SK025

CHEMISTRY 2
PRACTICE BOOK

Name:……………………………………….
Tutorial Group: …………………………….
Lecturer's Name: ……………………........

2022/2023
 CHEMISTRY
TUTORIAL BOOK
SK025
Chief Editor
Ummi Usaini

Editors
Shazwan Razak
Juniza Jasin
Haikal Fitri Harun
Izzati Asyikin
Shakila Ibrahim
Wan Nurul Bahiyah

Graphic Designer
Shazwan Razak
Mohd Rusydi Rosli

Special thanks to the writers of the

following chapters:
Chapter 1 &11 Chapter 4 & 7
Izzati Asyikin Mohd Pazli Pauzi
Soon Yit Leng Siti Aishah
Wan Nurul Bahiyah Rozaimie Wahab
Byron Kadum
Chapter 2 & 9 Chapter 5 & 8
Shazwan Razak Ummi Usaini
Shakila Ibrahim Juniza Jasin
Raudatul Jannah Amira
Renny Lee Irwan Shah Adnan
Chapter 3 & 12 Chapter 6 & 10
Asyandi Mohd Nor Syukri Zakaria
Khairul Afiq Haikal Fitri Harun
Amalina Aznan Atiyah Fauzin
Norazlinda Mardiana Amir
 Contents
Academic Calendar SK025 …………………. ………………………………………………..…... 3

Relative Atomic Masses of Selected Elements ………………………………………………..…... 4

List of Selected Constants Value ……………..……………………………………………….…... 5

Assessments in SK025 ,,,,,,,,,,,,,,, ……………..……………………………………………….…... 6

Chapter 1: Reaction Kinetics ...………………..…………………………………………….……... 7

Chapter 2: Thermochemistry …………………..……………………………………………….... 13

Chapter 3: Electrochemistry …..………………..………………………………………………... 19

Chapter 4: Introduction to Organic Chemistry…..……………………………………………….. 24

Chapter 5: Hydrocarbons ...…………………..……………………….………………………….. 29

Chapter 6: Benzene and Its Derivatives .………..……………………………………………….. 35

Chapter 7: Haloalkanes …..…….………………..……………………………………………….. 40

Chapter 8: Hydroxy Compounds.………………..……………………………………………….. 44

Chapter 9: Carbonyl Compounds………………..……………………………………………….. 48

Chapter 10: Carboxylic Acids and Its Derivatives ………………………………………………. 53

Chapter 11: Amines ..…..…….………………..…………………………………………………. 58

Chapter 12: Amino Acids ..…….….…………..…………………………………………………. 62

2
3
R.A.M of Selected Elements
Element Symbol Proton number Relative atomic mass
Aluminium Al 13 27.0
Silver Ag 47 107.9
Argon Ar 18 40.0
Arsenic As 33 74.9
Gold Au 79 197.0
Barium Ba 56 137.3
Beryllium Be 4 9.0
Bismuth Bi 83 209.0
Boron B 5 10.8
Bromine Br 35 79.9
Iron Fe 26 55.9
Fluorine F 9 19.0
Phosphorus P 15 31.0
Helium He 2 4.0
Mercury Hg 80 200.6
Hydrogen H 1 1.0
Iodine I 53 126.9
Cadmiun Cd 48 112.4
Potassium K 19 39.1
Calcium Ca 20 40.1
Carbon C 6 12.0
Chlorine Cl 17 35.5
Cobalt Co 27 58.9
Krypton Kr 36 83.8
Chromium Cr 24 52.0
Copper Cu 29 63.6
Lithium Li 3 6.9
Magnesium Mg 12 24.3
Manganase Mn 25 54.9
Sodium Na 11 23.0
Neon Ne 10 20.2
Nickel Ni 28 58.7
Nitrogen N 7 14.0
Oxygen O 8 16.0
Platinum Pt 78 195.1
Lead Pb 82 207.2
Protactinium Pa 91 231.0
Radium Ra 88 226.0
Radon Rn 86 222.0
Rubidium Rb 37 85.5
Selenium Se 34 79.0
Cerium Ce 58 140.1
Cesium Cs 55 132.9
Silicon Si 14 28.1
Scandium Sc 21 45.0
Tin Sn 50 118.7
Antimony Sb 51 121.8
Strontium Sr 38 87.6
Sulphur S 16 32.1
Uranium U 92 238.0
Tungsten W 74 183.9
Zinc Zn 30 65.4

4
Ionisation constant for water at 25C Kw = 1.00  10−14 mol2 dm−6

List of Selected Constants

Molar volume of gases Vm = 22.4 dm3 mol−1 at STP
= 24 dm3 mol−1 at room temperature

Speed of light in a vacuum c = 3.0  108 m s−1

Specific heat of water = 4.18 kJ kg−1 K−1
= 4.18 J g−1 K−1
= 4.18 J g−1 C−1

Avogadro’s number NA = 6.021023 mol−1

Faraday constant F = 9.65 x 104 C mol−1
Planck constant h = 6.625610−34 J s
Rydberg constant RH = 1.097  107 m−1
= 2.18  10−18 J

Molar of gases constant R = 8.314 J K−1 mol-1

= 0.08206 L atm mol−1 K−1

Density of water at 25C  = 1 g cm−3

Freezing point of water = 0.00 C

Vapour pressure of water at 25C Pwater = 23.8 torr

UNIT AND CONVERSION FACTOR

VOLUME 1liter = 1 dm3
1mL = 1 cm3

ENERGY 1J = 1 kg m2 s−2 = 1 N m = 1  107 erg

1 calorie = 4.184 J
1eV = 1.602 x 10-19 J
PRESSURE 1 atm = 760 mmHg =760 torr = 101.325 kPa = 101 325 N m-2
OTHERS 1 faraday (F) = 96 500 coulomb
1 newton (N) = 1 kg m s−2

5
Assessments in SK025
UPS by Chapter
UPS 1 UPS 2
Chapter 1 - 5 Questions Chapter 4 - 5 Questions
Chapter 2 - 5 Questions Chapter 5 - 10 Questions
Chapter 3 - 7 Questions Chapter 6 - 3 Questions

UPS 3
Chapter 7 - 3 Questions
Chapter 8 - 3 Questions
Chapter 9 - 3 Questions
Chapter 10 - 7 Questions

PSPM by Chapter Overall

Chapter 1 - 10 Marks Assignment - 15 %
Chapter 2 - 10 Marks Lab Report - 15 %
Chapter 3 - 7 Marks Practical Skills - 10 %
Chapter 5 - 6 Marks UPS - 20 %
Chapter 6 - 7 Marks Final Exam - 40 %
Chapter 7 - 7 Marks
Chapter 8 - 5 Marks
Chapter 9 - 7 Marks
Chapter 10 - 10 Marks
Chapter 11 - 7 Marks
Chapter 12 - 4 Marks

6
Chapter 1: Reaction Kinetics
TUTORIAL QUESTIONS CHAPTER 1

1. Write the differential rate equation for the following reactions.

(a) I− (aq) + OCl− (aq) ⎯→ Cl− (aq) + OI− (aq)
(b) 3O2 (g) ⎯→ 2O3 (g)
(c) 4NH3 (g) + 5O2 (g) ⎯→ 4NO (g) + 6H2O (g)

2. For the reaction

4NH3 (g) + 5O2 (g) ⎯→ 4NO (g) + 6H2O (g)
the rate of disappearance of oxygen is 0.020 M s-1
(a) determine the rate of formation of H2O and
(b) determine the rate of disappearance of NH3.
3. The reaction of peroxydisulfate ion (S2O82–) with iodide ion (I–) is
S2O82– (aq) + 3I– (aq) → 2SO42– (aq) + I3– (aq)

Experiment [S2O82–] [I–] Initial rate (M s-1)

1 0.080 0.034 2.2 x 10-4
2 0.080 0.017 1.1 x 10-4
3 0.160 0.017 2.2 x 10-4

From the following data collected at certain temperature,

(a) calculate the order with respect to each reactant.
(b) determine the rate constant
(c) write the rate equation

4. The conversion of cyclopropane to propene in the gas phase is a first order reaction with a rate
constant of 6.710–4 s−1 at 500C.
CH2
⎯
⎯→ H2C CH CH3
H2C CH2

(a) If the initial concentration of cyclopropane was 0.25 M, calculate the concentration after
8.8 min.
(b) How long will it take for the concentration of cyclopropane to decrease from 0.25 M to
0.15 M?
(c) How long will it take to convert 74% of the starting material to propene?

