Acetaminophen (paracetamol, Tylenol) is a widely used analgesic and antipyretic that reduces pain and fever by inhibiting prostaglandin synthesis in the central nervous system. Its structure features a phenolic hydroxyl group and an amide functionality, making it a simple yet instructive example for studying aromatic substitution and acylation reactions.
In this exercise, add the missing reagents and draw the structures of the intermediates in the synthesis of Acetaminophen. The preparation highlights key reaction types, including:
- Electrophilic Aromatic Substitution (EAS) – used to introduce the hydroxyl group on the aromatic ring.
- Nucleophilic Aromatic Substitution (SNAr)
- Nucleophilic Acyl Substitution – used to form the key aromatic amide by reacting the aniline derivative with an activated carboxylic acid derivative.
These steps illustrate how controlling aromatic substitution patterns and performing acylation reactions allow the assembly of a widely used pharmaceutical compound from simple starting materials.
Practice
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