CONFIDENTIAL* SET 1 962/3

Class / Tingkatan : ……………… Name / Nama: ………………………………………

Identity card number: ……………… Centre number/index number :……………...............
(Nombor kad pengenalan) (Nombor pusat/angka giliran)

962/3 STPM 2019

JABATAN PELAJARAN NEGERI KELANTAN

MODUL g-CAKNA
CHEMISTRY 3 (KIMIA)
SET 1
One and a half hours (Satu jam setengah)

SIJIL TINGGI PERSEKOLAHAN MALAYSIA

(MALAYSIA HIGHER SCHOOL CERTIFICATE)
Instructions to candidates: For examiner‟s
DO NOT OPEN THIS QUESTION PAPER UNTIL YOU ARE use
TOLD TO DO SO. (Untuk kegunaan
There are fifteen questions in Section A. For each question, four choices of pemeriksa)
answers are given. Choose one correct answer and indicate it on the Multiple- Section A
choice Answer Sheet provided. Read the instructions on the Multiple-choice
Answer Sheet very carefully. Answer all questions. Marks will not be deducted for Section B
wrong answers. (Bahagian B)
Answer all questions in Section B. Write your answers in the spaces provided.
16
Answer any two questions in Section C. All essential working should be shown.
For numerical answers, unit should be quoted wherever appropriate.
Begin each answer on a fresh sheet of paper and arrange your answers in 17
numerical order.
Section C
(Bahagian C)
Answers may be written in either English or Bahasa Malaysia.

Arahan kepada calon

JANGAN BUKA KERTAS SOALAN INI SEHINGGA ANDA DIBENARKAN
BERBUAT DEMIKIAN
Ada lima belas soalan dalam Bahagian A. Bagi setiap soalan, empat pilihan jawapan Total
diberikan.Pilih satu jawapan yang betul dan tandakan jawapan itu pada Borang (Jumlah)
Jawapan Aneka Pilihan yang dibekalkan. Baca arahan pada Borang Jawapan Aneka
Pilihan itu dengan teliti. Jawab semua soalan.
Markah tidak akan ditolak bagi jawapan yang salah.
Jawab semua soalan dalam Bahagian B. Tulis jawapan anda di ruang yang
disediakan.
Jawab mana-mana dua soalan dalam Bahagian C. Semua jalan kerja yang sesuai
hendaklah ditunjukkan. Bagi jawapan berangka, unit hendaklah dinyatakan di
mana-mana yang sesuai. Mulakan setiap jawapan pada helaian kertas jawapan
yang baharu dan susun jawapan anda mengikut tertib berangka.Jawapan boleh
ditulis dalam bahasa Inggeris atau Bahasa Malaysia.

This question paper consists of 10 printed pages

(Kertas soalan ini terdiri daripada 10 halaman bercetak )

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CONFIDENTIAL* SET 1 962/3

Section A [15 marks]

1.Which atomic orbitals overlap to form the carbon-carbon Π-bond in ethane, CH2══CH2?

A 2p and 2p B 2s and 2p

C Sp2 and sp2 D 2p and sp2

2.What is not true regarding a pair of optical isomers?

A They are mirror-images.

B They are non-superimposable

C An equimolar mixture of both isomers is called a racemic mixture.

D They have identical physical properties.

3.A methyl carbonium ion is produced via the heterolytic fission of the C ̶ Cl bond in chloromethane.
What is the hybridized state of the carbon atom in the methyl carbonium ion?

A sp B sp2

C sp3 D None of the above

4. Which of the following statements does not explain why ethylamine is a stronger base than
phenylamine?

A The ethyl group is electron-donating.

B The phenyl group is electron- withdrawing.

C Ethylamine is soluble in water but phenylamine is not.

D The phenylamine molecule can undergo resonance but ethylamine cannot.

