CONFI

DENTI
AL* S
ET2962/
3
1

MODULSTPM PENGGAL3201
8
SET2

CHEMI
STRYMARKI
NG SCHEME

Sec
tionA(
15mar
ks)

Ques
tion
1 D Carboncar
bonsingl
ebondsar eallσbonds.Car
bon–c arbondoubl
e
bondsaremadeupof1σand1πbond. Innaphtalenet
hereare6C-C
bondsand5C=Cbonds. Th usther
earealltogether11σ bonds
2 C NoofmolofCO2=31 .
6= 0.
72mol
44
NoofmolofH2O=1 9
.4=1.07mol
18
MassofC=0.72x12= 8.
64g
MassofH= 2x1.
07x1= 2.1
4g
MassofO=1 6.
5-8.
64-2.
14= 5.
72g

NoofmolofO= 5.
72=0.
358mol
1
6
Molr
ati
oofC:H:O=0.
72:1
.07:
0.35
8
2:6: 1

Empi
ri
calf
ormul
aisC2H6O

3 BFlourineat omsar emor eelec t

roneg ativet h
anc hl
orineat omsh ence
thef l
our oethanoicac idsares trongert hant hec hloroethanoicacids.
Themor ef l
ourineat omsi nth emol ecul es,thes tr
ong eristheac i
d.
CH3COOHi sweakert hanHCOOHbec auset heel ectronreleasing
natureoft heCH3g roupi ncreas esthes tr
eng t
hoft heO- Hbondi n
–COOH. Thelargert hepKav al ue,t
h eweakeri stheac i
d
4 B Therei sonec arbonc h i
ralinlimonene
Limonenei sah ydrocarbon,h enceiti sins ol
ubl einwat er
Thedoubl ebondsi nth eli
monenemol eculec anbeox i
disedby
acidifi
edKMnO4t of or mdiol s.
5 At h
eC= Cdoublebondi sat t
ac kedbyel ectrofi
leswh i
lethec arbonyl
group, C=Oi sattackedbynuc l
eofiles

B Itisinsolubleinwat
erbecauseitcannotformtheh
ydrog
enbondi
ng
withwater .
Alsoduetothepresenc
eoft helarg
enon-pol
ar
hydrocarbong r
oup

C Th
eC=
Cdoubl
ebondc
anundr
egoaddi
ti
onalpol
ymer
izat
ion

D TheC=Cdoubl ebondandthealdehydegroupcanbeox i
dised.
The
al
dehydegroupcanalsobereduced
6 B Thechl
orineatomi nQmustbeat t
ac h
edt oasidechai
nandnot
di
rec
tlytothebenzeneri
ng.Hence,freeradi
calsubsi
tuti
ontakes
CONFI
DENTI
AL* S
ET2962/
3
2

placewhenmet hy
lbenzenereactswi
thchlorineinth
epr es
enc
eof
sunli
ght
7 B Primaryal
kylhali
deunder g
oSN2mec hani
s me
Secondaryalkylhali
deundergoamix t
ureofSN1andSN2mec hani
sme
Terti
aryalky
lhali
deunder goSN1mechanisme.
AandCar epr i
mar yalky
lhali
des.Disasec ondaryhal
ide

8 B C6H5OH+Na→CH3CO-Na++½H2

CH3COCl+C6H5O-Na+ → CH3COOC6H5+NaCl

9 B Yi sket one(bec auseitdoesnotr educeFehling’

ssolut
ion).HenceX
isas ec
ondar yalc
ohol
CH3CH( OH) CH3+[O]→ CH3COCH3+H2O
2-Pr opanol Propanone
CH3COCH3( A)doesnotunder goox i
dati
on
CH3CH2CH2OH( C)isoxi
disedt oanaldehyde.Wh i
chcanreduce
Feh ling’
ss olut
ion
(CH3) 3COH( D)at ert
iaryalcohol,
isresi
s t
encet ooxi
dation
1
0 D1.Sh owst hatXmus thaveeithertheCH3COorCH3CH( OH)g roupsini
ts
mol ecule
2.Xi sei therapr i
maryalcohol,secondaryalc
oh olorcar
bonylgroup
3.Sh owst hatXisnotalcohol

C6H5COCH3+
3I2+4NaOH→ C6H5COONa+CHI3+3NaI+3H2O
C6H5COCH3+4[O]
→ C6H5COOH +CO2+H2O

1
1 C YisCH3CH2COOH. HenceXmustbeCH3CH2COCl
[Onlyanacy
lchl
oridewoul
dreactwi
thwatert
oproduc
eac
arbox
yli
c
acid]
CH3CH2COCl+H2O→ CH3CH2COOH+HCl
CH3CH2COOH+C2H5OH→ CH3CH2COOC2H5+H2O

1
2 D Zisanac
ylc
hlor
idebec
aus
eitf
umesi
nai
r.Zal
somus
thav
eac
hir
al
c
arbon.

