Interactions | Reactions | Processes


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Classified as: Substitution: Electrophilic Aromatic



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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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