TUTORIAL CHEMISTRY SK025

CHAPTER 9.0 : THERMOCHEMISTRY SK O25

4HCl(g) + O2(g) ⎯→ 2H2O(l) + 2Cl2(g) ΔH = −148.4 kJ Ans: −988.4 kJ
HF(l) ⎯→ ½H2(g) + ½F2(g) ΔH = + 600.0 kJ
H2(g) + ½O2(g) ⎯→ H2O(l) ΔH = −285.8 kJ

6. Given:
Hf [CaSO4.½ H2O] = −1573 kJ mol−1

Hf [CaSO4. 2 H2O] = −2020 kJ mol−1

Hf [H2O] = −293 kJ mol−1

Calculate ∆H (in kJ) for the reaction:

CaSO4.½H2O(s) + 32 H2O(l) ⎯→ CaSO4.2H2O(s) Ans: −7.5 kJ

7. Lattice energy for potassium fluoride is −821 kJ mol−1 and its enthalpy of hydration is −819 kJ mol−1.

Calculate enthalpy of solution for potassium fluoride. Ans: + 2 kJ mol-1

8. Construct a Born-Haber cycle diagram from the data below to determine the electron affinity of
bromine atom.

Reactions ΔH° (kJ)

½Br2(l) ⎯→ Br(g) +112

Rb(s) ⎯→ Rb(g) +82

Rb(g) ⎯→ Rb+(g) + e +400

Rb+(g) + Br-(g) ⎯→ RbBr(s) −658

Rb(s) + ½Br2(l) ⎯→ RbBr(s) −389

Ans: -325 kJ mol-1

9. 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

CHAPTER 9.0 : THERMOCHEMISTRY SK O25

Second ionisation energy of copper : +1960 kJ mol−1 Ans: - 4097 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

10.

Ca2+(g) + O2-(g)

Ca2+(g) + O(g) + 2e 5
Ca2+(g) + 1/2O2(g) + 2e
4 = +248 kJ

Ca+(g) + 1/2O2(g) + e 3 = +1150 kJ 6 = -3513 kJ
Ca(g) + 1/2O2(g)
Ca(s) + 1/2O2(g) 2 = +590 kJ
1 = +193 kJ
CaO(s) 7 = -635 kJ

(a) Calculate ∆H5. Ans: +697 kJ mol−1

(b) Calculate the first electron affinity if the second electron affinity of oxygen is +844 kJ mol−1.
Ans: -147 kJ mol−1

(c) Would the value of ∆H2 be larger or smaller for magnesium than it is for calcium? Explain
your answer.

Edited By: NAG, MPJ Revised By: AO

Approved By: FU

3.0 : ELECTROCHEMISTRY SK O25

SECTION A

1. Consider the half-cells below:

System Half-cell reaction Eº /V

I Ba2+ + 2e− ⎯→ Ba -2.9

II Cr3+ + 3e− ⎯→ Cr -0.74

III Co2+ + 2e− ⎯→ Co -0.28

IV PbO2 + 4H+ + 2e− ⎯→ Pb 2+ + 2H2O +1.17

Which of the following combinations give the highest e.m.f?

A I and II

B II and III

C II and IV

D I and IV

2. In the electrolysis of dilute sulphuric acid, how many Faradays, F, are required to TUTORIAL 3.0: ELECTROCHEMISTRY
produce 112 cm3 of gas at the anode measured at s.t.p.?
[1 mol of gas occupies 22.4 dm3 at s.t.p]

A F/200
B F/100

C F/50

D F/25

3. A certain quantity of electric charge produces 5.0 g of silver from an aqueous
solution of silver nitrate. When the same amount of charge is passed through an
aqueous solution containing the Xn+ ions, 3.02 g of X is produced. What is the value
of n? [Mr X = 197]

A1

B2

C3

D4

Unit Kimia, KMKt 2020/2021 1

3.0 : ELECTROCHEMISTRY SK O25

4. Consider the following half-cells: E = +0.74 V
Fe3+ + e− ⎯→ Fe2+ E = +0.55 V
I2 + 2e− ⎯→ 2I− E = +0.15 V
Sn4++ 2e− ⎯→ Sn2+ E = −2.33 V
Ce3+ + 3e− ⎯→ Ce

It can be concluded that iodine will
A reduce Fe2+ to Fe3+
B reduce Sn4+ to Sn2+
C reduce Ce3+ to Ce
D oxidise Ce to Ce3+

5. The e.m.f. of the following cell under standard conditions is +2.46 V. TUTORIAL 3.0: ELECTROCHEMISTRY
Al(s) | Al3+(aq) || Ag+(aq) | Ag(s)
Which statement is true about the cell?
[ +/ = +0.80 ]
A Al acts as the cathode.
B Ag+ acts as an oxidising agent.
C The standard reduction potential of Al half-cell is +1.56 V.
D The dissolved mass of Al is the same as the produced mass of Ag.

6. The cell diagram for a galvanic cell is shown below.
Fe(s) | Fe2+(aq) || H+(aq) , H2O(l) | O2(g) | Pt(s)
Which statement is true about the cell?
A The standard e.m.f. of the cell is positive.
B A colourless solution is observed at the anode.
C The concentration of H+ increases at the cathode.
D Electrons flow from the platinum electrode to the iron electrode.

Unit Kimia, KMKt 2020/2021 2

3.0 : ELECTROCHEMISTRY SK O25

7 The Nernst equation is written as:

= − 0.059 log


For the reaction Mg(s) + 2H+(aq) → Mg2+(aq) + H2(g), Q may be expressed as

A [ 2+]
[ ][ +]2

B [ 2+] 2
[ ][ +]2

C [ 2+] 2
[ +]2

D [ +]2
[ 2+] 2

For questions followed by three answer options with one or more possible answers,
choose the most approriate answer from the options given below :

A B C D
I only I and II only II and III only I, II, and III

8. The diagram below shows the arrangement of an electrochemical cell. TUTORIAL 3.0: ELECTROCHEMISTRY
V

iron Metal M

FeSO4(1 salt deposit of
bridge Mx+

The standard electrode potentials of some metals are given below:

Electrode system Eº/V
Ag+(aq)|Ag(s) +0.80
Cu2+(aq)|Cu(s) +0.34
Fe2+(aq)|Fe(s) -0.44

Unit Kimia, KMKt 2020/2021 3

3.0 : ELECTROCHEMISTRY SK O25

Zn2+(aq)|Zn(s) -0.76

Which solution is suitable to be used as +?

