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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.


Lewis structure; formal charge; hybridization; resonance; conjugation; stabilization; reduction

Topical Areas


Educational Level

Undergraduate lower division



Type / Methods




Subject Headings

Organic Chemistry  |   Chemistry (General)  |  

Date Posted


Teaching Notes

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Teaching notes are intended to help teachers select and adopt a case. They typically include a summary of the case, teaching objectives, information about the intended audience, details about how the case may be taught, and a list of references and resources.