17

(ii)

be aware of functional group interconversions:

Nomethod for the direct introduction of “CO2H+” onto aromatic ring.
achieved through functional group interconversion (FGI):

This can only be

2nd example:

Friedel-Crafts alkylation would lead to rearranged products if the suitable primary alkyl
halide is used, instead the use of Friedel-Crafts acylation leads to the desired product:

(iii)

use reactivity to your advantage

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CH3

CO2H

KMnO4

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CO2H
NO2

CO2H

NO2

CH3

CH3

CO2H

CH3

NO2

CH3

NO2

vs

KMnO4

HNO3/
H2SO4

HNO3/
H2SO4

separate

KMnO4

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Br

Br

X

+

+AlCl3

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NH2

H2
NNO

N

N

O

H

H

N

N

O

H

H

N

N

HCl+NaNO2

HONO
"blue"

decomposes >5oC

H+

"NO+"+H

NO+ X-

- H+

+ H

+H2O

X

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Cl

O

O

O

Br

Br

+

AlCl3

Br2/ FeBr3

[H]

no over acylation