Migration (chemistry) | Wikipedia audio article
Channel: wikipedia tts
Date: 2019-05-04

This is an audio version of the Wikipedia Article:
https://en.wikipedia.org/wiki/Rearrangement_reaction


00:02:07 1 1,2-rearrangements
00:03:14 2 Pericyclic reactions
00:03:44 3 Olefin metathesis
00:04:17 4 See also



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SUMMARY
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A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule. In the example below the substituent R moves from carbon atom 1 to carbon atom 2:

  
    
      
        
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    {\displaystyle {-}{\underset {| \atop \displaystyle \color {Blue}{\ce {R}}}{{\ce {C}}}}{\ce {-C-C{-}- {-C-}}}{\underset {| \atop \displaystyle \color {Blue}{\ce {R}}}{{\ce {C}}}}{\ce {-C}}{-}}
  Intermolecular rearrangements also take place. 
A rearrangement is not well represented by simple and discrete electron transfers (represented by curly arrows in organic chemistry texts). The actual mechanism of alkyl groups moving, as in Wagner-Meerwein rearrangement, probably involves transfer of the moving alkyl group fluidly along a bond, not ionic bond-breaking and forming. In pericyclic reactions, explanation by orbital interactions give a better picture than simple discrete electron transfers. It is, nevertheless, possible to draw the curved arrows for a sequence of discrete electron transfers that give the same result as a rearrangement reaction, although these are not necessarily realistic. In allylic rearrangement, the reaction is indeed ionic.
Three key rearrangement reactions are 1,2-rearrangements, pericyclic reactions and olefin metathesis.