Rearrangement reaction

In organic chemistry, a rearrangement reaction is a broad class of organic reactions "that involves a change of connectivity". Usually the term rearrangement refers to intramolecular processes involving modification of carbon skeleton.[1][2][3] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2:

A rearrangement is not well represented by simple and discrete electron transfers (represented by curved 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.

  1. ^ "molecular rearrangement". IUPAC Gold Book. 2014. doi:10.1351/goldbook.M03997.
  2. ^ March, Jerry (1985). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley. ISBN 9780471854722. OCLC 642506595.
  3. ^ Rojas, Christian M., ed. (2015). Molecular Rearrangements in Organic Synthesis. doi:10.1002/9781118939901. ISBN 978-1-118-34796-6.
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