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CONFIDENTIAL
5UI:rAN lDRIS EDUCATION UNIVBRS1TY
UNIVERSITI PENOIOIKAN SULTAN lORIS
FINAL EXAMINATION
SEMESTER 2 SESSION 2015/2016
CODE: SK01013
COURSE
:
INTRODUCTION TO ORGANIC
CHEMISTRY
0 7 MAR 2016
DATE:
DURATION: 2 HOURS
INSTRUCTIONS
1.
This
question
paper contains FOURTY
(40) questions
in PART A and TWO
(2) questions
in
PART B.
questions in PART A and PART
B.
2.
Answer ALL
3.
Questions in PART A must be answered in the OMR form
4.
Questions in PART 8 must be answered in the
answer
provided.
booklet
Use 28
provided.
pencil only.
Please do not
use
pencil.
This
question paper
contains 16 pages
including
the
cover
page and
appendix
NAME:
YEAR:
LECTURE GROUP:
A
REGISTRATION NO:
IDENTITY CARD NO:
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LECTURER: PM DR SARIPAH SALBIAH SYED ABDUL AZZIZ
DO NOT OPEN THIS QUESTION PAPER UNTIL YOU ARE
TOLD TO DO SO
CONFIDENTIAL
SK01013 Introduction To
Organic Chemistry
2
PART A
Answer ALL QUESTIONS
1.
2.
OMR
on
(40 Marks)
answer
sheet and choose the BEST
Which statement explains why the element carbon forms
A.
Carbon atoms combine readily with oxygen.
B.
Carbon atoms have very
C.
Carbon
readily
D.
Carbon
readily forms
In
a
so
many
answer
compounds?
high electronegativity.
forms ionic bonds with other carbon atoms.
molecule of CH4• the
covalent bonds with other carbon atoms.
hydrogen
atoms
are
spatially oriented
toward the centers of
a
regular
3
A.
square
B.
pyramid
C.
rectangle
D.
tetrahedron
The correct
hybrid orbitals for carbon
a
and b in the structure below
are
-
H
-
C
I
a
A.
a
=
B.
a
=
C.
a
=
D.
a
=
sp; b
Sp2;
b
sp; b
Sp3;
=
b
-
CH2- N0.2
I
b
Sp2
=
=
C
sp
Sp3
=
sp
[See next page
SK01013 Introduction To Organic
4.
5.
6.
7.
3
Chemistry
Which is the correct molecular formula of the
A.
C7H14
B.
C7H12
C.
C6H12
D.
C6H1O
Which
compounds
are
ethane and ethanol
B.
methanol and methanal
C.
1-propanol
D.
methanoic acid and ethanoic acid
Which of the
diene?
isomers?
A.
and
following
2-propanol
compounds below
are
cis-trans isomers?
CH3CH=CH2
CH3CH=CHCH2CH3
CH3CH=CHCH3
(1 )
(2)
(3)
A.
Only
B.
Both 1 and 2
C.
Both 2 and 3
D.
All three
Which of the
2
following compounds display optical
A.
CH2=CHCI
B.
CHCI=CHCI
C.
CH3-CHCI-COOH
D.
CH2(OH)-CH2(OH)
isomerism?
{See
next page
SK01013 Introduction To
B.
In which
Organic Chemistry
pair of hydrocarbons
4
does each
compound
contain
only
one
double bond per
molecule?
9.
A.
CsHs andC7Ha
B.
C4Ha and C2H4
C.
C2H2 and C3HS
D.
C2H2 and C2HS
Which Newman projection does NOT
represent the following compound?
A.
B.
C.
CH>-h
H
11�<:1
<:113
<:1
D.
Hyfy:H3
c�
H
[See next page
SK01013 Introduction To
10.
Which group
on
Organic Chemistry
5
the atom marked with
an
asterisk
(*) has the highest priority
in the
molecule below?
HO
o
11.
A.
The alcohol
B.
The chlorine
C.
