CONFIDENTIAL AS/APR 2008/CHM257

UNIVERSITI TEKNOLOGI MARA

FINAL EXAMINATION
COURSE
COURSE CODE
EXAMINATION
TIME
: ORGANIC CHEMISTRY 1
: CHM257
: APRIL 2008
: 3 HOURS
INSTRUCTIONS TO CANDIDATES
1. This question paper consists of three (3) parts : PART A (10 Questions)
PART B (10 Questions)
PART C (4 Questions)
2. Answer ALL questions from all three (3) parts.
i) Answer PART A in the Objective Answer Sheet.
ii) Answer PART B and PART C in the Answer Booklet. For PART C start each
answer on a new page.
3. Do not bring any material into the examination room unless permission is given by the
invigilator.
4. Please check to make sure that this examination pack consists of:
i) the Question Paper
ii) an Answer Booklet - provided by the Faculty
iii) an Objective Answer Sheet - provided by the Faculty
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO
This examination paper consists of 9 printed pages
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CONFIDENTIAL 2 AS/APR 2008/CHM257
PART A
The carbon-carbon sigma bond in ethane is formed by overlap of which two orbitals?
A. 2sp-2p
B. sp-sp
C. sp
2
-sp
1
D. sp
3
-sp
3
2. The reaction of propane with chlorine in the presence of UV light is an example of
A. an addition reaction.
B. a substitution reaction.
C. a hydrolysis reaction.
D. a Friedel -Crafts reaction.
3. When 2-butanol is treated with of concentrated sulphuric acid at 180 C, the structure
of main product could be
CH
3
CH
3
A. C
2
H
5
- CH-O-CH-C
2
H
5
B. CH
3
CH
2
COOCH
3
C. CH
3
CH
2
COCH
3
D. CH
3
CH = CHCH
3
4. The rate of the S
N
1 reaction is the fastest in the hydrolysis of
A. 1-bromopropane
B. 2-bromopropane
C. 1-bromo-2-methylbutane
D. 2-bromo-2-methylpropane
5. Which one of the following pairs of compounds are isomers of each other?
A. CH
3
CH
2
OCH
2
CH
3
and CH
3
CH
2
CH
2
CH
3
B. CH
3
CH
2
CH
2
OH and CH
3
CH
2
OCH
2
CH
3
C. CH
3
CH
2
NH
2
and CH
3
NHCH
3
D. CH
3
CH
2
CHBrCH
3
and CH
3
CHBrCH
3
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CONFIDENTIAL 3 AS/APR 2008/CHM257
6. Which of the following statements is TRUE?
A. Achiral refers to isomers that have atoms bonded in the same order, but with
different arrangement in space.
B. Stereoisomers are molecules with mirror images that are superimposable.
C. Enantiomers are stereoisomers that are mirror images that cannot be
superimposed on each other.
D. Chiral carbon is a carbon that is bonded to two different atoms or groups of
atom
7. Which of the following is not a characteristic of an electrophile?
A. It is a Lewis acid.
B. It is a Lewis base.
C. It is an electron acceptor.
D. It is positively charged
8. Nitration of benzene is carried out using nitric acid and sulfuric acid. The function of
NO
2
+
as a/an
A. catalyst
B. reducing agent
C. nucleophile
D. electrophile
9. Which of the following is a tertiary haloalkane?
A. C
6
H
5
CI
B. CH
3
C(CH
3
)(CI)(CH
3
)
C. CH
3
CH(CI)CH
3
D. CH
3
CH(CH
2
CI)CH
3
10.
HgSO
4
X
keto
H- - C=CR + H
2
O
Process X is known as
A.
B.
C.
D.
hydration
polymerization
hydrolysis
tautomerization
HgSO
4
H
2
SO
4
enol
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CONFIDENTIAL AS/APR 2008/CHM257
PARTB
QUESTION 1
a) List the following carbonium ions in order of increasing stability.
+
CH3-CH2-CH-CH3 ] CH3CH2CH2 I CH3-C-CH3 ] CH3
+
CH
3
b) Give two major resources of alkane.
QUESTION 2
Give the IUPAC name for each of the following organic compounds.
a)
b)
)H
QUESTION 3
Draw the structural formula for each of the following compounds:
a) 4-ethyl-1,2-dimethylcyclohexane
b) 4-isopropyloctyne
(4 marks)
(4 marks)
(4 marks)
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CONFIDENTIAL
AS/APR 2008/CHM257
QUESTION 4
Classify the following P,Q,R and S reaction
a)
b)
c)
d)
H
2
SO
4
P + H
2
O
+ H
2
(Lindlar catalyst)
Cl
2
uv light
H
2
O(H
2
SO
4
+HgSO
4
)
C
2
H
5
CI
> Q
R
(4 marks)
QUESTION 5
Give an appropriate reagents and conditions to prepare each of the following compounds
from butyne
a) butane
b) 2,2-dibromobutane
QUESTION 6
Consider the following reaction
(4 marks)
Br
"O(CH
3
)
3
f-butanol
