Interactions | Reactions | Processes

Classified as: Proton transfer: Brønsted reaction

The Brønsted acid/base protonation reaction involves the transfer of a proton from a Lewis base complex to a Lewis base with a higher proton affinity. The process is a special case nucleophilic substitution (at an H+ centre).

This analysis is explained in detail in the Chemogenesis webbook.

NaNO2
  +  
H+
         
HNO2
  +  
Na+

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RCOOH
  +  
Base–
Proton abstractor
         
RCOO–
  +  
Base-H
Protonated base

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  +  
HBr
         
R–OH
  +  
RBr

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RMgCl
  +  
H2O
         
R–H
  +  
Mg2+
  +  
[OH]–

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CH3MgI
  +  
H2O
         
CH4
  +  
Mg2+
  +  
[OH]–
  +  
I–

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  +  
Base–
Proton abstractor
         
  +  
Cl–

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  +  
Base–
Proton abstractor
         
  +  
Br–

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  +  
Base–
Proton abstractor
         
  +  
HI

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  +  
NaOH
         

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  +  
[OH]–
         
  +  
H2O

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  +  
NaH
  +  
         
  +  
H2
  +  
Na+

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[(C6H5)3P–CH2R]+
  +  
NaH
         
  +  
H2

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  +  
[OH]–
         
  +  
H2O

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  +  
HBF4(aq)
  +  
H2O
  +  
         
  +  
[BF4]–

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H+
  +  
         

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H+
  +  
H2C=CH2
         
[CH3CH2]+

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H+
  +  
CH3CH2OH
         

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HNO3
  +  
2
H2SO4
         
[NO2]+
  +  
2
[HSO4]–
  +  
[H3O]+

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NH3
  +  
H2O
         
[NH4]+
  +  
[OH]–

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NH3(aq)
  +  
H2O
         
[NH4]+
  +  
[OH]–

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.880 NH3
  +  
H2O
         
[NH4]+
  +  
[OH]–

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  +  
H2O
         
  +  
CH3OH

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CuO
  +  
H2SO4(aq)
         
CuSO4
  +  
H2O

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CaC2
  +  
2
H2O
         
HC≡CH
  +  
Ca(OH)2

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  +  
2
Base–
Proton abstractor
         
R–C≡C–R
  +  
2
Base-H
Protonated base
  +  
2
Cl–

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  +  
NaNH2
  +  
NH3
         
R–C≡C–R
  +  
NH3
  +  
NaCl

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R–C≡C–H
  +  
RLi
         
R–C≡C–
  +  
Li+
  +  
R–H

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RLi
  +  
H2O
         
R–H
  +  
Li+
  +  
[OH]–

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H+
  +  
[R–S–CH2]–
         
R–S–CH3

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R–S–CH3
  +  
Base–
Proton abstractor
         
[R–S–CH2]–
  +  
Base-H
Protonated base

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  +  
         
  +  
Li+
  +  

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  +  
Base–
Proton abstractor
         
  +  
Base-H
Protonated base

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  +  
Base–
Proton abstractor
         
  +  
Base-H
Protonated base

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R–H
  +  
Base–
Proton abstractor
         
R–
  +  
Base-H
Protonated base

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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  +  
H2O
         
  +  
Li+
  +  
[OH]–

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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3
H+
  +  
3
         
3

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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H+
  +  
         

