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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).![](http://www.chemthes.com/mech/61.gif)
(CH3CO)2CO |
+ |
2 |
[OH]– |
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2 |
[CH3COO]– |
+ |
H2O |
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(CH3CO)2CO |
+ |
2 |
R–OH |
+ |
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CH3COOR |
+ |
CH3COOH |
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(CH3CO)2CO |
+ |
NH3 |
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CH3CONH2 |
+ |
CH3COOH |
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RCOCl |
+ |
H2O |
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RCOOH |
+ |
HCl |
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RCOCl |
+ |
R–OH |
+ |
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+ |
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RCOCl |
+ |
2 |
NH3 |
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+ |
NH4Cl |
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RCOCl |
+ |
Li[Al(OtBu)3H] 1.0M in THF |
+ |
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RCHO |
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RCOCl |
+ |
R2CuLi |
+ |
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RCOOH |
+ |
R–OH |
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+ |
H2O |
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+ |
[OH]– |
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RCOO– |
+ |
NH3 |
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+ |
R–NH2 |
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+ |
R–OH |
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RCOCl |
+ |
RCOO– |
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(RCOO)2O |
+ |
Cl– |
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+ |
[OH]– |
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RCOO– |
+ |
R–OH |
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+ |
NH3 |
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+ |
R–OH |
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+ |
LiAlH4 |
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RCH2OH |
+ |
R–OH |
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+ |
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RCHO |
+ |
R–OH |
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+ |
RMgX |
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R3COH |
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+ |
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+ |
R–OH |
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+ |
RO– |
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2 |
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+ |
CH3CH2O– |
+ |
CH3CH2OH |
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+ |
CH3CH2O– |
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RCOCl |
+ |
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+ |
Cl– |
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RCOCl |
+ |
[SCN]– |
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+ |
RO– |
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CH3COOH |
+ |
CH3CH2OH |
+ |
H+ |
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+ |
H2O |
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+ |
H2O |
+ |
H+(aq) |
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+ |
RCOOH |
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+ |
2 |
NaOH |
+ |
OH–(aq) |
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+ |
RCOO– |
+ |
2 |
Na+ |
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+ |
NaOH |
+ |
OH–(aq) |
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RCOO– |
+ |
CH3OH |
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CH3COOR |
+ |
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+ |
Base– Proton abstractor |
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+ |
(CH3CO)2CO |
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+ |
CH3COOH |
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+ |
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+ |
CH3OH |
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+ |
2 |
(CH3CO)2CO |
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+ |
2 |
CH3COOH |
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+ |
(CH3CO)2CO |
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+ |
CH3COOH |
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+ |
2 |
NH3 |
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+ |
2 |
HCl |
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RCOCl |
+ |
H2S |
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+ |
HCl |
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+ |
(CH3)2NH |
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+ |
CH3OH |
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1000 |
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+ |
1000 |
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Terylene |
+ |
2000 |
H2O |
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+ |
NH3 |
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HCONH2 |
+ |
CH3OH |
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2 |
HCONH2 |
+ |
H2SO4 |
+ |
2 |
H2O |
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2 |
HCOOH |
+ |
(NH4)2SO4 |
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+ |
CH3NH2 |
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+ |
CH3OH |
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+ |
CH3OH |
+ |
H+ |
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+ |
H2O |
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CH3COCl |
+ |
NH3 |
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CH3CONH2 |
+ |
HCl |
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(CH3CO)2CO |
+ |
H2O |
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2 |
CH3COOH |
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CH3COCl |
+ |
H2O |
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CH3COOH |
+ |
HCl |
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CH3COCl |
+ |
2 |
CH3CH2NH2 |
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+ |
[CH3CH2NH3]+ |
+ |
Cl– |
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+ |
(CH3CO)2CO |
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+ |
CH3COOH |
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CH3COCl |
+ |
2 |
NH3 |
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CH3CONH2 |
+ |
NH4Cl |
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+ |
CH3COCl |
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+ |
HCl |
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+ |
CH3CH2OH |
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+ |
HCl |
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+ |
CH3OH |
+ |
H2SO4 |
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+ |
H2O |
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CH3CH2COOH |
+ |
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+ |
H2SO4 |
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+ |
H2O |
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+ |
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+ |
H+ |
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+ |
H2O |
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+ |
[OH]– |
+ |
H2O |
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+ |
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+ |
NaOH(aq) |
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CH3COONa |
+ |
CH3CH2OH |
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+ |
H2O |
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+ |
HCl |
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+ |
2 |
NH3 |
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+ |
NH4Cl |
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+ |
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+ |
HCl |
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+ |
H2O |
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2 |
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+ |
NH3 |
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+ |
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+ |
[NH4]+ |
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+ |
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+ |
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(CH3CO)2CO |
+ |
2 |
CH3NH2 |
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+ |
[CH3NH3]+ |
+ |
[CH3COO]– |
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CH3COCl |
+ |
2 |
CH3NH2 |
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+ |
[CH3NH3]+ |
+ |
Cl– |
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2 |
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+ |
CH3COCl |
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+ |
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+ |
Cl– |
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© Mark R. Leach 1999 –
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