]

(iii) Hence, suggest what the ∆G value in (e)(ii) indicates about the direction of the
reaction. [1]

(iv) Sulfuric acid is added as catalyst for the reaction. Suggest how would the addition
of sulfuric acid affect the equilibrium constant for the hydrolysis of ethyl ethanoate.
[1]

…………………………...…………………………………………………………………..

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

……………………………………………………………………………………………….
[Total : 20]

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

3 (a) Electroplating copper spoon with a layer of silver can improve the corrosion resistance
of the spoon, ensuring a non-reactive surface when in contact with food and gain
anti-microbial properties. Fig 3.1 shows one such set up for the electroplating of copper
spoon with a layer of silver.

Fig 3.1

(i) Write the half equations for the reaction that happens at each electrode. [1]

(ii) A current of 5A was passed through the system to electroplate the copper spoon
with a total surface area of 100 cm2.

Given the density of silver is 10.5 g cm–3, calculate the amount of time needed to
coat the copper spoon with 0.01 mm thickness of silver. [2]

(iii) A way to speed up the electroplating process is by increasing the current supplied.
Suggest the disadvantage of increasing the current supplied. [1]

(iv) Under suitable conditions, silver can be oxidised to silver(I) oxide, Ag2O. With the
use of Data Booklet and information in Table 3.1, construct an energy cycle to
calculate the lattice energy of silver(I) oxide.

Table 3.1

∆H /kJ mol–1
Standard enthalpy change of atomisation of Ag(s) +285
Standard enthalpy change of formation of Ag2O(s) –31
First Electron Affinity of O(g) –141
Second Electron Affinity of O(g) +744
[4]

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) The values of solubility product for some silver compounds are shown in Table 3.2.

Table 3.2

compound colour of precipitate solubility product

AgCl white 1.8  10−10
AgBr cream 5.2  10−13
AgI yellow 8.3  10−17
Ag2CrO4 red 1.1  10−12

(i) Describe what would be observed when aqueous AgNO3 is added drop-wise into a
solution containing 1  10−4 mol dm−3 of Cl− and 1  10−4 mol dm−3 of CrO42−. Explain
your answer. [2]

(ii) AgCl is soluble in excess of NH3(aq) but AgI is insoluble in excess of NH3(aq).
Explain the observation. [2]

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

(c) Write an equation to represent the thermal decomposition of hydrogen halide, HX.
Hence, explain the thermal stability of hydrogen halide down Group 17. [2]

……………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(d) A sample of pure N2O5 (g) is placed in an evacuated container and allowed to decompose
at a constant temperature of 300K.

2N2O5 (g) → 4NO2(g) + O2(g)

The concentration of N2O5 in the container is measured over a period of time, and the
measurement are recorded in Table 3.3. The rate equation for the reaction is found to
be Rate = k[N2O5].

Table 3.3

Time (min) [N2O5]/ moldm-3

0 0.480
10 0.381
20 0.302
30 0.240
40 0.190
50 0.150

(i) With the use of the data in Table 3.3, show that the order of reaction with respect
to N2O5 is one. [1]

(ii) Determine the value of the rate constant, k, for the reaction. Include units in your
answer. [1]

(iii) The following mechanism is proposed in the decomposition of N2O5(g)

Step 1 : N2O5 (g) → NO2(g) + NO3 (g)

Step 2 : NO2(g) + NO3(g) → NO2(g) + NO(g) + O2(g)
Step 3 : N2O5(g) + NO(g) → 3NO2(g)

Identify and explain which step of the proposed mechanism is the rate determining
step. [2]

(iv) If this experiment was repeated at the same condition but with twice the
concentration of N2O5, explain how would the value of k change. [2]

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

……………………………………………………………………………………………….
[Total : 20]

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

Section B
Answer one question from this section.

4 (a) Table 4.1 shows the pKa values of glycolic acid and ethanedioic acid.

Table 4.1

O H O O
C C H C C
Acid HO HO OH
OH
glycolic acid ethanedioic acid
pKa1 3.83 1.27
pKa2 - 4.28

(i) Explain why pKa1 of glycolic acid is larger than that of ethanedioic acid. [2]

(ii) Calculate the pH of 0.100 mol dm−3 of glycolic acid. [1]

Small portions of 0.100 mol dm−3 NaOH(aq) are added to 25.0 cm3 of 0.100 mol dm−3 of
glycolic acid.

(iii) Explain, with the aid of an equation, why the pH of the mixture is 7.6 when 25.0 cm3
of NaOH(aq) is added to glycolic acid. [2]

(iv) When 50.00 cm3 of 0.100 mol dm−3 NaOH(aq) was added, the pH value of the
reaction mixture is at 12.5.

Sketch the shape of the pH curve on suitable axis, using all the relevant information
given or calculated. Indicate the point at which a buffer of maximum capacity is
formed. [2]

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) Glycolic acid undergoes reactions as shown in Fig. 4.2.

Fig. 4.2

(i) Give the structures of compounds A and B in Fig 4.2. [2]

(ii) Give the reagents and conditions for step 2 in Fig. 4.2. [1]

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

Question 4 continues on the next page

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(c) Compound D is an ester with the molecular formula, C15H20O3.

When D was treated with different reducing agents, the following observations were
made.

On heating with acidified potassium manganate(VII), D gives 3 organic products,

E, C8H6O5, F, C4H10O and G, C3H6O.

• 1 mole of E reacts with 2 moles of SOCl2.

• E reacts fully with aqueous bromine in the ratio 1:1.
• G gives an orange precipitate, H, with 2,4-dinitrophenyhydrazine.

