Coupling reactions: azo dyes
Amines and Diazonium Salts · Chemistry
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Why does diazonium couple with phenol but not with nitrobenzene? Step 1: Coupling is electrophilic aromatic substitution by ArN₂⁺ (weak electrophile). Step 2: Phenol's ring is strongly activated (+M –OH) → attacks readily. Step 3: Nitrobenzene's ring is deactivated (–M –NO₂) → too unreactive. Step 4: Only activated rings (phenols, aromatic amines) couple — reactivity matching!