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