SECTION A [15 marks]

Answer all questions in this section. Indicate the correct answer on the space provided in page 4
1. The citrus flavour of lemons is due to the compound limonene, present in both the peel and the juice.

What is the mole ratio of carbon dioxide to water produced when limonene is completely burnt in oxygen?

A B C D

number of moles carbon dioxide 4 5 5 9

number of moles water 3 4 8 7

2. The diagram shows the structure of an alkene molecule. Which statements about this molecule are correct?

I. All the carbon atoms are in the same plane. II. It has geometrical isomers.
III. It is optically active. IV. It undergoes electrophilic addition reaction

A. I, II and III are correct B. I, II and IV are correct

C. I, III and IV are correct D. II, III and IV are correct

3. Which intermediate ion forms in the greatest amount during the addition of HBr to 2-methylpropene?
A. (CH3)3C+ B. (CH3)2CHCH2+ C. CH3CH2CH2CH2+ D. (CH3)2CHCH2

4. Which compounds will react with HCl under suitable condition to give the compound R?

A. I, II and III are correct B. I, II and IV are correct

C. I and II are correct D. II, III and IV are correct

5. A bromoalkane, indicated here by C–Br , reacts with aqueous NaOH. The mechanism has the reaction
pathway below. Which point in the diagram is correctly identified?
6. Which reagent will give a different observation with compounds X and Y?

A. hot SOCl2 B. hot acidified K2Cr2O7

C. NaOH (aq) D. warm alkaline iodine solution

7. Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H?
A. butyl ethanoate B. ethyl butanoate
C. ethyl propanoate D. propyl ethanoate

8. Menthol and menthone are both found in peppermint oil.

Which statement about these compounds is correct?

A. Both compounds can undergo mild oxidation.
B. Both compounds will give an orange precipitate with Brady's reagent.
C. Menthol can be formed from menthone by reaction with LiAlH4.
D. Menthone gives a positive test when warmed with Tollens’ reagent.

9. Propanone and hydrogen cyanide react together by this mechanism. Which statements about this
mechanism are correct?
I. CN– is an electrophile. II. It is an addition reaction.
III. Heterolytic bond breaking is involved IV. CN– act as catalyst
A. I, II and III are correct B. I, II and IV are correct
C. I and II are correct D. II, III and IV are correct

10. Citric acid is found in lemon juice.

What is the volume of 0.4 mol dm–3 sodium hydroxide solution required to neutralise a solution containing
0.005 mol of citric acid?
A. 12.5 cm3 B. 25.0 cm3 C. 37.5 cm3 D. 50.0 cm3

11. What is the organic product when N-propylethanamide, CH3CONHCH2CH2CH3, is boiled with excess
alkaline aqueous solution?
A. CH3COOH and CH3CH2CH2NH2 B. CH3CH2NH2 and CH3CH2CH2COOH
C. CH3CH2NH2 and CH3CH2CH2COO- D. CH3COO- and CH3CH2CH2NH2

12. The cyclic compound M is heated with dilute hydrochloric acid. What are the products of the reaction?
A. HOCH2CO2H and H2NCH2CO2H
B. HO2CCH2OH and HO2CCH2NH3+
C. H2NCOCH2OH and HOCH2CHO
D. HOCH2CONH3+ and HOCH2CHO
13. Which of the following compounds can be used to prepare a diazonium salt when it reacts with nitrous acid,
HNO2, at 5°C?

14. The amino acids aspartic acid and glutamic acid can react with each other to form amide inkages.

What is the maximum number of different compounds, each containing one amide linkage, that can
be formed from one molecule of aspartic acid and one molecule of glutamic acid?

A. 1 B. 2 C. 4 D. 6

15. The following diagram represents the structure of a possible polymer.

By which method might this polymer be made?

