CONFI

DENTI
AL*peng
gal3 2 SET296
2/3

Sec
tionA[
15mar
ks]

1 Naph
thal
eneC10H8i
sanac
tiv
ecomponenti
nmot
hbal
ls.
Itss
truc
tur
alf
ormul
ais
sh
ownbelow.

HowmanyC-
Csi
gmabondsar
eint
hemol
ecul
es
A 5
B 6
C 1
0
D 1
1

2 Anorganicl
iqui
dc ont
ainscarbon,
hydrog
enandox ygen.
Thecomplet
e
combusti
onof16.5goftheliqui
dgives31
.6gofcarbondiox
ideand19.
3gof
water
.Whatistheempiricalfor
mulaoftheorg
anicliqui
d?
A CH4O
B C2H4O
C C2H6O
D C3H8O

3 Th
es tr
uctur
alfor
mul
aeoff
iveor
gani
cac
idsar
egi
ven bel
ow.
I HCOOH
II CH3COOH
II
I FCH2COOH
IV F2CHCOOH
V Cl CH2COOH

Whi
choft
h efol
lowingi
sthecorr
ectar
rang
ementf
ort
hef
iveac
idsi
nth
e
or
derofincr
eas i
ngpKavalues
?

A I
,II
,V,I
II,
IV
B I
V,I
II,
V,I
,II
C I
V,I
Il,
,
V,I
I,I
D V,
III
,IV,
II,
I

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 3 SET296
2/3

4 Li
monenei
stheessent
ialoi
lfoundi
nth
eski
nofl
emonandor
ange.
Its
s
truc
tur
eisgi
venbelow

Wh
ichoft
hef
oll
owi
ngi
snott
ruer
egar
dingl
imonene?
A I
thasopt
ici
somer
.
B I
thasc
is-
transi
somer
s.
C I
tisi
nsol
ubl
einwat
er.
D I
tcanbeox
idi
sedbyac
idi
caqueouspot
ass
iummang
anat
e(V1
1).

5 Cit
ral,
anoi
lobtai
nedt
hroughtheext
rac
tionofl
emonl
eav
es,
hast
he
fol
lowi
ngst
ruc
ture.
CH3C=
CHCH2CH2C=CHCHO
I I
CH3 CH3

Basedont h
estruc
tur
eabov
e,c
itr
ali
sex
pec
tedt
ohav
eth
efol
lowi
ng
proper
tiesexc
ept

A i
tisat
tac
kedbynuc
leoph
ilesandel
ect
roph
iles
B i
tiss
olubl
einbot
hwat
erandor
gani
csol
vent

C i
tunder
goesaddi
ti
onandc
ondens
ati
onr
eac
tions
D i
treac
tswi
thox
idi
singag
ent
sandr
educ
ingag
ent
s

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 4 SET296
2/3

6 Whenc h
lori
neg asi sbubbled th
roughmet
hylbenzene under
cer
tai
nc ondit
ions,acompoundQ wi t
hthemolecularformula
C7H7Clisproduced.CompoundQ formsawhi
tepr eci
pit
ateon
warmi
ngwithethanoli
csil
verni
trate.

Whic
hoft hefol
lowingaboutth
econdi
ti
onsofthereac
tionof
methyl
benz
enec hlori
nat
ion andth
es t
ruc
tur
al f
ormula of
compoundQiscorr
ect?

Condi
ti
onsofr
eac
tion CompoundQ

A A1
Cl3/r
oomt
emper
atur
e

B Sunl
igh
t/r
efl
ux

C Sunl
igh
t/r
efl
ux CH3
Cl

D Al
Cl/r
oom t
emper
atur
e CH3
Cl

7 Whi
ch of t
hef
oll
owi
ng r
eac
tions t
akes pl
ace es
pec
ial
lyt
hroug
h SNl
mechani
sm?

A C6H5CH2Br + NH3 C6H5CH2NH2 + HBr

B (
CH3)
3CBr+NaOH (
CH3)
3COH +NaBr

C CH3CH2CH2Br+KOH CH3CH2CH20H+KBr

D CH3CHBr
CH3+KCN CH3CH(
CN)
CH3+KBr

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 5 SET296
2/3

8 Phenoli
susedtopreparet
hecompoundCH3COOC6H5 t
hroug
han
i
ntermedi e X ass
at howni
nth
ef oll
owings
cheme.

Reag
ent1 Reag
ent2
C6H5OH X
Wh
ati
sreag
entIandr
eag
entI
Iint
heabov
esc
heme?
Reag
ent1 Reag
ent2

A PC15 CH3COC1
B Na CH3COC1
C NaOH CH3COOH
D PCl5 CH3COOH

9 CompoundX i
soxidi
sedtocompoundY t
hatdoesnotr
educ
e
Fehl
ing
'ssol
uti
on.Xcoul
dbe

A CH3COCH3
B CH3CH(
OH)
CH3
C CH3CH2CH2OH
D (
CH3)
3COH

0 CompoundX g
1 ivest
hef
oll
owi
ngobs
erv
ati
onswh
eni
treac
tswi
tht
hes
pec
ifi
c
reag
ents.
1
.For
msy
ell
owpr
eci
pit
atewi
thal
kal
inei
odi
ne
2.
Isox
idi
sedbyac
idi
fi
edpot
ass
iummang
anat
e(VI
I)t
oac
arbox
yli
c
aci
d
3.
Doesnotl
iber
ateh
ydr
ogeng
as wi
ths
odi
um

