BKF1323-ORGANIC CHEMISTRY 21213.PDF
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Universiti
Malaysia
P H NG
nIneeiing
reatMty
FACULTY OF CHEMICAL NATURAL RESOURCES ENGINEERING
FINAL EXAMINATION
COURSE RGANIC CHEMISTRY
COURSE
CODE
KF1323
LECTURER
BDUL AZIZ MOHD AZODDEIN
CHE KU MOIIAMMAD FA IZAL BIN CHE
KU
YAHYA
DATE
9 JUNE 2013
DURATION
HOURS
SESSION/SEMESTER
ESSION 2012/2013 SEMEST ER II
PROGRAMME CODE
KB/BKC/BKG
INSTRUCTIONS TO CANDIDATE:
1 This question paper con sists of
FOUR 4)
questions Answer ALL questions
2
All answers to a new question should start on new page
3
All the calculations and assumptions must be clearly stated
4
Candidates are not allowed to bring any material other than those allowed by
the invigilator into the exam ination room
EXAMINATION REQUIREMENTS: -
DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO
This examination paper consists of
EIGHT 8)
printed pages including front page
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CONFIDENTIAL
BKBIBKC/BKG/121311JBKF1323
QUESTION 1
a Give the IUPAC names for the following compounds.
i
1 Mark)
ii
iii
1 Mark)
8r
r
1 Mark)
iv
r
1 Mark)
V
1 Mark)
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CONFIDENTIAL
BKB BKC BKG 1213111BKF1323
vi
Br
H
1 Mark)
b)
raw structures corresponding to the following TUPAC names:
i)
5-bromo-3-propylhex- 1 -ene
1 Mark)
ii)
5-chloro-4-methyl-2-hydroxy-hex-3-ene
1 Mark)
iii)
4,4,4-trifluorobut- 1 -ene
1 Mark)
iv )
2-methylbut-3 -enal
1 Mark)
v) Toluene
1 Mark)
C)
hat is the correct oxidation-level ordering of the following compounds, staring
will lowest oxidation level?
A: CH 0 B: HO)
C 0
: H
CO D: CH4
2 Marks)
d)
rrange the following phenols in order of increasing acidity least to most).
3
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CONFIDENTIAL
BKB/BKC/BKG/121311/BKF
1323
ct:, C N
NO
2
NH2
C
D
2 Marks)
e)
ydrocarbon A C
7H )
was treated with BH
3
followed by H
0
INaOH to provide
B C
7
H
4
0) as the only product. Reaction of B w ith TsC1/pyridine followed by
KOH gives C isomer with A) in addition to other olefin s). Treatment of C with
ozone followed by Zn/AcOH produces only the compound shown:
H3CY ̂ ^^CHO
CHO
i)
What is the correct formula for A?
ii)
What is the correct formula for B?
iii)
What is the correct formula for C?
6 Marks)
f)
ank the following in order of stability lowest to highest):
4 Marks)
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CONFIDENTIAL
BKB BKC BKG 121311 BKF1323
QUESTION
2
a) Draw the molecules structure of triethylamine and diisopropylamine.
4 Marks)
b) Explain the increasing in the boiling point of the organic compounds below.
CH 3 CH
20CH
CH
3
CH3CH2CH2CH2NH2
H3CH2CH2CH20H
4 Marks)
c) Using structure m olecules, explain wh y tertiary amines
30)
have lower boiling point
than 1
and 2° amines of comparable molecular weight.
4 Marks)
d If we compare an
alkylamine
and an
arylamine
we must look at the availability of the
nonbonded electron pair on N.
With CH
3
CH2
TT
for example, the electron pair is
localized on the N atom. Explain by describing the delocalized electron pair on the
benzene ring of an
wylamine
and what is the implication to the chemical properties
of amine.
8 Marks)
e Give an explanation for Hofmann elimination by showing the steps to synthesis
propene from propylamine.
5 Marks)
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CONFIDENTIAL
BKBIBKCIBKG/1213111BKF1323
QUESTION 3
a The reaction of an aldehyde or ketone with Grignard reagent, RMgX is a
nucleophilic addition to the carbon-oxygen double bond. Based on your
understanding, answer the following question
i . Give the definition of nucleophile?
2 Marks)
ii .
What is the function of G rignard reagent in this reaction?
2 Marks)
iii .
What product is formed initially and product forms when water is added.
Show the mechanism to produce a both products.
6 Marks)
b
y using the suitable example, discuss about concept of inductive and re sonance
effect that effluent the location and rate of aromatic substitution reactions.
6 Marks)
C
raw a stepwise m echanism for the reaction below
H
CH
H
H2SO4
1120
a H
4 Marks)
d
rite out the steps describing the mechanism of the free-radical bromination of
methane. Classify each step as initiation, propagation or term ination.
5 Marks)
6
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ii).
CH30H
2SO4
H20
CONFIDENTIAL
BKB/BKCIBKG/1213111BKF1323
QUESTION
a)
raw the organic products formed in each reaction
1
D-, ,^
Cr03
?
H2SO4/H20
2 Marks)
2 Marks)
iii).
Cr03
? ?
H2SO41H20
4 Marks)
iv).
[ ] cHI
excess)
]
Ag20
[3] Heat
2 Marks)
b)
nswer the following questions.
i . Give curved arrow mechanisms that show how both of the products A and
B of the following reaction are formed Indicate which is the major and
which the minor product.
7
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CONFIDENTIAL
BKB BKC BKG 1213111BKF1323
r
HBr
C i
4 Marks)arks)
ii .
riefly explain why one of the products is major and the other minor.
4 Marks)
c
Draw a detailed mechanism for the chlorination of benzene using C1
and FeCl3.
4 Marks)
d
Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards
nucleophilic attack.
HO
C HO
benzaldehyde
cyclohexanecarbaldehyde
3 Marks)
END OF QUESTION PAPER
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