Key Terms

• acyl group
• acylation
• alkylation
• benzyne
• combinatorial chemistry
• electrophilic aromatic substitution
• Friedel–Crafts reaction
• inductive effect
• nucleophilic aromatic substitution
• resonance effect

Summary of Reactions 16

• Electrophilic aromatic substitution
• Fluorination (Section 16.2)

• Bromination (Section 16.1)

• Chlorination (Section 16.2)

• Iodination (Section 16.2)

• Nitration (Section 16.2)

• Sulfonation (Section 16.2)

• Friedel–Crafts alkylation (Section 16.3)

• Friedel–Crafts acylation (Section 16.3)

• Reduction of aromatic nitro groups (Section 16.2)

• Nucleophilic aromatic substitution
• By addition to activated aryl halides (Section 16.6)

• By formation of benzyne intermediate from unactivated aryl halide (Section 16.7)

• Oxidation of alkylbenzene side chain (Section 16.8)

• Benzylic bromination of alkylbenzene side chain (Section 16.8)

• Catalytic hydrogenation of aromatic ring (Section 16.9)

• Reduction of aryl alkyl ketones (Section 16.9)