I AgNO3

II CuSO4

III ZnSO4

9. Which of the following solution(s) will produce hydrogen gas when electrolysed
using platinum electrode?
I dilute sodium hydroxide
II dilute sodium chloride
III dilute hydrochloric acid

10. Which of the following statements is/are correct regarding the anode of a
galvanic cell?
I It is the negative terminal of the cell

II Oxidation takes place at the anode

III Electrons flow from the anode of the galvanic cell

SECTION B

1. (a) Define standard electrode potential. TUTORIAL 3.0: ELECTROCHEMISTRY

(b) Given :

Al3+(aq) + 3e- ⎯→ Al(s) Eo = -1.66 V

Pb2+(aq) + 2e- ⎯→ Pb(s) Eo = -0.13 V

A galvanic cell consists of an Al electrode in 1.00 M Al(NO3)3, a Pb electrode

in 1.00 M Pb(NO3)2 and a KCl salt bridge.

i. Draw and label the cell diagram.

ii. Write cell notation of the reaction.

iii. Write the overall cell reaction.

iv. Calculate the standard cell potential.

v. Which electrode will increase in weight? Explain your answer.

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3.0 : ELECTROCHEMISTRY SK O25

2. (a) Standard electrode potentials for Ag+|Ag and Pb2+|Pb are +0.799 V and

-0.126 V respectively.

i. Determine the anode and the cathode.

ii. Calculate the standard cell potential. (+0.925 V)

(b) For the reaction,

2Ce4+ (aq) + Co(s) ⎯→ 2Ce3+ (aq) + Co2+ (aq) E° = +1.89 V

The standard reduction potential for Co2+ is −0.28 V. Calculate the standard

reduction potential for the change of Ce4+ to Ce3+. Of the following, which

species is reducing agent? (+1.61V)

3. (a) What will happen if Fe3+ is added to a solution containing I− at 25°C? Give

your prediction by assuming all of the species involved are at their standard

state. E0 = +0.53V
I2(s) + 2e- → 2I-(aq) E0 = +0.77V
Fe3+(aq) + e- → Fe2+(aq)

(b) Based on the cell notation below,

Ag(s) | Ag+ (aq, 1.0M) || M3+(aq, 1.0M) | M(s) ° = +1.00 V

i. write a balanced equation for the spontaneous reaction in the cell.

ii. name the oxidising agent. (+1.80 V) TUTORIAL 3.0: ELECTROCHEMISTRY
iii. calculate ° 3+|
[ ° +| = +0.80 V]

4. The magnitudes of the standard reduction potentials of two metals X and Y are as

follows: Y2+ + 2e- → Y | °|= 0.34V

X2+ + 2e- → X | °|= 0.25V

| °| denotes only the magnitude (not the sign) of the E value shown. When the

half-cells of X and Y are connected, electrons flow from X to Y. However, when X

is connected to a Standard Hydrogen Electrode (SHE), electrons flow from X to

SHE.

Unit Kimia, KMKt 2020/2021 5

3.0 : ELECTROCHEMISTRY SK O25

(a) Are the E° values of the half-cell reactions positive or negative?

(b) What is the standard emf of a cell consisting of X and Y electrodes?

(+0.59 V)

5. Consider a Galvanic cell consisting of a Zn2+/Zn and hydrogen electrode half cells.

An experiment is carried out to determine the emf ( ) of the cell. The zinc
electrode is immersed in a 1.0 M Zn2+ solution and the pressure of hydrogen gas

is 1 atm. The cell potential obtained at 250C is 0.54 V.

( ° 2+|Zn= -0.76 V and ° +| = 0.00 V)

(a) Calculate the concentration of hydrogen ion. (1.923 x 10-4 M)

(b) Write cell notation for the reaction.

6. The standard reduction potentials of Zn2+ and Mg2+ are given below:

Mg2+(aq) + 2e- Mg(s) ° = -2.37 V

Zn2+(aq) + 2e- Zn(s) ° = -0.76 V

Calculate the equilibrium constant, K for the reaction when = 0 (2.47x1054)

7. Determine the products formed at each electrode in the electrolysis of: TUTORIAL 3.0: ELECTROCHEMISTRY

(a) Molten NaCl
(b) concentrated aqueous solution of NaI.
(c) aqueous solution of NaNO3.
(d) aqueous solution of Cu(NO3)2 using:

i platinum electrodes
ii a copper anode and a platinum cathode

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

(a) State Faraday’s law of electrolysis.

(b) Write the half-reactions of the electrolysis.

(c) If a current of 0.50 A was supplied for 30 minutes, how many grams of barium

metal deposited. (0.64 g)

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3.0 : ELECTROCHEMISTRY SK O25

9. One of the half-reactions for the electrolysis of water is
2H2O(l) ⎯→ O2 (g) + 4H+(aq) + 4e−

If 10.00 L of oxygen gas is collected at 25°C and 755 mmHg,

(a) Calculate the electrical charge in coulombs that had passed through the

solution. (156 677.4 C)

(b) How long does it takes for collecting oxygen gas if a current of 12 A is used?

(217.61 minutes)

10. A student passes the same quantity of current through two electrolytic cells, one
containing silver (Ag) salt and the other containing gold (Au) salt. Over a period of
time, she finds that 2.64 g Ag and 1.61 g of gold are deposited at the cathode.

