Name: .........................................

Class: ..........................................

Section I /20
Section II /80
2021 Total /100
HIGHER SCHOOL CERTIFICATE
TRIAL EXAMINATION

Chemistry

General Instructions Total marks − 100

• Reading time − 5 minutes
• Working time − 3 hours Section I Pages 2 − 10
• Write using blue or black pen
20 marks
Black pen is preferred
• Attempt Questions 1 − 20
• Draw diagrams using pencil
• Allow about 35 minutes for this part
• Board-approved calculators may be used
• A data sheet and a Periodic Table are Section II Pages 11 − 29
provided at the back of this paper
• Write your name and class at the top of 80 marks
this page • Attempt Questions 21 − 33
• Allow about 2 hours and 25 minutes for this
section

−1−
Section I: Multiple Choice Questions (20 marks)
Attempt Questions 1 − 20
Allow about 35 minutes for this section

Use the multiple choice answer sheet for Questions 1 − 20.

1. A B C D
2. A B C D
3. A B C D
4. A B C D
5. A B C D
6. A B C D
7. A B C D
8. A B C D
9. A B C D
10. A B C D
11. A B C D
12. A B C D
13. A B C D
14. A B C D
15. A B C D
16. A B C D
17. A B C D
18. A B C D
19. A B C D
20. A B C D

−2−
1. Compounds X, Y and Z are in equilibrium. The graph below shows how the equilibrium yield
of compound Z changes with variations in temperature and pressure.

Which equation is consistent with this graph?

(A) X(g) + 3 Y(g) 2 Z(g) ΔH < 0
(B) X(g) + 3 Y(g) 2 Z(g) ΔH > 0
(C) 2 X(g) 2 Y(g) + Z(g) ΔH < 0
(D) 2 X(g) 2 Y(g) + Z(g) ΔH > 0

2. Which of the following is a conjugate acid/base pair that contains an amphiprotic species?
(A) HCl/Cl–
(B) HPO42–/PO43–
(C) H2CO3/CO32–
(D) CH3COOH/CH3COO–

3. Which of the following compounds are a pair of functional group isomers?

(A) Hex-1-ene and cyclohexene
(B) Butan-1-ol and 2-methylpropan-2-ol
(C) Pentane and 2-methylbutane
(D) Pentanal and pentan-2-one

4. A sample of solid magnesium hydroxide was added to a sodium hydroxide solution with a pH
of 12.00 and only some of the magnesium hydroxide dissolved.

What is the equilibrium concentration of magnesium ions in the resultant solution?

(A) 5.6 × 10−8 mol L–1
(B) 5.6 × 10−9 mol L–1
(C) 5.6 × 10−10 mol L–1
(D) 5.6 × 10−11 mol L–1

−3−
5. Consider the following compound:

Cl
CH3 C CH3
CH3 C

What is the systematic name of this compound?

(A) 2-chloro-2-methylbutanal
(B) 2-chloro-2,2-dimethylpropanal
(C) 3-chloro-3-methylbutan-2-one
(D) 3-chloro-3,3-dimethylpropan-2-one

6. A conductometric acid-base titration was carried out and the following conductivity curve was
obtained.

Which row of the following table contains an indicator that would be suitable for this titration?

Indicator pH range
(A) Crystal violet 0.0 − 2.0
(B) Methyl red 4.4 − 6.2
(C) Cresolphthalein 8.2 − 9.8
(D) Indigo carmine 11.4 − 13.0

7. A 50.0 mL sample of contaminated water was analysed for its lead ion content. Excess sodium
chloride was added to this sample and the lead(II) chloride precipitate that formed was filtered,
dried and weighed. It had a mass of 0.110 g.

What is the concentration of lead ions in the water sample?

(A) 1640 ppm
(B) 1880 ppm
(C) 2120 ppm
(D) 2360 ppm

−4−
 8. Consider the following compounds which have been labelled as X, Y and Z:
H H H O H H H H
H C C O H H C C N H C C N

H H H H H H H
X Y Z
Which of the following arranges these compounds in order of increasing boiling point?
(A) X<Y<Z
(B) X<Z<Y
(C) Y<X<Z
(D) Z<X<Y

9. A sodium hydroxide solution was prepared by weighing out 1.00 g of solid sodium hydroxide
and dissolving it in sufficient distilled water to make a 250.0 mL solution. A hydrochloric acid
solution was then titrated with the sodium hydroxide solution using an appropriate indicator.
The titration was repeated three more times and the results are shown below.

