The "Big Dog-Puppy Dog" Analogy for Resonance

Todd P. Silverstein
Chemistry Department, Willamette University, Salem, OR 97301
J. Chem. Educ., 1999, 76 (2), p 206
DOI: 10.1021/ed076p206
Publication Date (Web): February 1, 1999

Abstract

In this analogy, puppy dogs are restricted to a specific dog run; they represent s-bond electron pairs. Big dogs are allowed to roam freely over several consecutive dog runs; they represent delocalized p-bond electron pairs. By adding a bunny rabbit who is chased by the big dog, the analogy can be expanded to account for delocalized formal charge in a resonance hybrid.

Keywords (Audience):

High School / Introductory Chemistry

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

Applications and Analogies

Keywords (Pedagogy):

Analogies / Transfer

Keywords (Subject):

Covalent Bonding

Citing Articles

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This article has been cited by 6 ACS Journal articles (5 most recent appear below).

  • Cover Image

    Assessment of Organic Chemistry Students’ Knowledge of Resonance-Related Structures

    Rosa Betancourt-Pérez and Luis Javier Olivera, Julio E. Rodríguez
    Journal of Chemical Education2010 87 (5), 547-551
    • Assessment of Organic Chemistry Students’ Knowledge of Resonance-Related Structures

      Rosa Betancourt-Pérez and Luis Javier Olivera, Julio E. Rodríguez
      Journal of Chemical Education2010 87 (5), 547-551

      This study examines how well second-year nonmajor organic chemistry students are learning to draw, interpret, and understand resonance-related structures. Students were tested seven times throughout an academic year using a set of four tasks that ...

  • Cover Image

    Acid-Catalyzed Enolization of β-Tetralone

    Brahmadeo Dewprashad , Anthony Nesturi and Joel Urena
    Journal of Chemical Education2008 85 (6), 829
    • Acid-Catalyzed Enolization of β-Tetralone

      Brahmadeo Dewprashad , Anthony Nesturi and Joel Urena
      Journal of Chemical Education2008 85 (6), 829

      This experiment allows students to use 1H NMR to directly compare the relative initial rates of substitution of the benzylic and non-benzylic α hydrogens of β-tetralone and correlate their findings with the predictions made by resonance theory. The ...

  • Cover Image

    Aromatic Bagels: An Edible Resonance Analogy

    Shirley Lin
    Journal of Chemical Education2007 84 (5), 779
    • Aromatic Bagels: An Edible Resonance Analogy

      Shirley Lin
      Journal of Chemical Education2007 84 (5), 779

      A classroom demonstration involving the use of a bagel and cream cheese as an analogy for the two resonance contributors of benzene is described. This method emphasizes the deficiencies of using a single Lewis structure to describe the structure of ...

  • Cover Image

    If It's Resonance, What Is Resonating?

    Robert C. Kerber
    Journal of Chemical Education2006 83 (2), 223
    • If It's Resonance, What Is Resonating?

      Robert C. Kerber
      Journal of Chemical Education2006 83 (2), 223

      The resonance terminology that accompanies use of more than one Lewis-type structure to describe delocalized bonding in molecules has been leading students astray for more than half a century. In this article I review the origin of the terminology and how ...

  • Cover Image

    Intermediates, Transition States, Butterflies, and Frogs

    Trevor M. Kitson
    Journal of Chemical Education2001 78 (4), 504
    • Intermediates, Transition States, Butterflies, and Frogs

      Trevor M. Kitson
      Journal of Chemical Education2001 78 (4), 504

      An analogy that may be useful in the classroom is described. The changes that occur in typical simple SN1 and SN2 reactions are compared to the metamorphoses undergone by caterpillars and tadpoles, respectively.

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History

  • Received: August 03, 2009

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