A I
tisnotopt
icall
yacti
ve
B I
tisnotopt
icall
yacti
ve
C I
tisnotanacylchl
ori
deandal
sonotoptic
al l
yacti
ve
D CH3CH2*
CH(CH3)COCl+H2O→ CH3CH2*
CH( CH3)
COOH+HCl
CONFI
DENTI
AL* S
ET2962/
3
3

1
3 A Th
ech
iralc
ent
rei
nas
par
tami
ssh
ownbyan*i
nth
edi
agr
ambel
ow

H O H O

H2N-
C*–C–N–C*-C–OCH3

CH2 H CH2

C-
OH

↓Hy
drol
ysi
s
H O H O

H2N-
C–C-OH H2N-
C–C-OH + CH3OH

CH2 CH2

C–OH

1
4 C

CH3-
CH-CH3 + KCN → CH3-
CH-CH3 +Br
l l
Br CN

CH3-
CH-CH3 +4[
H] → CH3-
CH-CH3
l l
CN CN2NH2

[Note:
Amix
tureofsodi
umandethanoli
sar
educ
ingag
ent
:
2Na+2C2H5OH → 2C2H5ONa +H2]
CONFI
DENTI
AL* S
ET2962/
3
4

1
5 D
Repeat
inguni
tofpol
ypr
openei
s:

nCH3-CH=
CH2→ CH(
CH3)–CH2

Repeat
inguni
tofny
lon6
,6i
s:

HOOC(
CH2)
4COOH +H2N(
CH2)
6NH2

OC(
CH2)
4CONH(
CH2)
6NH

Repeat
inguni
tofTer
ylenei
s:

O O
ll ll
O-
CH2-
CH2-
O-C- -
C

Repeat
inguni
tofpol
ysr
yrenei
s:

H H H H
l l l l
C–C–C–C
l l l l
H H
 CONFI
DENTI
AL* S
ET2962/
3
5

Sec
tionB(1
5mar
ks)

1
6
Ques
tion
Sug
ges
tedans
wer Mar
k
Number
Sec
tionB[
15mar
ks]

H
H
1
6(a) C N
H
H [
1]

NH3i
sanel
ect
ronr
ichnuc
leoph
ile [
1]

NH3under
goesnuc
leoph
ili
csubs
tit
uti
onatC-
C/ [
1]
(
b)(
ii)
Bondinsteadofat
tac
kingt
heel
ect
ronr
ichbenz
ener
ingf
orel
ect
roph
ili
c
subs
titut
ion

CH2C
l

Conc
. HNO3,
conc
.H2S
O4 [
1]
◦
55C

NO2

CH2Cl [
1]
(
c)

S
n,c
onc
.HCl
[
1]
NH2

CH2Cl
[
1]

CompoundX
 CONFI
DENTI
AL* S
ET2962/
3
6

7mar
ks
Tot
al

TOTALMARKS:
7MARKS
1
7
Ques
tion
Sug
ges
tedans
wer Mar
k
Number
Sec
tionB[
15mar
ks]
1
7(a)
(i)
H H

C C
[
1]
F F

H CH2CH3 H

C C C C [
1]
H CH2CN CH3

(
ii) Addi
ti
onpol
ymer
izat
ion [
1]

(
iii
) Res
tri
ctedr
otat
ionaboutt
hedoubl
ebondsoft
hepol
ymer
;inf
lex
ibl
e [
1]

COOH

HOCH2CH2OH + [
1]+[
1]

COOH
(
b)(
i)

O O

O CH2CH2O C C [
1]

(
ii) Condensati
onpol
ymer
izat
ion [
1]
Est
erlinkage [
1]
CONFI
DENTI
AL* S
ET2962/
3
7

Tot
al 9mar
ks

TOTALMARKS:
8MARKS
Sec
tionC(30mar
ks)
18
NO ANSWER MARKS

H+ -
HCN + CN [
1]
(
a)

H m2
-
C O + CN

H3C m3 s
low

H m4 H m5

H3C C O- H CN H3C C OH +CN-

f
ast
C N C N [
4]

Ai
shal
oal
kaneandh
asabenz
ener
ingbec
aus
eC:
H≈1
:1 [
1]

Carbon-car
bondoubl
ebondinBcleav
estogi
veal
deh
ydeorket
one,
Con [
1]
(
b) oxi
dation
Cunder g
oingnuc
leophi
li
caddi
ti
onwithHCNtof
ormD [
1]

Dhasc
hir
alc
arbon,
Cispr
opanal [
1]
A : [
1]
CH(Br)
CH2CH2CH3

B : [
1]
CH=CHCH2CH3

C : CH3CH2CHO [
1]