(a) Calculate the charge passed through the cells. (0.0245 F)
(b) What is the oxidation state of gold in the salt? (+3)

(Hint: the oxidation state of silver is +1)

TUTORIAL 3.0: ELECTROCHEMISTRY

Unit Kimia, KMKt 2020/2021 7

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

SECTION A

1. Isomers that have the same formula but differ in their structure are called
A. structural isomers
B. Stereoisomers
C. Geometric isomers
D. Optical isomers

2. What type of isomers are CH3CH2OCH3 and CH3CH2CH2OH?
A. Chain
B. Constitutional
C. Positional
D. Functional groups

3. Which one of the following molecules do cis-trans isomers exist? TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY
A. H2C=CH2
B. (Br)HC=CHCl
C. CH2(Cl)CHBr l
D. H2C=CCl2

4. Which of the following is the definition of a pair of enantiomers?
A. A pair of structures that are superimposable mirror images of one another
B. A pair of stereoisomers that non superimposable mirror images of one
another
C. A pair of stereoisomers that are not mirror images of one another
D. A pair of stereoisomers that have equal specific rotations

Unit Kimia, KMKt 2020/2021

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

5. Which of the following is a chiral molecule? TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY
A. CH2BrI
B. CH3CBr2Cl
C. (CH3)2CHCl
D. CH3CHBrCH2CH3

6. In heterolytic fission, _____ are formed. In homolytic fission, _____ are formed.
A. one free radical and one cation; one free radical and one anion
B. free radicals; a cation and anion
C. one free radical and one anion; one free radical and one cation
D. a cation and anion; free radicals

7. Which of the following free radical is the most stable?
A. CH3
B. CH3CH2
C. (CH3)2CH
D.
CH3

8. Which of the following statements about nucleophiles and electrophiles are
always true?
A. Nucleophile has a lone pair of electrons while electrophile accepts a pair of
electrons
B. Nucleophile is a negative ion while electrophile is a positive ion
C. Nucleophile attacks double bonds while electrophile is only involved in
substitution reactions
D. Nucleophile accepts a pair of electrons while electrophile has a lone pair of
electrons

Unit Kimia, KMKt 2020/2021

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

9. Which of the following species is NOT an electrophile? TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY
A. NH3
B. Br2
C. HBr
D. AlCl3

10. What type of reaction does the conversion of A to B represent?

CH3CHClCH3 ⎯K⎯OH⎯, alc⎯o⎯hol→ CH2=CHCH3 + HCl
AB

A. Addition reaction
B. Elimination reaction
C. Substitution reaction
D. Rearrangement

Unit Kimia, KMKt 2020/2021

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

SECTION B

1. (a) Define the term isomerism, constitutional isomerism and stereoisomerism.

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

2. (a) What are the essential requirements for a molecule to exhibit cis-trans
(b) isomerism?
Which of the following compounds can exist as a pair of cis-trans
isomers? Draw the cis-trans isomers. TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY

i. ClCH=CHCl
ii. CH3CH=CH2
iii. CH3CH2CH=CHCH3
iv. (CH3)2C=C(CH3)CH2CH3

Br Br
v.

3. (a) Draw and label the cis-trans isomers of 1,2-dichloroethene.
(b) Suggest which of the isomers has:

i. higher boiling point
ii. higher melting point.
Explain your answers.

Unit Kimia, KMKt 2020/2021

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

4. (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

5. (a) State the structural features of a molecule in order 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).

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

7. Arrange the following carbocations in order of increasing stability. TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY

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

H+ +

8. (a) Define the terms electrophile and nucleophile.

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

i. NH3 vi. BF3

ii. Br• vii. CO2

iii. H2O viii. CH3CH=CH2
iv. NO2+ ix. CH3OH
v. Cl+ x. PCl5

Unit Kimia, KMKt 2020/2021

CHAPTER 4.0 : INTRODUCTION TO ORGANIC CHEMISTRY SK O25

9. State the type of reactions:

(a) O O
C Cl
C OH SOCl2

(b) CH2=CH2 + HCl ⎯→ CH3CH2Cl

(c)

CH2=CH2 + H2O H2O CH3CH2OH
H2SO4

(d) CH3CHBrCH3 ⎯K⎯OH⎯, alc⎯o⎯hol→ CH2=CHCH3 + HBr

(e) CH4 + Br2 ⎯⎯uv→ CH3Br + HBr

(f) NO2 TUTORIAL 4.0 INTRODUCTION TO ORGANIC CHEMISTRY
+ conc.HNO3 conc. H2SO4

(50-55)0C

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

10. Based on the reaction scheme below, state the type of reaction corresponding to

steps A, B and C.

CH3 CH CH2 CH3 Br2 Br
CH3 CH3CCH2CH3
uv
CH3
A
B KOH/ethanol

Br HBr CH3 C CH CH3
CH3
CH3 C CH2 CH3 C
CH3

Unit Kimia, KMKt 2020/2021

5.0 : HYDROCARBON SK O25

5.1 ALKANE

SECTION A
1. The following compounds are alkanes EXCEPT

A C5H12
B C6H12
C C7H8
D C7H14

2. Choose the true statement about an alkane.
A It undergoes electrophilic addition with chlorine gas.
B It undergoes nucleophilic substitution with chlorine gas.
C It undergoes free radical substitution when reacts with chlorine gas.
D It undergoes electrophilic substitution with an aqueous chlorine solution.

3. What is the IUPAC name for the following compound?
CH3

CH3 CH2 CH2 CHCH2 C CH3
CH2 CH3

A 5-cyclohexyl-3,3-dimethyloctane TUTORIAL 5.0 : HYDROCARBON
B 4-cyclohexyl-6,6-dimethyloctane
C 4-cyclohexyl-6-ethyl-6-methylheptane 1
D 2-ethyl-4-phenyl-2-methylheptane

4. Which of the following reaction is a free radical substitution?
A Hydrolysis of alkanes
B Combustion of alkanes
C Halogenation of alkanes
D Hydrogenation of alkanes

Unit Kimia, KMKt 2020/2021

5.0 : HYDROCARBON SK O25

5. Which of the following alkane has the lowest boiling point?
A C5H10
B (CH3)4C
C (CH3)2CHCH2CH3
D CH3CH2CH2CH2CH3

6. Ethane and bromine react in the presence of sunlight but not in the dark. Sunlight
is needed to initiate
A the heterolytic fission of C-H bonds to form carbanion.
B the homolytic fission of C-H bonds in ethane molecule.
C the homolytic fission of Br-Br bonds in bromine molecule.
D the heterolytic fission of bromine molecule to form bromide ions.