A polymerise ethene followed by hydration
B polymerise ethene followed by oxidation with cold acidified KMnO4
C polymerise 1,2-dichloroethene followed by hydrolysis
D polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO4.
 SMK TASEK UTARA, JOHOR BAHRU
UJIAN PENILAIAN PRA-PENTAKSIRAN (3) SEM 3 2017
SUBJECT : CHEMISTRY
Name : ____________________________________ Tingkatan : UPPER 6 ____________
Section A [15 marks]

1 6 11

2 7 12

3 8 13

4 9 14

5 10 15

Section B [15 marks]

Answer all questions in this section

16. Menthol, a cyclohexane derivative, is used in skin lotions since it counteracts itching. It can be prepared
from compound P by the reaction scheme below :

(a) Name compound P [1 mark]

……………………………………………………………………………………………………………...
(b) State the condition A required to convert compound P to menthol [1 mark]
……………………………………………………………………………………………………………...
(c) Explain why compound P is more acidic than menthol [2 marks]
……………………………………………………………………………………………………………...
……………………………………………………………………………………………………………...
……………………………………………………………………………………………………………...
(d) State a chemical test that can be use to distinguish compound P than that of methol [3 marks]
……………………………………………………………………………………………………………...
……………………………………………………………………………………………………………...
……………………………………………………………………………………………………………...
……………………………………………………………………………………………………………...
17. A reaction scheme to synthesis butter yellow, a dye once used to give a yellow colour to margarine. It has
been shown to be carcinogenic, and its use in food is prohibited.

(a) State the condition required in I, II and III [3 marks]

Condition I : ……………………………………………………………………………………….
Condition II : ……………………………………………………………………………………….
Condition III : ……………………………………………………………………………………….
(b) Draw the structure of X and Y in the box provided [2 marks]
(c) Name the type of reaction between X and Y to form butter yellow [1 marks]
……………………………………………………………………………………………………………...
(d) Compound Y when heated with water, forms compound Z, which can also be use to produce another
azo dye A, when reacted with Y under suitable condition. The reaction scheme for the formation of
compound Z and azo dye A is shown below.

In the boxes provided below, draw the structure of compound Z and azo dye A [2 marks]
Compound Z Azo dye A
Section C

18. Compound P has molecular formula C8H16. Hydrogenation of compound P produces 2,4-dimethylhexane.
Oxidation of compound P under suitable condition produces a racemic mixture of compound Q (shown
below) and compound R which give a positive test to alkaline iodine solution.

(a) Using suitable equations, explain and deduce the structure of P. [8 marks]
(b) Explain and draw the racemic mixture of compound Q. [3 marks]
(c) State and explain the product(s) obtained when compound P is treated with aqueous acid (H3O+) under
reflux [4 marks]

19. DEET (N,N-diethyl-m-toluamide) is the active ingredient in many insect repellants. Structure of DEET is
given in the diagram below.

(a) Starting from m-bromotoluene, propose a reaction scheme to synthesis N,N-diethyl-m-toluamide.

[9 marks]
(b) Draw the structure of the product formed when N,N-diethyl-m-toluamide is treated with the following
reagents
(i) potassium hydroxide under reflux [2 marks]
(ii) hydrochloric acid under reflux [2 marks]
(iii) hydrogen gas catalysed by nickel at 1700C under atmospheric pressure [1 mark]
(iv) boiled alkaline potassium manganate(VII) followed by acidification [1 mark]

20. Natural rubber is classified as a type of terpenes, which can be build up from its monomer isoprene as
shown in the structure below.

(a) Give the IUPAC name of isoprene and state the number of sigma-bonds and pi-bonds in a molecule of
isoprene [3 marks]
(b) Draw the structure of polymer for natural rubber with three repeating units. State the polymerisation
involved and suggest a catalyst that is possible to permit stereochemical control of polymerisation
reactions [4 marks]
(c) By referring to the structure of (b)

(i) explain two of the properties of natural rubber [4 marks]

(ii) suggest a method to enhance the properties of rubber by drawing the structure formed when two
polymeric rubber chain are interacting [4 marks]