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Interactions | Reactions | Processes
Classified as: Substitution: Nucleophilic Second Order
Second order nucleophilic substitution is a concerted processes in which a nucleophilic Lewis base displaces a nucleofugal Lewis base from a Lewis acid centre.
In organic chemistry, SN2 processes usually occur at a delta+ sp3 carbon centre. SN2 processes cause the tetrahedral carbon to invert like an umbrella via a five valent carbonium ion transition state. For more information look in the Chemogenesis webbook sections on substitution reactions and substitution, transfer, abstraction, displacement (STAD).![](http://www.chemthes.com/mech/3.gif)
R–I |
+ |
RO– |
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+ |
NaI |
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RCH2CHO |
+ |
Br2 |
+ |
CH3COOH |
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+ |
HBr |
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RCOO– |
+ |
RCl |
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+ |
Cl– |
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RCOOH |
+ |
CH2N2 |
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+ |
N2 |
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RBr |
+ |
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R–Nu |
+ |
Br– |
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+ |
Br2 |
+ |
CH3COOH |
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+ |
HBr |
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R2CuLi |
+ |
RBr |
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R–R |
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+ |
RBr |
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+ |
Br– |
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R2S |
+ |
R–I |
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[R3S]+ |
+ |
I– |
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+ |
CH3I |
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[R–S]– |
+ |
R–I |
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R2S |
+ |
I– |
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2 |
[R–S]– |
+ |
Br2 |
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R–S–S–R |
+ |
2 |
Br– |
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[R2OH]+ |
+ |
Br– |
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RBr |
+ |
R–OH |
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R–CH2–Br |
+ |
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[(C6H5)3P–CH2R]+ |
+ |
Br– |
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+ |
[OH]– |
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+ |
H2S |
+ |
[OH]– |
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+ |
NH3 |
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+ |
RMgBr |
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R–CH2CH2OH |
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+ |
LiAlH4 |
+ |
2 |
[H] |
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CH3CH2OH |
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+ |
[OH]– |
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+ |
[N3]– |
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+ |
Cl– |
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+ |
CH3COOH |
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+ |
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+ |
HCl |
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CH3I |
+ |
[OH]– |
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CH3OH |
+ |
I– |
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CH3I |
+ |
(CH3)3N |
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[(CH3)4N]+ |
+ |
I– |
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[(CH3)4N]+ |
+ |
[OH]– |
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CH3OH |
+ |
(CH3)3N |
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[(CH3)4N]+ |
+ |
H2S |
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[CH3–SH2]+ |
+ |
(CH3)3N |
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(CH3)2CHBr |
+ |
CH3CH2O– |
+ |
CH3CH2OH |
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CH3–CH=CH2 |
+ |
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+ |
Br– |
+ |
CH3CH2OH |
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+ |
[OH]– |
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+ |
(CH3)3N |
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CH2ClCH2Cl |
+ |
2 |
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PhS(CH2)2SPh |
+ |
2 |
Cl– |
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(CH3)2CHBr |
+ |
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+ |
Br– |
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+ |
CH3I |
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+ |
I– |
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+ |
Br2 |
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+ |
[Et3O]+[BF4]– |
+ |
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+ |
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+ |
Li+ |
+ |
[BF4]– |
+ |
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+ |
CH3CH2I |
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+ |
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+ |
Li+ |
+ |
I– |
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CH3I |
+ |
[SCN]– |
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N≡C–S–CH3 |
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RCOCl |
+ |
[SCN]– |
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CH3I |
+ |
[NO2]– |
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CH3–NO2 |
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CH3I |
+ |
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+ |
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R–I |
+ |
NaCN |
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R–CN |
+ |
NaI |
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R–I |
+ |
AgCN |
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R–NC |
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R2NH |
+ |
HNO2 |
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R2N–NO |
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[R–S]– |
+ |
N≡C–Cl |
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R–S–C≡N |
+ |
Cl– |
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2 |
R–SH |
+ |
N≡C–Br |
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R–S–S–R |
+ |
HCN |
+ |
HBr |
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RMgX |
+ |
N≡C–Cl |
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R–CN |
+ |
Cl– |
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RMgX |
+ |
I–C≡N |
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R–I |
+ |
[CN]– |
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+ |
[CN]– |
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+ |
