CONFIDENTIAL SET 1 962/3

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

Identity card number: ……………… Centre number/index number :……………...............

962/3 STPM 2020

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

JANGAN BUKA KERTAS SOALAN INI SEHINGGA ANDA DIBENARKAN

BERBUAT DEMIKIAN
Ada lima belas soalan dalam Bahagian A. Bagi setiap soalan, empat pilihan
jawapan diberikan.Pilih satu jawapan yang betul dan tandakan jawapan itu
pada Borang Jawapan Aneka Pilihan yang dibekalkan. Baca arahan pada
Borang Jawapan Aneka Pilihan itu dengan teliti. Jawab semua soalan. Total
Markah tidak akan ditolak bagi jawapan yang salah. (Jumlah)
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 9 printed pages

(Kertas soalan ini terdiri daripada 9 halaman bercetak )

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Section A [ 15 marks ]

Answer all questions

1 Which of the following compound exhibits optical isomerism?

A. CH3CH2C(Cl)2CH3 B. CH3CH2CH2OH
C. CH3CH2CH(OH)CH3 D. HOCH2CH(OH)CH2OH

2 Which IUPAC nomenclature corresponding to the structural formula of the alkene?

Structural formula IUPAC nomenclature
A. CH3 CH C CH3 2-ethyl-2-butene

CH2 CH3
CH3 CH2 CH3
B. 2,3-dimethyl-2-pentene
CH3 C C
CH3
C. CH3 CH CH CH CH3 2-methyl-2-pentene

CH3

D. CH 2 CH CH CH 1-ethyl-1,3-butadiene

CH 2
CH3

3 Which pair of compounds corresponds to the reagent used to differentiate the two compounds?
Pair of compounds Reagent
A. (CH3)3COH and (CH3)2CHCH2OH Sodium metal
B. CH3CH2OH and C6H5OH Bromine water
C. CH3CH2OH and CH3COOH Phosphorus(V) chloride
D. C6H5OH and CH3COOH Aqueous solution of sodium hydroxide

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4 The reaction below is classified as

Cl2
Cl Cl
AlCl3
Cl

A. An electrophilic substitution B. An electrophilic addition

C. A nucleophilic substitution D. A nucleophilic addition

5 Which of the following reactions takes place especially through SN1 mechanism?
A. C6H5CH2Br + NH3 → C6H5CH2NH2 + HBr
B. (CH3)3CBr + NaOH → (CH3)3COH + NaBr
C. CH3CH2CH2Br + KOH → CH3CH2CH2OH + KBr
D. CH3CHBrCH3 + KCN → CH3CH(CN)CH3 + KBr

6 Compound X decolorized acidified potassium manganate(VII) and forms a yellow precipitate with
alkaline iodine. Compound X is
A. CH3COCH3 B. (CH3)3COH
C. CH3CH2CHO D. CH3CH(OH)CH3

7 An excess of aqueous sodium hydroxide is added to the compound below.

HO COCl

Which of the following structures represents the organic ion produced ?

-
A O COCl C HO COO-

-
B O COO- D -
O COOH

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8 Which of the hydrocarbons given below has the highest boiling point?
A. CH3(CH2)4 CH3 B. CH3CH2CH CH2 CH3

CH 3
C. CH3CHCH2 CH2 CH3

CH 3 D. CH3(CH2)3 CH3

9 In which of the following series, are the compounds arranged in the order of increasing basic
strength?

CH3NH2 NH2 NH2

A. , ,
Cl

NH2
NH2 CH3NH2
B. , , Cl

C. NH2 , NH2 , CH3NH2

Cl

D. NH2 , CH3NH2 , NH2

Cl

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OH
10 The compound 2-(phenylmethyl)-2-butanol, CH3CH2 C CH3 , can be prepared
CH 2

from the reaction between Grignard reagent, X, and compound Y below except for

X Y
O
A. CH3MgBr CH2 C CH2CH3

O
B. CH3CH2MgBr CH2 C CH 3

O
C. CH3CH2CH2MgBr C CH3

O
D. CH2MgBr
CH3 CH2 C CH 3

11 What could X and Y be in the reaction below?

O
H2O C2H5OH
X Y CH3CH2C O C2H 5
Conc . H2SO4

X Y
A. CH3CH2COCl CH3CH2COOH
B. CH3CH2CH2Cl CH3CH2COOH
C. CH3CH2CH2Cl CH3CH2COCl
D. CH3COCl CH3COOH

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CONFIDENTIAL SET 1 962/3

12 Which of the following compounds does not produce benzoic acid when hydrolysed by acids?

A B
CN COCl

C COOCH2 D CH2COO

13 Which of the following is true regarding aminoethanoic acid?

A. In alkaline solutions, aminoethanoic acid exists in the cationic form.
B. In aqueous solutions, aminoethanoic acid forms the zwitterions.
C. Aminoethanoic acid is readily soluble in tetrachloromethane.
D. The amino group in aminoethanoic acid reacts with sodium hydroxide to form salt.