5. What is the IUPAC name of the following compound?

A 2-Chloro-5-methyl-1,3- cyclohexadiene

B 3-Chloro-6-methyl-1,3-cyclohexadiene

C 1-Methyl-4-chloro-2,4-cyclohexadiene

D 3-Methyl-6-chloro-1,3-cyclohexadiene

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CONFIDENTIAL* SET 1 962/3

6. Which of the following compounds is not an arene?

A C6H6 B C8H10 C C12H16 D C13H20

7. How many isomers (structural isomers and stereoisomers) are possible for a compound with the
formula C4H9Cl ?

A2 B4

C5 D6

8.The structure of compound X is shown below?

A It has three chiral centres.

B It is insoluble in water.

C It contains a secondry alcohol group.

D It decolourises acidified KMnO4

9.Which of the following is most susceptible to electrophilic substitution?

A Cyclohexanol

B Cyclohexenol

C Phenol

D 2-Nitrophenol

10.Formalin is an aqueous solution of

A methanol B methanal

C formic acid D sodium formate.

11. In the presence of concentrated sulphuric acid, ethanoic acid reacts with ethanol to form an ester.
During the esterification which bond of the ethanoic acid breaks?

A C―C B C═C C C―O D O―H

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CONFIDENTIAL* SET 1 962/3

12. Which reagent can be used to separate a mixture of benzene and aniline?

A Sodium hyroxide. B Hydrochloric acid.

C Ether D Sodium carbonate.

13. Serine has the structure shown below:

How many chiral centre(s) is/ are present in serine?

A0 C2

B1 D3

14. What reagent can be used to cleave the peptide bonds in proteins?

A Dilute H2SO4 B NH3 C Alkaline I2 D K2Cr2O7

15. What is a mixture of triethylaluminium and titanium(IV) chloride used as?

A Setting agent C Platiciser

B Ziegler- Natta catalyst D Vulcanising agent

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CONFIDENTIAL* SET 1 962/3

Section B [15 marks]

Answer all questions.

Write the answers in the spaces provided.

16 Benzene, toluene and nitrobenzene each undergoes chlorination reaction in the

presence of iron(III) chloride
(a) Write an equation for the chlorination of nitrobenzene. [1]

…………………………………………………………………………………………………

(b) State the function of iron(III) chloride in the reaction. [1]

…………………………………………………………………………………………………

(c) Write the mechanism of chlorination of nitrobenzene. [3]

(d) Arrange the three compounds in the increasing order of reactivity towards the
chlorination . Explain your answer. [2]

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

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

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

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CONFIDENTIAL* SET 1 962/3

17 The formula of two compounds X and Y are given below.

X Y
(a) By giving reagents and conditions, show the synthesis of Y from X [5]

(b) Describe a chemical test to distinguish X and Y [3]

………………………………………………………………………………………………

……………………………………………………………………………………………….

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

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

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CONFIDENTIAL* SET 1 962/3

Section C [ 30 marks]
Answer any two questions in this section.

18 (a) What is meant by stereoisomerism?[2]

(b) An amount of 0.01 mole of a hydrocarbon is burnt in excess oxygen. The products of the
combustion are passed through anhydrous calcium chloride and then through potassium
hydroxide solution. The masses of anhydrous calcium chloride and potassium hydroxide
solution increase by 0.72 g and 1.76 g respectively.

(i) Determine the molecular formula of the hydrocarbon. [7]

(ii) Draw the structural formulae of all the isomers of the hydrocarbon. [4]

(iii) If one of the isomers shows stereoisomerism, draw and name the streoisomer. [2]

19 Ethylbenzene, C6H5C2H5 is an important intermediate in the manufacture of

poly(phenylethene), which is commonly known as polystyrene. When ethylbenzene is treated
with chlorine under different conditions, two isomeric chlorides, C and D are formed. C reacts
with hot concentrated ethanolic potassium hydroxide to form E but, with aqueous sodium
hydroxide, it forms F, C8H10O. F gives a yellow precipitate with aqueous alkaline iodine. D is
inert with respect to aqueous sodium hydroxide but it oxidised by aqueous potassium
manganate (VII) to give acid G, C7H5ClO2.