7. Which of the following is a propagation step in the reaction between ethane and
chlorine
A Cl2 ⎯→ 2Cl•
B •CH2CH3 + •Cl ⎯→ClCH2CH3
C •Cl + CH3CH3 ⎯→ •CH2CH3 + HCl
D •CH2CH3 + HCl ⎯→ CH3CH2Cl + H•

For questions followed by three answer options with one or more possible answers,
choose the most approriate answer from the options given below :

A B C D TUTORIAL 5.0 : HYDROCARBON
I only I and II only II and III only I, II, and III

8. Combustion of alkanes may produce
I water
II carbon dioxide
III carbon monoxide

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5.0 : HYDROCARBON SK O25

9. Which of the following is/are true about the C-H bond in alkane?
I It is not polar.
II It undergoes substitution with chlorine.
III It reacts faster with bromine than chlorine.

10. Which of the compound(s) below give(s) 3 monobromoalkanes when reacted
with bromine in the presence of light?
I hexane

II 2,2-dimethylbutane

III 2,3-dimethylbutane

SECTION B TUTORIAL 5.0 : HYDROCARBON
1. Name the following compounds according to the IUPAC nomenclature:

a) CH3
CH3 C CH2 CH2 CH3
CH3 CHCH3

b) CH3CHCH3

CH3CHCH2CHCHCH3

CH2CH3 CH2CH3

c) CH3

CH3CH2 CH3

d) Br CH3
H3C
CH2CH3

Unit Kimia, KMKt 2020/2021 3

5.0 : HYDROCARBON SK O25

2. Draw the structural formula for each of the following compounds:
a) 1,1-dichloro-3-methylcyclohexane
b) 2,2-dimethyl-3-cyclohexylbutane
c) 1-bromo-5-chloro-3-ethyl-3-methylpentane
d) 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, cyclopentane

c) (CH3)2CHCH3, (CH3)4C, CH3(CH2)2CH3, CH3(CH2)3CH3

4. Explain why butane is soluble in benzene but insoluble in water.

5. Write a balanced chemical equation for the combustion of propane in
a) excess oxygen
b) limited oxygen

6. A mixture of propane and bromine is exposed to sunlight. The reaction equation
is given below.
CH3CH2CH3 + Br2 ⎯⎯uv→ A

a) State the type of the reaction. TUTORIAL 5.0 : HYDROCARBON
b) What is the function of sunlight in the reaction?
c) Draw the structure of the monosubstituted product, A.
d) Write the mechanism for the formation of the product.
e) Give the observation of the reaction.
f) What would happen if the mixture is kept in the dark at room temperature?

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5.0 : HYDROCARBON SK O25

7. Reaction between an alkane with molecular formula C5H12 with Cl2 in the presence
of sunlight gives only product C5H11Cl. Write the reaction equation and mechanism
for the formation of the product.

5.2 ALKENE

SECTION A

1. The IUPAC name for the following compound is

CH3 CH3
C= C CH2CH(CH3)CH3

C2H5

A cis-3, 4, 6-trimethylhept-3-ene
B trans-3, 4, 6-trimethylhept-3-ene
C cis-2-ethyl-3, 5-dimethylhex-2-ene
D trans-2-ethyl-3, 5-dimethylhex-2-ene

2. By using Saytzeff’s rule, the most stable alkene is TUTORIAL 5.0 : HYDROCARBON
A (C2H5)2C=CH2
B CH2=CHC4H9
C (CH3)2C=C (CH3)2
D C2H5CH=CHC2H5

3. Dehydration of an alcohol is shown below.

CH3 OH conc. H2SO4 major product
H3C C C CH3 

CH3 H

The major product formed is

Unit Kimia, KMKt 2020/2021 5

5.0 : HYDROCARBON SK O25

A CH3

CH3 C C CH2

CH3 H

B CH3

CH3 C C CH3

CH3

C CH3 CH C CH2

CH3 CH3

D CH3

CH3 C CH CH2
CH3

4. Which alkene produces ethanoic acid and butanone when reacted with hot acidified
KMnO4 solution?
A CH3CH=CHCH3
B CH3CH=C(CH3)2
C CH3CH=CHCH2CH3
D CH3CH=C(CH3)CH2CH3

5. When propene is oxidised by cold, dilute KMnO4 in NaOH solution, the product TUTORIAL 5.0 : HYDROCARBON
formed is

A CH3 CH CH3

OH

B CH3CH CH2

O

C CH3CH2CH2OH

D CH3CH(OH)CH2OH

Unit Kimia, KMKt 2020/2021 6

5.0 : HYDROCARBON SK O25

6. Ozonolysis of an alkene produces ethanal, CH3CHO, and propanal, CH3CH2CHO.
The alkene is

A 1-pentene
B 2-pentene
C 3-pentene
D 2-methyl-2-butene

For questions followed by three answer options with one or more possible answers,
choose the most approriate answer from the options given below :

A B C D
I only I and II only II and III only I, II, and III

7. Cyclohexane and cyclohexene can be differentiated by using
I NaOH(aq)
II Bromine water
III Cold KMnO4/OH−

8. Propene reacts with hydrogen halide, HX, according with the equation:

CH3CH = CH2 + HX CH3CHCH3
X

Which of the following statement is/are correct? TUTORIAL 5.0 : HYDROCARBON

I The intermediate is a carbocation.
II The product formed follows Markovnikoff’s rule.

III The rate of reaction increases in order: HCl < HBr < HI

9. Choose the correct statement(s) about anti-Markovnikov addition of propene.

I Platinum can be used to replace peroxides.

II The reaction does NOT occur with HCl in the presence of peroxide.

III The product is 1-bromopropane when it reacts with HBr in presence of
peroxide.

