CHEMISTRY

One hour and a half hours

SMK TENGKU INTAN ZAHARAH
23000 UNGUN TERENGGANU


MARKING SCHEME

SUMMATI!E ASSESSMENT
THIR TERM
ST"M
20#3
STPM CHEMISTRY 962/2

MARKING SCHEME
SECTION A

Question
No.
Answer E!"#n#tion
$
C This compound has one chiral carbon with four different groups. Thus
it can show optical isomers.

COOH COOH
| |
C C
H CH
3
H
3
C H
NH
2
NH
2
2
A
Phenol reacts with bromine water to produce a white precipitate.

OH
OH Br Br

Room temp
$ 3Br
2
a!"


Br
2# $# %&tribromophenol
white precipitate"
whereas phen'lmethanol CH
2
OH does not react with bromine
water
%

The reaction between methane and chlorine in the presence of light

in(ol(es a free radical mechanism.
The propagation step is
Cl ) CH
$
HCl ) CH
3
Cl
2
) CH
3
CH
3
Cl ) Cl

2
Question
No.
Answer E!"#n#tion
&
%
&
O
) &
CH
2
Br answer *" and C CH
3
answer C" are susceptible to
)
nucleophilic attac+ because the carbon atom in these carries a partial
positi(e charge# CH
3
is susceptible to free radical substitution
reactions. Ben,ene ring answer B" and carbon&carbon double bonds
contain electrons. Hence# the' are susceptible to electrophilic attac+.
Re&e&'er ( The electron densit' of an electrophile is (er' low.
Therefore# it will attac+ an electron rich centre# such as# the ben,ene
ring since the electron densit' is (er' high in the ben,ene ring.
'
OH OH
Cl Cl
) 3Cl
2
) 3HCl

Cl
2# $# % - trichlorophenol
Phenol undergoes electrophilic substitution.
6
% O Cl
|| |
CH
3
C CH ) PCl
.
CH
3
C CH
3
) POCl
3
|
Cl
(
C
/ster produces alcohol and carbo0'lic acid when acidic h'drol'sis is
performed.
CH
3
CH
2
"
2$
COOCH
2
"
21
CH
3
) H
2
O
CH
3
CH
2
"
2$
COOH ) CH
3
CH
2
"
21
OH
Carbo0'lic acid *lcohol
)

Remember2 The amino group acti(ates the ben,ene ring towards

substitution# at the ortho and para positions. Therefore# bromine will
replace h'drogen at the ortho and para positions.

3
Question
No.
Answer E!"#n#tion
9

Carbon'l group is found in aldeh'des and +etones.

$*
A
The pol'mer is produced from the addition pol'merisation reaction.
3olecules with double bonds are 4oined together to form a long
chain of the pol'mer.
$$

)#* 2* 3+
Optical isomers are onl' different in the aspect of polari,ed light
rotation.
$2
A
)# onl,+
Butan&2&ol is a secondar' alcohol. O0idation of the alcohol produces a
+etone.
H H H
| | |
CH
3
C C CH
3
) 5O6 CH
3
C C CH
3
) H
2
O
| | | ||
H OH H O
Butanone
$%

)#* 2* 3+
The C 7 C undergoes electrophilic addition.
The carbon'l group undergoes nucleophilic addition.
The ben,ene ring undergoes electrophilic substitution.
$&
%)#*2+
The particular pol'mer can be drawn as follows...
Thus this pol'mer can be s'nthesised from



$
Question
No.
Answer E!"#n#tion
This pol'mer is pol'amide because it contains

The group in this molecule ma+es it a pol'ester. 8t is not
resistant against al+aline h'drol'sis because esters and amides can
easil' be h'drol'sed.
$'
A)#+ Pol'2&meth'lbuta&l #3&diene"
CH3
&&CH
2
&C7CH&CH
2
"
n
is unsaturated# with C7C double bond and can be o0idised b'
3nO
$
&
9H
)
. Pol'ethene" and pol'phen'lethene" are saturated# cannot
be o0idised.
5:TP3 2;<;6


