Interactions | Reactions | Processes


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Classified as: Substitution: Addition-followed-by Elimination



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Net substitution occurs when an electrophile adds to a pi-bond, followed by the elimination of an electrofuge, often H+.

For more information look in the Chemogenesis webbook sections on substitution reactions and substitution, transfer, abstraction, displacement (STAD).
(CH3CO)2CO
  +  
2
[OH]–
        
2
[CH3COO]–
  +  
H2O

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(CH3CO)2CO
  +  
2
R–OH
  +  
        
CH3COOR
  +  
CH3COOH

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(CH3CO)2CO
  +  
NH3
        
CH3CONH2
  +  
CH3COOH

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RCOCl
  +  
H2O
        
RCOOH
  +  
HCl

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RCOCl
  +  
R–OH
  +  
        
  +  

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RCOCl
  +  
2
NH3
        
  +  
NH4Cl

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RCOCl
  +  
Li[Al(OtBu)3H]
1.0M in THF
  +  
        
RCHO

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RCOCl
  +  
R2CuLi
  +  
        

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RCOOH
  +  
R–OH
        
  +  
H2O

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  +  
[OH]–
        
RCOO–
  +  
NH3

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  +  
R–NH2
        
  +  
R–OH

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RCOCl
  +  
RCOO–
        
(RCOO)2O
  +  
Cl–

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  +  
[OH]–
        
RCOO–
  +  
R–OH

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  +  
NH3
        
  +  
R–OH

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  +  
LiAlH4
        
RCH2OH
  +  
R–OH

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  +  
        
RCHO
  +  
R–OH

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  +  
RMgX
        
R3COH

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  +  
  +  
R–OH
        
  +  
RO–

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2
  +  
CH3CH2O–
  +  
CH3CH2OH
        
  +  
CH3CH2O–

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RCOCl
  +  
        
  +  
Cl–

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RCOCl
  +  
[SCN]–
        

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  +  
RO–
        

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CH3COOH
  +  
CH3CH2OH
  +  
H+
        
  +  
H2O

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  +  
H2O
  +  
H+(aq)
        
  +  
RCOOH

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  +  
2
NaOH
  +  
OH–(aq)
        
  +  
RCOO–
  +  
2
Na+

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  +  
NaOH
  +  
OH–(aq)
        
RCOO–
  +  
CH3OH

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CH3COOR
  +  
  +  
Base–
Proton abstractor
        

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  +  
(CH3CO)2CO
        
  +  
CH3COOH

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  +  
        
  +  
CH3OH

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  +  
2
(CH3CO)2CO
        
  +  
2
CH3COOH

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  +  
(CH3CO)2CO
        
  +  
CH3COOH

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  +  
2
NH3
        
  +  
2
HCl

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RCOCl
  +  
H2S
        
  +  
HCl

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  +  
(CH3)2NH
        
  +  
CH3OH

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1000
  +  
1000
        
Terylene
  +  
2000
H2O

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  +  
NH3
        
HCONH2
  +  
CH3OH

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2
HCONH2
  +  
H2SO4
  +  
2
H2O
        
2
HCOOH
  +  
(NH4)2SO4

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  +  
CH3NH2
        
  +  
CH3OH

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  +  
CH3OH
  +  
H+
        
  +  
H2O

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CH3COCl
  +  
NH3
        
CH3CONH2
  +  
HCl

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(CH3CO)2CO
  +  
H2O
        
2
CH3COOH

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CH3COCl
  +  
H2O
        
CH3COOH
  +  
HCl

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CH3COCl
  +  
2
CH3CH2NH2
        
  +  
[CH3CH2NH3]+
  +  
Cl–

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  +  
(CH3CO)2CO
        
  +  
CH3COOH

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CH3COCl
  +  
2
NH3
        
CH3CONH2
  +  
NH4Cl

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  +  
CH3COCl
        
  +  
HCl

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  +  
CH3CH2OH
        
  +  
HCl

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  +  
CH3OH
  +  
H2SO4
        
  +  
H2O

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CH3CH2COOH
  +  
  +  
H2SO4
        
  +  
H2O

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  +  
  +  
H+
        
  +  
H2O

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  +  
[OH]–
  +  
H2O
        
  +  

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  +  
NaOH(aq)
        
CH3COONa
  +  
CH3CH2OH

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  +  
H2O
        
  +  
HCl

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  +  
2
NH3
        
  +  
NH4Cl

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  +  
        
  +  
HCl

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  +  
H2O
        
2

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  +  
NH3
        
  +  
  +  
[NH4]+

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  +  
        
  +  

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(CH3CO)2CO
  +  
2
CH3NH2
        
  +  
[CH3NH3]+
  +  
[CH3COO]–

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CH3COCl
  +  
2
CH3NH2
        
  +  
[CH3NH3]+
  +  
Cl–

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2
  +  
CH3COCl
        
  +  
  +  
Cl–

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© Mark R. Leach 1999 –

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