Titration Volume of NaOH added (mL)

1 15.20
2 15.15
3 15.10
4 15.10

Which row of the following table best describes the results of this experiment?

Calculated HCl
Reliability Accuracy
concentration
(A) Unreliable Accurate Correct
(B) Reliable Inaccurate Underestimated
(C) Reliable Inaccurate Overestimated
(D) Reliable Accurate Correct

10. Consider the following compound where one of the 1 H environments has been labelled as Ha :
H H Ha

H C C C O H

H H Ha
What would be the splitting pattern of the signal produced by the Ha environment on a 1 H
nuclear magnetic resonance (NMR) spectrum under standard conditions?
(A) Singlet
(B) Doublet
(C) Triplet
(D) Quartet

−5−
11. A 40.0 mL solution of 0.20 mol L–1 barium nitrate is mixed with 40.0 mL of 0.20 mol L–1 sodium
hydroxide solution at 25◦ C.

Which row of the following table correctly predicts if barium hydroxide will form as a precipitate
and the reason for this?

Will a precipitate form? Reason

(A) No Qsp < Ksp
(B) No Qsp > Ksp
(C) Yes Qsp < Ksp
(D) Yes Qsp > Ksp

12. The table below shows the heat of combustion of three different alcohols in kJ g–1.

Alcohol Heat of combustion (kJ g–1)

Methanol 22.7
Ethanol 29.7
Propan-1-ol 33.6

What is the most likely molar heat of combustion of butan-1-ol?

(A) 2019 kJ mol–1
(B) 2671 kJ mol–1
(C) 5286 kJ mol–1
(D) 36.0 kJ g–1

13. The polymer below can be produced from a reaction between two different monomers.

O O H H
 
C C N N
n

Which of the following is one of the monomers used to produce the above polymer?

(A) H2 N COOH

(B) HO COOH

(C) H2 N CONH2

(D) H2 N NH2

−6−
14. The mass spectrum of propan-1-amine is shown below.

Which species is most likely responsible for the base peak on this mass spectrum?
(A) C2H5+
(B) C2H6+
(C) CH2NH2+
(D) C3H7NH2+

15. A solution of sucrose (C12H22O11) was allowed to undergo fermentation in a conical flask that
was stoppered with cotton wool. During this process, yeast enzymes first hydrolyse sucrose into
simple carbohydrates according to the following equation:

yeast
C12H22O11(aq) + H2O(l) −−−→ 2 C6H12O6(aq)

The simple carbohydrates produced are then converted into ethanol and carbon dioxide.

The initial mass of the conical flask with its contents was 365.8 g and after several days,
the final mass was found to be 354.3 g.

What is the theoretical mass of sucrose that got consumed during this time period?
(A) 22.4 g
(B) 33.6 g
(C) 44.8 g
(D) 56.0 g

−7−
16. Consider the following series of reactions where A, B and C are different organic compounds.

H2/Pt

NaOH

KMnO4/H2SO4

No reaction

Based on the above information, a possible identity for compound A is:

(A) 1-bromo-2-methylbut-1-ene
(B) 2-bromo-2-methylbut-1-ene
(C) 3-bromo-2-methylbut-1-ene
(D) 4-bromo-2-methylbut-1-ene

17. A laboratory contains solutions of hydrochloric acid and acetic acid, both at equal volumes
with the same pH of 2.00. A chemist made the following statements regarding these solutions:

(i) Both solutions have the same hydronium ion concentration

(ii) A 10-fold dilution of both acids would cause both their pH values to increase by 1 unit
(iii) The hydrochloric acid solution would require a smaller volume of 0.10 mol L–1 sodium
hydroxide solution to be completely neutralised than the acetic acid solution

Which of the above statement(s) are correct?

(A) (i) only
(B) (i) and (ii) only
(C) (i) and (iii) only
(D) (i), (ii) and (iii)

−8−
18. The table shows some properties of two organic compounds, X and Y.