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Li3N
  +  
3
H2O
         
3
LiOH
  +  
NH3

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Na2O2
  +  
2
H2O
         
HOOH
  +  
2
NaOH

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Na2O2
  +  
2
HCl
         
HOOH
  +  
2
NaCl

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2
K2O
  +  
2
H2O
         
HOOH
  +  
2
KOH
  +  
O2

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CO2
  +  
2
[OH]–
         
[CO3]2–
  +  
H2O

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LiH
  +  
H2O
         
LiOH
  +  
H2

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NaH
  +  
H2O
         
NaOH
  +  
H2

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KH
  +  
H2O
         
KOH
  +  
H2

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RbH
  +  
H2O
         
RbOH
  +  
H2

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CsH
  +  
H2O
         
CsOH
  +  
H2

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CH3CH2OH
  +  
KOH
         
CH3CH2O–
  +  
K+
  +  
H2O

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2
NaOH
  +  
H2S
         
Na2S
  +  
2
H2O

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2
NaCl
  +  
H2SO4
         
2
HCl
  +  
Na2SO4

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[CO3]2–
  +  
CO2
  +  
H2O
  +  
H2O
         
2
[HCO3]–

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LiOH
  +  
H2S
         
LiSH
  +  
H2O

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NaOH
  +  
H2S
         
NaSH
  +  
H2O

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KOH
  +  
H2S
         
KSH
  +  
H2O

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RbOH
  +  
H2S
         
RbSH
  +  
H2O

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CsOH
  +  
H2S
         
CsSH
  +  
H2O

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2
LiOH
  +  
H2S
         
Li2S
  +  
2
H2O

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2
KOH
  +  
H2S
         
K2S
  +  
2
H2O

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2
RbOH
  +  
H2S
         
Rb2S
  +  
2
H2O

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2
CsOH
  +  
H2S
         
Cs2S
  +  
2
H2O

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Li2S
  +  
H2O
         
LiSH
  +  
LiOH

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Na2S
  +  
H2O
         
NaSH
  +  
NaOH

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K2S
  +  
H2O
         
KSH
  +  
KOH

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Rb2S
  +  
H2O
         
RbSH
  +  
RbOH

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Cs2S
  +  
H2O
         
CsSH
  +  
CsOH

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2
LiNH2
  +  
NH3
         
LiNH2
  +  
NH3

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Be3N2
  +  
6
H2O
         
3
Be(OH)2
  +  
2
NH3

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Mg3N2
  +  
6
H2O
         
3
Mg(OH)2
  +  
2
NH3

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Ca3N2
  +  
6
H2O
         
3
Ca(OH)2
  +  
2
NH3

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Sr3N2
  +  
6
H2O
         
3
Sr(OH)2
  +  
2
NH3

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Ba3N2
  +  
6
H2O
         
3
Ba(OH)2
  +  
2
NH3

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Ca2+
  +  
2
[HCO3]–
  +  
Ca(OH)2
         