The
ethyl group
D.
The
carboxylic acid group
Two
optically
active isomers of
mirror image of each other
12.
A.
conformers
B.
enantiomers
C.
diastreomers
D.
meso
are
a
substance which
called
are
related to each other
as
plane
_
compounds
Which molecule contains
A.
butane
B.
propane
C.
2-methylbutane
D.
2-methylpropane
a
total of three carbon atoms?
[See
next page
SK01013 Introduction To Organic
13.
Chemistry
6
Structure of 2, 3, 3-trimethylpentane is
_
A.
B.
C.
CHg-CH-CH-CH2-CH3
I
D.
14.
I
CH2-CHg
CHg
The IUPAC
name
for the
following compound is
CH3
I
_
CH3
I
CHrC-CHrCH
\
I
CH3·
15.
A.
2,4,4-trimethylbutane
B.
2,2,4-trimethylpentane
C.
1,3-pentamethylpropane
D.
1,1 ,3,3-tetramethylbutane
Which
compound is
A.
Ethane
B.
Ethene
C.
Ethyne
D.
Ethanol
a
saturated
CH3
hydrocarbon?
[See
next page
SK01013 Introduction To Organic
16.
Consider
the
three
isomeric
Which of the
methylpentane.
7
Chemistry
alkanes
n-hexane,
following correctly
2,3-dimethylbutane,
lists these
compounds
and
2-
in order of
increasing boiling point?
17.
18.
19.
A.
2,3-dimethylbutane
B.
2-methylpentane
<
n-hexane
C.
2-methylpentane
<
2,3-dimethylbutane
D.
n-hexane
The
<
melting point
<
2-methylpentane
2-methylpentane
and
<
<
<
n-hexane
2,3-dimethylbutane
<
n-hexane
2,3-dimethylbutane
boiling hydrocarbon compounds
A.
hydrogen bonds
B.
ion-dipole attraction
C.
dipole-dipole
D.
London
B.
HBr
C.
Br2, hv
D.
HBr, H202
Which of the
following
halogenation
best describes the carbon-chlorine bond of
A.
Ionic
B.
Nonpolar;
C.
Polar; d+
D.
Polar; d- at carbon and d+ at chlorine
no
by
_
forces
Choose the suitable reagents and conditions for the
Br2
determined
attraction
dispersion
A.
were
reaction below.
an
alkyl
chloride?
dipole
at carbon and d- at chlorine
[See
next page
SK01013 Introduction To Organic Chemistry
20.
21.
22.
23.
Which of the
following
A.
t-Butyl
B.
Propyl bromide
C.
Methyl
D.
Isopropyl
secondary alkyl
halide?
bromide
Acids
B.
Ether
C.
Esters
D.
Alcohols
of
chloride
organic compounds
A.
an
can
be represented
alcohol leads to the formation of
A.
alkene
B.
alkane
C.
alkyne
D.
alkyl halide
Which of the
a
iodide
Which class of
Dehydration
is
8
following
alcohols forms
A.
Methanol
B.
1-Propanol
C.
2-Propanol
D.
2-Methyl-2-propanol
a
as
R
-
OH?
an
_
ketone when oxidized?
[See
next page
SK01013 Introduction To Organic
24.
Which of the
following
9
Chemistry
is the ether?
A.
o
B.
All
�-C-OR
c.
D.
25.
What is the best
name
for the
following compound?
H
H
'c'"
II
CHrCHrC-CHrCHrCH3
26.
A.
2-ethyl-1-pentene
B.
4-ethyl-4-pentene
C.
2-propyl-1-butene
D.
3-methylenehexane
Examples of addition reactions include
A.
combustion of propene
B.
polymerization
C.
reaction of Cb with propene
D.
reaction of HBr with but-2-ene
all the
following EXCEPT
_
of ethene
[See
next page
K01013 Introduction To
27.
What is the
Organic Chemistry
major product
of the
10
following reaction?
2HCI
(g)
A.
B.
