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Reactive Intermediates and Polar Rearrangement (Carbocations and…

- - - - Formations
        
        Hydride shift by Base
        
        Halogen leaving with SN1
        
        Alkene attack
      - Reactions
        
        Attacked by nucleophile
        
        Alkene formation by Elimination
    - - Formations
        
        Electrophilic elimination (SE1)
        
        Alkene attacked by nucleophile
        
        Eliminate hydrogen
      - Reactions
        
        Nucleophilic attack
        
        Alkene formation
    - - SE1
      - Metals-dehalogenation
      - Lithium-halogen exchange
      - Elimination of hydride
      - Redox
  - - - Induction Effect
        3’ > 2’ > 1’
      - Hyperconjugation
    - - pKa of the conjugate acid
      - Resonance
      - Field effect
  - - - Wagner-Meerwein shift
      - Pinacol-Rearrangement
      - Semi-Pinacol rearrangement
    - - 1,2 shift is easy for C+ instead of C- or C.
      - Rearrangement occurs intramolecularily
      - Sigma bond must align with p-orbital
        
        Ex. Rearrangement assisted by neighboring groups.
  - - - 1,2 Aryl shift
      - Ramberg-Backlund (和Favorskii 一樣的mech.
      - Favorskii rearrangement
- - - - 1,2 shifts
        (Mainly C-H shifts)
      - Wolff rearrangement
      - Eschenmoser Fragmentation
- - - - 可能會與1,3-diplomat cycloaddition競爭
    - - Singlet
      - Triplet
- - - - With alkenes
      - With ketones
      - Dimerization