[R–S]– |
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+ |
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CH3COOH |
+ |
CH3CH2OH |
+ |
H+ |
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+ |
H2O |
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[BH4]– |
+ |
4 |
H2O |
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4 |
H2 |
+ |
[B(OH)4]– |
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+ |
H2O |
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R–OH |
+ |
HCHO |
+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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+ |
H2O |
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+ |
H+ |
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R–C≡C– |
+ |
R–Nfg |
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R–C≡C–R |
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+ |
H– |
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RCHO |
+ |
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+ |
Cl– |
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RCOCl |
+ |
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+ |
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+ |
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+ |
RCOO– |
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(RCOO)2O |
+ |
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+ |
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+ |
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+ |
[H2N]– |
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+ |
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+ |
[OH]– |
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RCOOH |
+ |
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+ |
[CH3–O]– |
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+ |
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+ |
R– |
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+ |
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+ |
H2O |
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RCOOH |
+ |
H+ |
+ |
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+ |
R–Nfg |
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+ |
Li+ |
+ |
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R–Nfg |
+ |
[SCN]– |
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R–S–C≡N |
+ |
R–N=C=S |
+ |
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R–TeH |
+ |
R–Nfg |
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H2Te |
+ |
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RMgX |
+ |
SO2Cl2 |
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RSO2Cl |
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RSO2Cl |
+ |
H2O |
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R–SO3H |
+ |
HCl |
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[R–SO2]– |
+ |
RCl |
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+ |
Cl– |
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[R–Se]– |
+ |
R–Nfg |
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R2Sb |
+ |
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[R3O]+ |
+ |
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R–Nu |
+ |
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+ |
I– |
+ |
Li+ |
+ |
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RCOO– |
+ |
Li+ |
+ |
CH3I |
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+ |
R–Nfg |
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+ |
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R–Nfg |
+ |
[NCO]– |
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R–N=C=O |
+ |
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RO– |
+ |
N≡C–Cl |
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R–O–C≡N |
+ |
Cl– |
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R+ |
+ |
[NCO]– |
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R–N=C=O |
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R–NH2 |
+ |
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R–N=C=O |
+ |
2 |
HCl |
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+ |
Br2 |
+ |
CH3COOH |
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+ |
HBr |
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+ |
(CH3CO)2CO |
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+ |
CH3COOH |
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+ |
(CH3CO)2CO |
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+ |
CH3COOH |
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Cl2O |
+ |
H2O |
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2 |
HClO |
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SiCl4 |
+ |
4 |
CH3MgI |
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Si(CH3)4 |
+ |
4 |
Mg2+ |
+ |
4 |
Cl– |
+ |
4 |
I– |
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N≡C–C≡N |
+ |
2 |
[OH]– |
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[NCO]– |
+ |
[CN]– |
+ |
H2O |
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H2NCl |
+ |
NH3 |
+ |
NaOH |
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H2N–NH2 |
+ |
NaCl |
+ |
H2O |
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2 |
H2NCl |
+ |
H2N–NH2 |
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N2 |
+ |
2 |
NH4Cl |
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3 |
H2NCl |
+ |
2 |
NH3 |
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N2 |
+ |
3 |
NH4Cl |
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PCl3 |
+ |
3 |
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+ |
3 |
Cl– |
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PCl3 |
+ |
3 |
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+ |
3 |
Cl– |
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PCl3 |
+ |
3 |
[(CH3)3C]– |
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+ |
3 |
Cl– |
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PCl3 |
+ |
3 |
R– |
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R3P |
+ |
3 |
Cl– |
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PCl3 |
+ |
3 |
[CH3]– |
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(CH3)3P |
+ |
3 |
Cl– |
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PCl3 |
+ |
3 |
[CH3CH2]– |
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(CH3CH2)3P |
+ |
3 |
Cl– |
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Cl2 |
+ |
[OH]– |
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[ClO]– |
+ |
Cl– |
+ |
H+ |
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Br2 |
+ |
[OH]– |
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[BrO]– |
+ |
Br– |
+ |
H+ |
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I2 |
+ |
[OH]– |
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[IO]– |
+ |
I– |
+ |
H+ |
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+ |