7
5. Iodine atoms combine to form molecular iodine in the gas phase:
I (g) + I (g) ⎯→ I2 (g)
The rate constant for the above reaction is 7.0  109 M−1 s−1 at 23C.
(a) If the initial concentration of iodine atoms is 0.086 M, calculate the concentration after
2.0 min.
(b) Calculate the half-life of iodine atoms if the initial concentration is
i. 0.42 M
ii. 0.60 M

6. The decomposition of dinitrogen pentoxide with the rate constant of 5.1 ×10–4 s–1 at 45 oC is
given below:
2N2O5 (g) ⎯→ 4NO2 (g) + O2 (g)
(a) Calculate the concentration of N2O5 after 3.2 min if the initial concentration is 0.25 M.
(b) If the initial concentration of N2O5 is 0.35 M, calculate the time needed for the
concentration to be reduced
i. to 0.08 M
ii. by 62%

7. A catalytic reaction of ammonia gas decomposes into nitrogen gas and hydrogen gas with a
platinum catalyst is one example of zero order reaction. In one reaction, the initial concentration
of ammonia gas is 1.5 M and after 120 seconds the concentration is 0.75 M.
(a) Calculate the rate constant and half life
(b) If the original concentration is reduced to 1.0 M, does the half-life decrease, increase, or
stay the same? If the half-life changes what is the new half-life?

8. The data listed in the table below were obtained from the following decomposition:
A ⎯→ products
Time/ min 0 5 10 15 25
[A]/ M 1.00 0.63 0.46 0.36 0.25

(a) By plotting an appropriate graph, show that the reaction is second order
(b) From your graph, determine the rate constant, k, of the reaction.
(c) Determine the half-life, t1/2, if [A]o = 1.00 M

9. (a) What are the conditions for an effective collision to occur between reactant molecules to
form product?
(b) How does transition state theory describe activated complex and activation energy?

10. Explain the effect of temperature on reaction rate based on Maxwell-Boltzmann distribution
curve.

8
11. The following equation shows the decomposition of HI(g):
Pt
2HI (g) H2 (g) + I2 (g) ΔH = –ve

(a) What is the function of platinum?

(b) Draw and label the potential energy profile for the reaction with and without platinum.
(c) Give another two factors that can influence the reaction rate and explain your answer.

12. The rate constant of a reaction is 3.46 × 10-2 s-1 at 298 K. Calculate the rate constant at 350 K
if the activation energy for the reaction is 50.2 kJ mol-1.

13. Rate constants, k for decomposition of hydrogen iodide at different temperatures are given in
the table below:

Rate constant, k
3.7510−9 6.6510−6 1.1510−3 7.7510−2
(mol−1 dm3 s−1)
Temperature
500 600 700 800
(K)

(a) Write the Arrhenius equation.

(b) Determine the activation energy for the decomposition of hydrogen iodide graphically
from the above data.

14. (a) What is meant by activation energy?

(b) The rate constant of a reaction at 463 K is 2.52 10−5 s−1 and at 503 K is 6.30  10−4 s−1.
Determine the activation energy for the reaction.

9
 PAST YEARS COLLECTIONS CHAPTER 1

PSPM 2020/2021

Decomposition of gaseous hydrogen iodide, HI at 508 oC is represented by the following equation:

2 HI (g) → H2 (g) + I2 (g)
The molar concentration of HI was measured at time interval in second(s) and the graph of
concentration against time for the decomposition of HI at 508 oC is shown in FIGURE 1.
Concentration of HI (M)

FIGURE 1

(a) (i) Based on FIGURE 1, determine the order of reaction and write the rate equation for the
decomposition.
(ii) Calculate the rate constant, k, and initial rate for the decomposition of HI.
[8 marks]
(b) State two (2) requirements for effective molecular collisions in producing a chemical change.
[2 marks]

10
PSPM 2019/2020

(a) The data for the reaction between methyl ethanoate, CH3COOCH3, with hydroxide ion, OH-, at
a certain temperature is shown in TABLE 1.
TABLE 1
Experiment [CH3COOCH3] / M [OH-] /M Initial rate /Ms-1 ×10-3
1 0.050 0.120 1.58
2 0.050 0.154 2.03
3 0.084 0.154 3.40
4 0.084 0.200 4.42

(i) Determine the order of reaction with respect to each reactant.

(ii) Write the rate law for the reaction.
(iii) Calculate the rate constant.
(iv) How many times will the rate increase if the concentration of both CH3COOCH3 and OH-
are doubled?
[9 marks]

(b) The decomposition of NH3 to N2 and H2 at 450 oC was studied on the surfaces of tungsten and
osmium catalysts. The profile diagram for the reaction using each catalyst is given in FIGURE
1.

(i) Which catalyst is better for this reaction? Explain.

(ii) The activation energy for the above reaction using tungsten catalyst is 163 kJ mol-1. How
many times faster is the reaction if the temperature is increased to 550 oC?
[5 marks]

11
PSPM 2018/2019

(a) On heating, dinitrogen pentoxide, N2O5 decomposes as follow:

2N2O5 (g) → 4NO2 (g) + O2 (g)
The reaction is first order with respect to N2O5.

(i) Determine the rate of formation of O2 if the rate of disappearance of N2O5 is 1.25 ×10-2
M min-1.
(ii) Calculate the rate constant for this reaction if 25% of N2O5 is decomposed within 10
minutes.
(iii) Determine the half-life for this decomposition reaction.
[7 marks]

(b) TABLE 1 shows the rate constants for the decomposition of N2O5 at two different temperatures.
TABLE 1
Temperature (oC) Rate constant (s-1)
25.0 1.74 ×10-5
35.0 6.61 ×10-5

(i) Determine the activation energy, Ea for this reaction in kJ mol-1.

(ii) Activation energy can also be determined graphically. Sketch the graph and explain
briefly.
[7 marks]

12
Chapter 2: Thermochemistry
TUTORIAL QUESTIONS CHAPTER 2

1. Define and write an example of thermochemical equation for each of the following terms:
(a) Standard enthalpy of formation
(b) Standard enthalpy of combustion
(c) Standard enthalpy of atomisation
(d) Standard enthalpy of neutralisation
(e) Standard enthalpy of hydration
(f) Standard enthalpy of solution (dissolution)

2. From the following data,

2Fe (s) + O2 (g) → Fe2O3 (s) ΔHf = -822.2 kJ mol-1
determine the enthalpy of combustion of iron.

3. A bomb calorimetric experiment is performed with powdered xylose, C5H10O5 as the

combustible substance. The data obtained are:

Mass of xylose burned = 1.183 g

Heat capacity of calorimeter = 4.728 kJ oC-1
Initial calorimeter temperature = 23.29 oC
Final calorimeter temperature = 27.19 oC

(a) Calculate the heat of combustion of xylose, in kJ mol-1.

(b) Write the thermochemical equation for combustion of xylose.

4. A quantity of 1.922 g of methanol (CH3OH) was burned in a constant-volume bomb

calorimeter. Consequently, the temperature of the water rose by 4.20 oC. If the quantity of water
surrounding the calorimeter was exactly 2000 g and the heat capacity of the calorimeter was
2.02 kJ oC-1, calculate the molar heat of combustion of methanol.
[The specific heat of water is 4.18 J g-1 oC-1]

5. When 200 mL of 1.00 M NaOH was mixed with 150 mL of 1.00 M HCl in a Styrofoam ‘coffee
cup’ calorimeter, the temperature rose from 25.00 °C to 30.00 °C. Calculate the heat of
neutralisation. Assume that the specific heat of solution is 4.18 J g-1 °C-1 and density of solution
is 1 g mL-1.

13
6. (a) State Hess’s Law.

(b) The enthalpies of formation of ammonia, hydrogen chloride and ammonium chloride are
-46.1 kJ mol-1, -92.3 kJ mol-1, -14.4 kJ mol-1 respectively
(i) Write the thermochemical equation for the formation of each of the above
substances

(ii) Calculate the enthalpy change for the reaction.

