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NAME MATRIC. NUMBER CLASS NAME OF TUTOR SK027 Topical Test 2 (Set B) Session 2008/2009 Perak

NAME MATRIC. NUMBER CLASS NAME OF TUTOR

SK027

Topical Test 2 (Set B) Session 2008/2009

Perak Matriculation College Chemistry Unit Session 2008/2009 Semester 2 20 Quiz 5 (40 minutes) : ________________________________________________
Perak Matriculation College
Chemistry Unit
Session 2008/2009
Semester 2
20
Quiz 5
(40 minutes)
: ________________________________________________
: ________________________________________________
: ________________________________________________
: _____________________________________________

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 CH 3 CH(CH 3 ) 2
Cl
CH 3
CH(CH 3 ) 2

c)

Chemistry Unit KMPk 2008/09

1

CH 2 CHCH=CH 2
CH 2 CHCH=CH 2

F

SK027

Topical Test 2 (Set B) Session 2008/2009

___________________________

2. Complete the following reaction scheme:

CH 2 CHCH=CH 2 F SK027 Topical Test 2 (Set B) Session 2008/2009 ___________________________ 2. Complete
O CH 3 C AlCl 3 Cl Br 2 , FeBr 3
O
CH 3 C
AlCl 3
Cl
Br 2 ,
FeBr 3
CH 2 CHCH=CH 2 F SK027 Topical Test 2 (Set B) Session 2008/2009 ___________________________ 2. Complete

Chemistry Unit KMPk 2008/09

(3 marks) CH 3 H 2 SO 4 , HNO 3 , CH 3 Cl ,
(3 marks)
CH 3
H 2 SO 4 ,
HNO 3 ,
CH 3 Cl ,
AlCl 3
(4 marks)
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)

Chemistry Unit KMPk 2008/09

3

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.

SK027 Topical Test 2 (Set B) Session 2008/2009 4. By giving suitable chemical reactions, explain how

CH 3

from

SK027 Topical Test 2 (Set B) Session 2008/2009 4. By giving suitable chemical reactions, explain how

CH 3

[4 marks]

5. Which compound between benzoic acid and methylbenzene, will have higher rate of nitration when reacted with HNO 3 /H 2 SO 4 at 55 o C? Explain.

Set B

Chemistry Unit KMPk 2008/09

 

[3 marks]

~ END OF QUESTION PAPER~

 

4

SK027

Topical Test 2 (Set B) Session 2008/2009

No

sec

 

Answer

Marks

1.

(i)

   
 

CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3

 

CH 3

CH 3

a)

b)

H

H

H
 
 

CH 2

CH
 

C=O

1+1

 

CH 3

CH 3

(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

 

CH 3

2.

2.

O

C
C

CH 3

or

 

O

CH 3

CH 3

CH O C

O

C
C

CH 3

CH 3 C Cl
CH 3 C
Cl

AlCl 3

CH 3

CH

H 2 SO 4 ,

HNO 3
HNO 3

CH 3

H SO , HNO 3 CH NO or

NO 2

or

CH O C CH CH 3 C Cl AlCl CH H SO , HNO 3 CH

1+1+1

+1

 

,

NO 2

CH 3

CH Br

Br

 

Br 2 , FeBr 3

Br FeBr CH

CH 3

CH Br Br FeBr CH CH Cl , AlCl CH CH

CH 3 Cl , AlCl 3

CH 3

CH 3

or

or Br CH or CH

Br

or Br CH or CH

CH 3

or

or CH

CH 3

 

Chemistry Unit KMPk 2008/09

 

5

SK027

Topical Test 2 (Set B) Session 2008/2009

     

NO 2

NO
 

NO 2

 

3.

(a)

3. (a) H SO , Cl

H 2 SO 4 ,

Cl 2

HNO ,

HNO 3 ,

HNO ,
 

AlCl 3

AlCl Cl 1+1

Cl

1+1

(b)

 
(b) CH CH

CH 2 CH 3

CH 3 CH 3

Br 2

Br

CH 3 CH 2 Br

CH 3 CH 3 Br CH CH Br 1+1

1+1

uv

AlBr 3

4.

OXIDATION TEST

 
CH KMnO ,H+ COOH +

CH 3

KMnO 4 ,H+

CH KMnO ,H+
CH KMnO ,H+ COOH +

COOH

+

 

MnO 2

(brown precipitate)

1

Observation : Purple colour of KMnO 4 decolourised & form brown precipitate (MnO 2 )

1

KMnO 4 ,H+

KMnO

4

,H+

CH 3

CH no reaction

no reaction

 

1

Observation : Purple colour of KMnO 4 remained unchanged

 
 

1

5

 

COOH

COOH

   
H SO NO
 

H 2 SO 4

NO

NO 2

+ HNO 3

+ HNO
 

Chemistry Unit KMPk 2008/09

6

SK027

Topical Test 2 (Set B) Session 2008/2009

- COOH is meta director & deactivating group 1 CH 3 CH 3 CH 3 H
-
COOH is meta director & deactivating group
1
CH 3
CH 3
CH 3
H 2 SO 4
NO 2
+ HNO 3
+
NO 2
-
CH 3 is ortho-para director and activating group.
1
Therefore:
CH 3
COOH
react faster with HNO 3 / H 2 SO 4 @ 25 o C compare to
1
CH 3 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

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