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SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
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SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
962/3 STPM 2023
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
CHEMISTRY
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
PAPER 3
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
One and a half hours
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN
SMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSINSMJKJITSIN

SEKOLAH MENENGAH JENIS KEBANGSAAN JIT SIN

(JIT SIN HIGH SCHOOL)

PEPERIKSAAN PERCUBAAN SIJIL TINGGI PERSEKOLAHAN MALAYSIA

(MALAYSIA HIGHER SCHOOL CERTIFICATE TRIAL EXAMINATION)

Instructions to candidates :
DO NOT OPEN THIS QUESTION PAPER UNTIL YOU ARE ALLOWED TO DO SO.
Answer all questions in Section A.
Answer all questions in Section B.
Answer two questions only in Section C. All working should be shown. For numerical
answers, units should be quoted wherever appropriate.

For examiner’s use

Section A
1-15
Section B
16
17
Section C

Total

This question paper consists of 12 printed pages

© SMJK Jit Sin 2023

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SECTION A [ 15 marks]
Answer all the questions in this section.

1. The structural formula of noradrenaline is shown below

Which is not true about the above noradrenaline?

A Optically inactive
B Has four functional groups
C Undergoes dehydration reaction
D Undergoes coupling reaction with a diazonium salt.

2. Which hydrocarbon can form a monochloro-substitution derivative which shows

both chirality and cis-trans isomerism?
A CH3CH=CH2
B (CH3)2C=CH2
C CH3CH=C(CH3)2
D CH3CH=CHCH2CH3

3. When ethene reacts with bromine in tetrachloromethane, 1,2-dibromoethane is

formed. What is the intermediate formed in this reaction?

A B

C D

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4. At which of the carbon atoms in the molecule below will undergo nucleophilic
addition most likely? B
A

5. Which one of the following formulae represents the organic compound formed
when (chloromethyl)benzene is heated under reflux with alkaline potassium
manganate(VII) solution and the mixture then acidified. .

A B C D

6. Chlorine was passed into methylbenzene under reflux in the presence of

aluminium chloride.
The compound was found to be present
in the product.

How is the mechanism for the formation of this product best described?

A electrophilic and nucleophilic substitution.

B nucleophilic and free radical substitution
C electrophilic and free radical substitution
D nucleophilic substitution only.

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7. The reaction scheme outlines the production of one of the monomers of

nylon 6,6 from compound X.

Which compound could be X?

A CH2=CHCH=CH2
B BrCH2CH2CH2CH2Br
C HOCH2CH2CH2CH2OH
D HOOCCH2CH2CH2CH2COOH

8. Which one of the following reagents can be used to distinguish between the
two compounds shown below?

A dilute hydrochloric acid B sodium metal

C ethanoyl chloride D iron(III) chloride solution

9. Which alcohol(s) on oxidation with acidified potassium dichromate(VI) solution

to give an organic product which causes an effervescence when reacted with
sodium carbonate? .
1 butan-1-ol
2 2-methylpropan-1-ol
3 2-methylpropan-2-ol

A 1 only B 1 and 2 only

C 2 and 3 only D 1, 2 and 3

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10. An organic compound has the following properties:

 It gives a positive iodoform test
 It gives a yellow precipitate with 2,4-dinitrophenylhydrazine
 It does not react with either Tollens’ reagent or Fehling’s reagent

Which compound would give these results?

A CH3CHO B CH3CH2OH
C CH3CH2COCH3 D CH3CH2CH2CHO

11. The unsaturated diketone shown is excreted by the bombardier beetle?

What is formed when this compound reacts with hydrogen cyanide?

A B

C D

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12. When an organic compound X was treated with phosphorus pentachloride,

fumes of hydrogen chloride were evolved. When X was warmed with acidified
aqueous potassium dichromate(VI), the solution turned green.

Which of the following was X ?

A CH3CH2CHO B CH3CH2COOH
C CH3CH(OH)CH3 D C6H5COCH3

13. Which liquid, when shaken with AgNO3(aq), will give a white precipitate in
the shortest time?

A carbon tetrachloride B chlorobenzene

C 2-chlorobutane D ethanoyl chloride

14. Benzenediazonium chloride is prepared by reacting phenylamine dissolved in

concentrated hydrochloric acid with aqueous sodium nitrite, keeping the
temperature below 10oC.

Which of the following occurs if the temperature rises above 10oC?

A loss of phenylamine.
B loss of hydrogen chloride.
C decomposition of benzenediazonium chloride
D crystallisation of benzenediazonium chloride

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15. Aspartic acid is an amino acid.

Which structure is predominant when aspartic acid is in aqueous solution at

pH 11?