.
STPM CHEMISTRY 962/2
MARKING SCHEME
SECTION + , Stru-ture. Question /
Q0ESTION
NO
S0GGESTE1 ANS2ERS MARK
<%a"i"
)-+ &%r $ NH
3
$ .%r
/

<
<%a"ii"
)CH
3
+
2
C%r
2
$ NaOH CH
3
/ C / CH
3

O
<
=%a"iii"
/CHO CH/CH
2
CH
3
OH
<
<%b"i"
<
<%b"ii"

<
<%b"iii"
O
>
and
<
<%b"i("
<
TOTA3
)
MARKS

%
/thanol
N
$
i" CH
3
CH
2
3gBr
ii" H
3
O
)
Na
)
O
&
CH
2
CHCH
3
O
&
Na
)
Na
)
O
&
CH
2
CCH
3
OH
CH8
3
Na
)
O
&
CH
2
?C?O&Na)

HO
COOH

Q0ESTION
NO
S0GGESTE1 ANS2ERS MARK
<@a"i" *n electrophile is an electron deficient species which accepts a lone
pair electrons from another species to form a coordinate bond#
/lectrophile are Aewis acids
<
<@a"ii"
CH
2
7CH
2
) Br
2
B BrCH
2
&CH
2
Br
2
<@b"i" C 2 HOCH
2
CHCH
3
"OH or
HOOCCH
2
CH
2
COOH
D 2 CH
2
7CCH
3
"COOCH
3
<
<
<
<@b"ii"
Pol'mer C2 Condensation pol'meri,ation
Pol'mer D2 *ddition pol'merisation
<
<
Total E
mar+s

@
SECTION C ,Ess#4 Question/
Q0ESTIO
N NO
S0GGESTE1 ANS2ERS S0GGESTE
1 MARKS
<Ea" 2&butanol Optical isomerism.
8t has a chiral carbon atom bonded to four different groups.
8t has a pair of enantiomers that are non superimposable mirror
images.




<
<
<
Butenedioic acid geometrical isomerism
This isomerism arises due to restricted rotation about the
C7C bond.
HOOC COOH HOOC H
C 7 C C 7 C
H H H COOH
Cis& butenedioic acid Trans& butenedioic
acid
<
<
<
<Eb"
3olecular formula 2 C
.
H
<2
O
P 2 CH
3
CH
2
CH
2
CHOH"CH
3
O
>
F 2 CH
3
CH
2
CH
2
CCH
3


CH
3
CH
2
CH
2
CHOH"CH
3
) 5O6 B CH
3
CH
2
CH
2
COCH
3

P is an alcohol with the CH
3
CHOH" - group which reacts with

E
H
CH
3
CH
2
CH
3

OH
C
H
3
CH
2
C
OH
C
CH
3
H
3irror plane
Q0ESTIO
N NO
S0GGESTE1 ANS2ERS S0GGESTE
1 MARKS
al+aline iodine to produce CH8
3
.
CH
3
CH
2
CH
2
CHOH"CH
3
) $8
2
) OH
&
B CH
3
CH
2
CH
2
COO
&

) CH8
3
) .H8
F is a +etone with the CH
3
CO&" which reacts with al+aline
iodine to produce CH8
3
.
CH
3
CH
2
CH
2
COCH
3
) 38
2
) OH
&
B CH
3
CH
2
CH
2
COO
&
)
CH8
3
) 3H8
F ia a carbon'l compound which forms a precipitate with 2#$ -
dinitrophen'lh'dra,ine.
O
2
N
CH
3
CH
2
CH
2
COCH
3
) H
2
NNH NO
2

