Nitration
Benzene is nitrated by concentrated nitric and sulfuric acids to form nitrobenzene.
- Reagents
- concentrated HNO3 and concentrated H2SO4
- Conditions
- warm at about 50-55 C
- Reaction class
- electrophilic substitution
- Equation
- C6H6 + HNO3 -> C6H5NO2 + H2O
Overview
Benzene is nitrated by concentrated nitric and sulfuric acids to form nitrobenzene.
Transformation
- Equation
- C6H6 + HNO3 -> C6H5NO2 + H2O
- Reagents
- concentrated HNO3 and concentrated H2SO4
- Environment
- warm at about 50-55 C
- Reaction class
- electrophilic substitution
- Mechanism
- electrophilic aromatic substitution
- Evidence level
- textbook core
Scope and limitations
- Scope
- The acid mixture generates the nitronium ion electrophile for nitration of benzene.
- Limitations
- Higher temperatures encourage further nitration; directing effects are outside this route record.
Related reactions
- Combustion: Benzene → Carbon dioxide
Benzene combusts to carbon dioxide and water and tends to burn with a smoky flame.
- Bromination: Benzene → Halogenoarenes
Benzene undergoes bromination with a halogen carrier catalyst to form bromobenzene.
- Friedel Crafts alkylation: Benzene → Alkylarenes
Friedel-Crafts alkylation attaches an alkyl group to benzene.
- Friedel Crafts acylation: Benzene → Acylbenzenes
Friedel-Crafts acylation attaches an acyl group to benzene.
- Reduction: Nitroarenes → Aromatic amines
Nitroarenes are reduced to aromatic amines using tin and hydrochloric acid followed by alkali.
- Ring hydrogenation: Benzene → Cyclohexane
Benzene gives cyclohexane through ring hydrogenation.
- Nitration: Benzene → Nitrobenzene
Benzene gives nitrobenzene through nitration.
References
- Organic Chemistry: Other Aromatic SubstitutionsJohn McMurry · OpenStax Organic Chemistry · 2023
Supports nitronium-ion formation from concentrated nitric and sulfuric acids, benzene attack, and deprotonation to regenerate aromaticity in nitration.