BRAINCAKEAromatic Synthetic Routes
Aromatic synthetic routes start from benzene or phenol. Benzene reacts by electrophilic substitution, so each step adds or changes a group on the ring. The key conversions are:
• benzene → nitrobenzene: conc. HNO3 and conc. H2SO4, 50 °C
• nitrobenzene → phenylamine: tin and conc. HCl, heat under reflux, then NaOH(aq)
• benzene → bromobenzene: Br2 with a halogen carrier such as FeBr3 or AlBr3
• benzene → alkylbenzene: haloalkane and AlCl3 (Friedel-Crafts alkylation)
• benzene → aromatic ketone: acyl chloride and AlCl3 (Friedel-Crafts acylation)
• phenol → 2,4,6-tribromophenol: bromine water at room temperature, no halogen carrier
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Key terms in this lesson
- electrophilic substitution
- A reaction mechanism in which an electrophile is attracted to and attacks a region of high electron density, such as the delocalised ring in benzene, displacing a hydrogen atom.
More in Organic Synthesis
- Practical Techniques in Organic Synthesis
- Quickfit Apparatus
- Filtration under Reduced Pressure
- Recrystallisation
- Melting Point Determination
- Identifying Functional Groups
- Aliphatic Synthetic Routes
- Planning Multi-Stage Syntheses
All 9 lessons in Organic Synthesis · All OCR A-level Organic Chemistry topics