O
2
N
CH
3
CH
2
CH
2
C7NNH NO
2
) H
2
O
G
CH
3
Total <. mar+s
19(a)(i)
%-&ole0ular nu0leo1h-l-0 su's2-2u2-on :
N
2"
#$#
#
19(a)(ii) The ra2e of rea02-on -n0reases because 2he 'rea3-n4 of C/%r 'ond
needs less ener4, 2han 2ha2 of C/Cl 'ond. This is due to 2he len42h
of C/%r 'ond -s less 2han 2he C/Cl 'ond len42h &a3-n4 -2 5ea3er
and eas-er 2o 'rea36
#
#
#

1

H CH
3
CH
2
& H
HO2
/


$ CH
3
CH
2
?C?Cl HO? C ? Cl CH
3
CH
2
?C?OH ) Cl
&

H H H H

CH
3
CH
2
CH
2
Cl ) NaOH
reflu0
CH
3
CH
2
CH
2
OH ) NaCl
CH
3
CH
2
CH
2
OH

CH
3
CH7 CH
2

CH
3
CH7 CH
2
) HCl CH
3
CHClCH
3

conc. H
2
:O
$

<E;HC
Q0ESTIO
N NO
S0GGESTE1 ANS2ERS S0GGESTE
1 MARKS
19(b)(i) #$#
#$#
#
19(b)(ii)
Catal'tic crac+ing is used 2o 1ro7-de e82ra 1e2rol and as a sour0e of
al3enes for 2he &anufa02ure of &an, 1e2ro0he&-0als6
#
#
19(b)(iii)
Catal'tic crac+ing is carried out at .90:C using the 0a2al,s2s s-l-0on
)I!+ o8-de and alu&-n-u& o8-de6
#
#
TOTA;
#9 MARKS
2;a" *dd solid phosphorous I" chloride to ethanol at room temperature.
C
2
H
.
OH $ PCl
.
C
2
H
.
Cl
3
$ HCl
Bubbled chloroethane into hot potassium c'anide dissol(ed in
ethanol.
C
2
H
.
Cl $ JCN C
2
H
.
CN $ JCl
Boiling propanenitrile with dilute sulphuric acid.
C2H
.
CN $ 2H
2
O $ H
$
C
2
H
.
COOH $ NH
$

$
Correct steps
< m
< m for
correct
reagent and
condition of
each step."
<$<$<" m
2;b" Heat </propanol with e0cess of concentrated sulphuric acid at <E;
o
C.
CH
3
CH
2
CH
2
OH CH
3
CH 7 CH
2
$ H
2
O
Pass propene together with steam o(er heated phosphoric acid
adsorbed on the surface of silicon dio0ide".
O H
2
CH
3
CH CH
2
)
CH
3
CH CH
3
OH
Correct steps
< m
< m for
correct
reagent and
condition of
each step."
<$<" m
2;c" Boiling 2/bromopropane with a!ueous sodium h'dro0ide. Correct steps

<;
Q0ESTIO
N NO
S0GGESTE1 ANS2ERS S0GGESTE
1 MARKS
) JOH
CH
3
CH CH
3
Br
CH
3
CH CH
3
OH
) JBr
O0idise 2/propanol with hot acidified potassium dichromate.
CH
3
CH CH
3
OH
) 5O6 CH
3
CH CH
3
O
O H
2
)
< m
< m for
correct
reagent and
condition of
each step."
<$<" m
2;d" Heat </propanol with e0cess of concentrated sulphuric acid.
CH
3
CH
2
CH
2
OH CH
3
CH CH
2
)
O H
2
Reaction with h'drogen chloride at room temperature.
CH
3
CH CH
2
Cl H )
CH
3
C CH
3
Cl
Heat 2/choloropropane with ethanolic potassium c'anide.
CH
3
C CH
3
Cl
JCN
)
CH
3
C CH
3
CN
JCl
)
Boiling 2 c'nopropane with dilute sulphuric acid.
CH
3
C CH
3
CN
2 H
2
O
) H
)
)
CH
3
C CH
3
COOH
NH
$
)
)
Correct steps
< m
< m for
correct
reagent and
condition of
each step."
<$<$<$<" m
EN1 O5 MARKING SCHEME

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