CONFI

DENTI
AL ANSWERSCHEMESET196
2/3201
8

Sec
tionA[
15mar
ks]

1
.D

2.
B

3.
A

4.
D

5
.D

6
.A.

7.
B–Th
eCH3g
roupi
nmet
hyl
benz
ene(
ort
oluene)i
sa2,
4-di
rec
tingg
roup.

8.
D

9.
D

1
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

1
0.C

2
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

1
1.A

1
2.D

1
3.A

1
4D

3
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

1
5

SECTI
ONB[
15mar
ks]

1
6.(
a)Per
cent
agebymas
sofTer
ylene

%C=1
0C/COC6H5COOCH2CH2O

=1
0(1
2)/1
0(1
2)+
8(1
)+4(
16) @1
20/1
92 1mar
k

=6
2.5
% 1
mar
k

b) HOOC- COOH 1
mar
k

HO-
CH2-
CH2-
OH 1
mar
k

c)Nameofg
as:
Hydr
ogenc
hlor
ideg
as 1
mark

ClOC - COCl 1
mar
k

4
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

Cl-
CH2-
CH2-
Cl 1
mar
k

d)Us eofTer
ylene:Tos
tor
edr
inks
/PETbot
tle/us
einmag
net
ict
ape/s
olar
tape/synt
het
icfabr
ic
1mark

17.
a)Nameofmec
hani
sm:
uni
mol
ecul
arnuc
leoph
ili
csubs
tit
uit
ion(
SN1
)
1mark

Nucleoph
il OH-/Hy
e: rox
idei
on
1mar
k

b)Mec
hani
sm:
Step1

CH3 CH3
-
H3C–C–Br s
low H3C–C+ + Br
CH3 CH3 1mar
k

St
ep2

CH3 f
ast CH3
H3C–C+ + OH- H3C–C-OH
CH3 CH3 1mar
k

Wri
tesl
owandf
astr
eac
tion 1
mark

c
)rat
e=k[
(CH3)
3CBr] 1mar
k

d)Conc
ent
rat
ionofOH-wi
llnotc
hang
eth
erat
eofr
eac
tion 1mar
k

5
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

SECTI
ONC(
30mar
ks)

1
8.(
a)i
)1mol
eXpr
oduc
e5mol
eCO2and4mol
eH20 1mar
k

So,
X=C5H8 1mar
k

Y=C5H10 1mar
k

i
i)X= 1mar
k

Y= 1mar
k

i
ii
)C5H8(
g)+7O2(
g) 5
CO2(
g)+4H2O(
l) 1mar
k

i
v) Ni

+H2(
g) 1mar
k

b)Mec
hani
sm:
Freer
adi
cals
ubs
tit
uti
on 1mar
k

I
nit
iat
ion:

6
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

Br
-Br uv 2Br . 1mar
k

Pr
opag
ati
on

H +Br . ..
+HBr

1mar
k

.+ Br–Br Br .
+Br

Imar
k

Ter
minat
ion

Br.+ .
Br Br
2 1mar
k

Br.+ . Br 1mar
k

. .
+. 1mar
k

7
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

Th
eov
eral
lequat
ion:

+Br
2 uv Br +HBr 1mar
k

19(a)Reagentsandcondit
ions:Ac
idif
iedpotas
siummang anate(VI
I)s
olut
ionand
warm
1
mark
Methanoi
cacid:Purpl
ec ol
ourofacidi
fiedKMnO4 dec
olouri
sed.
eth
anoicaci
d: Purplecolourofaci
difi
edKMnO4r emainunchang
ed
1mark

1mar
k
+
[
O]r
epl
acedbyKMnO4/H ,
heati
nth
eequat
ion

1
(b)Reag
ent
sandc
ondi
ti
ons:
Aci
dif
iedpot
ass
iummang
anat
e(VI
I)s
olut
ionand
warm
1mark

