Exercício de Química Sintética e Organica Mista (634)

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(b) Acetanilide is a reactive substrate toward electrophilic aromatic substitution. An acetamido
group is ortho, para-directing.
(c) Sulfonation of the ring occurs.
(d) Bromination of the ring takes place.
(e) Acetanilide undergoes Friedel–Crafts alkylation readily.
( f ) Friedel–Crafts acylation also is easily carried out.
Acetanilide Acetyl chloride
�� ortho isomerC6H5NHCCH3
O
CH3CCl
O
AlCl3
p-Acetamidoacetophenone
O
NHCCH3
CCH3
O
Acetanilide tert-Butyl
chloride
�� ortho isomerC6H5NHCCH3
O
(CH3)3CCl
AlCl3
p-tert-Butyl-
acetanilide
O
NHCCH3
C(CH3)3
Acetanilide p-Bromoacetanilide
�C6H5NHCCH3 ortho isomer
O
Br2
acetic acid
O
NHCCH3
Br
Acetanilide p-Acetamidobenzenesulfonic acid
�C6H5NHCCH3
O
SO3
H2SO4
O
NHCCH3
SO3H
ortho isomer
Acetanilide o-Nitroacetanilide p-Nitroacetanilide
�C6H5NHCCH3
O
HNO3
H2SO4
O
NHCCH3
NO2
O
NHCCH3
NO2
AMINES 629