NH3 (g) + HCl (g) ⎯→ NH4Cl(s)

7. Nitrogen oxides undergo many interesting reactions. Calculate ΔH for the overall equation.
1
N2O5 (s) → 2 NO2 (g) + 2 O2 (g)
From the following equations:
3
N2O5 (s) → 2 NO (g) + 2 O2 (g) ΔH = +223.7 kJ
1
NO (g) + O2 (g) → NO2 (g) ΔH = -51.7 kJ
2

8. Given:
S(s) + O2 (g) → SO2 (g) ΔH = -297 kJ
1
SO2 (g) + 2 O2 (g) → SO3 (g) ΔH = -99 kJ

Calculate ΔH for the following reaction using energy cycle method:

3
S(s) + 2 O2 (g) → SO3 (g)

9. Acetylene, C2H2, is a gas used in welding torches. It is produced by the action of water on
calcium carbide, CaC2. Calculate for acetylene in kJ mol-1 by using the thermochemical
equations given below.

CaO (s) + H2O (l) → Ca(OH)2 ΔH1 = -65.3 kJ

CaO (s) + 3 C (s) → CaC2 (s) + CO (g) ΔH2 = +462.3 kJ
CaC2 (s) + 2 H2O (l) → Ca(OH)2 (s) + C2H2 (g) ΔH3 = -126.0 kJ
1
C (s) + 2 O2 (g) → CO (g) ΔH4 = -220.0 kJ
2 H2O (l) → 2 H2 (g) + O2 (g) ΔH5 = +572.0 kJ

10. (a) Define lattice energy.

(b) Which substance in the following pairs has larger lattice energy? Explain.
KCl or RbCl

14
11. Based on the data given:
Enthalpy of hydration of Na+ = -390 kJ mol-1
Enthalpy of hydration of Cl- = -380 kJ mol-1
Enthalpy of solution of NaCl = +6 kJ mol-1

Construct an energy cycle diagram to calculate the lattice energy of NaCl.

12. Use a Born Haber cycle for KF and the following values to calculate a value for the standard
enthalpy of formation of KF(s)
K (s) → K (g) ΔH = +90 kJ
–
K (g) → K (g) + e
+
ΔH = +419 kJ
F2 (g) → 2 F (g) ΔH = +160 kJ
– –
F (g) + e → F (g) ΔH = -336 kJ
–
K (g) + F (g) → KF (s)
+
ΔH = -821 kJ

13. Use the data below to construct a Born-Haber cycle for copper (II) oxide and determine its
lattice energy.
Enthalpy of atomisation of copper: +339 kJ mol-1
First ionisation energy of copper: +745 kJ mol-1
Second ionisation energy of copper: +1960 kJ mol-1
Enthalpy of atomisation of oxygen: +248 kJ mol-1
First electron affinity of oxygen: –141 kJ mol-1
Second electron affinity of oxygen: +791 kJ mol-1
Enthalpy of formation of copper (II) oxide : –155 kJ mol-1

15
 PAST YEAR COLLECTIONS CHAPTER 2

PSPM 2020/2021

(a) TABLE 1 shows the lists of standard enthalpy change associated with the solubility of silver
chloride, AgCl.
TABLE 1
Enthalpy ΔHo (kJ mol-1)
Lattice energy of AgCl +915
Hydration energy of Ag+ -465
-
Hydration energy of Cl -364

(i) Construct the thermochemical cycle to show the relationship between lattice energy,
hydration energy and enthalpy of solution of AgCl.
(ii) Calculate the enthalpy of solution of AgCl.
[6 marks]

(b) Arrange the following substances in ascending order of lattice energy. Explain your answer.
AlCl3, MgCl2, NaCl
[4 marks]

16
PSPM 2019/2020

(a) Ethanol, CH3CH2OH, is produced from fermentation of sugarcane and widely used as an
alternative fuel to replace petrol. A 1.00 g sample of ethanol was burned in a bomb calorimeter,
which has a total heat capacity of 11.0 kJ oC-1. The temperature of the calorimeter and its
contents increased from 25.0 oC to 27.7 oC.
(i) Write a balanced chemical equation for the reaction that takes place in the bomb
calorimeter.
(ii) Calculate the enthalpy of combustion of ethanol per mol.
[6 marks]

(b) Born-Haber cycle for the formation of calcium sulphide is given in FIGURE 2 (The cycle is
not drawn to scale)

(i) Name the enthalpy changes for ΔH7 and ΔH8.

(ii) Identify the species X formed from ΔH5.
(iii) Use the data in FIGURE 2 to calculate the value of ΔH6.
(iv) Will the lattice energy for CaO be larger or smaller than CaS? Explain briefly.
[6 marks]

17
PSPM 2018/2019

(a) In an experiment to measure the enthalpy change of neutralisation, 25.0 mL of 1.0 M HCl is
placed in a polystyrene cup. At the same temperature, 25.0 mL of 1.0 M NaOH is added and
stirred. The temperature of the resulting solution increases by 7.0 oC. Calculate the enthalpy of
neutralisation for this reaction.
[Assume the density and specific heat capacity of the final solution are the same as water]
[6 marks]

(b) The thermochemical data for the formation of sodium oxide, Na2O is given in TABLE 2.
TABLE 2
Enthalpy ΔHo (kJ mol-1)
Ionisation energy of sodium +496
Enthalpy of formation of sodium oxide -414
First electron affinity of oxygen -141
Second electron affinity of oxygen +750
Enthalpy of atomisation of oxygen +249
Lattice energy of sodium oxide -2478

Based on TABLE 2,
(i) Construct a Born-Haber cycle for sodium oxide.
(ii) Calculate the enthalpy of atomisation of sodium.
[8 marks]

18
Chapter 3: Electrochemistry
TUTORIAL QUESTIONS CHAPTER 3

1. (a) Define
(i) Galvanic cell.
(ii) Standard reduction potential.
(b) A galvanic cell consists of an Al as anode electrode in 1.0 M Al(NO3)3, a Pb as cathode
electrode in 1.0 M Pb(NO3)2 and a KCl salt bridge.
(i) Draw and label the cell diagram.
(ii) State the function of salt bridge.
(iii) Write the overall cell reaction.
(iv) Calculate the standard cell potential.
(v) Which electrode will increase in mass? Explain your answer.
[ E  Al 3+ |Al = –1.66V ; E  Pb2+ |Pb = –0.13V]

2. (a) Standard electrode potentials for Ag+|Ag and Pb2+|Pb are +0.80V and –0.13V
respectively.
(i) Determine the anode and the cathode.
(ii) Calculate the standard cell potential.
(b) For the reaction,
2Ce4+ (aq) + Co (s) → 2Ce3+ (aq) + Co2+ (aq) Eo = +1.89V
the standard reduction potential for Co2+ is - 0.28 V. Calculate the standard reduction
potential for the change of Ce4+ to Ce3+.

3. The standard reduction potential of a half-cell can be determined when connected with a
standard hydrogen electrode. Describe how the standard hydrogen electrode is used to
determine the standard reduction potential of copper half-cell.

4. Based on the cell notation below,

Ag (s) | Ag+ (aq, 1.0M) || M3+ (aq, 1.0M) | M (s) E° = +1.00V
(a) Write a balanced equation for the spontaneous reaction in the cell.
(b) Name the oxidising agent.
E 3+
(c) Calculate M |M .
E +
[ Ag | Ag = +0.80V]

19
5. A cell notation of a galvanic cell is as follows:
Zn (s) | Zn2+ (aq,1.0M) || Sn2+ (aq, 1.0 M) | Sn (s)
(a) Write the overall cell equation.
(b) Identify the oxidizing and reducing agent.

6. Predict whether the following reactions would occur spontaneously in aqueous solution at 25°C.
Assume that the initial concentrations of the dissolved species are all 1.0 M.
(a) Ca (s) + Cd2+ (aq) → Ca2+ (aq) + Cd (s)
(b) 2Br-(aq) + Sn2+ (aq) → Br2 (l) + Sn (s)
E  2+ E Cd 2+ |Cd E Br |Br - E  Sn 2+ |Sn
[ Ca |Ca = –2.87V; = –0.40V; 2
= +1.07V; = –0.14V]

7. Predict whether Fe3+ can oxidise I to I2 under standard state conditions.

E  3+ 2+ E I |I -
[ Fe |Fe = +0.77V; 2
= +0.53V]

8. A galvanic cell consists of magnesium electrode immersed in 1.0 M magnesium nitrate solution
and a silver electrode immersed in 1.0 M silver nitrate solution and a salt-bridge.
[𝐸°Mg2+|Mg = –2.36V , 𝐸°𝐴𝑔+|𝐴𝑔 = +0.80V]
(a) Write the half reaction at anode and cathode.
(b) Write the cell notation for the above reaction.
(c) State the oxidizing agent.
(d) Calculate the cell potential if 1.0 M magnesium nitrate is replaced with 0.1 M magnesium
nitrate.