Unit Kimia, KMKt 2020/2021 7

5.0 : HYDROCARBON SK O25

10. Which compound(s) show(s) cis-trans isomerism?
I CH3 – CH2 – CH = CH2
II ClCH2CH = CHCH2Cl
III CH2CH3

Br

SECTION B

1. Give the IUPAC names for the following alkenes:
a) CH3
CH3 C CH2

b) CH3 CH2 CH2 CH2 CH3
CC

HH

c) H3C CH3

d)

e) TUTORIAL 5.0 : HYDROCARBON

2. Draw the structural formula for each of the following alkenes: 8
a) trans-2-hexene
b) cis-4-octene
c) 1,2-dichlorocyclobutene
d) trans-1-chloro-2-butene

Unit Kimia, KMKt 2020/2021

5.0 : HYDROCARBON SK O25

3. The following names are incorrect. Suggest the correct names and give your
reason(s).

a) trans-3-pentene

b) 2-methylcyclohexene

4. Write the equation for the preparation of propene from (a) 2-chloropropane (b) 1-
propanol

5. Draw the structural formulae of compounds A to M in the following reactions:

a) OH CH3 H2SO4 A+ B
H3C C C CH3 heat
CH3 H major minor

b) CH2
C KOH,CH3CH2OH H2C
Heat

c) CH3 CH2 ⎯⎯Pd→ D
C CH2 + H2 E

CH3 CH2 CH2
d) CH3

+ HCl

e) + HBr ⎯C⎯H⎯3O⎯O⎯CH⎯3 → F
H3C CH3
TUTORIAL 5.0 : HYDROCARBON
f) H3O+ CH3 CH3
G + H2O
C CH3

OH

g) H H

H + Cl2 ⎯C⎯C⎯l4→ H3C C C CH3

Cl Cl

h) H H

H3C C C CH2 + Br2 ⎯H⎯2⎯O→ I

H

Unit Kimia, KMKt 2020/2021 9

5.0 : HYDROCARBON SK O25

i) H3C CH3 KMnO4, H+

CH3  J +K

j) CH3 i. O3 L +M
CH3 C CHCH3 ii. CH3 S CH3

6. Outline the synthetic pathway for the formation of
a) 1,2-dibromocyclopentane from bromocyclopentane
b) chlorocyclohexane from cyclohexanol

7. a) Define Saytzeff’s rule.

b) Draw the structural formulae and name the major and minor products for
the following reaction:

OH conc.H2SO4 A+ B
CH3CH2CHCH(CH3)2
Major Minor

c) Write the reaction mechanism for the formation of the major product.

8. Draw the structural formulae of alkenes that would be formed when 2-bromo-3-
methylbutane is subjected to dehydrohalogenation with potassium hydroxide in
ethanol. Predict the major product.

9. a) Define Markovnikov’s rule. TUTORIAL 5.0 : HYDROCARBON

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.

10. Propose a chemical test to differentiate between butane and butene. State the
observation and write the reaction equation involved.

Unit Kimia, KMKt 2020/2021 10

5.0 : HYDROCARBON SK O25

11. 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.

12. Complete the following reaction scheme.

H A B

HBr, ROOR + Br2, H2O

H2O, H

conc. H2SO4 H3C +

G CH3 KMnO4, H , heat C



H2, Pt KOH, etOH -

F E KMnO4, OH , cold

D

Edited by Revised by Approved by TUTORIAL 5.0 : HYDROCARBON
AAA MS FU

Unit Kimia, KMKt 2020/2021 11

6.0: BENZENE AND ITS DERIVATIVES SK O25

SECTION A:
1. Which of the following is NOT a number of Hückel’s rule?

A. 2
B. 6
C. 14
D. 16

2. A hydrocarbon with six carbon atoms is said to be aromatic if
A. It is a cyclic compound.
B. The compound has more than one C=C bond.
C. All of the atoms in the molecule are on the same plane.
D. It is cyclic, planar and has six delocalised π electrons.

3. Name the given structure below

Br

A. p-bromopropylbenzene TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES
B. m-bromopropylbenzene
C. m-bromoethylbenzene
D. o-bromopropylbenzene

4. Choose the correct statement for the reaction below.

NO 2

conc.HNO3 , conc.H2SO4
50 - 55 °C

A. The electrophile is H2SO4.
B. H2SO4 is a Brønsted–Lowry base.
C. Benzene undergoes electrophilic addition reaction.
D. Benzene undergoes electrophilic aromatic substitution.

5. What is the function of Lewis acid in halogenation of benzene?
A. It initiates the formation of halogen radical.
B. It increases the polarity of halogen molecule.

Unit Kimia, KMKt 2020/2021 36

6.0: BENZENE AND ITS DERIVATIVES SK O25

C. It decreases the polarity of halogen molecule.
D. It makes the halogen a stronger nucleophile.

6. The product of the reaction below is

H3C C(CH3)3 KMnO4/H+
Δ

A. COOH
HOOC

B. C(CH3)3
HOOC C(CH3)3

C.
HO

D. C(CH3)3
H3C

A B C D
I only I and II only II and III only I, II, and III

7. What is/are the possible name(s) for the following compound? TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES

OH

OH

I. 1,3-dihydroxybenzene
II. Benzene-1,3-diol
III. 3-hydroxyphenol

8. X, Y CH2Cl
CH3

Choose the correct statement about the above reaction.
I. X and Y are Cl2 and uv light respectively.
II. The reaction is a free radical substitution reaction.

Unit Kimia, KMKt 2020/2021 37

6.0: BENZENE AND ITS DERIVATIVES SK O25

III. The reaction is an electrophilic substitution reaction.

9. The compound that can be used as a catalyst for the Friedel-Crafts alkylation
of benzene is/are

I. AlCl3

II. H2SO4

III. V2O5

10. Which of the following compound(s) can undergo a free radical substitution
reaction with bromine?

I. Hexane

II. Toluene

III. Benzene

SECTION B
1. (a) What is an aromatic compound?

(b) Cyclopropenyl cation is the simplest aromatic compound.
+

i. Draw two other possible resonance structures of this cation. TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES
ii. Describe the aromaticity of cyclopropenyl cation.

2. (a) Name the compounds below according to the IUPAC nomenclature.
i. CH3CH2CHCOOH

ii. I

Br

Unit Kimia, KMKt 2020/2021 38

6.0: BENZENE AND ITS DERIVATIVES SK O25

iii. O
CCH3

F
iv. NH2

(b) Write the structural formulae for each of the following compounds.
i. 1,3,5-trinitrobenzene
ii. m-isopropylphenol
iii. 4-chloro-2,3-dinitrotoluene
iv. Benzaldehyde

3. Complete the following reaction equations and name the compound A, B and C.

(a) Br2 A
(b) H3C FeBr3
(c)
NO2 K2Cr2O7 / H+ B TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES
Δ

H3C FeCl3 C

+ CHCH3
Cl

Unit Kimia, KMKt 2020/2021 37

6.0: BENZENE AND ITS DERIVATIVES SK O25

4. Give the complete equation for the chlorination reaction of benzene and
cyclohexene. State the type of reaction involves.

