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Malaysia
PAHANG
EnIneeiing
CreatMty
ORGANIC CHEMISTRY
COURSE CODE
BKF1323
LECTURER
DATE
19 JUNE 2013
DURATION
3 HOURS
SESSION/SEMESTER
PROGRAMME CODE :
BKB/BKC/BKG
INSTRUCTIONS TO CANDIDATE:
1.
2.
3.
4.
This question paper consists of FOUR (4) questions. Answer ALL questions.
All answers to a new question should start on new page.
All the calculations and assumptions must be clearly stated.
Candidates are not allowed to bring any material other than those allowed by
the invigilator into the examination room.
EXAMINATION REQUIREMENTS: -
BKBIBKC/BKG/121311JBKF1323
CONFIDENTIAL
QUESTION 1
a) Give the IUPAC names for the following compounds.
i)
(1 Mark)
ii)
(1 Mark)
iii)
8r
Br
(1 Mark)
iv)
Bri
Br
(1 Mark)
V)
(1 Mark)
BKB/BKC/BKG/1213111BKF1323
CONFIDENTIAL
vi)
Br
CH
Me
(1 Mark)
b)
C)
C: H2CO D: CH4
(2 Marks)
d)
BKB/BKC/BKG/121311/BKF 1323
CONFIDENTIAL
OH
OH
ct:,'
'NH2
NO2
A
OH
(2 Marks)
e)
H3CY'^^^CHO
CHO
i)
ii)
iii)
f)
(4 Marks)
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.
CH3 CH20CH2CH3
CH3CH2CH2CH2NH2
CH3CH2CH2CH20H
(4 Marks)
c) Using structure molecules, explain why tertiary amines (30) have lower boiling point
than 1 0 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 CH3CH2NTTI2 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)
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).
ii).
iii).
What product is formed initially and product forms when water is added.
Show the mechanism to produce a both products.
(6 Marks)
b)
By using the suitable example, discuss about concept of inductive and resonance
effect that effluent the location and rate of aromatic substitution reactions.
(6 Marks)
C)
CH3
H2SO4
CH3
+ 1120
aCH3
(4 Marks)
d)
Write out the steps describing the mechanism of the free-radical bromination of
methane. Classify each step as initiation, propagation or termination.
(5 Marks)
BKB/BKCIBKG/1213111BKF1323
CONFIDENTIAL
QUESTION 4
a)
H2SO4/H20
(D-,*,^
(2 Marks)
ii).
H2SO4
? + H20
+ CH30H
(2 Marks)
iii).
Cr03
H2SO41H20
? + ?
(4
Marks)
iv).
[1] cHI (excess)
0-
[2] Ag20
[3] Heat
(2 Marks)
b)
BKB/BKC/BKG/1213111BKF1323
CONFIDENTIAL
Br
Ci+
HBr
(4 Marks)
ii).
Briefly 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 2 and FeCl3.
(4 Marks)
d) Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards
nucleophilic attack.
1CHO
C HO
cyclohexanecarbaldehyde
benzaldehyde
(3 Marks)