A B C D

Answer for Section A

1 6 11

2 7 12

3 8 13

4 9 14

5 10 15

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Section B [15 marks]

Answer all questions.
Write the answers in the spaces provided.

16 Vanilloids are a group of organic compounds naturally in spices such as ginger

and cloves.
The general structure and some reactions of a vanilloid are shown below
whereby ‘R’ represents a side chain.

(a) Identify the following

(i) Reagent A : _______________________________________ [1]

(ii) Reagent B : _______________________________________ [1]

(b) Suggest the structure of organic structure C. [1]

(c) State two observation that you would be expect to see when a small amount
of aqueous bromine is added to a sample of a vanilloid. [2]

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(d) Write the chemical equation for the reaction of vanilloid with
aqueous bromine.
(Assume the –OCH3 and ‘R’ groups do not react with bromine). [2]

17 Phenylamine can be made from nitrobenzene in the laboratory using the method
given below.

4.84g of nitrobenzene and 10g of tin (an excess) are placed into a flask. The
flask is fitted with a reflux condenser. 20cm3 of concentrated hydrochloric acid is
then added dropwise to the flask. The water bath is heated for 30 minutes to complete
the reaction. Once the mixture has cooled, concentrated sodium hydroxide is added
until the mixture is alkaline.
Pure phenylamine can be obtained from the mixture.

(a) (i) State the role of the mixture of tin and concentrated hydrochloric acid. [1]

(ii) Write an equation for the conversion of nitrobenzene to form

phenylamine. [1]

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(b) Explain why the acidic mixture must be made alkaline before the phenylamine
can be separated out and purified. [2]

(c) In the experiment, 2.88 g of pure phenylamine was produced.

Calculate the percentage yield of phenylamine. [2]

(d) Predict the solubility of phenylamine in water. Explain. [2]

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Section C [30 marks]

Answer two questions only.

You may answer all the questions but, only the first two answers will be marked.
Write the answers on the answer sheets. Begin each answer on a new page of the
answer sheet.

18(a) When 2-chloro-2-methylbutane reacts with water, compound F is formed.

F undergoes dehydration to give compound G and H.

(i) State the suitable reagent and reaction condition for the dehydration of F.[2]

(ii) Draw the structure of F, G and H. [3]

(iii) State the Saytzeff’s rule and name the major product for the
dehydration of F. [2]

(iv) State the type of mechanism and draw the reaction mechanism to show
formation of F. [3]

(v) Predict the effect of on the rate reaction of (iv) if the water is replaced by
sodium methoxide, CH3ONa. Explain your answer. [2]

(b) If 1,1-dichlorocyclohexane is heated with an excess of ethanolic potassium

hydroxide, a product R, C6H9Cl is obtained and no further loss of chlorine
occurs. R decolourises bromine water.
Suggest the structure of R and explain why the expected loss of chlorine
atom does not occur. [3]

19 (a) Compound R and S are two isomers with molecular formula C 8 H8 O.

Compound R reacts with Fehling’s solution to give a red precipitate whereas
S does not. When both compounds are heated with acidified potassium
manganate(VII) solution, R is oxidised to compound M while S is oxidised to
compound N. Compound M requires 1 mole of sodium hydroxide to neutralise
completely while N requires 2 moles of sodium hydroxide to neutralise completely.
Deduce and determine the structural formula of R and S. Write equations for
any 2 of the reactions of the above. [6]

(b) Phenylmethanol undergoes chlorination in the presence of iron(III) chloride

without sunlight.
(i) Describe the reaction mechanism involved. [5]
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(ii) Compound K is an isomer of phenylmethanol. K reacts with aqueous

bromine. Draw the structural formula of K. Give a chemical test to prove the acidic
property of compound K. [4]

20 (a) Methanoic acid shows positive result towards Tollens’ reagent but ethanoic
acid does not. Explain the above statement and write the appropriate equation for
this reaction. [3]

(b) Write a synthetic route for the convers ion of cyclopropane to

cyclopropanecarboxylic acid via Grignard reagent. [5]

(c) When 2-phenylethanoic acid reacts with alcohol Q, a fruity smell compound,
R with molecular formula C 11H14O2 is formed. Oxidation of alcohol Q
yields S, whereas treatment with alkaline iodine solution gives a yellow
precipitate

(i) Draw the structures of Q, R, S. [3]

(ii) Give the IUPAC name of R. [1]
(iii) Write all the chemical equations involved. [3]

Prepared by : Checked by: Verified by:

______________________ ____________________ ________________

Lau Chein Chong Ng Peh Leang Ng Gim Kooi

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