Interactions | Reactions | Processes

Classified as: Elimination: Second Order

Second order elimination involves the concerted (concurrent) ejection of a nucleofuge and an electrofuge, or a pair of radicals to generate a pi-system.

As the mechanism is concerted, it is an orbital symmetry controlled process. FMO symmetry arguments predict (and experiment demonstrate) that the Efg and Nfg must be diaxial (at 180°) for the elimination to proceed.

For more information look in the Chemogenesis webbook sections on fragmentation reactions and elimination reactions.
  +  
[OH]–
         
  +  
(CH3)3N
  +  
H2O

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(CH3)2CHBr
  +  
CH3CH2O–
  +  
CH3CH2OH
         
CH3–CH=CH2
  +  
  +  
Br–
  +  
CH3CH2OH

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  +  
[OH]–
         
  +  
(CH3)3N
  +  
H2O

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CH2ClCH2Cl
  +  
CH3CH2O–
         
H2C=CHCl
  +  
Cl–
  +  
CH3CH2OH

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(CH3)2CHBr
  +  
CH3CH2O–
         
CH3–CH=CH2
  +  
Br–
  +  
CH3CH2OH

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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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  +  
RLi
         
  +  
LiF
  +  
R–H

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HCOOH
  +  
H2SO4
         
CO
  +  
H2O

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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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CHCl3
  +  
NaOH
         
CCl2
  +  
NaCl
  +  
H2O

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CHCl3
  +  
Base–
Proton abstractor
         
CCl2
  +  
Base-H
Protonated base
  +  
Na+

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  +  
2
  +  
         
  +  
2
(CH3)3COH
  +  
2
KCl

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  +  
NaOH
         
  +  
NaCl
  +  
H2O

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2
CHCl2CH2Cl
  +  
Ca(OH)2
  +  
H2O
         
2
H2C=CCl2
  +  
CaCl2
  +  
2
H2O

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CH3CHO
  +  
HCN
         
  +  
H2O

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  +  
KOH
  +  
CH3CH2OH
         
  +  
KBr
  +  
H2O

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  +  
NaOH
  +  
CH3CH2OH
         
  +  
NaBr
  +  
H2O

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2
  +  
2
KOH
  +  
CH3CH2OH
         
  +  
  +  
2
KBr
  +  
2
H2O

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(CH3)2CHBr
  +  
KOH
  +  
CH3CH2OH
         
CH3–CH=CH2
  +  
KBr
  +  
H2O

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3
  +  
3
KOH
  +  
CH3CH2OH
         
  +  
  +  
  +  
3
KBr

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H2C=CH2
  +  
H2O
  +  
H+

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2
  +  
2
NaOH
         
  +  
CH3–CH=CH2
  +  
2
NaCl
  +  
H2O

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2
(CH3)2CHBr
  +  
2
KOH
         
  +  
CH3–CH=CH2
  +  
2
KBr
  +  
H2O

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© Mark R. Leach 1999 –

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