D : CH3CH2CH(
OH)
CN
[
1]

E : CH3CH2CH(
OH)
CH2NH2
[
1]
F : CH3CH2CHCH2NHCOCH3

OCOCH3 [
1]

TOTALMARK 1
5
CONFI
DENTI
AL* S
ET2962/
3
8

===
====
=
Tot
almar
ks:
15
===
====
=

1
9
NO ANSWER MARKS

(
a)( Whit
efume sevol
veswhenRreactwi
ththionylc
hlori
de(SOCl
2)showstha
t [
1]
i
) Ri sal
cohol
Thef
orma t
ionofyel
lowpre
cipi
tat
ewit
hi odineshowstha
tRcons i
stof

OH
│ [
1]
CH3─C─group
│
H
Si
sphe
nol
be c
auseSdi
ssol
vesi
nKOHs
olut
ion [
1]

S
truc
tur
alf
ormul
aofRa
ndS

OH
HO CH2CH3
│
CH3─C─
[
1+1
]
│
H S

Re
act
ioni
nvol
ved
OH Cl
│ │
CH3─C─ +S
OCl
2  +HCl+ S
O2
CH3─C─ [
1]
│ │
H H
R
(
ii)

OH O
│
CH3─C─ 2+Na
+I OH C6H5─C─ONa + CHI
3

│ [
1]
H

R
CONFI
DENTI
AL* S
ET2962/
3
9

HO CH2CH3 + Na
OH(
aq)  +Na
-
O CH2CH3 +H2O
[
1]

Thes
ynt
hes
isofRf
rombr
omobe
nze
ne

Br Dr
yet
her Mg
Br
+Mg [
1]

Mg
Br +CH3CHO CHCH3
│ [
1]
(
iii
)
OMgBr

H
CHCH3 +H2O CHCH3
[
1]
│ │
OMgBr OH

CH3CH2CH2OH Cu CH3CH2CHO
Δ
[1] [1] [
1+1
]
ngKMnO4/H+ orK2Cr +
*
ifus
i O
2 7/H mus
tcont
rolc
ondi
ti
on

(
b) CH3CH2CHO +HCN CH3CH2CH(
OH)
CN
[
1+1
]
[
1] [
1]

CH3CH2CH( CN +H3O+
OH) CH3CH2CH(
OH)
COOH
Δ
[
1]

TOTALMARK 1
5
 CONFI
DENTI
AL* S
ET2962/
3
10

TOTALMARKS:1
5
=
====
===
===
===
=

20
NO ANSWER MARKS

(
a)(
i) 2-
ami
no-
3-phe
nyl
propa
noi
cac
id [
1]

+
NH3
│
(
ii)
CH2─CHCOOH

[
1]

Re
act
ione
qua
tion:

O O O H O
│ [
1]
H2N─CH─C─OH+ H2N─CH─C─OH H2N─CH─C─N─CH─C─OH
│ │ │ │
(
iii
)(a CH2 CH2 CH2 CH2
) │ │ │ │

+ H2N─CH─C─OH
│
CH2
│

O H O

H2N─CH─C─N─CH─C─OH
│ │
CH2 CH2
│ │
O H OH O

H2N─CH─C─ N─CH─C─N─CH─C─OH [
1]
│ │ │
CH2 CH2 CH2
│ │ │
 CONFI
DENTI
AL* S
ET2962/
3
11

(
a) (
iii
)
(b) O

CH2CH2COOH CH2CH2─C─Cl
S
OCl
2/PCl
3/PCl
5

[
1]
[
1]

O H O
│
CH2CH2─C─N─CH─C─OH
│
CH2
│

[
1]
[
1+1
+1]

(
a)(i
V
)
Re
age
nt:
Nit
rousa
cid HNO2/Na
NO2+HCl [
1]

Obs
ervat
ion:Aevol
vesg
asnoe
ffe
rve
sce
ncewhe
rea
snoobs
erva
tionnoc
hang
e
f
or3-phe
nylpr
opanoi
caci
d [
1]

Equa
tion: NH2 NH2
│ │
CH2─CH─COOH +HNO2 CH2─CH─COOH

[
1]

(
b)(
i) Ybec
aus
eYf
ormshydr
oge
nbondi
ngbe
twe
enmol
ecul
es [
1+1
]
Or
 CONFI
DENTI
AL* S
ET2962/
3
12

(
b)(
ii) Obs
erva
tion:
Ydiss
olvebutXnotdi
ssol
ve [
1]
Re
acti
onequati
on:

H2N CO2H +HCl H3N+

Cl CO2H
[
1]

(
b)(i
ii
) Y [
1]

(
b) [
1]
H3N+ CO2-

TOTALMARK 1
6
TOTALMARKS:1
5
=
====
===
===
===
=