CompoundXc
oul
dbe

A CH3CH2CHOHCH3
B (
CH3)
3COH
C CH3CH2CHO
D C6H5COCH3

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 6 SET296
2/3

1
1 Wh
atc dXandYbei
oul nth
er eact
ionbelow?
0
H20 C2H50H l
l
X Y--- - CH3CH2C O-
C2H5

X Y

A CH3CH2CH2Cl CH3CH2COCl
B CH3CH2CH2Cl CH3CH2COOH
C CH3CH2COC1 CH3CH2COOH
D CH3COC1 CH3COOH
.

1
2 Zhasthemolecul
arformulaofC4H9COC1.
Zr eac
tswit
hcol
dwatert
o
pr
oduceanac i
dicsol
ution.
Zisopti
call
yacti
veandfumesi
nair
.The
st
ruct
uralf
ormulaofZi s

A CH3CH2CH2CH2COCl
B CH3CH(
CH3)
CH2COC1
C CH3COCH2CH2CH2Cl
D CH3CH2CH(CH3)
COCl

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 7 SET296
2/3

1
3 Aspart
ameisanar tif
ici
als weetenerwhic
h1sus
edtorepl
ace
sugarfordi
abet
ics
.Thestruc
turalformul
aofas
par
tamei
sasfol
lows
.

HO H0
I II I II
H2N-
C- C- N-
C-C-
O- CH3
l ll
CH2H CH2

C-OH
ll
O

Wh
ichoft
hef
oll
owi
ngs
tat
ement
sisnott
rueaboutas
par
tame?

A Opt
ical
lyi
nac
tiv
e

B Amet
hyles
ter

C Hasonepept
idel
inkag
e

D For
mst
wodi
ffer
entami
noac
idswh
enh
ydr
oly
sed

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 8 SET296
2/3

1
4 Wh
ichs
truc
tur
erepr
esent
sth
erepeat
inguni
tofapr
otei
n?

CH3 H O

A O–C–C C

H NH2

0 O

B
-
C- - C-
O-CH2-CH2-O

H CH3
C -
C C-

H COOCH3

H O O

D N C C N CH2 C

H CH2 H

OH

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 9 SET296
2/3

1
5 Wh
ichoft
hef
oll
owi
ngpai
rsofpol
ymerandi
tsr
epeat
inguni
tist
rue?

Pol
imer
s Repeat
inguni
ts

A Pol
ypr
opene -
CH2CH2CH-

B Ny
lon6
,6 -
CO(
CH2)
5NH-

C Ter
ylene OCH2CH2OCO- -CO

D Pol
yst
yrene CHCH2CHCH2

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 1
0 SET296
2/3

Sec
tionB[ 15marks]
Ans
weral lques
tionsi
nthiss
ect
ion.

1
6 As
tudentat
tempt
edt
omakeXf
rom(
chl
oromet
hyl
)benz
eneass
hown:

NH2
Conc
.NH3
CH2Cl Seal
ed CH2Cl

(c
hlor
omet
hyl
)benz
e X
ne

Howev
er,
adi
ffer
entpr
oduc
twi
thmol
ecul
arf
ormul
aC7H9Nwasobt
ained.

a)Gi
vet
hedi
spl
ayedf
ormul
aoft
hepr
oduc
tobt
ained. [
1
mar
k]

b)Ex
plai
nwh
yXwasnotobt
ained. [
2
mar
ks]

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
.

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
.

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
.

c
)Wi
tht
heus
eofar
eac
tions
cheme,
showh
owh
emi
ghts
ynt
hes
iseXf
rom
(
chl
oromet
hyl
)benz
ene,
giv
ingt
her
eag
ent
sandc
ondi
ti
ons
. [
4
mar
ks]

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 1
1 SET296
2/3

1
7 a) Th
edi
agr
ams
howst
her
epeatuni
tforas
ynt
het
icpol
ymerD:

H H H CH2CN CH3

C C C C C C

F H H CH2CH3 H

i
) Drawthest
ruc
tur
eoft
het
womonomer
sfr
omwh
icht
hepol
ymerDis
deri
ved. [
2marks
]

ii
) St at
eth
ety
peofpol
ymer
izat
ioni
nvol
vedi
nth
efor
mat
ionofth
e
poly
merD. [1mark]

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.

i
ii
) Sug
ges
twh
yth
epol
ymerDi
stoug
handr
igi
d. [
1mar
k]

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..

b) Terylenewast hefi
rstwholl
ys y
nthet
icf
ibreinv
entedbytheBri
ti
sh
chemi stJRWhinfi
eldin1941.Si
nce1976
, i
thasbeenthemostwidel
y
produc edsynt
heti
cfibre.Cl
othesmadefromTer y
lenekeepth
eirshape
afterwas h
ingandar ehard-
wear i
ng.

i
) Drawthemonomersfr
omwh i
chTery
leneisder
ivedf
romandh
enc
e
dr
awar epeatuni
tofthepol
ymerTery
lene. [3
marks
]

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 1
2 SET296
2/3

i
i)Stat
ethetypeofpoly
meri
zat
ioninvol
vedint
hef
ormati
onof
Tery
leneandnamet h
eli
nkagebetweenth
emonomerunit
sint
his
poly
mer.[2mar ks
]

.
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
.
..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
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..
.
..
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..
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..
.
..
.
..
.
..
.
..
.
..
.
..

