Interactions | Reactions | Processes

Classified as: Substitution: Addition-followed-by Elimination

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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