9. Refer the reaction below:

3H2O2 (aq) + 6H+ (aq) + 2Au (s) → 2Au3+ (aq) + 6H2O (l)
(a) Write the Nernst equation for the cell at 25 °C.
(b) Calculate the E°cell.
(c) Determine the pH of the half-cell if e.m.f of the cell is +0.2711V, [Au3+] = 0.25 M and
[H2O2] = 1.50 M
[Given: 𝐸°𝐴𝑢3+|𝐴𝑢 = +1.50V, 𝐸°𝐻2 𝑂2|𝐻2 𝑂 = +1.77V]

10. A galvanic cell is constructed by connecting a nickel plate that was immersed into 1.50 M
Ni(NO3)2 solution and an aluminium plate was immersed into a solution containing x M of Al3+
ions. If the cell voltage is 1.40 V,
(a) Calculate the standard cell potential.
(b) Determine the value of x.
[Given: 𝐸°𝑁𝑖 2+ |𝑁𝑖 = –0.25V, 𝐸°𝐴𝑙3+ |𝐴𝑙 = –1.66V]

11. The standard electrode potential is given below:

O3 (g) + 2H+ (aq) + 2e- → O2 (g) + H2O (l) E° = +2.07V
Cl2 (g) + 2e- → 2Cl- (aq) E° = +1.36V
Pressure of all gasses are at 1.0 atm
(a) Write an equation for the spontaneous reaction.
(b) Calculate the 𝐸°𝑐𝑒𝑙𝑙 .
(c) Calculate the Ecell at 25oC if the [Cl–] = 0.01M and [H+] =1.0 M.

20
12. An experiment is carried out to determine the pH of an unknown solution using a galvanic cell
consisting of copper and hydrogen electrodes. The pressure of hydrogen gas is 1 atm. The
copper electrode is immersed in 1.0 M Cu2+ solution and the Ecell at 25oC is +0.48 V.
(a) Write the balanced equation for the cell reaction.
(b) Determine the pH of the unknown solution.
[𝐸°𝐶𝑢2+ |Cu = +0.34V; E  H + |H = +0.00V]
2

13. Calculate the equilibrium constant, K for the following reactions using standard reduction
potentials at 25 oC.
(a) Mg(s) + Zn2+(aq) → Mg2+(aq) + Zn(s)
(b) Br2(l) + 2I (aq) → 2Br (aq) + I2(g)
E  2+ E  Zn 2+ | Zn E Br |Br - E  I 2 |I −
[ Mg |Mg = –2.37V; = –0.76V; 2
= +1.07V; = +0.53V]

14. Explain products formed at the anode and the cathode in the electrolysis of,
(a) Dilute NaCl solution.
(b) Concentrated NaCl solution.
(c) Aqueous Na2SO4 solution.

15. (a) State the Faraday’s first law.

(b) The half-reaction at an electrode is,
Mg2+ (molten) + 2e- → Mg (l)
Calculate the mass of magnesium that can be produced by supplying 1.00 F to the
electrode.

16. Consider the electrolysis of molten barium chloride, BaCl2.

(a) Write the half-reactions of the electrolysis.
(b) How many grams of products can be produced at cathode by supplying 0.50 A for 30
minutes?

17. One of the half-reactions for the electrolysis of water is

2H2O (l) → O2 (g) + 4H+ (aq) + 4e-
If 0.076 L of O2 is collected at 25°C and 755 mmHg, calculate the electrical charge in coulombs
that had passed through the solution?

18. Hydrogen gas is produced when water is electrolysed

2H2O (l) + 2e- → H2 (g) + 2OH- (aq)
A student wants to fill a balloon with hydrogen gas. How long must a current of 12 A be used
in the electrolysis of water to fill the balloon to a volume of 10.00 L and a pressure of 0.924
atm at 22°C?

19. A current of 2.00 A is passed for 30 minutes through a galvanic cell consisting of graphite
electrode and a solution of potassium sulphate at 25°C. Calculate the volume of oxygen gas
evolved at the anode at 1 atm.

21
 PAST YEAR COLLECTIONS CHAPTER 3

PSPM 2020/2021

An electrochemical cell is constructed from the following two half-cell reaction:

VO2+ (aq) + 2H+ (aq) + e → VO2+ (aq) + H2O (l) Eo= +1.00 V
Pb2+ (aq) + 2e → Pb (s) Eo= - 0.13 V
(a) Write a balanced equation for the overall reaction when the two half-cells are connected.
[2 marks]
(b) Calculate the standard electrode potential for the reaction.
[2 marks]
o + +
(c) Calculate the cell potential at 25 C if the initial concentration of VO2 = 0.10 M, H = 0.05 M,
VO2+= 0.10 M and Pb2+ = 0.25 M.
[3 marks]

PSPM 2019/2020

(a) The standard reduction potentials for copper(II), chromium(III) and nickel(II) ions are given
below:
Cu2+ (aq) + 2e- → Cu (s) Eo = +0.34 V
Cr3+ (aq) + 3e- → Cr (s) Eo = - 0.74 V
Ni2+ (aq) + 2e- → Ni (s) Eo = - 0.25 V

(i) Arrange the metal in order of increasing strength of reducing agents. Give your reason.
(ii) Determine whether the reaction below is spontaneous under standard conditions.
Cu2+ (aq) + Cr (s) → Cu (s) + Cr3+ (aq)
(iii) Explain what will happen if chromium container is used to store copper sulphate solution.
[6 marks]

(b) Zinc plating (galvanising) is an important means of corrosion protection. One of the possible
ways in which this can be achieved is through electrolysis. How many grams of zinc can be
deposited on steel object if a current of 1.2 A is passed through zinc sulphate solution for one
hour?
[4 marks]

22
PSPM 2018/2019

(a) A galvanic cell is constructed based on the notation below:

Zn (s) | Zn2+ (aq) || Ag+ (aq) | Ag (s)

The cell potential is 1.58 V when concentration of Zn2+ and Ag+ are x M and 0.15 M,
respectively. Calculate the value of x.
[Given Eocell = +1.56 V]
[4 marks]

(b) A current of 0.025 F was passed through an aqueous solution of Mn+ using a current of 2.00 A.
An amount of 0.79 g of M was deposited at cathode.
[Given molar mass of M is 63.2 g mol-1]
(i) Calculate the time taken in minutes for the deposition of M.
(ii) Calculate the volume of oxygen gas liberated at the anode at STP.
[6 marks]

23
Chapter 4: Introduction to
Organic Chemistry
TUTORIAL QUESTIONS CHAPTER 4

1. Identify the class of carbon that is tagged with the (*) symbol and identify the class of hydrogen
that is attached to the carbon:
*
(a) CH3CH2CH2CH2CH3
*
(b) CH2=CHCH2CH2CH3
(c)

(d)

*
(e)
*

(f) CH(CH3)2
*

2. (a) Define the term structural formula.

(b) Draw the condensed structure for each of the following compounds:
(i) OH

(ii) O

(iii)

(iv) OH

Cl O

24
 (c) Draw the skeletal structure for each compound given below:
(i) O
CH3 CH2 CH2 C CH3

(ii) CH3 CH3

CH3CH CH2CH2CHCH2CH3

(iii) (CH3)3CCH2CH2CH2OH

(iv) Br
CH3CH2CHCH2C OH
O

3. (a) Explain the terms functional group and homologous series.

(b) Draw the structural formula for
(i) an aldehyde (C5H10O)
(ii) a ketone (C4H8O)
(iii) a carboxylic acid (C3H6O2)
(iv) an amine (C5H13N)
(v) an amide (C2H5NO)
(vi) an alcohol (C2H6O)
(vii) an ester (C3H6O2)
(viii) an ether (C2H6O)

4. Identify and name the functional groups present in the following molecules:
(a) CH2OH

NHCH3

(b) CH2OCH3

NHCOCH3

(c) O Cl
COOH
C C H
C
O
C O
O

25
5. (a) Define the term isomer.
(b) Draw all possible isomers of compound with the molecular formula C4H10O and identify
the types of isomerism present.

