Skip to Content

An Adventure in Stereochemistry

Alice in Mirror Image Land


Author(s)

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 Areas

N/A

Educational Level

High school, Undergraduate lower division

Format

PDF

Type / Methods

Directed

Language

English

Subject Headings

Organic Chemistry  |   Biochemistry  |  


Date Posted

08/30/04

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.

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.

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.

Comments