Name: …………………………………………………….. Class: ………………………….

MODUL PENTAKSIRAN PDPC SEMESTER 3 MODUL PENTAKSIRAN PDPC SEMESTER 3

962/3 SEMESTER 3 MODUL PENTAKSIRAN PDPC STPM 2023 MODUL
PENTAKSIRAN PDPC SEMESTER 3 MODUL PENTAKSIRAN PDPC SEMESTER 3 MODUL
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MODUL PENTAKSIRAN PDPC SEMESTER 3 MODUL PENTAKSIRAN PDPC SEMESTER 3

MODUL PENTAKSIRAN PDPC

SEMESTER 3
NEGERI PAHANG
Instructions to candidates:
DO NOT OPEN THIS QUESTION PAPER UNTIL YOU ARE TOLD TO DO SO.
Answer all questions in Section A and Section B
Section A – Objective questions (15 marks). Darken your answers in the OMR section below

Section C : Answer two question only. All working should be shown. For
numerical answers, unit should be quoted wherever appropriate.

Answers may be written in either English or Malay.

Tear off pages 1, and tie it together with your answer sheets of section B and
with your answer sheets of Section C.

This question paper consists of 11 printed pages

1
 Section A
[15 marks]
Answer all questions in this section.

1. Which is not true about a nucleophile?

A A nucleophile is a Lewis acid

B Nucleophiles do not seek electron
C Ammonia is a nucleophile
D Nucleophiles attack low electron density site

2. In a reaction which gave a 45.0% yield, 8.00 g of methylbenzene were converted

into the explosive 2,4,6-trinitromethylbenzene (TNT) (Mr = 227.0). The mass of
TNT formed was

A 1.46
B 3.33
C 6.79
D 8.88

3. Which one of the following mechanisms is not involved in the reaction sequence
below?
CH3CH3 → CH3CH2Cl → CH3CH2OH → CH2=CH2 → CH3CH2Br

A Electrophilic addition
B Electrophilic substitution
C Nucleophilic substitution
D Free radical substitution

4. A reaction sequence is shown below.

KOH in ethanol KMnO4/H+

X C4H8 CH3COOH reflux
reflux

What could be X?

A 1-bromobutane
B 1-bromo-2-methylpropane
C 2-bromobutane
D 1,2-dibromobutane

2
5.
O
1. O3
X
2. Zn/H2O

Determine X.

D CH3

6. Which of the following statements explains best why fluoroalkanes are the least
reactive haloalkanes?

A The C-F bond is the most polar carbon halogen bond.

B The C-F bond is the strongest carbon-halogen bond.
C Fluorine is more electronegative than carbon.
D Fluoride ion is the most stable halide ion.

7. K, L and M are carbonyl compound

K CH3CHO
L C2H5COCH3
M CH3COCH3

3
Which series of carbonyl compound is arranged in order of their decreasing
reactivity with HCN

A K>M>L
B L>M>K
C M>K>L
D M>L>K

8.

9.

4
 10.

11.

12.

13.

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14. Menthol is found in peppermint oil and it has a following structure.

OH

H3C CH(CH3)2

When menthol is heated with chromic acid and the organic product is distilled over,
the structure of the product is

A OH

HOOC COOH

B O
C H

H3C CH(CH3)2

C O

HOOC COOH

D O

H3C CH(CH3)2

6
15.

7
 Section B [15 marks]
Answers all questions in this section.

16. A hydrocarbon X, contains 90.9 % by mass of carbon. The mass of 1.0 g X occupied 283 cm3 at
177° C and 100 kPa.

[ Gas constant, R is 8.31 JK-1 mol-1]

(a) Determine the empirical formula of X. [2]

(b) Determine the molecular formula of X. [3]

(c) When X is refluxed with acidified potassium manganate (VII), benzoic acid and propanoic
acid are formed.
(i) Draw the structural formula of X [1]

(ii) X has an isomer that is optically active. Draw the structural formula of the isomer. [1]

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17. (a) A tertiary alcohol, A has a molecular formula, C5H12O. It reacts with hot concentrated
sulphuric acid to form B and C.

B and C have the same molecular formula, C5H10.

(i) Draw the structural formula of A, B and C. [3]

A B C

(ii) Give the IUPAC name of tertiary alcohol A. [1]

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

(b) Phenylmethanol and 4-methylphenol are isomeric hydroxyl compounds.

(i) Draw the structural formula of each of the isomers. [2]

Phenylmethanol 4-methylphenol

(ii) Name the reagent used to distinguish the two isomeric hydroxyl compounds and state the
observation involved. [2]

Reagent: ………………………………………………………………

Observation:
…………………………………………………………………………………………………………

…………………………………………………………………………………………………………

9
 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 provided. Begin each answer on it new page of the answer sheet.

18 (a) Trichlorofluoromethane, CFCl3 or Freon was introduced in the 1930s to be used in

foam insulation, cleaning, sterilisation, refrigeration and other industries. Using the
concept of hybridisation and overlapping of orbitals, describe the formation of bonds in
the CFCl3 and draw a labelled diagram of the molecule. [6]

(b) What is meant by stereoisomerism? [2]

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

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

19.

20. (a) Write the synthetic pathway for the formation of phenol from benzene. [7]

(b) Compare and explain the relative acidities of hexanoic acid, hexan-1-ol and[4]
phenol.
[4]
(c) An organic compound C8H9Br has three isomers P, Q, R. Isomers P and Q
gave the white precipitate when warmed with alcoholic AgNO3 solution in
alkaline medium but isomer R does not. P is optically active. Compound Q
form dicarboxylic acid compound when reacts with acidified potassium
manganate (VII) solution. Identify compounds P, Q and R. Write the
chemical equation evolved

KERTAS SOALAN TAMAT

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