Compound Solubility in water Litmus paper test

X Partially soluble Blue litmus turns red
Y Soluble Red litmus turns blue

Which row of the following table best identifies compounds X and Y?

X Y
(A) HCOOH C6H13NH2
(B) C5H11COOH CH3NH2
(C) CH3NH2 C5H11COOH
(D) C6H13NH2 HCOOH

19. In aqueous solution, iodide ions (I–) can react with iodine (I2) to form triiodide ions (I3–) and
an equilibrium is established.

I–(aq) + I2(aq) I3–(aq)

When hexane is added to this system, two separate layers form and some iodine dissolves into
the hexane layer which becomes purple due to the dissolved iodine. The following distribution
equilibrium is then established:

I2(aq) I2(hexane)

The diagram below shows the appearance of the equilibrium mixture.

Which row of the following table shows the most likely colour changes that would occur in the
hexane layer when potassium iodide and silver nitrate are added to the aqueous layer?

KI added AgNO3 added

(A) Purple colour fades Purple colour fades
(B) Purple colour fades Purple colour intensifies
(C) Purple colour intensifies Purple colour fades
(D) Purple colour intensifies Purple colour intensifies

−9−
20. A 25.0 mL solution of 0.15 mol L–1 nitric acid was mixed with a 20.0 mL solution of 0.10 mol L–1
barium hydroxide.

What is the pH of the resultant solution?

(A) 7.70
(B) 9.06
(C) 10.40
(D) 11.74

−10−
Section II: Short Answer Questions (80 marks)
Attempt Questions 21 − 33
Allow about 2 hours and 25 minutes for this part

Answer the questions in the spaces provided. These spaces provide guidance for the expected
length of response.

Show all relevant working in questions involving calculations.

Question 21 (4 marks)
A chemist placed two pieces of cotton wool at opposite ends of a sealed horizontal glass tube.
One piece of cotton wool was soaked in concentrated ammonia solution, and the other was
soaked in concentrated hydrochloric acid solution. Over time, a ring of white powder is formed
inside the tube. This is shown in the schematic diagram below.
Glass tube

Cotton
Cotton
Cott on wool
woo
ooll Ring of Cotton wool
soaked in white soaked in
concentrated powder concentrated
hydrochloric ammonia
acid

(a) Explain why this reaction is well accounted for by the Brönsted-Lowry theory of acids 3
and bases, but not by the Arrhenius theory. Include a relevant chemical equation in your
answer.

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(b) Describe ONE limitation of the Brönsted-Lowry theory of acids and bases. 1

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−11−
Question 22 (7 marks)
N2O4 is a colourless gas that can dissociate into brown NO2 gas according to this equation:
N2O4(g) 2 NO2(g)

(a) When an equilibrium mixture of N2O4 and NO2 is placed into an ice bath, the brown colour 2
of the mixture fades.

Explain whether the decomposition of N2O4 into NO2 is endothermic or exothermic.

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(b) A reaction vessel initially contained the following concentration of gases at equilibrium. 2
Gas Initial equilibrium concentration (mol L−1 )
N2O4 0.15
NO2 0.25

At time T1 , the volume of the reaction vessel was halved and the system was then allowed
to reach equilibrium at time Teq .

Sketch two curves on the provided graph to show how the concentrations of N2O4 and
NO2 gas will vary as a function of time between t = 0 and t = Tf .

Note that absolute concentration values at Teq are not important.

0.60
Concentration (mol L−1 )

0.50

0.40

0.30

0.20

0.10

0.00
0 T1 Teq Tf

Time (units)

−12−
(c) Explain how the equilibrium position changes after T1 using collision theory. 3

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Question 23 (4 marks)
A student carried out an experiment to test the effectiveness of soap in hard water which 4
contains a high content of calcium and magnesium ions.

The student prepared two beakers, one containing distilled water and the other containing
hard water. A fabric soaked in oil was added to both beakers followed by a soap solution. The
resultant mixtures were then stirred and the results of the experiment are shown below:

Type of water Observations

Distilled water • Oily stains on fabric were removed

• White precipitate formed in solution

Hard water
• Oily stains remained on the fabric

Account for the results obtained in this experiment with reference to the molecular structure
and cleaning action of soap.

