AROMATIC FUNCTIONAL GROUP INTERCONVERSIONS

BENZENE

R
N

KI (aq), room temp.

Br

Br2 & FeBr3 cat., room temperature

BROMOBENZENE
HBF4 - filter off solid, dry & heat

OH

Powdered Zn, heat

Cl

HNO3, H2SO 4 cat., 55C

NO2

HCl, reflux, Sn; NaOH

OXIDATION

NITROBENZENE

REDUCTION
NH2

KMnO4, H2SO4, heat

ALKYLBENZENE

REACTIONS KEY

BENZENEDIAZONIUM

HCl, CuCl cat., room temp.

CHLOROBENZENE

CuCN, polar solvent, reflux (also for Ar-Br)

0.1M H2SO 4, H2O

KNH2, NH3, -33C; then dilute acid

Na & RI, dry ether

Chloroalkane, AlCl3 cat., room temperature

H2O, 160C

PHENOL

Cl2 & AlCl3 cat., room temperature

HYDROLYSIS

HBr, CuBr cat., room temperature

NaOH with Cu salt cat., 200 atm & 350C, then HCl

SUBSTITUTION

AZOBENZENE

Coupling reaction

FLUOROBENZENE

IODOBENZENE

C6H5R, NaOH, <10C

PHENYLSULFONIC ACID

H2SO 4, heat under reflux

I2 & conc. HNO3, reflux

KCN & copper powder

OH

BENZONITRILE

O
Cl

BENZOYL CHLORIDE

SOCl2, heat

CH3

H 2O

PHENYLKETONE

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

H2SO 4 cat., H2O, heat

O
OH

BENZOIC ACID

BENZALDEHYDE

PHENYLAMINE

ACYLATION
CO, HCl & AlCl3 cat, CuCl

OTHER

RCOCl, AlCl3 cat., reflux 60C

Diazotisation: NaNO2 (aq), dilute HCl, temp. 0-5C

Cold H3PO2 (aq)

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