AROMATIC FUNCTIONAL GROUP INTERCONVERSIONS

O
OH I F R

S I2 & conc. HNO3, reflux

PHENYLSULFONIC ACID IODOBENZENE FLUOROBENZENE N AZOBENZENE
N
O

H2SO 4 cat., H2O, heat

Coupling reaction
H2SO 4, heat under reflux

C6H5R, NaOH, <10˚C

KI (aq), room temp.

Br2 & FeBr3 cat., room temperature Br

BROMOBENZENE
HBF4 - filter off solid, dry & heat
N
HBr, CuBr cat., room temperature N
BENZENEDIAZONIUM
OH H2O, 160˚C
Powdered Zn, heat
BENZENE PHENOL

KCN & copper powder

NaOH with Cu salt cat., 200 atm & 350˚C, then HCl Cl HCl, CuCl cat., room temp.
CHLOROBENZENE
CuCN, polar solvent, reflux (also for Ar-Br)
Cl2 & AlCl3 cat., room temperature

Na & RI, dry ether

Chloroalkane, AlCl3 cat., room temperature N
0.1M H2SO 4, H2O C
HNO3, H2SO 4 cat., 55˚C BENZONITRILE

KNH2, NH3, -33˚C; then dilute acid

O

SnCl2 (ether), HCl, 20˚C, then boil with H2O

R Cl BENZOYL CHLORIDE
ALKYLBENZENE

REACTIONS KEY
KMnO4, H2SO4, heat
O
SOCl2, heat
SUBSTITUTION NO2
CH3 PHENYLKETONE
H 2O
NITROBENZENE
OXIDATION
HCl, reflux, Sn; NaOH

O O
REDUCTION
BENZOIC ACID H BENZALDEHYDE
OH
NH2
HYDROLYSIS PHENYLAMINE

ACYLATION
CO, HCl & AlCl3 cat, CuCl

OTHER
RCOCl, AlCl3 cat., reflux 60˚C
Diazotisation: NaNO2 (aq), dilute HCl, temp. 0-5˚C

Cold H3PO2 (aq)

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