aromatic functional group interconversions · c 6 h 5 r, l n a o h, < 1 0 ˚ c aromatic...
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C 6H5R
, NaO
H, <
10˚C
AROMATIC FUNCTIONAL GROUP INTERCONVERSIONS
BENZENE PHENOLOH
CHLOROBENZENECl
BROMOBENZENEBr
F
BENZOIC ACID BENZALDEHYDE
PHENYLKETONE
BENZONITRILE
PHENYLSULFONIC ACID AZOBENZENENN
R
BENZENEDIAZONIUMN
N
BENZOYL CHLORIDE
IODOBENZENEI
FLUOROBENZENE
REACTIONS KEYSUBSTITUTION
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
H2S
O4,
heat
und
er re
f ux
HCl
, ref
ux,
Sn; N
aOH
Diazotisation: NaNO2 (aq), dilute HCl, temp. 0-5˚C
CO, HCl & AlCl3 cat, CuCl
H2S
O4 ca
t., H
2O, h
eat
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
Na
& R
I, dr
y et
her
Coup
ling
reac
tion
NaOH with Cu salt cat., 200 atm & 350˚C, then HCl
KCN
& c
oppe
r pow
der
KMnO
4, H
2SO
4, he
at
SnCl
2 (et
her)
, HCl
, 20˚
C, th
en b
oil w
ith H
2O
CuCN, polar solvent, ref ux (also for Ar-Br)
SOCl2, heat
KNH
2, N
H3,
-33˚
C; th
en d
ilute
aci
d
H2O
0.1M H2SO4, H2O
SO
O OH
CH3
O
O
H
O
OH
O
Cl
CN
BY NC ND
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C
NITROBENZENENO2
PHENYLAMINENH2
ALKYLBENZENER
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