Electrophilic Aromatic Substitution
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Periodic Table of Synthesis of Benzene Derivatives

EAS = via Electrophilic Aromatic Substitution
DS = via Diazonium Salt Coupling
NAS = via Nucleophilic Aromatic Substitution

C

Friedel-Craft Alkylation, EAS, Carbocation from alcohols, alkenes or alkyl halides and a Lewis acid = alkylbenzene

Friedel-Craft Acylation, EAS, RCOCl/AlCl3 = phenylketone

DS, CuCN = cyanobenzene

Kolbe Synthesis, EAS, Phenol/-OH/CO2 = salicylic acid

Claisen Rearrangement = ortho-alkylphenol

N

Nitration, EAS, HNO3/H2SO4 = nitrobenzene

Diazo Coupling, EAS, Diazonium/Heat = diazo dyes

O

Cumene Hydroperoxide Rearrangement, EAS = phenol & acetone

DS, CuOH = phenol

NAS of Sulfonate or Halobenzene Derivatives = phenol derivative

F

DS, NaBF4 = fluorobenzene

    S

Sulfonation, EAS, H2SO4 = benzene sulfonic acid, reversible tends to form para adduct

Cl

Chlorination, EAS, Cl2/FeCl3 = chlorobenzene

DS, CuCl = chlorobenzene

      Br

Bromination, EAS, Br2/FeBr3 = bromobenzene

DS, CuBr = bromobenzene

      I

Iodination, EAS, I2/HNO3 = iodobenzene

DS, HI = iodobenzene

 

 

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Thursday, August 05, 2010 20:18