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Developing a Holistic Understanding of Hybridization and Resonance


Manisha Nigam
Department of Chemistry
University of Pittsburgh at Johnstown


This case study is the result of the author's efforts to help students master the complex concept of resonance by unifying multiple concepts across general chemistry and organic chemistry courses. Resonance is a key building block for students' understanding of acids and bases, stabilization of reactive intermediates, and all aromatic reactions of benzene and its derivatives in organic chemistry. This case presents a set of problems that challenges students to think holistically about the concept of resonance together with the concepts of Lewis dot structure, formal charge, and hybridization. This approach, which has been successfully implemented within the curriculum of a first-semester organic chemistry course, can also be adapted for a general chemistry course. An answer key is included within the teaching notes.

  • Correctly use arrows to draw all important resonance structures.
  • Identify major (extra stable) resonance structures and identify why a particular structure is major.
  • Assign correct hybridization to all non-hydrogen atoms.
  • Improve understanding of conjugation, acids and bases; stabilization of reactive intermediates; and mechanisms of reaction of benzene and its derivatives.
Keywords: Lewis structure; formal charge; hybridization; resonance; conjugation; stabilization; reduction
Topical Area: N/A
Educational Level: Undergraduate lower division
Formats: PDF
Type/Method: Directed
Language: English
Subject Headings: Organic Chemistry   Chemistry (General)  
Date Posted: 11/8/2016
Date Modified: N/A
Copyright: Copyright held by the National Center for Case Study Teaching in Science, University at Buffalo, State University of New York. Please see our usage guidelines, which outline our policy concerning permissible reproduction of this work.

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