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−13−
Question 24 (4 marks)
Consider the following equilibrium reaction: 4
Fe3+(aq) + SCN–(aq) FeSCN2+(aq)
The following procedure was used to determine the equilibrium constant for this reaction.
• 2.0 mL of 2.5 × 10−3 mol L–1 Fe(NO3)3 and 2.0 mL of 2.5 × 10−3 mol L–1 KSCN was mixed
in a 10.0 mL volumetric flask and then filled to the mark with distilled water.
• The resultant solution was allowed to reach equilibrium and its absorbance at 480 nm was
measured with colourimetry and found to be 0.280.
• A series of standard solutions was used to construct the calibration curve below.
Calibration curve for FeSCN2+
0.45

0.40

0.35

0.30
Absorbance

0.25

0.20

0.15

0.10

0.05

0.00
0 1 2 3 4 5 6
Concentration of FeSCN (ppm)
2+

Calculate the equilibrium constant for the reaction.

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−14−
Question 25 (10 marks)
Ethanol, propanoic acid and concentrated sulfuric acid were mixed into a flask and then heated
under reflux.

(a) Write a chemical equation, using structural formulae, for the reaction that occurs. 2

(b) Outline why refluxing is used to carry out this reaction. 2

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After the reaction, the reaction mixture was separated using the apparatus shown below.

−15−
Three pure organic compounds were collected in separate beakers and were labelled as X, Y
and Z in order of collection. Each compound was analysed with mass spectrometry and the
resultant mass spectra are shown below.

−16−
(c) What are the identities of compounds X, Y and Z, and which of these has the lowest boiling 1
point as indicated by the order of collection?

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(d) Explain the differences in boiling point between compounds X, Y and Z. 5

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−17−
Question 26 (8 marks)
An unknown organic acid with a molecular formula of C4H4O4 reacts with sodium hydroxide
to form a salt and water according to the following general equation:

C4H4O4(aq) + xNaOH(aq) → Nax C4H4−x O4(aq) + xH2O(l)

To determine the stoichiometric ratio between C4H4O4 and sodium hydroxide, ten 10.0 mL
samples were prepared by mixing together various volumes of C4H4O4 and sodium hydroxide.
All of the C4H4O4 and sodium hydroxide solutions used had identical concentrations and
temperatures. The temperature change of each sample was measured and the results are given
below.

Sample 1 2 3 4 5 6 7 8 9 10
Volume of
0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0
NaOH (mL)
Volume of
10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0
C4H4O4 (mL)
Temperature
0.00 0.56 1.14 1.70 1.80 2.85 3.40 3.42 2.28 1.13
increase (◦ C)

(a) Construct an appropriate graph of the data and hence determine the value of x to the 4
nearest integer.

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−18−
(b) When a few drops of bromine water is added to the unknown organic acid, the bromine 1
water is decolourised.

Draw a possible structural formula for the unknown organic acid that is consistent with all
the information provided.

(c) The enthalpy change per mole of water formed in the neutralisation reaction is −56 kJ mol–1. 3

If 15% of the heat released by the reaction was lost to the surroundings, calculate the
concentration of the sodium hydroxide solution before it was mixed with the organic acid.

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−19−
Question 27 (9 marks)
A student transferred 25.00 mL of a benzoic acid solution into a beaker and titrated it against
a 0.1389 mol L–1 sodium hydroxide solution. As the titrant was being delivered, changes in
pH were monitored using a pH meter immersed in the beaker solution and attached to a data
logger. In total, 40.00 mL of sodium hydroxide was added before the recording was stopped
(This does NOT represent the equivalence point). The benzoic acid solution was found
to have a pH of 2.60 and a concentration of 0.1000 mol L–1.

(a) Given that benzoic acid is a weak monoprotic acid with a molecular formula of C6H5COOH, 1
show that the amount of salt produced at the equivalence point is 2.500 × 10−3 mol.

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(b) The half-equivalence point of a titration occurs when the volume of titrant that has been 8
added is half of what is required to reach the equivalence point. It can be shown that the
pH at the half-equivalence point on the titration curve is equal to the pKa of the weak acid
being titrated. Note that you are NOT required to prove this.