6. For each of the following compounds, draw its isomeric pair that represents a chain, positional
and functional group isomerism:
(a) CH3CH2CH=CH2
(b) CH3CH(CH3)CH(CH3)CH3
(c) CH3CH2CH2CH2CH2OH

7. (a) What are the essential requirements for a molecule to exhibit cis-trans isomerism?
(b) Which of the following compounds can exist as a pair of cis-trans isomers? Draw the cis-
trans isomers.
(i) ClCH=CHCl
(ii) BrCH=CHCl
(iii) CH3CH=CH2
(iv) (CH3)2C=CHCH3
(v) CH3CH2CH=CHCH3
(vi) (CH3)2C=C(CH3)CH2CH3
(vii)
Br Br

8. Draw all the structural formulae of alkenes C5H10. Identify the structure that exhibits cis-trans
isomerism

9. Draw and label the cis-trans isomers of 1,2-dichloroethene.

10. (a) What is meant by chirality centre?

(b) From the following list, identify the compounds that exhibit optical activity:
(i) CH3CH=C(CH3)CH2CH3
(ii) CH3CH(OH)CH2CH3
(iii) CH3CH2CH(Br)CH2CH3
(iv) CH3CH(NH2)COOH

26
11. (a) State the structural features of a molecule to be optically active.
(b) Draw the structural formula of 2-bromobutane and indicate the chiral carbon using an
asterisk (*).
(c) Use a three-dimensional formula to show the structural formulae of enantiomers in (b).

12. Explain the differences between homolytic cleavage and heterolytic cleavage. Give one
example for each cleavage.

13. (a) Define the terms electrophile, nucleophile, Lewis acid, and Lewis base.

(b) Classify each of the following as electrophile, nucleophile or free radical.

(i) NH3 (vii) BF3
(ii) Br• (viii) CO2
(iii) H2O (ix) CH3CH=CH2
(iv) NO2+ (x) CH3OH
(v) NO2− (xi) PCl5
(vi) Cl+

14. Arrange the following carbocations in order of increasing stability.

CH3 CH3 H
+ +
H3C C CH2 H3C C CH2CH3 CH3 H3C C CH2CH3
+ +
H

15. Chloromethane reacts with hydroxide ion to form methanol as shown in the equation below.
OH− + CH3Cl ⎯→ CH3OH + Cl−
(a) Identify the nucleophile and electrophile.
(b) State the type of reaction.

27
16. State the type of reactions:
(a) O O
C OH C Cl
SOCl2

(b) CH2=CH2 + HCl ⎯→ CH3CH2Cl

CH2=CH2 + H2O ⎯⎯ ⎯ ⎯ ⎯→ CH3CH2OH

H SO , catalyst
(c) 2 4

(d) CH3CHBrCH3 ⎯⎯ ⎯ ⎯⎯→ CH2=CHCH3 + HBr

KOH , alcohol

(e) CH4 + Br2 ⎯⎯→ CH3Br + HBr

uv

(f) NO2
+ HNO3 H2SO 4

(g) Br H
CH3COOH
CH3CH CH CH3 + Zn CH3C CH CH3

Br

28
Chapter 5: Hydrocarbons
TUTORIAL QUESTIONS CHAPTER 5

1. Name the following compounds according to the IUPAC nomenclature

(a) (b)

(c) (d)

2. Draw the structural formula for each of the following compounds:

(a) 3–cyclohexyl–2,2–dimethyloctane
(b) 5–sec–butyl–2,4–dimethylnonane

3. Arrange the following alkanes in order of increasing boiling points. Explain your answer.
(a) nonane, pentane, decane, heptane
(b) pentane, 2-methylbutane, 2,2-dimethylpropane

4. Write the chemical equation for the combustion of cyclohexane in

(a) excess O2
(b) limited O2

5. A mixture of 2-methylpropane and bromine is exposed to sunlight. The reaction equation is

given below.

(a) State the type of the reaction.

(b) What is the function of sunlight in the reaction?
(c) Draw the structure of the monosubstituted products, D and E. Identify the major product.
(d) Write the mechanism for the formation of the major product.
(e) Give the observation of the reaction.
(f) What would happen if the mixture is kept in the dark at room temperature?

29
6. Give the IUPAC names for the following alkenes:
(a) (b)

(c) (d)

7. Draw the structural formula for each of the following alkenes:

(a) 1–butene
(b) 2,3–dimethyl–2–butene
(c) cis–4–octene
(d) trans–1,2–dibromoethene
(e) 2–pentene
(f) Methylcyclobutene

8. The following names are incorrect. Suggest the correct names.

(a) trans–3–pentene
(b) 2–methylcyclohexene

9. Write the equation for the preparation of propene from:

(a) 2–chloropropane
(b) propanol

10. Outline the preparation of

(a) 1,2–dibromocyclopentane from bromocyclopentane
(b) chlorocyclohexane from cyclohexanol

11. (a) State the rule used to determine the major product in dehydration of alcohol reaction.
(b) Explain the rule above.
(c) Draw the structure of the organic products below and identify the major product (if any):

(i)

(ii)

30
 (iii)

(iv)

(v)

12. (a) Define Markovnikov’s rule.

(b) Write an equation of the reaction between 2-methylpropene and hydrogen bromide to
form the product.
(c) State the type of reaction involved.
(d) Write the mechanism that accounts for the formation of the product.

13. Write the structural formulae of the products of a reaction of U with:

(a) H2, Ni (d) H2O, H+

(b) HBr (e) KMnO4, OH–, cold
(c) Br2, CH2Cl2 (f) HBr, H2O2

14. Complete the following reaction scheme.

31
15. Compound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon
treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B
decolourises potassium permanganate solution. Ozonolysis of B gives C, C2H4O, and D, CH2O.
Suggest the structural formulae of A, B, C and D. Write the equations for all the reactions
involved.

16. Describe a chemical test to differentiate the following compounds.

(a) butane and 1–butene
(b) methylcyclopentene and methylcyclopentane

17. The structural formula of two organic compounds are given below:
Structure I Structure II
CH2=CHCl CF2=CF2
Explain the preparation of synthetic homopolymers through addition polymerisation.

32
 PAST YEAR COLLECTIONS CHAPTER 5

PSPM 2020/2021
A hydrocarbon, C6H12, exists in two isomeric forms, A and B. Compound A decolourises bromine
water, whereas B does not. Compound A undergoes ozonolysis to give a single product C. Compound
C forms a brick red precipitate when treated with copper (II) sulphate and sodium potassium tartrate
in alkaline solution.
(a) Deduce the structural formula of A.
(b) Draw the structural formula of B.
[5 marks]
Polytetrafluoroethene (PTFE), commonly known as Teflon® is used as a non-stick coating for pans
and other cookware.

(a) State the type of this polymer.

(b) Draw the structural formula of the monomer used.
[2 marks]
PSPM 2019/2020

(a) Propane undergoes free radical bromination to produce compound A. Draw the intermediates
formed and the structural formula of A.
[3 marks]

(b) Hydrocarbon B, C6H12 reacts with one mole of hydrogen gas over platinum catalyst to produce
compound C. Oxidation of B forms carbon dioxide and carboxylic acid D. Draw the structural
formulae of B, C, and D. Name a simple chemical test to differentiate B from C.
[4 marks]

(c) The structural formula of natural rubber is shown below. Draw the structural formula of its
monomer.

[1 marks]

33
PSPM 2018/2019

Compound A is a four-membered ring alkane with molecular formula C5H10.

(a) Draw the structural formulae for all possible monosubstituted products for the reaction between
C5H10 and chlorine in the presence of light.
(b) Write the reaction mechanism for the formation of the most stable reaction intermediate in (a).
[7 marks]

34
Chapter 6: Benzene and Its
Derivatives
TUTORIAL QUESTIONS CHAPTER 6

1. Draw the structural formula for each of the following compounds.

(a) 1,3,5-trinitrobenzene
(b) m-bromophenol
(c) p-methylbenzaldehyde
(d) 4-chloro-2,3-dinitrotoluene
(e) o-nitrotoluene
(f) isopropylbenzene

2. Write the IUPAC names for the following compounds.

(a) (b)

(c) (d)

(e) (f)

35
3. Draw the structural formulae of compounds P to T in the following reactions.
(a)

(b)

(c)

(d)

(e)

4. Suggest a chemical test to differentiate the following pairs:

(a) cyclohexene from benzene.
(b) toluene from benzene.