CH3C=CH
I
.
H
I
CI
C.
D.
28.
Reduction of
a
ketone with NaBH4 will result in the formation of
A.
an
alkene
B.
an
alkane
C.
a
primary alcohol
D.
a
secondary alcohol
_;,_",..---.--�'
[See
next page
SK01013 Introduction To
29.
30.
31.
32.
Organic Chemistry
The reaction below is a/an
A.
oxidation
B.
reduction
C.
substitution
D.
rearrangement
A
compound which shows
A.
propane
B.
pentanal
C.
2-pentanol
D.
2-pentanone
Which compound is
an
A.
CH30H
B.
CH30CH3
C.
CH3COOH
D.
CH3COOCH3
The
following
11
______
a
process.
positive Tollen test is
_
organic acid?
reaction will
produce
LiAIH4)
A.
CO2
B.
CH3CH2CH2CH3
C.
CH3CH2CH2COCI
D.
CH3CH2CH2CH20H
__
eter
[See
next page
SK01013 Introduction To
Organic Chemistry
33.
carboxylic acid derivatives, EXCEPT
34.
35.
All of these
are
A.
ester
B.
amide
C.
alkyl
halide
D.
acid
anhydride
The
materials for the
organic starting
A.
only
B.
an
acid and
C.
an
alkane and
D.
a
an
12
preparation of
----
an
ester could be
_
acid
an
ketone and
Give the IUPAC
alcohol
a
an
naming
ketone
alcohol
of ester
compound
below.
o
CH3-CH'-CH'-�-O---O
36.
A.
Cyclobutanoate
B.
Cyclic
C.
Butyl cyclobutanoate
D.
Cyclobutyl
What is the
butanoate
name
A.
Butene
B.
Butane
C.
Butyne
D.
Benzene
butanoate
of the compound that has the molecular formula C6H6?
[See
next page
SK01013 Introduction To
37.
38.
Organic Chemistry
The CI atom attached to benzene
13
ring
is
A.
meta
directing
B.
ortho
directing
C.
ortho and para
directing and activating
D.
ortho and para
directing
What is the
product(s) of the
and
_
deactivating
reaction below?
OR
6
39.
40.
A.
m-Chlorophenol
B.
m-Hydroxytoluene
C.
o-Chlorophenol
D.
o-Hydroxytoluene
and
and
Which
polymers
A.
Starch and
B.
Protein and nylon
C.
Protein and
D.
Starch and cellulose
Which of the
occur
p-Chlorophenol
p-Hydroxytoluene
naturally?
nylon
plastic
following
A.
Dacron
B.
Nylon 6,6
C.
Polyethylene
D.
Natural rubber
contain
isoprene units?
[See
next page
SK01013 Introduction To
14
Organic Chemistry
PART 8
(20 Marks)
Answer ALL QUESTIONS in the
1.
a)
Based
on
Figure 1,
answer
the
Reagent
D
answer
booklet
provided
questions below:
A
1
�H3
OH
�
c
Figure
compound A, Band C.
i)
Give the IUPAC
ii)
Suggest reagent
iii)
Select either the law of Markonikov
production
b)
1
Suggest
butanol.
a
of
name
of
D.
[1 Mark]
or
Anti-Markonikov used in the
compound C.
chemical test to differentiate
Explain
[3 Marks]
[1 Mark]
1-pentanol, 2-pentanol
and
2-methyl-2-
the detail observation.
[5 Marks]
[See
next page
SK01013 Introduction To Organic Chemistry
2.
a)
15
Arrange the following compounds
your
in order of
increasing boiling point
and
explain
answer.
�OH
�OH
[5 Marks]
b)
Draw all the
c)
Based
on
resonance
structures of benzene.
[2 Marks]
the reaction below:
o
+
compound
i)
Draw the structure of
ii)
Give the IUPAC
iii)
State
one
compound F.
name
of
compound F.
function of FeBr3 in this reaction.
END OF QUESTIONS
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