5. According to the following reactions. CH3
i.
+ CH3Cl AlCl3 + HCl

ii. NO2
+
+ conc.HNO3 conc.H2SO4 H2O
50- 55°C

(a) State the electrophile involved in (i).

(b) State the catalyst in (i) and (ii). What is the function of the catalyst in the
reaction?

(c) Write the reaction mechanism in (ii)

6. Based on the following reaction scheme below;
COCH3

reagent I CH3CH2CH2Cl E Br2, CH2Cl2

F

AlCl3 uv

(a) Write the structural formula of E and F and specify reagent I. TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES
(b) Write the mechanism for the formation of E.

7. Suggest a chemical test to differentiate cyclohexene from benzene. Give the
equation involved and its observations.

8. (a) When an aromatic hydrocarbon G, C8H10 is heated with acidified
potassium manganate (VII), a compound H, C7H6O2 is obtained.
i. Draw the structural formula of G.
ii. Write an equation to show the reaction in (a).

(b) J is an isomer of G. When J is heated with the reagent in (a), a
compound K, C8H6O4 is obtained.
i. Draw the structural formula of J.
ii. Write an equation to show the reaction in (b).

Unit Kimia, KMKt 2020/2021 37

6.0: BENZENE AND ITS DERIVATIVES SK O25

9. Compound L has formula, C7H7Cl
(a) Draw all possible structures of L
(b) Which of the isomer is formed from free radical substitution of toluene?

10. Outline the synthesis of the following compounds from benzene
(a) Benzoic acid
(b) 1-phenylethanol

TUTORIAL 6.0 BENZENE AND ITS DERIVATIVES

Unit Kimia, KMKt 2020/2021 38

7.0: HALOALKANES SK O25

SECTION A
1. What is the IUPAC name for the following compound?

F Cl
Cl C C Cl

H Cl

A. chlorofluorocarbon.
B. trichlorofluoroethane.
C. 1-fluoro-1,2,2,2-tetrachloroethane
D. 1,1,1,2-tetrachloro-2-fluoroethane

2. Haloalkanes are more reactive than corresponding alkanes because
A. haloalkanes are ionic compounds.
B. haloalkanes are polar compounds.
C. haloalkanes are more soluble in water.
D. the size of the halogen atoms are bigger.

3. Iodoethane reacts with hydroxide ion, OH , through SN2 mechanism.What is
the effect of doubling the concentration of OH ?
A. The rate of reaction is doubled
B. The rate of reaction is quadrupled
C. The rate of reaction remains the same.
D. The rate of reaction decrease by factor of 2.

4. A bromoalkane, RBr, is hydrolysed by aqueous sodium hydroxide.The rate
equation for the reaction is
Rate = k[RBr][OH ]
R could be

A.
CH2Br

Unit Kimia, KMKt 2020/2021 40

7.0: HALOALKANES SK O25

B.
Br

C.

Br

D. (CH3)3CBr

5. Which of the following compound is formed when chlorocyclohexane is boiled
with alcoholic potassium hydroxide?

A. OH

OH

B.

C. Cl

OH

D.

A B C D
I only I and II only II and III only I, II, and III

6. Which statement(s) is/are true about the reaction of 2-chloro-2-methylpropane
with aqueous sodium hydroxide?

I. The rate is dependent on the temperature.
II. The rate is proportional to the concentration of 2-chloro-2- methylpropane.
III. The rate is proportional to the concentration of aqueous sodium hydroxide.

7. What is the possible product, M of the following reaction?

Br +

+ H2O H M

Unit Kimia, KMKt 2020/2021 41

7.0: HALOALKANES SK O25

I. OH
II. OH

III.

OH

8. Which of the following reagents can react with haloalkanes in a nucleophilic
substitution reaction?
I. OH
II. CN
III. NH3

9. Which of the following haloalkanes will undergo SN1 reaction?
I. 2-Chloro-2-methylpropane
II. 2-Bromo-2-methylbutane
III. 1-Bromo-4,5-dimethylheptane

10. Which of the following are needed to prepare ethyl ethanoate, CH3COOC2H5?
I. CH3CH2Br
II. CH3COO-
III. C2H5O-

Unit Kimia, KMKt 2020/2021 42

7.0: HALOALKANES SK O25

SECTION B

1. Classify the following compounds as primary, secondary or tertiary haloalkane
and give their IUPAC names.

(a) CH3 (CH2)4Cl
(b) CH3

CH3 CH2 CF
CH(CH3)2

(c) CH2CH2Br

CH3 CH2 CH2 CHCH2 CH2 CH3

(d) CH3C(Cl)2CH3
(e)

CH2Cl

2. Draw the structural formulae of the following compounds:
(a) tert-butyl bromide
(b) isopentyl chloride
(c) 1-bromo-1-isopropylcyclobutane
(d) 4-bromo-3-methyl-2-pentene
(e) 3-(iodomethyl)-3-phenyl-1-pentene

3. Draw the structural formulae of A to G .

(a) 2-bromobutane A B

NaOH(aq) C
(b) 1-chloropropane

(c)

(d) bromocyclopentane F

(e) 2-chloropropane NaOH,Ethanol G
∆

Unit Kimia, KMKt 2020/2021 43

7.0: HALOALKANES SK O25

4. Grignard reagent is an example of organometallic compound which is very
useful in the synthesis of many organic compounds.
(a) Show the preparation of a Grignard reagent from 1-bromo-2-methlypropane.
(b) Use the above Grignard reagent to prepare the corresponding:
i. alkane
ii. 1º, 2º and 3º alcohols
iii. carboxylic acid

5. Complete the following reaction scheme.
C(CH3)2COOCH3

A

C(CH3)2OCH3 C(CH3)2MgCl

CH3COO- B

F CH OH Mg ether B
F 3 dry


C(CH3)2Cl

NH 3 NareOflHux, EtOH
C
excess 

E C(CH3)2NH2 H2O C(CH3)2

E D C(CH3)2OH C (major)

D

6. What is meant by SN1 and SN2?

7. Give three differences between SN1 and SN2 reactions.

Unit Kimia, KMKt 2020/2021 44

7.0: HALOALKANES SK O25

8. Arrange the following compounds in order of increasing reactivity towards SN1
hydrolysis reaction. Explain your answer.

