Industrial Applications of EAS Reactions:

1. Nitration → Aniline → Dyes and Pharmaceuticals

• Nitrobenzene ([O-][N+](=O)c1ccccc1) is reduced to aniline (Nc1ccccc1)
• Aniline is the precursor to azo dyes, sulfa drugs, paracetamol (acetaminophen)
• Synthesis route: $C_{6}H_{6}$ --[$HNO_{3}$/$H_{2}SO_{4}$]-→ $C_{6}H_{5}NO_{2}$ --[Fe/HCl, then base]-→ $C_{6}H_{5}NH_{2}$

2. Nitration → TNT (2,4,6-Trinitrotoluene)

• Toluene undergoes sequential nitration (3×) to give TNT
• SMILES: Cc1c([N+](=O)[O-])cc([N+](=O)[O-])cc1[N+](=O)[O-]
• Industrial explosive and military application

3. Sulfonation → Detergents (Linear Alkylbenzenesulfonate)

• Long-chain alkylbenzenes undergo sulfonation → alkylbenzenesulfonic acids → sodium salts = biodegradable detergents
• Biodegradable because linear chains (not branched)

4. Friedel-Crafts Acylation → Pharmaceuticals

• Acetophenone (CC(=O)c1ccccc1) synthesis via FC acylation: industrial intermediate
• Ibuprofen synthesis involves FC acylation as a key step
• Aspirin (acetylsalicylic acid) pathway: phenol → salicylic acid → aspirin (involves electrophilic substitution of the ring)

5. Halogenation → Agrochemicals

• Chlorobenzene (Clc1ccccc1) and bromobenzene (Brc1ccccc1) are intermediates in pesticide and herbicide synthesis
• DDT synthesis involves electrophilic chlorination

Pharmaceutical SMILES Summary: