Aromatic Functional Group Interconversions

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C 6
H
5R
, N
aO
H
, <
10
˚C
AROMATIC FUNCTIONAL GROUP INTERCONVERSIONS
BENZENE PHENOL
OH
CHLOROBENZENE
Cl
BROMOBENZENE
Br
F
BENZOIC ACID BENZALDEHYDE
PHENYLKETONE
BENZONITRILE
PHENYLSULFONIC ACID AZOBENZENEN N
R
BENZENEDIAZONIUM
N
N
BENZOYL CHLORIDE
IODOBENZENE
I
FLUOROBENZENE
REACTIONS KEY
SUBSTITUTION
OXIDATION
REDUCTION
HYDROLYSIS
ACYLATION
OTHER
Br2 & FeBr3 cat., room temperature
Cl2 & AlCl3 cat., room temperature
HNO3, H2SO4 cat., 55˚C
RCOCl, AlCl3 cat., ref ux 60˚C
Chloroalkane, AlCl3 cat., room temperature
H
2S
O
4, 
he
at
 u
nd
er
 re
f u
x
H
Cl
, r
ef
 u
x, 
Sn
; N
aO
H
Diazotisation: NaNO2 (aq), dilute HCl, temp. 0-5˚C
CO, HCl & AlCl3 cat, CuCl
H
2S
O
4 
ca
t.,
 H
2O
, h
ea
t
I2 & conc. HNO3, ref ux
Cold H3PO2 (aq)
KI (aq), room temp.
HBF4 - f lter of solid, dry & heat
HBr, CuBr cat., room temperature
HCl, CuCl cat., room temp.
H2O, 160˚CPowdered Zn, heat
N
a 
&
 R
I, 
dr
y 
et
he
r
Co
up
lin
g 
re
ac
tio
n
NaOH with Cu salt cat., 200 atm & 350˚C, then HCl 
KC
N
 &
 c
op
pe
r p
ow
de
r
KM
nO
4, 
H
2S
O
4, 
he
at
Sn
Cl
2 (
et
he
r)
, H
Cl
, 2
0˚
C,
 th
en
 b
oi
l w
ith
 H
2O
CuCN, polar solvent, ref ux (also for Ar-Br)
SOCl2, heat
KN
H
2, 
N
H
3, 
-3
3˚
C;
 th
en
 d
ilu
te
 a
ci
d
H2O
0.1M H2SO4, H2O
S
O
O OH
CH3
O
O
H
O
OH
O
Cl
C
N
BY NC ND
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C
NITROBENZENE
NO2
PHENYLAMINE
NH2
ALKYLBENZENE
R