Question I

&

2-methyl-5-phenylhexane

m-bromobenoic acid

1-bromo-3,5-dimethylbenzene

o-bromopropylbenzene
1 -
fluoro- 2,4-dimitrobenzene

p-chloroaniline
 OH
as NH2
b) I

-xNHu
I
#CHE
Kor
of

c)
&Hy d) o
#
or
I I ,TX
X NHz

e) f)

H OH

IEI
NO2 I
#XN0z
-
ar
kF I
NOz
a) Reaction intermediates
O, p-activator stabilized
E NCCHz)z by
are e-

donation by amine

nitrogen.

b) Reaction intermediates
0,p-activator
5 by
are stabilized
electron donating
inductive effect ofalkyl

C Reaction intermediates
o,p-activator are stabilized by e-

- :CtzCHs donation by other

oxygen

d)
ian-deactivator
Reaction intermediate s
are destabilized by e-

1 I withdrawal by carbony/
& oxygen.
a)

EITPrAnou, EIFB+-X
I 11

b)

Icalls NXcN
1 a
C)
#XcOsH NOz
# C02H
I 11 HNOS -

I
XX H2504
>
x 1
d)
N82
EITNonHaos, Ien
e)
XXc0zH
111 HNO3,
#250x
my sost
4)

Epatatures IIIoft + I pocHs

n-
Only
*
methoxybenzene reacts faster than benzene.
a) Benzene > chlorobenzene > O-Dichlorobenzene

b) phenol> nitrobenzene > p-bromonitrobenzene

C) O-xylene > Fluorobenzene) benzaldehyde.

d) p-methoxybenzonitrile > p-methylbenzonitrile > benzonitrile

 ⑪
a-
a
y at
He
->
XXCHICHs
Ix1
XNO, Pd
nHz

Catalytic Hydrogenation

3)

BrTimsisoyBmAA
Br
I 7 1

Nitration, followed by reduction with substituted amilies.

Fe, produces

"EIFI kMnO4
->

H20
-
Xc0ct
I 11
*CO2H

a)
O-T PCHCCARI
PTTCALCH
- CASCHICHD ⑨
I I
X/Locks
-

/ ACI
OCH
 a

TIF"Ac->
CHzCHzC I
EIF ACH
I +
=Xx
I 11
ci
3)

FYP Etc
-
-

1
X-
11 114 -

t
2
-1

EIT. YII
C) cout
XX n8z
k1 z7fcate
HHO3
->
H2SOy
I

as

EITNCcHzco
NCaHacHsSn

I IT
so EIFNCCAUCER
-> +
a) -"Bu -

starts from phenol

EH of
O 0H

CH3
EI) ->
Fife Is -

ITB
b) I

1=Y
-
-
starts from
phenol
& CA3
pH3
·CHz I

ElctIHSN
I ->
-

↓H dcHs
C) 200H

moylmon
I
-
starts from
phenol
2H-

R
IomOrcR
I
NO2
I
*
11. I
-
I

NO2

↓ kMnOY

North,amor
-
hos
d) NH2
from
I can starts both phenol and
-

EIIar
I benzene

OH
NOz
/
⑤
I I
x
I
->
EII os Ix
↓
BV2 /

FeBrg
NO2

Far
<-
=Br
sn,H4

Is
I
 21 2/
"

EITIEICOM ->
EII
I

! -

cit.

NOz

#InosENOES
b) I

I Xyp 1
Br

Br

ER o IE
c)

EIIs
SOsH
d)
SOsH SUSH

EI El F<-
I
,
X
 CHz

xysi
CH3
as
#Br
, HN03

kit
)
H2SO+

NOz

1
FT
b -
-
, I 11
#H2SOy #XNOz
NO2

NO2

I
"

EITINO,
BV2 Br
MHz

FITBr
I
Br

EOT
OH OH
d)

EI
I

inP > ·
EIF
CHz
a) CHCHzCOC1, AICls (Friedel -
Crafts Acylation

b)
Ha,Pd (Catalytic Hydrogenation)

a) Brc, FeBrg (Bromination

d) Brc, FeBrs (Bromination)

e) KOH (alcohol) (Dehalogenation)