Sect
ionC[30marks
]
Ans
weranytwoques
tionsi
nthi
ssec
tion.

18(a)Et
hanalunderg
oesnuc
leophi
li
caddi
ti
onwi
thh
ydr
ogenc
yani
de,
HCN.
Bri
efl
y
des
cri
bethestepsinthi
smec
hanis
m. [
5marks]

(b)Onboili
ngwit
hconcent
rat
edet hanol
ics
odi
umh
ydr
oxi
de,
compoundA,
C10H13Br
,gi
vesonl
yoneproduc
tB,C10H12.

Bundergoesox
idat
ionunderc
ert
ainc
ondi
ti
ont
ogi
vebenz
aldeh
ydeandc
ompoundC,
C3H6O.

Cr
eac
tswi
thh
ydr
ogenc
yani
det
ogi
veD,
C4H7NO,
whi
chi
sopt
ical
lyac
tiv
e.

Ont
reat
ingDwi
thl
it
hiumal
umi
numh
ydr
ide,
EC4H11NO,
ispr
oduc
ed.

Onemol
eofEr
eac
tswi
tht
womol
esofet
hanoy
lch
lor
idet
ogi
veF,
C8H15NO3.

Deducethestr
uct
uresofc
ompoundsA-
F.Explai
nthechemi
str
yofthereac
tions
descr
ibed.
Therei
snoneedtocommentont
h echemi
str
yoftheox
idati
onofB
[10marks]

!9( a)CompoundRandSar etwoisomer swithmol ecul

arformulaC8H10O. Rg iv
es
offwhit
ef umeswiththi
onylchl
orideandf ormsy ellowpreci
pitat
ewi t
hal kal
ine
aqueousiodinebutSdoesnot .Sdissolv
esi naqueouspot assi
umh ydroxi
debutR
doesnot,Ri ssy
ntesis
eds t
arti
ngf r
ombr omobenz enewhereasSfrom4- ethylani
line.
(i
) Ex plaintheaboveobser v
ationsandwr i
tethestr
ucturalformulaeofR
andS
[5mar ks]
(i
i) Wr i
teequati
onsfort h
er eactioninvolved [2
marks]
(i
ii
) Wr i
teequati
onsfort h
es ynthesi
sofR [3mar ks]

(b)Stat
et h
ereag
entsandreac
tioncondi
tionsf
ort
hes
ynt
hes
isof2-
h
ydr
oxybut
anoicaci
dst
art
ingfr
om1 -
propanol. .
[
5marks]

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 1
3 SET296
2/3

20(a)CompoundAisaphenylal
aninewhichisaness
enti
alaminoaci
dthatmustbe
pr
ovidedi
nthedietf
orheal
thygrowth
. Acanbesynt
hesi
sedfr
om3- ph
eny
lpropanoi
c
aci
d.Thes
truc
turalf
ormul
aofAi sgivenbelow
NH2
│
CH2─CHCOOH

(i
) NameAac cordingtotheIUPACnomenc l
ature. [
1mar k]
(i
i) Dr awt hes tructureofAatpH=2 [
1mar k]
(i
ii
) Gi vether eac tionequati
onf orth
ef ol
lowing:
(a)Th ef ormat ionoftr
ipeptideonlyfr
omA [2
mar k]
(b)Thef ormat ionofanami deus i
ngAandt h
e3- phenyl
propanoicacid
bya two-st
epr eactions [
3mar ks]
(i
v) Gi veac hemi c
alt estt
odi f
ferent
iatethe3-ph enyl
propanoicacidfr
om
A
[
3mar ks]
(b)TwoorganiccompoundsXandYh avethefol
lowingformulae

O2N CH3 H2N CO2H

X Y

( i
) Statewh i
chofthes
ec ompoundsh
ast hehig
h ermel t
ingpoi
nt.Explai
ny our
answer . [1
mar k]
( i
i) CompoundXandYc anbedist
igui
shedbyus i
nghydroc
h l
ori
cac id.
Statetheobservati
onandwr i
teequati
onforthereactionwh i
choccur
.
[2mar ks]
(ii
i) Whi
choft hecompoundsXandYex i
stsasz wit
t er
ion?Wri
tethes t
ructural
formulaofzwit
t eri
on.
[2mar ks]

96
2/1 CONFI
DENTI
AL*
CONFI
DENTI
AL*peng
gal3 1
4 SET296
2/3

96
2/1 CONFI
DENTI
AL*