CH3 Br CH2Br

CH3CBr , ,

CH3

9.The SN2 hydrolysis of (CH3)3CCH2Br with aqueous solution of NaOH is 105 times
slower than the hydrolysis of CH3CH2Br. Explain this observation.

10. State and write the reaction mechanism for each of the following reactions:

(a) CH2CH3 KOH(aq) CH2 CH3

Br OH

(b) CH3CH2Cl ⎯⎯Na⎯OH⎯(a⎯q⎯)→ CH3CH2OH

(c) CH3 CH3 CH3

CH3 C CH2 Br NaOH(aq) CH3 C CH2OH + CH3 C CH2 CH3

CH3 CH3 OH
major product

Unit Kimia, KMKt 2020/2021 45

CHAPTER 8.0 : HYDROXY COMPOUNDS SK O25

SECTION A
OBJECTIVE QUESTIONS
1. Which of the following alcohol gives 2-methylpropanoic acid when it is oxidized?

A. 1-butanol
B. 2-butanol
C. 2-methyl-1-propanol
D. 2-methyl-2-propanol

2. When compound X, which is optically active, is warmed with chromic acid, an optically
inactive compound Y is formed. Y does not react with alkaline iodine. X is
A. (CH3)2CHCH2OH
B. C6H5-CH(OH)CH2CH3
C. CH3CH2CH2CH(OH)CH3
D. CH3CH2CH(OH)CH2CH3

3. Compound V gives the following observations:
• It gives positive triiodomethane test.
• It evolves white fumes when reacted with SOCl2.
• It decolourises purple colour of hot acidified KMnO4 solution.

Compound V is
A. CH3CH2OH
B. (CH3)3COH
C. CH3COCH2CH3
D. HOCH2C(CH3)2CH3

4. When bromine is added to phenol, the brown colour of bromine is decolourised and a white
precipitate of 2,4,6-tribromophenol is formed. This is an example of
A. electrophilic addition
B. free radical substitution
C. electrophilic substitution
D. nucleophilic substitution

CHAPTER 8.0 : HYDROXY COMPOUNDS SK O25

A B C D
I only I and II only II and III only I, II, and III

5. Arrange the following compounds in order of increasing boiling point.
I HOCH2CH2OH
II CH3CH2CH2OH
III CH3CH(OH)CH3
IV HOCH2CH2CH2OH

A. II < III < IV < I
B. III < II < I < IV
C. I < IV < III < II
D. II < III < I < IV

6. Phenol and phenylmethanol differ in their reaction with
I. propene.
II. aqueous iron(III) chloride.
III. acidified potassium permanganate solution.

7. 1-butanol can be differentiated from 2-butanol by using
I. alkaline iodine
II. phosphorus(V) chloride
III. acidified potassium dichromate solution

8. Oxidation of 2-pentanol produces compound X. X gives
I. negative reaction with Tollen’s reagent.
II. a yellow precipitate with alkaline iodine.
III. an orange precipitate with 2,4-dinitrophenylhydrazine

9. Which of the following compound(s) could be formed by the dehydration of 1-butanol?
I. 2-butene
II. 1,3-butadiene
III. 2-methyl-1-propene

10. Compound X, C4H10O, can be oxidized to C4H8O2 by acidified potassium permanganate
solution. X could be

I. (CH3)2CHCH2OH

CHAPTER 8.0 : HYDROXY COMPOUNDS SK O25

II. CH3CH2CH2CH2OH
III. CH3CH(OH)CH2CH3

SECTION B
SUBJECTIVE QUESTIONS
1. Give the IUPAC names for each of the following compounds.

(a) Br CH3 (e) H3C CH2 OH
Br CH C OH
CH3 CC

HH

(b) CH3 (f)

CH3 CH2 C CH2OH HO

CH2 CH2 CH3 OH

(c) O2N OH

(d) CH2 CH3 (g) NO2
CHCHCH2 CH2OH O2N OH
CH3
NO2

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

3. 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

4. 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) methanol reacts with PCl5
(e) 1,2-ethanediol with potassium

CHAPTER 8.0 : HYDROXY COMPOUNDS SK O25

(f) 1-hexanol reacts with PCC/CH2Cl2
(g) cyclopentanol reacts with SOCl2

5. Predict the structural formulae of A to D in the reaction series below.

conc. H2SO4 C4H8 (i) O3 2C2H4O
 B (ii) Zn, H2O C

C4H10O
A

K2Cr2O7, H+ C4H8O2
 D

6. Outline the synthesis of the following compounds.
(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) 1-butanol and 2-propanol
(c) benzene and cyclohexanol
(d) 2-methyl-2-butanol and 2-butanol

8. 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.

9. An alcohol C4H10O which has several isomers gave the following observations:

I Isomer L gives negative result with Lucas reagent and forms butanoic acid
when oxidised with acidified potassium dichromate solution.

II Isomer M is optically active and gives positive result with I2/NaOH.

III Isomer N reacts instantly with Lucas reagent but does not decolourise
acidified solution of potassium dichromate.

Explain the above observations and suggest the structural formulae of isomers L, M and N.

10. The structural formula of X is shown below.

CHAPTER 8.0 : HYDROXY COMPOUNDS SK O25

OH

CH2 CH2OH
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 sulfuric acid

9.0 : CARBONYL COMPOUNDS SK O25

SECTION A

1. Acrolein has the following structural formula:
H2C CHCH
O

Which of the following is not true with regards to acrolein?
A It does not exhibit stereoisomerism.
B All the bond angles in the molecule are approximately 90.
C It undergoes electrophilic and nucleophilic addition reactions.
D It decolourises aqueous bromine and acidified potassium dichromate
solution.

