Name : …………………………………….

Class : …………

962/2 TRIAL STPM SEM 3 2022

CHEMISTRY

SMK GREEN ROAD

One and a half hours

Instructions to candidates:

For examiner’s use

Section B

16

17

Section C

Total

Section A
1 2 3 4 5 6 7 8

9 10 11 12 13 14 15

__________________________________________________________________________________

This question paper consists of 8 printed pages

Prepared by; checked by;

_____________________ _____________________
(Annie Afzan bt. Ariffin) (Chai Kim Lian)
 Section A [15 marks]

Answer all questions in this section.

1. Compound A undergoes catalytic hydrogenation according to the equation A + H 2 → AH2.

Give that AH2 contains trigonal planar shape molecule, what could be A?
A CH2=CH2 C CHCCH3
B D

2. The following mechanism shows the reaction between methane and bromine in the presence of
ultraviolet light.
Uv light
Step 1 : Br2 2 Br•
Step 2 : Br• + CH4 → HBr + •CH3
Step 3 : •CH3 + Br2 → CH3Br + Br•
Which of the following statements about the above reaction could be correct?
A The above reaction can be carried out in the dark at room temperature
B The above reaction can be initiated by adding methyl radical in the dark.
C The only product formed is CH3Br.
D The above reaction stops at step III.

3. When two organic compounds X and Y from two different homologous series are burnt
separately in an excess of oxygen at 150 ˚C and ordinary pressure, the volume of carbon dioxide
is the same as that of water vapour formed. X and Y could be

A B C D
X alkane alkane alkene cycloalkane
Y alkene aldehyde ketone alkene

4. Which property does benzene have as a consequence of the delocalisation of electrons in the
benzene molecule?
A Benzene is a good conductor of electricity.
B The carbon-carbon bond lengths are between those of C-C bonds and C=C bonds.
C Addition reaction of benzene take place more easily than substitution.
D Substitution in benzene takes place at one particular carbon atom.

5 A liquid P decolourised bromine water and formed a white precipitate with aqueous silver
nitrate. Y could be
I CH2=CHCH2Cl III CH2CH2Cl
II CH2Cl IV
CH2CH3
Cl
A I and II only correct C II and III only correct
B I and IV only correct D III and IV only correct

6 Which of the following reagents can react with ethanol and phenol?
A ethanoic acid C ethanoyl chloride
B aqueous bromine D aqueous sodium hydroxide
7 A compound R reacts with phosphorus pentachloride to give off an acidic gas. R also reacts
with S reagent to produce a compound T which gives a grey precipitate with Tollens’ reagent.
Which of the following combinations could apply to R, S and T?
R S T
+
A CH3CH2CH2OH KMnO4/H CH3CH2CHO
B CH3CH(OH)CH3 KMnO4/H+ CH3COCH3
+
C C6H5CH2OH KMnO4/H C6H5COCH3
+
D CH3CH2COOH K2Cr2O7/H CH3CH2CHO

8 Which of the following is true regarding methanoic acid?

A It is a stronger acid than ethanoic acid.
B It has higher boiling point than ethanoic acid.
C It can be produced when hydrolysing methyl ethanoate under acidic condition.
D It produces carbon dioxide when react with concentrated sulphuric acid under reflux.

9 Which compound is most readily hydrolysed by water?

A CH3COCH2Cl B C6H5CH2COCl
C CH3CHClCOOH D Cl
Cl COCH3
Cl
10 A food chemist wants to create the odour of pineapples for a product. An ester with this odour
has the formula C3H7COOC2H5. Which pair of the reactants would produce this ester?
A C2H5Cl and C3H7COOH B C2H5OH and C2H5COCl
C C2H5OH and C3H7COOH D C3H7OH and C2H5COCl

11 CH3CONH2 can be distinguished from CH3CH2NH2 by using

A acidified potassium manganate (VII) solution
B sodium hydroxide solution
C 2,4-dinitrophenylhydrazine
D alkaline iodine

12 Which of the following statements about aminoethanoic acid is incorrect?

A Its aqueous solution conducts electricity.
B It forms zwitterions.
C It has high boiling point.
D It is optically active.

13 In many countries, plastic waste is collected separately and sorted. Some of this is incinerated
to provide heat for power stations. Why is pvc; polyvinyl chloride; removed from any waste
that is to be incinerated?
A It can be melted down and re-used.
B Its combustion products are harmful.
C It destroys the ozone layer.
D It does not burn easily.