2
CaCO3
  +  
2
H2O

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BeH2
  +  
2
H2O
         
Be(OH)2
  +  
2
H2

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MgH2
  +  
2
H2O
         
Mg(OH)2
  +  
2
H2

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CaH2
  +  
2
H2O
         
Ca(OH)2
  +  
2
H2

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SrH2
  +  
2
H2O
         
Sr(OH)2
  +  
2
H2

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BaH2
  +  
2
H2O
         
Ba(OH)2
  +  
2
H2

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BeH2
  +  
2
H+
         
Be2+
  +  
2
H2

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MgH2
  +  
2
H+
         
Mg2+
  +  
2
H2

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CaH2
  +  
2
H+
         
Ca2+
  +  
2
H2

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SrH2
  +  
2
H+
         
Sr2+
  +  
2
H2

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BaH2
  +  
2
H+
         
Ba2+
  +  
2
H2

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CaF2
  +  
H2SO4
         
2
HF
  +  
CaSO4

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Be2C
  +  
4
H2O
         
2
Be(OH)2
  +  
CH4

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MgC2
  +  
2
H2O
         
HC≡CH
  +  
Mg(OH)2

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SrC2
  +  
2
H2O
         
HC≡CH
  +  
Sr(OH)2

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BaC2
  +  
2
H2O
         
HC≡CH
  +  
Ba(OH)2

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4
H+
  +  
C4–
         
CH4

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D2
  +  
H2
  +  
[OH]–
         
HD
  +  
DOH

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Mg2Si
  +  
2
H2SO4
         
SiH4
  +  
2
MgSO4

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NH3
  +  
HCl
         
NH4Cl

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NH4Cl
         
NH3
  +  
HCl

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Ca3P2
  +  
6
H2O
         
2
PH3
  +  
3
Ca(OH)2

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Cs3As
  +  
3
H2O
         
H3As
  +  
3
CsOH

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K3As
  +  
3
H2O
         
H3As
  +  
3
KOH

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Li3As
  +  
3
H2O
         
H3As
  +  
3
LiOH

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Na3As
  +  
3
H2O
         
H3As
  +  
3
NaOH

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Rb3As
  +  
3
H2O
         
H3As
  +  
3
RbOH

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Cs3Sb
  +  
3
H2O
         
H3Sb
  +  
3
CsOH

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K3Sb
  +  
3
H2O
         
H3Sb
  +  
3
KOH

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Li3Sb
  +  
3
H2O
         
H3Sb
  +  
3
LiOH

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Na3Sb
  +  
3
H2O
         
H3Sb
  +  
3
NaOH

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Rb3Sb
  +  
3
H2O
         
H3Sb
  +  
3
RbOH

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H2N–OH
  +  
HCl
         

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2
NH3
         
[NH4]+
  +  
[H2N]–

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3
HN3
  +  
2
Na
         
2
NaN3
  +  
NH3
  +  
N2

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N2O3
  +  
2
H2SO4
         
2
[NO]+
  +  
2
[HSO4]–
  +  
H2O

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Na2CO3
  +  
SO2
  +  
H2O
         
Na2SO3
  +  
CO2

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Na2SO3
  +  
2
HCl
  +  
H2O
         
SO2
  +  
2
NaCl
  +  
H2O

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  +  
H+
         
[HSO3]–
  +  
SO2
  +  
2
Na+

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Ag2CO3
  +  
2
HF
         
2
AgF
  +  
CO2
  +  
H2O

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K2CO3
  +  
4
HF
         
2
K[HF2]
  +  
CO2
  +  
H2O

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HCl
  +  
H2O
         
[H3O]+
  +  
Cl–

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2
HF
         
H+
  +  
[FHF]–

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CH3CH2OH
  +  
H2SO4
         
H2C=CH2
  +  
H2O

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  +  
H2SO4
         
CH3–CH=CH2
  +  
H2O

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(CH3)3COH
  +  
H2SO4
         
  +  
H2O

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  +  
  +  
2
Na
  +  
CH3CH2OH
         
  +  
2
NaBr
  +  
H2

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  +  
2
Base–
Proton abstractor
         

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[H3]+
  +  
Base:
Proton abstractor
         
  +  
H2

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H+
  +  
H2
         
[H3]+

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Na2[B4O5(OH)4]
.8H2O
  +  
2
HCl(aq)
         
4
H3BO3
  +  
2
NaCl
  +  
5
H2O

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2
H+
  +  
         

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Ca3(PO4)2
  +  
3
H2SO4
         
2
H3PO4
  +  
3
CaSO4

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NaOCl(aq)
  +  
2
HCl
         
Cl2
  +  
NaCl
  +  
H2O

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NaOH
  +  
HBr
         
NaBr
  +  
H2O

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NH3
  +  
HNO3
         
NH4NO3

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HCOOH
  +  
NaOH
         
HCOONa
  +  
H2O

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  +  
H2SO4
         
  +  
Na2SO4

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  +  
H+
         
  +  
H2O

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CH3NH2
  +  
H2O
         
[CH3NH3]+
  +  
[OH]–

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[Fe(H2O)6]2+
  +  
2
NaOH(aq)
         

Fe(H2O)4(OH)2
Fe(OH)2
  +  
2
Na+
  +  
2
H2O

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[Fe(H2O)6]2+
  +  
6
NaOH(aq)
         

