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Tautomers/Tautomerism

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In part, tautomers are "isomers that are rapidly interconverted." Frequently, however, the less stable of two tautomers is the important on terms of a compound's ability to exhibit a particular sort of chemical reactivity. If one does not recognize the intermediacy of tautomeric forms in such cases, the nature of the reaction will be obscured. This page examines some of the more common or important reactions that proceed by way of an unstable tautomer.

Strongly Related Topics

Somewhat Related Topics

Glossary Terms
  • alpha position
  • constitutional isomers
  • enol
  • isomers
  • rearrangement reactions
  • tautomers

  • Tautomers/Tautomerism

    The most important type of tautomerism in organic chemistry are keto-enol tautomers. Primarily because of the much greater strength of a carbonyl double bond as compared with an alkene double bond, the keto form is usualy the more stable of the two.

    Self-test question #1

    Show the enol tautomer of cyclohexanone:

    ?



    Related reading in textbook (McMurry, Organic Chemistry, 4th ed.)

    Related Computer-Based Learning Materials

    Links to Related Internet Resources


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    This page was prepared by Holly Buchinsky and Dhaval Patel of the Penn State University, Schuylkill Campus, Fall 1996 - Spring 1997

    Send questions, comments, or suggestions to:
    Dr. Thomas H. Eberlein
    the1@psu.edu
    Copyright © 1996 Thomas H. Eberlein

    Version 1.2.2, 3/17/97