2. Choose the suitable Grignard reagent that can be used to prepare
2-methyl-3-pentanol from propanal.
A (CH3)3CMgBr
B CH3CH2MgBr
C (CH3)2CHMgBr
D CH3CH2CH2MgBr

3. Butanal can be distinguished from butanone by using the following reagents TUTORIAL 9.0 CARBONYL COMPOUNDS
EXCEPT
A Schiff’s reagent
B Tollens’ reagent

C Iodoform test

D Bromine water

4. Which of the following would attack the carbon atom in the carbonyl group?
A Nucleophile
B Electrophile
C Free radical
D Carbocation

5. A compound P reacts with

Unit Kimia, KMKt 2020/2021 1

9.0 : CARBONYL COMPOUNDS SK O25

• sodium hydroxide solution
• 2,4-dinitrophenylhydrazine
• phosphorus(III) chloride
P could be

A HO COCH3

B OCOCH3
C HOOC
O
C CH3

D H3C C CH3
O

6. Which of the following alcohols can be oxidised to 2-methyl-3-pentanone? TUTORIAL 9.0 CARBONYL COMPOUNDS
A CH3CH2CH(OH)CH3
B CH3CH(OH)CH2CH2CH3
C (CH3)3CCH(OH)CH3
D (CH3)2CHCH(OH)CH2CH3

7. Which substance would test positively with 2,4-DNPH but negatively with Tollens’
reagent?
A Propanal
B Propanone
C Propanoic acid
D 1-propanol

8. Which reagent would you choose to convert 1-pentanol to pentanal? 2
A PCC in CH2Cl2
B K2Cr2O7 with aqueous H2SO4
C KMnO4 with aqueous H2SO4

Unit Kimia, KMKt 2020/2021

9.0 : CARBONYL COMPOUNDS SK O25

D KOH, ethanol, reflux

For questions followed by three answer options with one or more possible answers,
choose the most approriate answer from the options given below :

A B C D
I only I and II only II and III only I, II, and III

9. 2-Hexanone and hexanal can be distinguished by
I Brady’s reagent
II Tollens’ reagent

III Iodoform test

10. Compound Y gives an orange precipitate with 2,4-dinitrophenylhydrazine and
shows a positive iodoform test.
Y could be
I Ethanal

II Propanone

III 2-Propanol

TUTORIAL 9.0 CARBONYL COMPOUNDS

Unit Kimia, KMKt 2020/2021 3

9.0 : CARBONYL COMPOUNDS SK O25

SECTION B TUTORIAL 9.0 CARBONYL COMPOUNDS

1. Give the IUPAC name for each of the following aldehydes and ketones:

(a) Cl CH3

H3C C CH2 C C O

CH2 CH3 H H

(b) Br

CH3 CHCHC O

CH3 CH3

(c) O

CH3 C CHCH3

CH3

(d) CH3CH2CH2CH2C O
CH3

(e)
O

(f)
CO

CH3
(g)

CH2 C O

CH3

2 (a) Draw the structural formulae and give IUPAC names for
(i) the seven isomeric aldehydes and ketones with the molecular formula of
C5H10O.

(ii) aldehydes and ketones with molecular formula of C8H8O containing a benzene
ring.

(b) Draw the structural formula for each of the following compounds:

(i) 2-ethyl-3-methylpentanal
(ii) 4-methyl-2-pentanone
(iii) acetone
(iv) acetaldehyde

3. (a) What are reagent needed to convert each compound into butanal (CH3CH2CH2CHO)

Unit Kimia, KMKt 2020/2021 4

9.0 : CARBONYL COMPOUNDS SK O25

(i) CH3CH2CH2CH2OH
(ii) CH3CH2CH2CH=CHCH2CH2CH3

(b) What are reagent needed to convert each compound into acetophenone
(C6H5COCH3)
(i) Benzene
(ii) C6H5CH(OH)CH3

4. Draw structural formula for the products formed when propanal reacts with

(a) NaBH4 in methanol
(b) C6H5MgBr followed by hydrolysis
(c) LiAlH4 followed by hydrolysis
(d) hot, acidified KMnO4 solution

5. Complete the following reactions:

(a) i. LiAlH4 A
HO CH2 CH2 CH2 CHO
+
ii. H3O

(b) CN
B NaCN C OH
CH3
HCl

(c) -

CO

CH3 CH2 CH2 CH2 C O CH3 CH2 CH2 CH2 C O + Ag(s) TUTORIAL 9.0 CARBONYL COMPOUNDS
silver mirror
H
CH3 H
(d) CH3 D

CH3 C CH2 CH2OH CH3 C CH2 C O

OH OH
O
(e) C2H5COCl
E AlCl3 C C2H5

(f) O +

CH3 CH2 CH2 C H K2Cr2O7, H

F

Unit Kimia, KMKt 2020/2021 5

9.0 : CARBONYL COMPOUNDS SK O25

(g)
O + H2N NH NO2 G

(h) O O2N H
CH3 C CH3
i. CH3CH2MgBr

+

ii. H2O, H

6. Show how the following conversions can be carried out:
(a) propanone to propene

(b) cyclohexanone to cyclohexane-1,2-diol

(c) 3-pentanone to 3-chloropentane

7. Give a chemical test to distinguish between:
(a) benzaldehyde from benzyl alcohol

(b) hexanal from 2-hexanone

(c) 2-pentanone from 3-pentanone

8. 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.

9. Complete the following reaction scheme and write the structural formulae of A to E. Specify
the reagents I to III.

TUTORIAL 9.0 CARBONYL COMPOUNDS

Unit Kimia, KMKt 2020/2021 6

9.0 : CARBONYL COMPOUNDS SK O25

E

conc. H2SO4 I CH3 CH2 CH2 Br


CH3 CH2 CH2OH

PCC, CH2Cl2

i) LiAlH4 CH3 CH2 CHO i. CH3CH2MgBr B II O
D CH3 CH2 C CH2 CH3
A +

ii) H3O+ ii. H2O, H

III -

i. KMnO4, OH , 

+

ii. H3O

CH3 CH2 CH2 Cl CH3OH, conc. H2SO4
C



10. Propanone can be converted to various compounds as shown in the following reaction
scheme.

i. CH3CH2MgBr O NaCN A H3O+ B
C CH3 C CH3 HCl

ii. H3O+ i. LiAlH4

conc. H2SO4,  +

ii. H3O

D E TUTORIAL 9.0 CARBONYL COMPOUNDS
(major product)

(a) Draw the structural formulae of A, B, C, D and E.
(b) What is the rule used to predict the structure of D?

(c) One of the chemical tests that can distinguish D from E is by using Br2 in CH2Cl2. State
the observation and write the chemical equation for the reaction involved.

(d) State the reaction involved in the formation of E.

Unit Kimia, KMKt 2020/2021 7