a) What is the type of mechanism involved in the reaction?
b) What happen to the reaction rate with each of the following changes?
i) The concentration of "O(CH
3
)
3
is decreased.
ii) The halide is changed to CH
3
CH
2
CH
2
CH
2
CH(Br)CH
3
.
iii) The leaving group is changed to I".
(4 marks)
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CONFIDENTIAL
AS/APR 2008/CHM257
QUESTION 7
Consider the following bromination reaction
(CH
3
)
3
CH + Br
2
uv (CH
3
)
3
CBr HBr
Write a stepwise mechanism for the reaction including initiation, propagation and termination
steps.
(4 marks)
QUESTION 8
Identify the reagent needed to carry out each transformation for A and B
B
(4 marks)
QUESTION 9
Compare and contrast reactions between S
N
1 and S
N
2 in terms of
a) molecularity
b) reaction mechanism
QUESTION 10
(4 marks)
Predict the major product(s) that would be obtained for the following monosubstitution
reactions.
a) sulfonation of phenol
b) chlorination of benzenesulfonic acid
(4 marks)
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CONFIDENTIAL AS/APR 2008/CHM257
PARTC
QUESTION 1
In the reaction scheme below, compound V is formed when compound P, C4H8 undergoes S
reaction. Compound P reacts with Br
2
in CCI
4
to produce compound Q, C
4
H
8
Br
2
. When
compound P undergoes ozonolysis, compound T and U are the products formed. Compound
P reacts with HBr to produce compound R, C
4
H
9
Br (major).
H H H
-C - C - C -
H CH
3
H
V
CH
3
C(CH
3
)CH
2
P
Ozonolysis
HBr
Br
2
, CCU
a)
b)
c)
T + U
Draw the structures of compounds Q, R,T and U
What is the name of reaction S?
C
4
H
9
Br (major)
R
(4 marks)
(1 mark)
i) What is the functional group of compound P?
ii) Which reagent in the above scheme can be used as an indicative test for the
presence of the functional group of compound P? What is the positive result
that should be observed?
(3 marks)
d) There are two possible products from reaction of compound P with HBr.
i) What rule do you have to apply to get compound R as the only observed
product?
ii) What is the other possible product that is not observed?
(2 marks)
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CONFIDENTIAL 8 AS/APR 2008/CHM257
QUESTION 2
a) Under different experimental conditions, chlorine reacts with toluene to give
o-chlorotoluene and benzyl chloride (C
6
H
5
CH
2
CI) respectively.
i) State clearly the different experimental conditions for the above two reactions
ii) The reactions undergo different mechanisms. Name the mechanism for each
reaction above,
iii) Give equations to show clearly the mechanism involved in the formation of
o-chlorotoluene.
(7 marks)
b) Show how the following compounds can be prepared from benzene.
NH
2
(3 marks)
QUESTION 3
a) Cow's milk contains about 4% of lactose. Lactic acid is produced by the fermentation
of lactose by certain bacteria and is found in sour milk. The acid has the structural
formula : CH
3
CH(OH)COOH
i) Explain why lactic acid produced from cow's milk has optical activity.
ii) Draw the three-dimentional representations of lactic acid and its isomers to
explain the optical activity,
iii) Amino acids are acids that contain the -NH
2
and COOH groups. Write the
structural formula of an amino acid that shows optical activity and also
another amino acid that does not show optical activity
(6 marks)
b) By using equations show how cyclopentane can be prepared from
i) cyclopentene
ii) a suitable Grignard reagent
(4 marks)
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CONFIDENTIAL 9 AS/APR 2008/CHM257
QUESTION 4
a) Write the structural formula for each of the following alkyl halides.
i) Isobutyl bromide
ii) 1-Methylcyclopentyl iodide
iii) 1-Bromo-2,2-dimethylpropane
iv) terf-Butyl iodide
(4 marks)
b) Draw the structure of the major product of the following reactions. State the
mechanism (E1, E2, S
N
1 or S
N
2) for each reaction.
ethanol
i) CH
3
CH(CH
3
)CH(CI)CH
3
+ NaOH ?
O
ii) BrCH
2
CH(CH
3
)CH(CH
3
)
2
+
3
DMF ?

(4 marks)
c) Give 2 usages of alkyl halides
(2 marks)
END OF QUESTION PAPER
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