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CHEMISTRY LECTURES
Reactions of Phenols: Electrophilic
Aromatic Substitution
? Hydroxyl group strongly activates the ring towards
electrophilic aromatic substitution.
Electrophilic Aromatic Substitution in Phenols
? Halogenation
? Nitration
? Sulphonation
? Friedel-Craft¡¯s Alkylation
? Friedel-Craft¡¯s Acylation
Halogenation
H2O
OH
F + 3Br2
Br Br
Br
OH
F
25¡ãC
Nitration
O
H
CH3
OH
CH3
NO2
HNO3
Acetic acid
5¡ãC
OH
CH3H3C
SO3H
(69%)
H2SO4
100¡ãC
Sulphonation
OH
CH3H3C
Friedel-Craft¡¯s Alkylation
OH
C
CH3
CH3H3C
CH3
H3PO4
60¡ãC
(CH3)3COH
OH
CH3
Friedel-Craft¡¯s Acylation
AlCl3
OH
CH3CCl
O
OH
C
O CH3
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