5. Starting from benzene, outline a synthesis of

(a) benzyl chloride
(b) nitrobenzene

6. Write the mechanism for the following reaction.

NO 2

conc H 2SO 4
+ conc HNO 3
0
50-55 C

7. Write the synthetic pathway to synthesis the following compound from benzene.
(a) m-nitrotoluene
(b) o-nitrobenzoic acid

8. Show how each of the following compounds can be prepared from toluene.
(a) benzoic acid
(b) benzyl chloride

36
9. Draw the structural formulae of compounds A to F in the following reaction scheme

Br2 , FeBr3

KMnO4, H+, CH3Cl, conc. HNO3,

E D B
heat FeCl3 conc. H2SO4
Cl2, uv 50 - 55°C
CH3COCl,
F AlCl3

37
 PAST YEAR COLLECTIONS CHAPTER 6

PSPM 2020/2021

Benzene can be converted to its derivatives as shown in the reaction scheme below.

(a) Name the type of reaction D.

(b) Ethylbenzene can be converted into styrene by a two-step reaction. Suggest E and F.
(c) Draw the structural formula of compound H.
(d) Write the mechanism for reaction involving G.
[7 marks]

PSPM 2019/2020

(a) Based on the following reaction scheme, give reagents E, F, G and draw the structural formula
of H.

[4 marks]
(b) Write the mechanism for the formation of isopropylbenzene.
[4 marks]

38
PSPM 2018/2019

Compound B and C are hydrocarbons with the structural formulae as shown below.

(a) Name compounds B and C according to IUPAC nomenclature.

(b) Both B and C can undergo oxidation reaction with the same oxidising agent. Write chemical
equations involved and explain the differences between these two reactions.
(c) Name one reaction that converts B to methylcyclohexane.
[8 marks]

39
Chapter 7: Haloalkanes
TUTORIAL QUESTIONS CHAPTER 7

1. Classify the following compounds as primary, secondary or tertiary haloalkanes and give their
IUPAC names:
(a) CH3
CH3 CH2 CF
CH(CH3)2
(b)
CH2 CH2 Br
CH3 CH2 CH2 CH CH2 CH2 CH3
(c)

(d)
CH2Cl

2. Draw the structural formulae of the following compounds:

(a) tert-butylbromide
(b) 1-bromo-1-isopropylcyclobutane
(c) 4-bromo-3-methyl-2-pentene

3. State and write the reaction mechanism for each of the following reactions:
(a)
CH3 CH3
NaOH(aq)
H3C C CH3 H3C C CH3
Br OH

NaOH (aq)
(b) CH3CH2Cl ⎯⎯ ⎯ ⎯ ⎯⎯→ CH3CH2OH
(c)
CH3 CH3 CH3
NaOH(aq)
CH3 C CH2 Br CH3 C CH2 OH + CH3 C CH2 CH3
CH3 CH3 OH
major product

40
4. Arrange the following compounds in order of decreasing reactivity toward SN2 reaction with
aqueous solution of NaOH.
(CH3)2CHCH2Br, CH3CH2CH2CH2Br, (CH3)3CCH2Br

5. (a) Draw all four structural isomers of C4H9Br.

(b) Which of the isomers react most rapidly with aqueous NaOH through SN1 reaction?

(c) Choose two isomers which can react with KOH in ethanol to produce the same alkene.

6. Based on the given reaction scheme, suggest reagent X , structure P and Q.

C H=C H2 C H2C H2Br
X KCN
P

KOH ( aq)

7. (a) Show how a Grignard reagent is prepared from 1-bromopropane.

(b) Draw the structure formed when the above Grignard reagent reacts with:
i) CH2O followed by hydrolysis
ii) CH3CHO followed by hydrolysis
iii) CH3COCH3 followed by hydrolysis
iv) CO2 followed by hydrolysis
v) H2O followed by hydrolysis

41
8. Complete the mind map given:

KCN, ethanol

H2O, H+

ii) H2O, H+
+
ii) H2O, H

42
 PAST YEAR COLLECTIONS CHAPTER 7

PSPM 2020/2021

(a) Dehydration of 2-methyl-2-butanol produces alkenes.

(i) Draw the structural formulae of all alkenes formed.
(ii) Label the major product and explain your answer.
[4 marks]
(b) 2-bromo-methylbutane can be converted to 2-methyl-2-butanol. Write the mechanism for this
reaction.
[3 marks]

PSPM 2019/2020

(a) 1-chlorobutane reacts with sodium methoxide as shown in the chemical equation below.

CH3CH2CH2CH2Cl + NaOCH3 → CH3CH2CH2CH2OCH3

(i) Name and draw the mechanism involved.

(ii) Write the reaction rate equation.
[5 marks]
(b) Complete the reaction scheme below by giving the reagent J and structural formulae of K and
L.

[3 marks]
PSPM 2018/2019

Two organic compounds D and F with molecular formula C4H9Br reacts with suitable reagents to
form E and G via SN1 and SN2 reactions respectively. Both E and G have a molecular formula of
C4H10O.
(a) Draw the structural formulae for D, E, F, and G.
(b) Suggest reagents for the formation of E and G.
(c) Write the mechanism for the formation of E.
[8 marks]

43
Chapter 8: Hydroxy Compounds
TUTORIAL QUESTIONS CHAPTER 8

1. Classify the following compounds as primary, secondary, or tertiary and give their IUPAC
names.
(a) (b)

(c) CH2 CH3 (d)

CH CH CH2 CH2 OH
CH3

(e)

2. The following names are incorrect. Draw the structural formulae and give the correct IUPAC
names.
(a) 2-hydroxycyclohexanol
(b) 6-methyl-3-ethylcyclohexanol

3. Arrange the following compounds in increasing order of boiling point. Explain your answer.
(a) 1,3-propanediol, n-butane, 1-propanol
(b) (CH3)2CHCH2OH, (CH3)2CH(CH2)2CH2OH, (CH3)2CH(CH2)3CH2OH

4. Arrange the compounds in each set in decreasing order of solubility in water. Explain your
answer.
(a) ethanol, 1-pentanol, 1-hexanol
(b) hexane, 1-hexanol, 1,2-ethanediol

5. Write the complete equation for each of the following reactions.

(a) 2-butanol heated with acidified KMnO4 solution.
(b) 2-propanol heated with concentrated H2SO4.
(c) 2-methyl-1-propanol heated with acidified K2Cr2O7 solution.
(d) 1,2-ethanediol with potassium.
(e) Glacial ethanoic acid is refluxed with 2-propanol in the presence of concentrated H2SO4.

44
 (f) 1-hexanol reacts with PCC, CH2Cl2.
(g) cyclopentanol reacts with SOCl2, in pyridine
(h) butene reacts with acidified water.
(i) 1-bromo-1-methylcyclopentane reacts with aqueous potassium hydroxide, KOH.
(j) CH3MgBr reacts with methanal, CH2O followed by hydrolysis.
(k) CH3MgBr reacts with ethanal, CH3COH followed by hydrolysis.
(l) CH3MgBr reacts with propanone CH3COCH3 followed by hydrolysis.

6. Show the preparation of

(a) propanone from 2-bromopropane
(b) 1,2-dibromoethane from ethanol

7. Give a chemical test to distinguish between

(a) 2-methyl-1-propanol and 2-methyl-2-propanol
(b) 3-pentanol and 2-butanol
(c) phenol and cyclohexanol

8. The structural formula of alcohol A is given below:

(a) Give the IUPAC name of A.

(b) Classify alcohol A as 1, 2 or 3.
(c) Give the major product of the dehydration of A.

9. Compound P is an alcohol. Upon oxidation with acidified KMnO4 solution, a ketone, Q is

formed. P reacts with PBr3 to give R which is then purified and refluxed in dry ether along with
Mg metal to form a Grignard reagent, S. S is treated with Q followed by acidic hydrolysis to
yield 3,4-dimethyl-3-hexanol. Identify P, Q, R and S. Write all the equations for reactions
involved.