14 Which of the following statements about natural rubber is not true?

A Its monomer is 2-methyl-1,3-butadiene.
B It is the trans-isomer of polyisoprene.
 C It can be synthesised by the addition polymerisation of isoprene.
D It is a saturated hydrocarbon.

15 Plastic can be classified as thermoplastic and thermosetting plastic based on its thermal
properties. Which is a thermosetting plastic?
A Bakelite B Perspex
C Polystyrene D Polyvinyl chloride
 Section B [15 marks]
Answer all questions in this section.

16 Acetaminophen is a drug used to relieve pain and fever. The structural formula of
acetaminophen is shown below:

HO N – C – CH3
H O

a) Name one functional group of the acetaminophen. [1]

……………………………………………………………………………………………..

b) Write the IUPAC nomenclature of acetaminophen. [1]

……………………………………………………………………………………………..

c) Write the chemical equation when acetaminophen is heated with aqueous sodium
hydroxide solution. [1]

………………………………………………………………………………………………

d) Write the structural formulae of the products formed and state the observations when
acetaminophen reacts with the following reagents. [4]
i. Bromine water; ii. LiAlH4 followed by HCl(aq);

Structural formula: Structural formula:

Observation: Observation:
17 Tryptophan is a compound used by human body to make protein. The reactions of tryptophan
are shown in the reaction scheme below.

CH2CHCN CH2CHCN CH2CHCOOH

CH3 Cl CH3 NH2 CH3 NH2
P Q NaNO2, HCl, 5 ˚C
N N N R
H H H
Tryptophan

a) Give the reagents and conditions for reaction P and Q. [2]

Reaction P : ……………………………………………………………………………….

Reaction Q : ……………………………………………………………………………….

b) Draw the structural formula of R. [1]

c) Give the structural formulae of aqueous solution of tryptophan with; [2]

i) pH = 7 :

ii) pH = 9 :

d) Tryptophan forms isomers which rotate the plane polarised light. Deduce and draw the
structures of the isomers of tryptophan. [3]

…………………………………………………………………………………………………

…………………………………………………………………………………………………

…………………………………………………………………………………………………
 Section C [30 marks]
Answer any 2 questions in this section.

18
a) Para-aminobenzoic acid, PABA, is commonly found in human body, which can be generated
from bacteria found in intestinal tract such as E.Coli. Propose a reaction scheme of how PABA can be
prepared from benzene. [8]
b) The structural formulae of three hydroxyl compounds are shown below.

OH OH H3 C OH

Cyclohexanol phenol 4-methylphenol

Compare and explain the acidity between cyclohexanol, phenol and 4-methylphenol. [7]

19 A hydrocarbon, A, produces two isomers of B and D, C3H6O, when reacts with ozone followed
by hydrolysis. When heated with dilute sulphuric acid, compound A produces a major product, E.
compound E does not give observable change when reacts with acidified potassium manganate(VII)
solution. When compound G reacts with Mg in dry ether followed with compound D and is hydrolysed,
compound E is formed. Compound G contains 45.9% by mass of carbon, 45.2% of chlorine and 8.9%
of hydrogen.
a) Determine the empirical formula of compound G. [2]
b) Identify the structural formulae of compounds A, B, D, E and G. [5]
c) Suggest a chemical test to distinguish between compound B and D. [3]
d) Write the reaction mechanism when compound G is refluxed with ethanolic potassium cyanide.
[5]

20 An alcohol J reacts with hot concentrated sulphuric acid and gives compounds K and L, C 9H10,
which are isomers of each other. Both compounds K and L react with bromine, where K forms
compound N whereas compound L reacts to give compound M. Compound L gives effervescence when
treated with hot acidified potassium manganate(VII) solution. While compound J gives yellow
precipitate when reacts with alkaline iodine solution. Compound P is produced when compound J reacts
with copper heated at 400 ˚C.
a) Draw the structural formulae of compounds J, K, L, M, N and P. [6]
b) Compound K also isomeric with compound Q. Explain the type of isomerism shown by
compound K and Q. [3]
c) Write the reaction mechanism for the formation of compound M from compound L. [4]
d) Write the chemical equations for the formation of yellow precipitate from compound J and
effervescence from compound L. [2]