C

6
H
5
R
, N
a
O
H
, <
1
0

C
A R O M AT I C R E A C T I O N S M A P
BENZENE
2014 COMPOUND INTEREST - WWW.COMPOUNDCHEM.COM
PHENOL
OH
CHLOROBENZENE
Cl
BROMOBENZENE
Br
ALKYLBENZENE
R
NITROBENZENE
NO2
PHENYLAMINE
NH2
F
BENZOICACID
COOH
BENZALDEHYDE
CHO
PHENYLKETONE
COR
BENZONITRILE
CN
PHENYLSULFONICACID
SO3H
AZOBENZENE
N
N
R
BENZENEDIAZONIUM
N
+
N
BENZOYLCHLORIDE
COCl
IODOBENZENE
I
FLUOROBENZENE
REACTIONS KEY
SUBSTITUTION
OXIDATION
REDUCTION
HYDROLYSIS
ACYLATION
OTHER
Br
2
& FeBr
3
cat., room temperature
Cl
2
& AlCl
3
cat., room temperature
HNO
3
, H
2
SO
4
cat., 55C
RCOCl, AlCl
3
cat., refux 60C
Chloroalkane, AlCl
3
cat., room temperature
H
2
S
O
4
,
h
e
a
t

u
n
d
e
r

r
e
f

u
x
H
C
l, r
e
f u
x
, S
n
; N
a
O
H
Diazotisation: NaNO
2
(aq), dilute HCl, temp. 0-5C
CO, HCl & AlCl
3
cat, CuCl
H
2
S
O
4
c
a
t
.
,
H
2
O
,
h
e
a
t
I
2
& conc. HNO
3
, refux
Cold H
3
PO
2
(aq)
KI (aq), room temp.
HBF
4
- flter of solid, dry &heat
HBr, CuBr cat., room temperature
HCl, CuCl cat., room temp.
H
2
O, 160C Powdered Zn, heat
Air
N
a
&
R
I
, d
r
y
e
t
h
e
r
C
o
u
p
lin
g

r
e
a
c
t
io
n
NaOH with Cu salt cat., 200 atm & 350C, then HCl
K
C
N
&
c
o
p
p
e
r
p
o
w
d
e
r
K
M
n
O
4
, H
2
S
O
4
, h
e
a
t
S
n
C
l2
(e
t
h
e
r
)
, H
C
l, 2
0

C
, t
h
e
n
b
o
il w
it
h
H
2
O
CuCN, polar solvent, refux (also for Ar-Br)
SOCl
2
, heat
K
N
H
2
, N
H
3
, -
3
3

C
; t
h
e
n
d
ilu
t
e
a
c
id
H
2
O
0.1M H
2
SO
4
, H
2
O