NaOH |
+ |
H2O |
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+ |
NaCl |
+ |
H2O |
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+ |
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+ |
2 |
Na |
+ |
CH3CH2OH |
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+ |
2 |
NaBr |
+ |
H2 |
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+ |
NaOH |
+ |
H2O |
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+ |
NaCl |
+ |
H2O |
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+ |
[SCN]– |
+ |
CH3CH2OH |
+ |
H2O |
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+ |
[NCO]– |
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+ |
[SCN]– |
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+ |
[NCO]– |
+ |
CO2 |
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+ |
LiI |
+ |
CH2Cl2 |
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+ |
.880 NH3 |
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![]() |
![]() |
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![]() |
+ |
H2O |
![]() |
![]() |
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![]() |
+ |
(NH4)2CO3 |
![]() |
![]() |
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![]() |
+ |
CO2 |
+ |
2 |
H2O |
+ |
NH3 |
![]() |
![]() |
2 |
![]() |
+ |
Ca(OH)2 |
![]() |
![]() |
![]() |
![]() |
2 |
![]() |
+ |
CaCl2 |
+ |
2 |
H2O |
![]() |
![]() |
![]() |
1000 |
![]() |
+ |
1000 |
![]() |
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![]() |
Polycarbonate |
+ |
2000 |
HCl |
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+ |
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+ |
HCl |
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![]() |
+ |
CH3NH2 |
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+ |
HCl |
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![]() |
+ |
H2 |
+ |
2 |
NaOH |
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![]() |
![]() |
+ |
2 |
NaCl |
![]() |
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![]() |
CH2ClCH2Cl |
+ |
NH3 |
+ |
CaO |
![]() |
![]() |
![]() |
![]() |
+ |
H2O |
+ |
CaCl2 |
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![]() |
![]() |
CH2ClCH2Cl |
+ |
4 |
NH3 |
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![]() |
![]() |
![]() |
+ |
2 |
NH4Cl |
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![]() |
+ |
NH3 |
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![]() |
+ |
H2O |
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![]() |
+ |
HCN |
+ |
[OH]– |
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![]() |
![]() |
+ |
NaOH |
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![]() |
![]() |
+ |
NaCl |
![]() |
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![]() |
![]() |
![]() |
+ |
H2O |
+ |
NaOH |
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+ |
NaCl |
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+ |
HNO3|H2SO4 concentrated |
+ |
H2 |
+ |
![]() |
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![]() |
![]() |
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![]() |
1000 |
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+ |
1000 |
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![]() |
Terylene |
+ |
1000 |
H2O |
![]() |
![]() |
![]() |
![]() |
CH3CH2Br |
+ |
2 |
NH3 |
![]() |
![]() |
![]() |
![]() |
CH3CH2NH2 |
+ |
NH4Br |
![]() |
![]() |
![]() |
![]() |
CH3Br |
+ |
KCN |
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![]() |
CH3CN |
+ |
KBr |
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![]() |
+ |
I2 |
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+ |
HI |
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![]() |
![]() |
![]() |
+ |
2 |
NH3 |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
NH4Cl |
![]() |
![]() |
![]() |
![]() |
CH2ClCH2Cl |
+ |
2 |
KCN |
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![]() |
![]() |
![]() |
+ |
2 |
KCl |
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![]() |
![]() |
![]() |
+ |
2 |
KCN |
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![]() |
![]() |
![]() |
+ |
2 |
KBr |
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![]() |
![]() |
![]() |
CH3NH2 |
+ |
3 |
CH3CH2Br |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
Br– |
+ |
2 |
HBr |
![]() |
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![]() |
![]() |
+ |
[OH]– |
![]() |
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![]() |
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![]() |
+ |
HBr |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
KCN |
![]() |
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![]() |
![]() |
![]() |
+ |
KBr |
![]() |
![]() |
![]() |
![]() |
CH3–CH=CH2 |
+ |
Br2 |
![]() |
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![]() |
![]() |
![]() |
+ |
Br– |
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![]() |
![]() |
![]() |
(CH3)2CHBr |
+ |
2 |
NH3 |
![]() |
![]() |
![]() |
![]() |
(CH3)2CHNH2 |
+ |
NH4Br |
![]() |
![]() |
![]() |
![]() |
CH3CH2OH |
+ |
2 |
![]() |
![]() |
![]() |
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![]() |
![]() |
![]() |
![]() |
![]() |
(CH3)2CHBr |
+ |
NaOH(aq) |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
NaBr |
![]() |
![]() |
![]() |
![]() |
2 |
![]() |
+ |
2 |
NaOH |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
CH3–CH=CH2 |
+ |
2 |
NaCl |
+ |
H2O |
![]() |
![]() |
CH3CH2OH |
+ |
![]() |
![]() |
![]() |
![]() |
![]() |
Polyethylene Glycol |
![]() |
![]() |
![]() |
![]() |
![]() |
CH3Br |
+ |
[CN]– |
![]() |
![]() |
![]() |
![]() |
CH3CN |
+ |
Br– |
![]() |
![]() |
![]() |
![]() |
CH2ClCH2Cl |
+ |
2 |
[CN]– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
Cl– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
[CN]– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
Br– |
![]() |
![]() |
![]() |
![]() |
(CH3)2CHBr |
+ |
KOH |
+ |
H2O |
![]() |
![]() |
![]() |
![]() |
+ |
KBr |
![]() |
![]() |
![]() |
![]() |
2 |
(CH3)2CHBr |
+ |
2 |
KOH |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
CH3–CH=CH2 |
+ |
2 |
KBr |
+ |
H2O |
![]() |
![]() |
![]() |
+ |
[CN]– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
NH3 |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
NH4Br |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
CH3CH2OH |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
[CN]– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
Cl– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
[OH]– |
![]() |
![]() |
![]() |
![]() |
![]() |
+ |
2 |
Br– |
![]() |
![]() |
![]() |
![]() |
© Mark R. Leach 1999 –
Queries, Suggestions, Bugs, Errors, Typos...
If you have any:
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Bug, typo or grammatical error reports about this page,please contact Mark R. Leach, the author, using mark@meta-synthesis.com