Using all of the information provided and relevant calculations, draw a titration curve
for this titration on the axes below. In particular, you should clearly mark:
• The initial pH
• The pH and volume of sodium hydroxide added at the half-equivalence point
• The pH and volume of sodium hydroxide added at the equivalence point
• The final pH when 40.00 mL of sodium hydroxide has been added

You may assume that the hydrolysis of the salt produced in part (a) is negligible at the end
when 40.00 mL of sodium hydroxide has been added.

14.00

12.00

10.00

8.00
pH

6.00

4.00

2.00

0.00
0 5 10 15 20 25 30 35 40
Volume of NaOH added (mL)

−20−
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−21−
Question 28 (6 marks)
The following thermodynamic data applies to the dissolution of solid potassium hydroxide in 6
water at 25◦ C.

Δsol H −◦− = −57 kJ mol–1

Δsol S −◦− = +11 J mol–1 K–1

With reference to this data and the resultant Δsol G−◦− , describe and analyse the changes in
structure and bonding that occur when potassium hydroxide is dissolved in water at 25◦ C.
Include a relevant diagram in your answer.

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−22−
Question 29 (6 marks)
A chemist conducted an experiment where they measured the pH of a sample of perchloric acid
(HClO4) and hypochlorous acid (HClO). A salt was then dissolved into each acid. The results
are summarised in the table below.
Acid Perchloric acid Hypochlorous acid
Concentration of
0.10 0.10
acid (mol L–1)
Initial pH 1.00 4.27
Salt dissolved Sodium perchlorate (NaClO4) Sodium hypochlorite (NaClO)

(a) Account for the pH readings measured in this experiment and explain how the pH of each 5
acid solution will be affected by the dissolution of the salts. Include relevant chemical
equations in your answer.

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(b) Predict which of the resultant mixtures can potentially act as a buffer solution and briefly 1
justify your answer.

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−23−
Question 30 (7 marks)
An unknown organic compound with a molecular formula of C7H14O2 was analysed with infrared 7
(IR) spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. The following spectra
were obtained from these techniques.

Analyse the spectra above to determine the structural formula of the organic compound.

Note: 1 H NMR chemical shift data has been included on your data sheet.

−24−
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−25−
Question 31 (5 marks)
A beaker is known to contain ONE of the following 0.10 mol L–1 solutions: 5

• Sodium sulfate
• Copper(II) nitrate
• Sodium hydroxide
• Silver nitrate
• Sodium carbonate

Describe a series of tests that could be used to confirm the identity of the solution in the beaker.
Include any expected observations and relevant net ionic equations in your answer.

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−26−
Question 32 (5 marks)
The following procedure was used to determine the phosphate content of a particular brand of
plant food.
• A 4.258 g sample of the plant food was mixed with 50.0 mL of 0.126 mol L–1 silver nitrate
solution. All of the phosphate ions were precipitated out, leaving an excess of silver ions.
• The precipitate formed was filtered off and the filtrate was diluted to 250.0 mL with
distilled water in a volumetric flask.
• Four 50.0 mL aliquots of the resulting solution were transferred to separate conical flasks
and, in each case, the excess silver ions was titrated against a 0.0625 mol L–1 potassium
thiocyanate (KSCN) solution according to the following equation:
Ag+(aq) + SCN–(aq) → AgSCN(s)
• The results are given in the table below:
Titration Titre volume (mL)
1 11.90
2 11.60
3 11.70
4 11.65

(a) Calculate the moles of silver ions that remained unreacted following the reaction with the 2
phosphate ions.

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(b) Calculate the concentration of phosphate ions in the plant food sample in mg/g. 3

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−27−
Question 33 (5 marks)
Oxidation and reduction reactions occur as opposing reactions as shown below. 5

Oxidation
−−
A)−−−−
−−−−
*
−−B
Reduction

In organic chemistry, a strong reductant that is commonly used to carry out reduction reactions
is sodium borohydride (NaBH4).

Using the information above and any other relevant reactions, construct a flowchart to show
a reaction pathway that can be used to synthesise the compound below using propanal as the
ONLY starting organic reagent.

H C H O H H

H C O C C C H

H C H H H

All reagents used must be clearly shown and the structural formula of all intermediates must
be drawn.

End of paper

−28−
Section II extra writing space

If you use this space, clearly indicate which question you are answering.

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