New search
download case
  • Overview
  • Teaching Notes
  • Answer Key
  • Comments/Replies

An Adventure in Stereochemistry

Alice in Mirror Image Land



Co Authors:

Frank J. Dinan
Department of Chemistry & Biochemistry
Canisius College
dinan@canisius.edu

Gordon T. Yee
Department of Chemistry
Virginia Polytechnic Institute and State University
gyee@vt.edu

Abstract:

Playfully alluding to Lewis Carroll’s tale of Alice Through the Looking Glass, this case study considers the problems that would arise if a person were to cross over into a mirror-image environment. Students read about a drowsy undergraduate studying for a stereochemistry exam who finds herself in a place where spearmint gum tastes like caraway seed. The case emphasizes the lock-and-key theory of enzyme action and stresses the need for molecules to have the proper chirality if they are to be biologically useful. Designed for introductory organic chemistry and biochemistry courses, the case could also be used in biology courses.

Objectives:
  • Understand that a link exists between stereochemistry, taste, and smell.
  • Distinguish between chiral and achiral objects.
  • Apply the lock-and-key model of enzyme action.
  • Recognize that an enzyme capable of acting upon a chiral molecule won’t necessarily act on its enantiomer.
  • Distinguish between stereogenic and non-stereogenic carbon atoms.
  • Determine whether a wide variety of biologically important molecules are chiral or achiral.
  • Apply the Cahn-Ingold-Prelog system to determine the R- or S-designation of molecules.
Keywords: Stereochemistry; chirality; lock and key enzymes; enantiomer; stereogenic carbon atoms; taste; smell; Cahn-Ingold-Prelog
Topical Area: N/A
Educational Level: High school, Undergraduate lower division
Formats: PDF
Type/Method: Directed
Language: English
Subject Headings: Organic Chemistry   Biochemistry  
Date Posted: 08/30/04
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.

Teaching Notes


Case teaching notes are password-protected and access to them is limited to paid subscribed instructors. To become a paid subscriber, begin the process by registering here.

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.

  Download Teaching Notes

Answer Key


Answer keys for the cases in our collection are password-protected and access to them is limited to paid subscribed instructors. To become a paid subscriber, begin the process by registering here.


  Get Answer Key



Name:
Email:
Department:
Institution:
City State:
Comments:
security code
Enter Security Code: