Chapter 16 Part 1

1
Chapter 16 Part 1

• Electrophilic Aromatic Substitution

2
General Mechanism

• Halogenation
• Nitration
• Sulfonation
• Friedel-Crafts

3
Halogenation (Cl2, Br2)

• FeBr3 is the actual catalyst.

4
REVIEW Halogenation of Alkenes

• Recall, halogenation of alkenes does not require
  a catalyst.
• WHY?
• Alkenes are more reactive than aromatic compounds

5
Iodination Requires Oxidation Catalyst

• Catalyst HNO3, HIO3, SO3, H2O2

6
Nitration with Nitric Acid

• Sulfuric Acid Catalyst is required.
• Recall, hybridization?

7
Nitration
8
Reduction of Nitro Compounds
9
Sulfonation

• Industrial Soaps!

• Sulfonations are carried out in one of two ways
• fuming sulfuric acid known as oleum is
  required for unactivated rings
• Rings containing electron donating substituents
  can be sulfonated with sulfuric acid

10
Sulfonation with Oleum
11
Sulfonic Acids
12
Alkali Fusion to form Phenols
13
Friedel-Crafts

• Requires AlCl3 catalyst
• Two kinds of Friedel-Crafts reactions
• Alkylation
• Acylation

14
Friedel-Crafts Alkylation

• Acylating Reagents

15
F-C Acylation
16
F-C Alkylation