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phenols: claisen rearragement. Structure and Nomenclature of Phenols Phenols have hydroxyl groups bonded directly to a benzene ring Naphthols and phenanthrols have a hydroxyl group bonded to a polycyclic benzenoid ring. The Claisen Rearrangement

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slide2

Structure and Nomenclature of Phenols

      • Phenols have hydroxyl groups bonded directly to a benzene ring
        • Naphthols and phenanthrols have a hydroxyl group bonded to a polycyclic benzenoid ring

Chapter 21

slide3

The Claisen Rearrangement

      • Allyl phenyl ethers undergo a rearrangement upon heating that yields an allyl phenol
      • The process is intramolecular; the allyl group migrates to the aromatic ring as the ether functional group becomes a ketone
        • The unstable keto intermediate undergoes keto-enoltautomerization to give the phenol group
      • The reaction is concerted, i.e., bond making and bonding breaking occur at the same time
slide4

Allyl vinyl ethers also undergo Claisen rearrangement when heated

    • The product is a g-unsaturated carbonyl compound
  • The Cope rearrangement is a similar reaction
  • Both the Claisen and Cope rearrangements involve reactants that have two double bonds separated by three single bonds
slide5

The transition state for the Claisen and Cope rearrangements involves a cycle of six orbitals and six electrons, suggesting aromatic character

    • This type of reaction is called pericyclic
  • The Diels-Alder reaction is another example of a pericyclic reaction