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Bilirubin

E-/Z-, But Not Easy


Author(s)

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

Abstract

In this case study, two students meet a professor who surprises them by telling them that a biochemically important molecule’s structure has been incorrectly represented in the published literature - in an article in the Proceedings of the National Academy of Sciences, a major biochemistry textbook, and even The Merck Index. The students are challenged to find the nature of the structural errors and correct them. In addition to demonstrating that the technical literature is not without its flaws, the case reviews important concepts related to geometric isomerism and tautomerism.


Objectives

  • To get students to think critically about the literature sources they use in chemistry.
  • To review concepts related to geometric isomerism and tautomerism.

Keywords

Bilirubin; Z-isomer; E-isomer; geometric isomerism; Cahn-Ingold-Prelog; tautomerism; scientific literature

Topical Areas

N/A

Educational Level

Undergraduate lower division

Format

PDF

Type / Methods

Directed

Language

English

Subject Headings

Organic Chemistry  |   Biochemistry  |  


Date Posted

10/17/03

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Comments


Susan Choi
schoi@camdencc.edu
Department of Chemistry
Camden County College
Blackwood, NJ
10/01/2006
I have used this case with my Organic Chemistry II class. Many of my students are pre-pharmacy, so having a medical tie-in increases the students’ interest in the case. The case also forces the students to recall material previously learned (E/Z designations) while learning new concepts (such as lactam/lactim). I allow the students to form groups and work together outside of class. They submit their answers to the questions which count toward part of their grade on their first exam.

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