Organic Chemistry : Electrophillic Sibstitution Reactions

1. CHEMISTRY LECTURES

2. Reactions of Phenols: Electrophilic
Aromatic Substitution
• Hydroxyl group strongly activates the ring towards
electrophilic aromatic substitution.

3. Electrophilic Aromatic Substitution in Phenols
• Halogenation
• Nitration
• Sulphonation
• Friedel-Craft’s Alkylation
• Friedel-Craft’s Acylation

4. Halogenation
H2O
OH
F + 3Br2
Br Br
Br
OH
F
25°C

5. Nitration
O
H
CH3
OH
CH3
NO2
HNO3
Acetic acid
5°C

6. OH
CH3H3C
SO3H
(69%)
H2SO4
100°C
Sulphonation
OH
CH3H3C

7. Friedel-Craft’s Alkylation
OH
C
CH3
CH3H3C
CH3
H3PO4
60°C
(CH3)3COH
OH
CH3

8. Friedel-Craft’s Acylation
AlCl3
OH
CH3CCl
O
OH
C
O CH3