Universiti

Malaysia
PAHANG

EnIneeiing

CreatMty

FACULTY OF CHEMICAL & NATURAL RESOURCES ENGINEERING

FINAL EXAMINATION
COURSE

ORGANIC CHEMISTRY

COURSE CODE

BKF1323

LECTURER

ABDUL AZIZ MOHD AZODDEIN

CHE KU MOIIAMMAD FAIZAL BIN CHE
KU YAHYA

DATE

19 JUNE 2013

DURATION

3 HOURS

SESSION/SEMESTER

SESSION 2012/2013 SEMESTER II

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: -

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO

This examination paper consists of EIGHT (8) printed pages including front page.

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)

Draw 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)

What is the correct oxidation-level ordering of the following compounds, staring

will lowest oxidation level?
A: CH30 B: (HO)2 C0

C: H2CO D: CH4
(2 Marks)

d)

Arrange the following phenols in order of increasing acidity (least to most).

BKB/BKC/BKG/121311/BKF 1323

CONFIDENTIAL

OH

OH

ct:,'

'NH2

NO2
A

OH

(2 Marks)
e)

Hydrocarbon A (C7H12) was treated with BH3 followed by H2 0 2INaOH to provide

B (C7H14 0) as the only product. Reaction of B with 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)

Rank the following in order of stability (lowest to highest):

(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).

Give the definition of nucleophile?

(2 Marks)

ii).

What is the function of Grignard 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)

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)

Draw a stepwise mechanism for the reaction below

CH3

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)

Draw the organic products formed in each reaction

1).
Cr03

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)

Answer 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

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)

END OF QUESTION PAPER