Suggest structures for D – H and explain the observations described above. [10]

……………………………………………………………………………………………………..

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………………..

……………………………………………………………………………………………………..
[Total : 20]

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

5 (a) PCl5 dissolves in water to give acidic solution. Write an equation for the reaction of PCl5
with water. [1]

…………………………………………………………………………………………………….

(b) When compound W, C12H12O3, is mixed with 2,4-dinitrophenylhydrazine, an orange

precipitate is formed. However, no precipitate is observed when W is heated with
Tollens’ reagent.

When W is heated with dilute hydrochloric acid, compounds X and Y are formed.
Compound X has the molecular formula C3H4O2.

When Y is warm with alkaline iodine, yellow precipitate is observed. Compound Z,

C9H9BrO2, is formed when Y is mixed with excess Br2(aq).

Deduce the structures of compounds W, X, Y and Z, and explain the observations

described above. [6]

…………………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

…………………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(i) The numerical value of Kb for propylamine is 4.8  10−4. Calculate the value of pKb
for propylamine. [1]

(ii) Calculate the initial pH of the 0.20 mol dm−3 propylamine solution. [1]

(iii) Explain with the aid of an equation, why the pH of the solution at equivalence point
is less than 7. [2]

(iv) Using your answer from (a)(i) - (iii), sketch the titration curve that would result from
this titration with the 0.100 mol dm−3 HCl. solution. Showing clearly the point of
maximum buffering capacity. [2]

(iv) With reference to the structure and bonding, account for the difference in the boiling
point between propylamine and trimethylamine.

Compound boiling point / C

propylamine, CH3CH2CH2NH2 49
trimethylamine, (CH3)3N 7
[2]

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

……………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(d) Ethene can be converted into propylamine via a three-step synthesis route.

Suggest the reagents and conditions for the synthesis route, showing clearly the
structure of the intermediate organic compounds. [3]

……………………………………………………………………………………………………..

(e) Propylamine can also be obtained from the reaction between 1-bromopropane and NH3
under suitable conditions.

Suggest a mechanism for the reaction between 1-bromopropane and NH3. Show all
relevant dipoles, lone pair electrons and curly arrows. [2]

…………………………………………………………………………………………………….

…………………………………………………………………………………………………….
[Total : 20]

NJC/H2 Chem Preliminary Examination/03/2024

Additional answer space

If you use the following pages to complete the answer to any question, the question number must be
clearly shown.

………………………………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

………………………………………………………………………………………………………………….

NJC/H2 Chem Preliminary Examination/03/2024

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2024 Prelims NJC H2 Chem P3 (QP)

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2024 Prelims NJC H2 Chem P3 (QP)

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1

NATIONAL JUNIOR COLLEGE

READ THE INSTRUCTIONS FIRST

A Data Booklet is provided. Section B

This document consists of 32 printed pages.

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

1 (a) Chlorinated phenols have seen growing applications as fungicides, herbicides,

It can be readily produced from compound A using chlorine in water.

(iii) Write a balanced equation for reaction III. [1]

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) Vanadium is a transition element that exhibits variable oxidation states.

(ii) Write the full electronic configuration for V3+ . [1]

VO3− +1.00 V VO2+

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

NJC/H2 Chem Preliminary Examination/03/2024

(ii) State one harmful effect of nitrogen oxides. [1]

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(i) Suggest the structures for compounds P, Q and R. [3]

NJC/H2 Chem Preliminary Examination/03/2024

NO2 NO2 NH2

(ii) An alternative synthesis pathway for procainamide is shown in Fig 2.3.

NO2 NH2 NH2

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(c) Nitrogen atoms in organic compounds are potential Brønsted-Lowry base.

The 3 nitrogen atoms on procainamide have different basicity.

NJC/H2 Chem Preliminary Examination/03/2024

(d) Ethyl ethanoate can undergo the following hydrolysis.

Equation 2.1 : ∆Soreaction = ∑ Sꝋ (products) – ∑ Sꝋ (reactants)

Standard enthalpy change Standard Molar Entropy

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(i) Prove that ∆Gꝋ = – RT ln K, when reaction is at equilibrium. [1]

An aqueous solution at 30 C is known to have the following composition.

compound concentration / mol dm–3

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

compound colour of precipitate solubility product

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

2N2O5 (g) → 4NO2(g) + O2(g)

Time (min) [N2O5]/ moldm-3

(iii) The following mechanism is proposed in the decomposition of N2O5(g)

Step 1 : N2O5 (g) → NO2(g) + NO3 (g)

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(ii) Calculate the pH of 0.100 mol dm−3 of glycolic acid. [1]

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) Glycolic acid undergoes reactions as shown in Fig. 4.2.

(i) Give the structures of compounds A and B in Fig 4.2. [2]

NJC/H2 Chem Preliminary Examination/03/2024

Question 4 continues on the next page

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(c) Compound D is an ester with the molecular formula, C15H20O3.

On heating with acidified potassium manganate(VII), D gives 3 organic products,

• 1 mole of E reacts with 2 moles of SOCl2.

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

(b) When compound W, C12H12O3, is mixed with 2,4-dinitrophenylhydrazine, an orange

When Y is warm with alkaline iodine, yellow precipitate is observed. Compound Z,

Deduce the structures of compounds W, X, Y and Z, and explain the observations

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

Compound boiling point / C

NJC/H2 Chem Preliminary Examination/03/2024

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

NJC/H2 Chem Preliminary Examination/03/2024

Additional answer space

NJC/H2 Chem Preliminary Examination/03/2024 [Turn over

NJC/H2 Chem Preliminary Examination/03/2024

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