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A R O M AT I C R E AC T I O N S M A P

BENZENE

KI (aq), room temp.


Br

Br2 & FeBr3 cat., room temperature

BROMOBENZENE
HBF4 - filter off solid, dry & heat

N
N+

HBr, CuBr cat., room temperature


OH

Powdered Zn, heat

BENZENEDIAZONIUM

H2O, 160C

PHENOL

HCl, CuCl cat., room temp.

Cl

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

CHLOROBENZENE

HNO3, H2SO 4 cat., 55C

REACTIONS KEY
SUBSTITUTION

NO2

NITROBENZENE
HCl, reflux, Sn; NaOH

OXIDATION
REDUCTION
HYDROLYSIS

KMnO4, H2SO4, heat

ALKYLBENZENE

BENZONITRILE

BENZOYL CHLORIDE

COR

SOCl2, heat

PHENYLKETONE

H 2O

CHO

COOH

BENZOIC ACID

Air

NH2

PHENYLAMINE

CO, HCl & AlCl3 cat, CuCl


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

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CN

COCl

ACYLATION
OTHER

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

0.1M H2SO 4, H2O


KNH2, NH3, -33C; then dilute acid

Na & RI, dry ether

Cl2 & AlCl3 cat., room temperature

Chloroalkane, AlCl3 cat., room temperature

Cold H3PO2 (aq)

C6H5R, NaOH, <10C

AZOBENZENE

Coupling reaction

FLUOROBENZENE

IODOBENZENE

KCN & copper powder

H2SO 4 cat., H2O, heat

H2SO 4, heat under reflux

PHENYLSULFONIC ACID

I2 & conc. HNO3, reflux

BENZALDEHYDE

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

SO3H

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