(a) (i) Deduce the identities of C and D. [2]

(ii) Suggest the conditions required to obtain each product from ethylbenzene and in each
case state the type of reaction occurred. [6]

(b) Deduce the identities of E, F and G and write all the chemical equations involved. [7]

20 (a) Glycine or 2-aminoethanoic acid is a solid with a high melting point. Draw the full
structural formula of glycine and Draw the structural formula of two repeating units between glycine
molecules. [3]

(b) The isomers M has structural formulae as follow.

CO2H

NH2
M

i. M reacts with dilute hydrochloric acid and aqueous solution of sodium hydroxide at room
temperature. Draw structure formula of product form. [2]

ii. By giving reagents and conditions, show the synthesis of M from 2-nitrotoluene. [4]

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CONFIDENTIAL* SET 1 962/3

(c) (i) State the reagents and write the equations for the preparation of ethylamine, C2H5NH2,
from CH3CN [2]

(ii) Write the equations for the reactions of ethanoyl chloride, CH3COCl, with aniline,
C6H5NH2. Name the organic products formed. [2]

(iii) Write the structural formula of the products obtained when the following polyester
O O
is heated with aqueous sodium hydroxide. [2]
OCH2CHOCCH2CH2C
CH3 n

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

CHEMISTRY MARKING SCHEME

Section A (15 marks)

Qn Answer Explanation
1 A Only the lateral ovelap of two p orbitals will produce a Π- bond.
Π-bond

σ bond
2 D Optical isomer differ in their specific rotation, the angle through which a
plane-polarised light is rotated.
3 B CH3Cl→ CH3++ Cl-
There are three bonf pairs surrounding the carbon atom in CH3+. It undergoes
sp2 hybridisation.
4 C The strength of a base depends on its Kb value and not its solubilty. The ethyl
group (an electron-donating group) increases the electron density of lone-pair
electrons on the nitrogen atom making them more available to combine with
H+. Whereas the phenyl group (an electron-withdrawing group)decrease the
electron density of the lone-pair electrons.The presence of the benzene ring
allows phenylamine to undergo resonance which also decreases the electron
density of the lone-pair electrons.
5 A

The ring must be numbered across the double bond such that the first
substituent encountered has the lowest number possible
6 C Arenes have the general formula of Cn H2n-6 .
When n=12, H=24-6=18. So, the correct formula should be C12H18.
C Draw the possible for C4H9Cl
7 CH3CH2CH2CH2Cl 1-Chlorobutane
CH3―C(CH3)(Cl)―CH3
2-Chloro-2- methylpropane
CH3CH2―*CH(Cl)―CH3
2-Chlorobutane
CH3―CH(CH3)―CH2Cl
1-Chloro-2-methylpropenane
8 A Compound X has four chiral centres.

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

9 C Cyclohexanol and cyclohexenol do not undergo electrophilic substitution as

there is no benzene ring in their structure. The ―NO2 group in nitrophenol
withdraws electron from the benzene ring and decreases its ability to be attacked
by electrophiles (spesies that attack region of high electron density).
B Formalin, a 40% aqueous solution of formalin (methanol) is used to preserve
10 biological specimen
11 C

B Aniline will dissolve in dilute HCl.

12 C6H5NH2 + HCl C6H5NH3+Cl-
The aqueous layer is then separated from the mixture. Excess NaOH is added
to the aqueous layer where aniline will separate out an oily layer.
C6H5NH3+Cl- + NaOH C6H5NH2 + NaCl +H2O

*Aniline is a base and thus is soluble in dilute mineral acids. Benzene is a

hydrocarbon which is insoluble in aqueous solutions.
B
13

A A peptide bond can be broken via hydrolysis with hot dilute acids or hot dilute
14 alkalis.

R―CONH―R + H2O → R―COOH + R―NH2

R―CONH―R + NaOH → R―COO-Na+ + R―NH2
15 B Ziegler- Natta catalyst

Take note: This must be memorized.