10. An alcohol C4H10O which has several isomers gave the following observations. Determine the
isomers and draw all equations involved.
(a) Isomer L gives negative result with Lucas reagent and forms butanoic acid when oxidised
with acidified potassium dichromate solution.
(b) Isomer M is optically active and gives positive result with I2, NaOH.
(c) Isomer N reacts instantly with Lucas reagent but does not decolourise acidified solution
of potassium dichromate.

11. T has a formula, C5H12O. It is oxidised to form U, C5H10O. T undergo dehydration to form V.
Ozonolysis of V gives propanone and ethanal. Deduce structures of T, U and V.

45
12. The structural formula of X is shown below.

Draw the structural formula of the product formed when X reacts with:
(a) sodium.
(b) aqueous sodium hydroxide.
(c) phosphorus pentachloride.
(d) propanoic acid refluxed with traces of concentrated sulphuric acid.

13. Explain the following observation:

(a) Phenol is soluble in aqueous solution of sodium hydroxide but cyclohexanol is not.
(b) Ethanol reacts with iodine in aqueous solution of sodium hydroxide to produce yellow
precipitate, but 1-propanol does not.

46
 PAST YEAR COLLECTIONS CHAPTER 8

PSPM 2020/2021

Compounds K and L are isomers of a branched alcohol with molecular formula of C4H10O. Oxidation
of K produces a carboxylic acid, whereas L resists oxidation.
(a) Deduce the structural formulae of K and L.
(b) Write a chemical equation for oxidation of K.
[5 marks]

PSPM 2019/2020

Compound M and N are isomers with molecular formula C5H12O. The reaction of M and N with
sodium metal forms gas bubbles. When M is heated with acidified solution of sodium dichromate,
orange solution turns green and compound P, C5H10O2 is formed. N does not decolourise acidified
sodium dichromate solution.
(a) Deduce the structural formulae of M, N and P.
(b) Write all chemical equations involved.
(c) Write the structural formula of product formed when P reacts with N. State the catalyst used.
[7 marks]

PSPM 2018/2019

The structural formula of compound H is shown below.

(a) Name the functional group of compound H.

(b) Suggest a synthetic pathway to prepare H via Grignard reagent and propanal.
(c) Compound H reacts with J to form K, C10H20O2, in the presence of a few drops of sulphuric
acid. Draw the structural formula of J. State the function of sulphuric acid.
[7 marks]

47
Chapter 9: Carbonyl Compounds
TUTORIAL QUESTIONS CHAPTER 9

1. Give the IUPAC name for each of the following aldehydes and ketones:
(a) (d)

(b) (e)

(c) (f)

2. Draw the structural formulae for each of the following compounds:

(a) 2-ethyl-3-methylpentanal
(b) 4-chloro-2-methyl-3-hexanone

3. Draw the structural formulae and give IUPAC names for

(a) seven isomeric carbonyls with molecular formula C5H10O
(b) aldehydes and ketones with molecular formula of C8H8O containing a benzene ring

4. Show the preparation of propanal from the following compound.

(a) 1-propanol
(b) 3-hexene
(c) Ethane

5. Draw the structural formula for the products formed when propanal reacts with:
(a) NaBH4 in methanol
(b) C6H5MgBr followed by hydrolysis

48
6. Complete the following reactions:
(a)

(b)

(c)

(d)

(e)

7. Complete the following reaction scheme. Draw the structural formulae of A to E. Identify
reagents I to III.

KMnO4, H+
Heat

49
8. Show the synthetic pathway for the following conversions.
(a) from propanone to propene
(b) from propanal to 1-bromopropane

9. Compound X has the molecular formula of C5H10O. It does not react with Fehling’s solution
but can be reduced to an alcohol with LiAlH4. Draw all the possible structural formula of X.

10. Suggest the chemical test to distinguish the following compounds. State the observation and
write the equation:
(a) Propanal and propanone
(b) 2-pentanone and 3-pentanone

11. Compounds W and X have the molecular formula of C8H8O. W reacts with hot Fehling’s
solution producing a red precipitate. X gives negative result towards Fehling’s test but it reacts
with LiAlH4 followed by hydrolysis to form alcohol Y. Both X and Y react with iodine in
NaOH solution to yield a yellow precipitate. Deduce the structural formulae of W, X and Y.

50
 PAST YEAR COLLECTIONS CHAPTER 9

PSPM 2020/2021

The structural formula of propiophenone is shown below.

Compound M and N are isomers of propiophenone. M reacts with a solution of iodine in aqueous
sodium hydroxide solution to form a yellow precipitate. Meanwhile N, which rotates plane polarized
light, forms a silver mirror when treated with Tollens’ reagent.
(a) Deduce the structural formulae of M and N.
(b) Draw the chemical equations for all the reactions involved.
[7 marks]

PSPM 2019/2020

(a) Based on the following reaction scheme, draw the structural formulae of Q, R and S.

[3 marks]

(b) Compound T, C4H8O forms an orange precipitate with Brady’s reagent. Treatment of T with
alkaline iodine solution gives a yellow precipitate.
(i) Explain the observation and draw the structural formula of T.
(ii) Ozonolysis of alkene U produces only T. State the reagent used and suggest alkene U.
[5 marks]

51
PSPM 2018/2019

(a) Arrange the following compounds in ascending order of boiling point. Explain your answer.

CH3CH2CH2COH CH3CH2CH2COOH CH3CH2CH2CH2OH

L M N

(b) Based on the following reaction scheme, draw the structural formulae of P and T, and give
reagents Q, R and S.

[8 marks]

52
Chapter 10: Carboxylic Acids
and Its Derivatives
TUTORIAL QUESTIONS CHAPTER 10

1. Give the IUPAC names for the following carboxylic acids.

(a) CH3(CH2)5COOH
(b) O

OH

(c) CH3(CH2)4CH(COOH)2
(d) CH2 CH3 O
CH CH2 CH2 CH2 CH2 C OH

(e) CH2 CH3

CH3 CH CH2 C OH
O

2. Draw the structural formula for each of the following compounds:

(a) 2-hydroxy-2-phenylethanoic acid
(b) 2-chlorobutanedioic acid
(c) o-hydroxybenzoic acid

3. Arrange the following in order of increasing boiling point. Explain your answer.
pentanal, butanoic acid, pentane, 1-butanol

4. Arrange the following compounds in order of increasing acidity and explain your answer.
(a) CH2ClCOOH, CH3COOH, CH3CH2OH, CH2FCOOH, CHF2COOH
(b) Ethanoic acid, phenol, 2-chloroetanoic acid and ethanol

53
5. Identify compounds A to J in the following reactions.
(a) Cl
i. KMnO4, OH−, 
CH3 CH CH2 CHO A
ii. H+

(b) +
K2Cr 2O7 , H
CH3 CH2 CH2OH B

(c) C + NaOH ⎯→ CH3CH2COONa + H2O

(d) conc H 2 SO4

CH3OH + D ⎯⎯⎯⎯⎯⎯→ CH3CH2COOCH3 + H2O

(e) CH2COOH E CH2COCl

+ HCl + SO2

i) LiAlH
i) LiAlH 4
4/ether
CH 3CH 2COOH
(f) ii) H3O+ F

(g)

(h)

(i) Mg
CH3CH 2CH 2COOH ⎯⎯⎯ → J

6. Based on the reaction scheme below:

(a) Draw the structural formulae for compound M.

(b) Give reagent R.

54
7. Show how propanoic acid may be converted to each of the following compounds:
(a) CH3CH2CH2COOH
(b) O
CH3 CH2 CH2 CH2 O C CH2 CH3

(c) O
CH3 CH2 C Cl

(d) 2-propanol

8. An Organic compound, P has the molecular formula, C3H6O. It reacts with Cr2O72-/H+ to form
Q. Q reacts with ethanol to give sweet smelling liquid, R. The reaction is catalyst by
concentrated sulphuric acid.
(a) Identify P, Q and R. Write the equation for the reaction involved.
(b) Suggest suitable Grignard reagent can be used to produce Q.

9. Explain why methanoic acid give positive result with Tollens’ test and acidified potassium
permanganate but ethanoic acid does not.

10. (a) Define condensation polymerization.

(b) When compound P, C8H10 is refluxed with acidified potassium permanganate solution,
the product is Q, C8H6O4. When Q reacts with methanol in the presence of an acid
catalyst, compound R C10H10O4 is formed, which is a monomer of Dacron. Predict the
structure of P, Q and R.