Fe(H2O)4(OH)2
Fe(OH)2
  +  
2
Na+
  +  
2
H2O
  +  
4
NaOH(aq)

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[Fe(H2O)6]2+
  +  
2
NH3(aq)
         

Fe(H2O)4(OH)2
Fe(OH)2
  +  
2
[NH4]+

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[Fe(H2O)6]2+
  +  
2
NH3(aq)
         

Fe(H2O)4(OH)2
Fe(OH)2
  +  
2
[NH4]+

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[Co(H2O)6]2+
  +  
2
NaOH(aq)
         

Co(H2O)4(OH)2
Co(OH)2
  +  
2
Na+
  +  
2
H2O

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[Co(H2O)6]2+
  +  
6
NaOH(aq)
         

Co(H2O)4(OH)2
Co(OH)2
  +  
2
Na+
  +  
2
H2O
  +  
4
NaOH(aq)

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[Co(H2O)6]2+
  +  
2
NH3(aq)
         

Co(H2O)4(OH)2
Co(OH)2
  +  
2
[NH4]+

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[Cu(H2O)6]2+
  +  
2
NaOH(aq)
         

Cu(H2O)4(OH)2
Cu(OH)2
  +  
2
Na+
  +  
2
H2O

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[Cu(H2O)6]2+
  +  
6
NaOH(aq)
         

Cu(H2O)4(OH)2
Cu(OH)2
  +  
2
H2O
  +  
2
Na+
  +  
4
NaOH(aq)

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[Cu(H2O)6]2+
  +  
2
NH3(aq)
         

Cu(H2O)4(OH)2
Cu(OH)2
  +  
2
[NH4]+

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[Fe(H2O)6]3+
  +  
3
NaOH(aq)
         

Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
H2O
  +  
3
Na+

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[Fe(H2O)6]3+
  +  
6
NaOH(aq)
         

Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
H2O
  +  
3
Na+
  +  
3
NaOH(aq)

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[Fe(H2O)6]3+
  +  
3
NH3(aq)
         

Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
[NH4]+

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[Fe(H2O)6]3+
  +  
6
NH3(aq)
         

Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
[NH4]+
  +  
3
NH3

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2

[Fe(H2O)6]3+
  +  
3
[CO3]2–
         
2

Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
CO2
  +  
3
H2O

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[Al(H2O)6]3+
  +  
3
NaOH(aq)
         
Al(H2O)3(OH)3
Al(OH)3
  +  
3
H2O
  +  
3
Na+

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[Al(H2O)6]3+
  +  
4
NaOH(aq)
         
[Al(OH)4]–
  +  
4
Na+
  +  
6
H2O

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Al(H2O)3(OH)3
Al(OH)3
  +  
NaOH(aq)
         
[Al(OH)4]–
  +  
Na+
  +  
3
H2O

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Al(H2O)3(OH)3
Al(OH)3
  +  
3
H+
         
[Al(H2O)6]3+

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[Al(H2O)6]3+
  +  
3
NH3(aq)
         
Al(H2O)3(OH)3
Al(OH)3
  +  
3
[NH4]+

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[Al(H2O)6]3+
  +  
6
NH3(aq)
         
Al(H2O)3(OH)3
Al(OH)3
  +  
3
[NH4]+
  +  
3
NH3

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2
[Al(H2O)6]3+
  +  
3
[CO3]2–
         
2
Al(H2O)3(OH)3
Al(OH)3
  +  
3
CO2
  +  
3
H2O

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[Cr(H2O)6]2+
  +  
3
NaOH(aq)
         

Cr(H2O)3(OH)3
Cr(OH)3
  +  
3
Na+
  +  
3
H2O

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[Cr(H2O)6]2+
  +  
6
NaOH(aq)
         

[Cr(OH)6]3–
  +  
6
H2O
  +  
6
Na+

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[Cr(H2O)6]2+
  +  
3
NH3(aq)
         