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

16
(a)

NO2

FeCl3
+ Cl2 Cl + HCl [1]

(b) Lewis acid catalyst / halogen carrier [1]

(c ) Cl2 + FeCl3  Cl+FeCl4- [1]

NO2

+ H
+ Cl+  Cl [1]

NO2
NO2
+ H
-H+ [1]
Cl
Cl

(b) Increasing order of reactivity towards the chlorination reaction:

Nitrobenzene < benzene < toluene [1]

Toluene – methyl group is electron donating // activating or
Nitrobenzene – nitro group is electron withdrawing // deactivating [1]

Total: 7 marks

17 (a)

[1] [1]
[2]

+ CH3CH(OH)CH3

[1] [1] [1] [3]

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

(a) Add 2,4-dinitrophenylhydrazine to each X and Y at room temperature. [1]

X form an orange precipitate while no observable change for Y [1]

[1]

Total : 8 marks

18 Phenomena where by two or more compounds having the same molecular and structural [1]
formula but different in arrangement of atom in spaces/ spatial arrangement [1]

(i) X CO2 + H2O

0.01 mol 1.76 g 0.72g [1]
1.76 g
Mass of C = x 12 = 0.48 g
44
0.72 g
Mass of H = x 2 = 0.08 g
18
Mass of hydrocarbon X = 0.56 g [1]

0.56
Relative molecular mass X = [1]
0.01
or = 56.0

Mass C H
0.48 0.08
0.48 0.08
Number of moles
12 1
or = 0.04 = 0.08
Ratio or =1 =2 [1]

Empirical formula = CH2 [1]

(CH2)n = 56
(14)n = 56
n =4 [1]
Molecular formula = C4H8 [1]

Alternative
y y
CxHy + (x+ )O2  xCO2 + H2O [1]
4 2
0.01 mol 1.76 g 0.72g [1]

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

1.76 0.72
Number of moles
44.0 18
= 0.04 = 0.04 [1+1]
ii.01 mol of X produces 0.04 mol of CO2 and 0.04 mol of H2O
∴ x =4 [1]
y =8 [1]
X is C4H8 [1]

(ii) CH2=CHCH2CH3 ; CH3CH=CHCH3 ;

5 structures correct [4]

4 structures correct [3]
3 structures correct [2]
2 structures correct [1]

[4]

(iii)

[1 + 1]

Total: 15 marks
Cl
19 (i) C2H5
│
H- C-CH3

Cl
C D [1+1]

(ii) C2H5 Cl
uv │
+ Cl2 H- C-CH3 + HCl Equation [1]
Reagents [1]

Free radical substitution [1]

C2H5
C2H5
AlCl3
+ Cl2 + HCl Equation [1]
5
Cl
CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

Reagents [1]

Electrophilic substitution [1]

(b)
H H COOH
│ │
C = CH2 OH- C – CH3

Cl
[1+1+1]
E F G

Cl H
│ │
ethanolic C = CH2
H- C-CH3
+ KOH + KCl + H2O
reflux
[1]

H H
│ │
C = CH2 + NaOH OH- C – CH3 + NaCl [1]
reflux

H
│ COONa
OH- C – CH3 + 4I2 + 6NaOH + CHI3 + 5NaI + 5H2O [1]

C2H5
COOH
KMnO4 / H+
+ CO2 + 2H2O [1]

Cl Cl

Total : 15 marks

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CONFIDENTIAL* ANSWER SCHEME SET 1 962/3

20. (a) H2N-CH2-COOH [1]

O H [2]
H2N-CH2-C N-CH2-COOH

20. (b) (i)

CO2H

[1]
NH3Cl
CO2Na

NH2 [1]

20. (b) (ii)

O
Sn / HCl OR
CH3 KMnO4/ H+ C OH CO2H
H2 / Ni

NO2 [1m] [1m]

NO2 NH3Cl
[1m] [1m] …… [4]

(c) (i) heat with hydrogen gas in the present nickel as catalyst [1]
CH3CN + H2 → CH3CH2NH2 [1]

(c) (ii) CH3COCl + C6H5NH2 → CH3CONHC6H5 + HCl [1]

N-phenyl ethanamide [1]

(c) (iii) O O HOCH2CHOH

HO C CH2 CH2 C OH CH3 [2]

Total : 15 marks