Aromatic Substitution
Home ]

 

Help end world hunger

 

 

 

 

Periodic Table of Synthesis of Benzene Derivatives

EAS = via Electrophilic Aromatic Substitution
DS = via Diazonium Salt Coupling (Sandmeyer?)
NAS = via Nucleophilic Aromatic Substitution
Benzyne 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

Reduction of Friedel-Craft Acylation Products to a Primary Alkyl Group (Carbonyl to Methylene) using Acidic (Clemmensen), Basic (Wolff-Kishner) and Neutral Conditions (Thio Ketal)

DS, CuCN = cyanobenzene

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

Claisen Rearrangement = ortho-alkylphenol

N

Nitration, EAS, HNO3/H2SO4 = nitrobenzene

Reduction of Nitrobenzene to Aniline

Conversion of an Aniline to a Diazonium Salt

Diazo Coupling, EAS, Diazonium/Heat = Azo dyes

Benzyne Intermediate from Halobenzenes

O

Cumene Hydroperoxide Rearrangement, EAS = phenol & acetone

DS, CuOH = phenol

NAS of Sulfonate or Halobenzene Derivatives = phenol derivative

Benzyne Intermediate from Halobenzenes

F

DS, NaBF4 = fluorobenzene

H

DS,H3PO2
  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 with HNO3 or H2O2= iodobenzene

DS, HI = iodobenzene

 

 

 

Up ] Nucleophilic Substitution ] [ Aromatic Substitution ] Free Radical Substitution ] Enol Enolate Reactions ] Peptides ]

Copyright 2003 and beyond intergrader.net

Thursday, April 06, 2017 13:18