1. 4-nitrophenol
2,4,6 tribromophenol
Excess Br2
Electrophilic substitution
Dilute Nitric acid
Phenol
Nitration – electrophilic substitution
NaOH at room temperature
Neutralisation Na
Redox
2-nitrophenol
Sodium phenoxide

2. Aminobenzene Nitrobenzene Methylbenzene Benzene Bromobenzene
Bromination– electrophilic substitution
Reduction
Aminobenzene
Nitrobenzene
[H] Tin + conc HCl in reflux (NaOH at end)
Methylbenzene
50°C + concentrated nitric acid and concentrated sulphuric acid catalyst
Haloalkane + halogen carrier in reflux (anhydrous for Cl)
Electrophilic substitution - nitration
Alkylation – electrophilic substitution
Excess of Bromine 3Br2 + Halogen Carrier (FeBr3)
Acyl chloride + halogen carrier in reflux (anhydrous for Cl)
Br2 + Halogen Carrier (FeBr3)
Benzene
Bromobenzene
Phenyl ethanone
Electrophilic substitution – bromination/halogenation
Acylation
NaBH4 [H]
Electrophilic substitution – chlorination/halogenation
Reduction
Cl2 + Halogen Carrier (FeCl3)
Phenyl ethanol
Chlorobenzene