11. (a) Draw the structural formula of

i. hexanedioic acid
ii. 1,6-hexanediamine
(b) Write an equation for the reaction between both compounds to form a polymer.
(c) Name the functional group of the polymer formed in (b).
(d) Write the repeating unit of this polymer.
(e) Give the general name of this polymer.
(f) Name the type of polymerisation.

12. Draw the monomers for the polymer given below.

55
 PAST YEAR COLLECTIONS CHAPTER 10

PSPM 2020/2021

Compound P and Q have molecular formula of C3H6O2. Compound P has a vinegar smell, while Q
has sweet smelling odour. Compound P reacts with phosphorus (V) chloride and releases white
fumes. Acidic hydrolysis compound Q gives two products, one of the products has reducing
properties.
(a) Deduce the structural formulae of P and Q.
(b) Write the chemical equation for all the reaction involved.
(c) Show how P can be prepared from bromoethane via two-step synthesis.
[9 marks]

PSPM 2019/2020

(a) Arrange the compounds below in order of increasing acidity. Explain your answer.
Propanoic Acid 2-chloropropanoic acid Phenol
[4 marks]

(b) Show a two-step synthesis for the following compounds:

(i) Pentanoic acid from 1-bromobutane
(ii) Butanoyl chloride from an alkene containing eight carbon atoms.
[6 marks]

(c) Draw the structural formula of the repeating unit when the monomers below undergo
condensation reaction.
H2N(CH2)6NH2 and ClCO(CH2)4COCl
[1 marks]

56
PSPM 2018/2019

(a) Treatment of 2-phenylethanoic acid with alcohol U gives an ester V with molecular formula of
C11H14O2. Alcohol U reacts with alkaline iodine solution to form a yellow precipitate W, where
as oxidation of U yields X.
(i) Draw the structures for U, V, and X.
(ii) Write all chemical equations involved.
(iii) Give IUPAC name of W.

(b) Explain why methanoic acid gives positive test towards Tollens’ reagent but ethanoic acid does
not. Write the equation for this reaction.
[10 marks]

(c) The structure of Kevlar is as shown below.

Write the structural formulae of its monomers.

[2 marks]

57
Chapter 11: Amines
TUTORIAL QUESTIONS CHAPTER 11

1. Classify the following amines as 1, 2 or 3 and give their IUPAC names:
(a) CH3CH2CH2NH2
(b) CH(CH3)2
CH3 CHNH
CH3
(c) C6H5CH(CH3)CH2NH2
(d) NH2

Cl
(e) C6H5 N CH2 CH3
CH2 CH2 CH3
2. Draw the structural formulae for the following compounds:
(a) 2-propanamine
(b) 3-aminobenzoic acid
(c) N-butyl-N-ethylaniline
(d) N,N-dimethyl-1-butanamine
(e) trimethylamine

3. (a) Explain why the boiling point of N, N-dimethylmethanamine is 4oC while 1-propanamine
is 49oC
(b) Compare the solubility of trimethylamine and methylamine in water. Explain your
answer.

4. Arrange the following compounds in ascending order of boiling point and explain your answer.
1-propanol, ethanoic acid, chloroethane, 1-propanamine

58
5. Identify A to E in the following reactions.

(a) CH3CONHCH2CH3 ⎯→ (CH3CH2)2NH

i. LiAlH4
(b) (CH3)3CCH2CN B
ii. H2O

(c) C
(CH3)2CHCONH2 ⎯⎯→ CH3CH(CH3)CH2NH2

(d) NH2
Sn, HCl
D
NH2

(e)

6. Based on the reaction below, draw the structure of J, K, L M, and N

NaNO2, HCl

59
7. Write the reaction equation for the reaction between nitrous acid, HNO2, and:
(a) Ethanamine
(b) N- Methylmethanamine
(c) N,N-dimethylethanamine
(d) Aniline

8. Show how each of following compounds can be synthesized:

(a) 2-methyl-1-propanamine from 2-propanol
(b)
N N O H from benzene

9. Suggest a chemical test to distinguish:

(a) aniline from benzamide
(b) ethanamine from N,N-diethylethanamine

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 PAST YEAR COLLCTIONS CHAPTER 11

PSPM 2020/2021

Amines can be classified into primary, secondary and tertiary amines. By using an amine with
molecular formula C4H11N:
(a) draw the structural formulae for primary, secondary and tertiary amines.
(b) Arrange the above amines in order of increasing boiling point. Explain your answer.
[7 marks]

PSPM 2019/2020

An amine, C3H9N has three isomers, V, W and X.

(a) Draw the structural formulae of V, W and X.
(b) Suggest a chemical test to distinguish between V, W and X. State the observation and write the
chemical equations involved.
[8 marks]

PSPM 2018/2019

(a) The reaction scheme below shows the formation of a dye DD from benzene.
(i) Give the reagents AA and CC and draw the structural formulae of BB and DD.
(ii) Name the reaction for the formation of DD.

(b) N-methylamphetamine is a potent central nervous system stimulant that is mainly used as a
recreational drug. The structure of N-methylamphetamine is shown below.

Name a chemical test to distinguish N-methylamphetamine from aniline. State the observation
and write the chemical equation.
[8 marks]

61
Chapter 12: Amino Acids
TUTORIAL QUESTIONS CHAPTER 12

1. (a) Define -amino acid.

(b) Name the following -amino acids using the IUPAC nomenclature:

NH2 CHCOOH
(i)
CH(CH3)2

NH2 CHCOOH
(ii)
CH2C6H5

NH2 CHCOOH
(iii)
CH2OH

NH2 CHCH2 CH2 COOH

(iv)
COOH

2. Draw the structural formulae of the following compounds:

(a) 2-amino-4-methylpentanoic acid
(b) 2-amino-3-hydroxybutanoic acid
(c) 2-amino-3-methylpentanoic acid

3. (a) What is zwitterion?

(b) Draw the structure of zwitterion for glycine, 2-aminoethanoic acid.

4. (a) What is meant by an isoelectric point?

(b) The isoelectric point of valine, 2-amino-3-methylbutanoic acid is 6. Predict the structural
formula of valine at:
(i) isoelectric point
(ii) pH 12
(iii) pH 1

62
5. The structural formula of tyrosine is
COOH
HO CH2 CH
NH2
Predict the structural formula of the product formed when tyrosine reacts with:
(a) NaOH(aq)
(b) HCl
(c) CH3OH in the presence of concentrated H2SO4, reflux
(d) NaNO2 in HCl

6. (a) What is a peptide bond?

(b) Write the reaction between phenylalanine and glycine to produce a dipeptide Phe-Gly.
H COOH
H2N C COOH
H2N CH CH2
H

Glycine Phenylalanine

7. (a) All amino acids are optically active except glycine, 2-aminoethanoic acid. Explain this
statement by using serine, 2-amino-3-hydroxypropanoic acid.
(b) Draw all possible stereoisomers of serine.

8. The structure of amino acid CC is shown below.

NH2

C H2C HC OOH

CC
Compound CC reacts with dilute mineral acid to form DD, whereas EE is formed when CC
is treated with nitrous acid. Condensation two moles of CC forms a dipeptide FF. Give
IUPAC name for CC and draw the structure of its zwitterions. Draw the structure of DD,
EE and FF. Show the peptide bond in FF.

63
 PAST YEAR COLLECTIONS CHAPTER 12

PSPM 2020/2021

Dipeptide R has molecular formula of C5H10O4N2. When R is heated with dilute sulphuric acid, two
amino acids, S, C2H5O2N and T, C3H7O3N , were produced. Compound T is optically active, while
S is not.
(a) Draw the structural formulae for S and T.
(b) Draw the structural formula for R and label the peptide linkage.
[4 marks]

PSPM 2019/2020

(a) The structural formula of tyrosine is shown below.

Write the chemical equations when tyrosine reacts with:

(i) NaOH solution
(ii) HCl solution
(iii) Methanol with traces of concentrated sulphuric acid.

(b) Explain why tyrosine can react with acid and base.
[4 marks]

PSPM 2018/2019

Amino acid has amphoteric properties. By using serine below as an example,

(a) Explain what is meant by amphoteric species.

(b) Write chemical equations to show the amphoteric properties.
[4 marks]

64