Cr(H2O)3(OH)3
Cr(OH)3
  +  
3
[NH4]+

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2

[Cr(H2O)6]2+
  +  
3
[CO3]2–
         
2

Cr(H2O)3(OH)3
Cr(OH)3
  +  
3
CO2
  +  
3
H2O

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Cr(H2O)3(OH)3
Cr(OH)3
  +  
6
NH3(aq)
         

[Cr(NH3)6]2+
  +  
3
H2O
  +  
3
[OH]–

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Fe(H2O)4(OH)2
Fe(OH)2
  +  
2
H+
         

[Fe(H2O)6]2+

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Co(H2O)4(OH)2
Co(OH)2
  +  
2
H+
         

[Co(H2O)6]2+

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Cu(H2O)4(OH)2
Cu(OH)2
  +  
2
H+
         

[Cu(H2O)6]2+

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Fe(H2O)3(OH)3
Fe(OH)3
  +  
3
H+
         

[Fe(H2O)6]3+

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Cr(H2O)3(OH)3
Cr(OH)3
  +  
3
H+
         

[Cr(H2O)6]2+

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[Fe(H2O)6]3+
  +  
H2O
         

[Co(NH3)6]2+
  +  
[H3O]+

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Fe2(SO4)3
.5H2O
  +  
7
H2O
         
2

[Fe(H2O)6]3+
  +  
3
[SO4]2–

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Cr(H2O)3(OH)3
Cr(OH)3
  +  
3
NaOH(aq)
         

[Cr(OH)6]3–
  +  
3
Na+
  +  
3
H2O

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[Cr(H2O)6]2+
  +  
H2O
         

Cr(H2O)5(OH)]2+

  +  
[H3O]+

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[Cr(H2O)6]2+
         

Cr(H2O)5(OH)]2+

  +  
H+

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H+
  +  
[AlCl4]–
         
AlCl3
  +  
HCl

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  +  
HBr
         
  +  
Br–

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  +  
H+

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  +  
Br–
         
  +  
HBr

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3
Na2O
  +  
2
H3PO4
         
2
Na3PO4
  +  
3
H2O

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Na2O
  +  
2
H+
         
2
Na+
  +  
H2O

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2
NaF
  +  
H2SO4
         
2
HF
  +  
Na2SO4

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2
NaBr
  +  
H2SO4
         
2
HBr
  +  
Na2SO4

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4
NaBr
  +  
3
H2SO4
         
2
HBr
  +  
2
Na2SO4
  +  
Br2
  +  
SO2
  +  
2
H2O

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2
NaI
  +  
H2SO4
         
2
HI
  +  
Na2SO4

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NaI
  +  
H2SO4
         
HI
  +  
I2
  +  
SO2
  +  
S
  +  
H2S

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  +  
2
HCl(aq)
         
  +  
2
Cl–

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  +  
NaOH(aq)
         
  +  
Na+
  +  
H2O

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CH3COOH
  +  
KOH
  +  
H2O
         
[CH3COO]–
  +  
K+
  +  
H2O

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  +  
[OH]–
         
  +  
H2O

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H2O
         
H+
  +  
[OH]–

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BaCl2
  +  
H2SO4(aq)
  +  
H2O
         
BaSO4
  +  
2
HCl

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2
NH3
  +  
H2SO4
         
(NH4)2SO4

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2
KF
  +  
H2SO4
         
2
HF
  +  
K2SO4

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  +  
[OH]–
         
  +  
HBr

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  +  
H+
         

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HNO3
  +  
H2SO4
         
  +  
[HSO4]–

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HNO3|H2SO4
concentrated
         
  +  
[HSO4]–

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RCOOH
  +  
2
LiCH3
         

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  +  
LiCH3
         
H2C=CH2
  +  
  +  
Li+
  +  
CH4

Go To Reaction Data Page

© Mark R. Leach 1999 –

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please contact Mark R. Leach, the author, using mark@meta-synthesis.com