8
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

4-
methy
lbenzoi
caci
d:Pur
plecol
ourofac
idi
fi
edKMnO4dec
olour
ised
Benz
oicacid:Pur
plecol
ourOfKMnO4remainunc
hang
ed
1
mar
k

3[
O]r
epl
acedbyKMnO4/H+,
heati
nth
eequat
ion
1
mar
k

(c
)Reag
ent
sandc
ondi
ti
ons:
Heatwi
thal
kal
inei
odi
nes
olut
ion.
1mar
k

2-h
ydrox
ybut
anoi
caci
d:Li
ghtyel
lowpreci
pit
ateformed
1-
hydr
oxybut
anoi
cac
id:Novi
sibl
echangeisobser
ved//Nol
igh
tyel
low
pr
ec i
ptat
e
1mar
k

1mark
(
d))Reagent
sandc ondit
ions: Addedwithdil
uteH2SO4i
nroomtemperatur
e
1mark
Sodi
umbenz oat
e: Whiteprecipit
ateformed
sodi
umet h
anoate: Nov i
siblechangeisobser
ved//Nowhi
teprec
ipit
ate.
1mark

1
mar
k

(
e)Reagent
sandcondi
ti
ons:Adddis
t i
ll
edwateratr
oomt
emper
atur
eth
ent es
t
t
hewhi
tefumerel
easedwit
hmoistbluelit
muspaper
;
[1mark]

9
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

Et
hanoy
lch
lor
ide :
Reac
tvi
gor
ous
lyandwh
itef
umer
eleas
edt
urnsmoi
st
bl
uell
it
mustored.
Et
hanami
de :
Nov
isi
blec
hang
eisobs
erv
ed;
[1mar
k]

(
Whi
tef
ume)
)

20.(
i)Thebenz
eneistreat
edwithamixt
ureofc
oncentr
atedni
tri
cac
idand
concent
rat
eds ul
phur
icacidatatemper
atur
enotexceedi
ng 
55°
C.
1mar
k

1mark
Ni
t r
obenzeneisreducedtophenyl
ammoniumionsusi
ngamixtur
eofti
nand
concentr
atedhydrochl
oricac
id.
Th emix
tur
eisheatedunderr
efl
uxinaboil
ingwater
bath
1mark

Thelonepaironthenit
rogeninthepheny
laminepicksupahydrogenionfr
omthe
ac
id.
Thenit
robenz
enehasbeenreduc
edbygai
ningel
ect
ronsint
hepresenc
eofth
eaci
d.
1mark

1mar
k

(
ii)Phenyl
ami
nereac
tswi
thc
oldNi
trousac
id,
HNO2t
opr
oduc
ea
benzenediaz
oni
um
ion.
. 1mar
k

1
0
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

1mar
k

Whenphenoli
saddedt
oabov
esoluti
on,c
oupli
ngreacti
onoc
cur
s
topr
oduceabrigh
tcol
our
edsol
id,4-
hydrox
yazobenz
ene. 1
mar
k

1mar
k

(ii
i)Pheny
l ner
ami eactswi
thdi
lut
eHClt
opr
oduc
ewat
er-
sol
ubl
eioni
csal
t,
ph
eny l
ammonium c
hlor
ide
1mar
k

1
mar
k
Ev
apor
ati
onoft
hes
olut
ionc
aus
est
hepr
eci
pit
ati
onoft
hei
oni
csal
t.
1mar
k

1
1
CONFI
DENTI
AL ANSWERSCHEMESET196
2/3201
8

(
b)
Reag
ent1 Reag
ent
2

Reag
ent1:
Aci
dif
iedpot
ass
iummang
anat
e(VI
I)s
olut
ion,
heat 1
mar
k

Reag
ent2:
Met
hanolwi
thc
onc
ent
rat
eds
ulph
uri
cac
id,
heat 1
mar
k

2s t
ruc
turalfor
mulaewrit
tencorr
ec t
ly 1
mar
k
(4–methy
lphenoland4-
hydrox
ybenzoicac
id)

1
2