Interactions | Reactions | Processes

Classified as: Substitution: Electrophilic Aromatic

Electrophilic aromatic substitution involves an electrophilic Lewis acid interacting with an aromatic pi-system Lewis base to form a Wheland intermediate.

This high energy species then rapidly ejects an electrofugal Lewis acid (usually H+) to form the substituted aromatic.

This analysis is explained in detail in the Chemogenesis webbook.
  +  
Cl+
         
  +  
H+

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  +  
Cl+ / [AlCl4]–
         
  +  
H+
  +  
[AlCl4]–

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  +  
Br+
         
  +  
H+

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  +  
Br+ [FeBr4]–
         
  +  
H+
  +  
[FeBr4]–

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  +  
I2
  +  
CuCl2
         

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  +  
[NO2]+
         
  +  
H+

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  +  
HNO3
  +  
H2SO4
         
  +  
H2O

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  +  
H2S2O7
         
  +  
H2SO4

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  +  
H2S2O7
  +  
H2O
         
  +  
H2SO4

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  +  
HSO3Cl
         
  +  
H2O

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  +  
R+
         
  +  
H+

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  +  
RCl
  +  
AlCl3
         
  +  
[AlCl4]–

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  +  
[RCO]+
         

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  +  
RCOCl
  +  
AlCl3
         
  +  
H+
  +  
[AlCl4]–

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  +  
Cl2
  +  
AlCl3
         
  +  
H+
  +  
[AlCl4]–

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  +  
         

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  +  
         
  +  
[AlCl4]–
  +  
H+

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CO2
  +  
         

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  +  
  +  
BF3
         
  +  
H+
  +  
[BF4]–

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  +  
CH3CH2Cl
  +  
AlCl3
         
  +  
H+
  +  
[AlCl4]–

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  +  
         
  +  
H+

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  +  
SOCl2
  +  
AlCl3
  +  
CS2
         

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  +  
         
  +  
H2O

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  +  
PCl5
  +  
SnCl4
  +  
         

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  +  
  +  
AlCl3
         
  +  
H2O

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  +  
CH3–CH=CH2
         

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2
  +  
  +  
H2SO4
         
  +  
H2O

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  +  
3
HNO3
         
  +  
3
H2O

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  +  
HNO3|H2SO4
concentrated
         
  +  
H2O

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  +  
  +  
AlCl3
         
  +  
H2O

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2
  +  
2
CO
  +  
FeCl3
         

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  +  
CO
  +  
FeCl3
         

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2
  +  
CO
  +  
FeCl3
         

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  +  
  +  
AlCl3
         
  +  
HCl

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  +  
H2C=CH2
  +  
HCl
  +  
AlCl3
         

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2
  +  
CCl3CHO
  +  
H+
         
DDT
  +  
H2O

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  +  
NH3
  +  
NiO
  +  
Ni
         
  +  
H2

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  +  
HNO3|H2SO4
concentrated
  +  
H2
  +  
         

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  +  
CH3COCl
  +  
AlCl3
         
  +  
HCl

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  +  
[CH3CO]+
         
  +  
H+

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  +  
HNO3
  +  
H2SO4
         
  +  
H2O

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  +  
  +  
AlCl3
  +  
HCl
         

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© Mark R. Leach 1999 –

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