Interactions | Reactions | Processes


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Classified as: Addition: Electrophilic Protonation



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The addition of Brønsted is a stepwise process. The first step involves a electrophilic proton complexing with a pi-system to generate Type 4 Lewis complex which collapses to a carbenium ion centre. This subsequently complexes with a nucleophilic Lewis base, usually, but not always, the counter ion of the Brønsted acid used to initiate the reaction.

For more information look in the Chemogenesis webbook section on addition reactions.

  +  
HCl
        

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  +  
HBr
        

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  +  
HI
        

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R–C≡C–R
  +  
HCl
        

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  +  
HCl
        

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  +  
CO
  +  
H2O
  +  
H+
  +  
H+(aq)
        
(CH3)3C–COOH

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RCHO
  +  
R–OH
  +  
        
  +  
H2O

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  +  
R–OH
  +  
        
  +  
H2O

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  +  
2
R–OH
  +  
        
  +  
2
H2O

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H+
  +  
        

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O=C=C=C=O
  +  
2
HCl
        

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  +  
HF
        

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  +  
HCl
        

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  +  
HBr
        
(CH3)3CBr

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  +  
HI
        
(CH3)3CI

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  +  
H2O
  +  
H2SO4
        
(CH3)3COH

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CH3–CH=CH2
  +  
HF
        

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CH3–CH=CH2
  +  
HCl
        

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CH3–CH=CH2
  +  
HBr
        
(CH3)2CHBr

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CH3–CH=CH2
  +  
HI
        
(CH3)2CHI

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CH3–CH=CH2
  +  
H2O
  +  
H+
        

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H2C=CH2
  +  
HF
        

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H2C=CH2
  +  
HCl
  +  
AlCl3
        
CH3CH2Cl

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H2C=CH2
  +  
HBr
  +  
AlBr3
        
CH3CH2Br

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H2C=CH2
  +  
HI
        
CH3CH2I

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H2C=CH2
  +  
H2O
  +  
H+
        
CH3CH2OH

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HC≡CH
  +  
H2O
  +  
H+
        
CH3CHO

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HC≡CH
  +  
HCl
  +  
HgCl2
        
H2C=CHCl

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H2C=CH2
  +  
HClO
        

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CH3–CH=CH2
  +  
HClO
        

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  +  
CH3OH
        

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  +  
HCN
  +  
[OH]–
        

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  +  
CH3OH
  +  
H2SO4
  +  
H2O
        
  +  
[NH4]+
  +  
[HSO4]–
  +  
H2O

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  +  
2
HCN
        

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  +  
HCl
        

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  +  
CO
  +  
H2O
  +  
H+
        

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HC≡CH
  +  
H2O
  +  
H+
        
CH3CHO

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2
H2C=CH2
  +  
H2SO4
  +  
Ag2SO4
        
(C2H5O)2SO2

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CH3COOH
  +  
H2C=CH2
        

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  +  
  +  
  +  
3
H2O
  +  
H2SO4
        
3

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H2C=CHCl
  +  
HCl
  +  
FeCl3
        
CH3CHCl2

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CH3CHCl2
  +  
Cl2
  +  
SiO2
        
CH3CCl3
  +  
HCl

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  +  
H2O
  +  
H+
        

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CH3CHO
  +  
HCN
        
  +  
H2O

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  +  
H2O
  +  
H+
        

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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2
  +  
2
HCN
  +  
2
H2
  +  
Pd
on BaSO4
  +  
2
H2O
        
  +  

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  +  
HBr
        

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  +  
H2SO4
        

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H2C=CH2
  +  
H2SO4
        

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  +  
HBr
        

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© Mark R. Leach 1999 –

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