SK027

Topical Test 2 (Set B)

Session 2008/2009

Perak Matriculation College

Chemistry Unit
Session 2008/2009 20
Semester 2
Quiz 5
25
(40 minutes)
NAME : ________________________________________________
MATRIC. NUMBER : ________________________________________________
CLASS : ________________________________________________
NAME OF TUTOR : _____________________________________________

ANSWER ALL QUESTIONS.

1. Write the structural formula of the following organic compound.

2,3,5,6-tetramethylbenzaldehyde

(ii) Give the IUPAC names of the following compounds.

a)

Cl
CH3

CH(CH3)2

c)

Chemistry Unit KMPk 2008/09 1

 SK027
Topical Test 2 (Set B)
Session 2008/2009

CH2CHCH=CH2

___________________________

(3 marks)

2. Complete the following reaction scheme:

O CH3
CH3C Cl H2SO4 ,
AlCl3 HNO3 ,

Br2 ,
CH3Cl ,
FeBr3
AlCl3

(4 marks)

Chemistry Unit KMPk 2008/09 2

 SK027
Topical Test 2 (Set B)
Session 2008/2009

3. By giving suitable chemical equation(s), show how

(a) 3-bromonitrobenzene can be synthesized from benzene

(b) benzoic acid can be synthesized from benzene

( 6 marks)

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 SK027
Topical Test 2 (Set B)
Session 2008/2009

4. By giving suitable chemical reactions, explain how the following pair of compounds
can be differentiated in the laboratory.

CH3 CH3
from

[4 marks]

5. Which compound between benzoic acid and methylbenzene, will have higher rate of
nitration when reacted with HNO3/H2SO4 at 55oC? Explain.

[3 marks]

~ END OF QUESTION PAPER~

Set B

Chemistry Unit KMPk 2008/09 4

 SK027
Topical Test 2 (Set B)
Session 2008/2009

No sec Answer Marks

1. (i)
CH3CH2CH2CH2CH2CH2CH3 CH3 CH3
a) b)
CH2 H

C=O

1+1

CH3 CH3

(ii)
a) 4-chloro-2-isopropyltoluene 1

b) 4-bromo-3-nitrotoluene @ 1-bromo-4-methyl-2-nitrobenzene 1

c) 3-fluoro-4-phenyl-1-butene 1

CH3
2.

O C CH3
or

CH3
CH3 O O CH3 CH3
C CH3 CH3C Cl H2SO4 , NO2 or 1+1+1
AlCl3 HNO3 , +1
NO2
Br2 ,
CH3Cl ,
FeBr3
AlCl3
CH3
CH3 CH3
CH3
or Br CH3 or

Br CH3

Chemistry Unit KMPk 2008/09 5

 SK027
Topical Test 2 (Set B)
Session 2008/2009

NO2 NO2
3. (a) H2SO4 , Cl2
1+1
HNO3 , AlCl3
Cl

(b) CH2CH3
Br2 1+1
CH3CH3 CH3CH2Br
uv AlBr3

4. OXIDATION TEST

KMnO4 ,H+
CH3 COOH + MnO2
1
(brown precipitate)

Observation : Purple colour of KMnO4 decolourised & form brown precipitate

1
(MnO2)

KMnO4 ,H+
CH3 no reaction 1

Observation : Purple colour of KMnO4 remained unchanged

1

5 COOH COOH
H2SO4
+ HNO3
NO2

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 SK027
Topical Test 2 (Set B)
Session 2008/2009

- COOH is meta director & deactivating group

1
CH3 CH3 CH3
H2SO4 NO2
+ HNO3 +

NO2
- CH3 is ortho-para director and activating group.

1
Therefore:

CH3 COOH

react faster with HNO3 / H2SO4 @ 25oC compare to

1
- CH3 is activating group that is electron donating group which stabilizes the sigma
complexes to the ortho and para-directing.

TOTAL 20

Chemistry Unit KMPk 2008/09 7