14 The repeating unit of a polymer is shown below

H H H CH3 H H
C C C C C C
H H H

Which of the following statements is not true of the polymer?

A. It is elastic B. It is thermally stable C. It can be vulcanized

D. Its monomers are CH CH2 and CH2=C(CH3)CH=CH2

15 Which of the following compounds can act as a monomer in condensation polymerization?

A. CH3COOH B. CH3COCH3
C. CH2=CHCl D. HOCH2CH2OH

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Section B [ 15 marks ]

Answer all questions

16 Compound X, with the molecular formula, C5H12O is a tertiary alcohol.

(a) Draw the structural formula and give the IUPAC name of X. [2]

IUPAC name :……………………………………………………………………………………….

(b) Compound X is formed when a haloalkane reacts with an aqueous solution of sodium hydroxide.
(i) Write the rate equation for the reaction. [1]

………………………………………………………………………………………………

(ii) State the mechanism for the reaction. [1]

………………………………………………………………………………………………

(c) Compund Y, an isomer of X is an optically active primary alcohol.

(i) Give IUPAC name of Y. [1]

………………………………………………………………………………………………

(ii) Draw the isomers of compound Y [2]

(iii) Compound Y reacts with a hot acidified solution of potassium manganate(VII), write the
equation for the reaction [1]

………………………………………………………………………………………………

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17 (a) A chiral primary amine, C4H11N and ammonia are basic.

(i) Draw the structural formula of the amine, [1]

(ii) Which compound is more basic ? [1]

……………………………………………………………………………………………….

(b) When phenylamine, C6H5NH2, reacts with nitric(III) acid in the presence of
concentrated hydrochloric acid at a temperature of 0 oC to 5 oC to produce a salt used in the dye
industry.

(i) Name this salt .. [1]

………………………………………………………………………………………………

(c ) When an aqueous solution of this salt is heated to 70 oC, a vigorous reaction occurs.

(i) Name the organic product formed. [1]

………………………………………………………………………………………………

(ii) Identify the gas evolved [1]

………………………………………………………………………………………………

(d) When an aqueous solution of this salt is added to an alkaline solution of phenol, a yellow
precipitate is formed immediately.

(i) Name the chemical reaction which occurs . [1]

………………………………………………………………………………………………

(ii) Draw the structure of the yellow precipitate . [1]

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CONFIDENTIAL SET 1 962/3

Section C [ 30 marks ]

Answer two questions only.

18 (a) Two organic compounds, P and Q , are formed when 2-pentene reacts with hydrogen bromide. P
isan optically active compound. Show how P and Q are formed and determine their structural formulae.
[7]
(b) Both benzene and phenol undergo nitration at 55℃ to form nitrated products. Describe the
solubility of benzene and phenol in water. [3]

(c) Benzene reacts with 2-bromopropane in the presence of aluminium bromide to form compound S.
Chlorination of compound Sin the presence of light produces compound T as the major product and
compound U. When compound S treated with hot acidified potassium manganate (VII) solution,
compound V is formed. Hydrolysis of compound T produces compound W. Draw the structural formulae
of compound S, T,U , V and W. [5]

19 (a) An organic compound P with relative molecular mass of 126.5 has the following composition by
mass: carbon , 66.4% ; chlorine, 28.1%, and hydrogen, 5.5%
(i) Determine the molecular of P. [2]
(ii) Draw the possible structure for P [2]
(iii) When P is refluxed with aqueous potassium hydroxide, Q is formed. Controlled oxidation
of Q produces R that gives an orange precipitate S with 2,4-dinitrophenylhydrazine. Continued oxidation
of R produces T, a white solid.. Determine the structural formula of P , Q, R, S and T. [5]
(b) Write a reaction scheme to show how 2-methyl-2-butanol could be prepared from
chloroethene.[6]

20 (a) (i) Propanoic acid and methyl ethanoate are structural isomers. Which isomer has a
higher boiling point ? Explain your answer. [6]
(ii) Show how N-ethylpropanamide can be prepared from propanoic acid. [5]
(b) Salicylamide is a non-narcotic analgesic and an antirheumatic drug. It is a member of
salicylamides and a member of phenols. Its IUPAC name is 2-hydroxybenzamide.
(i) Suggest the product formed when salicylamide is heated with aqueous hydrochloric
acid. [1]

(ii) Show how the organic product in (b)(i) can be used as the starting material in the preparation
of an ester. [3]