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Bilirubin

E-/Z-, But Not Easy

By Frank J. Dinan

Bilirubin


 

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.

   

Date Posted

10/17/2003

Overview

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

  

Subject Headings

Biochemistry
Organic Chemistry

EDUCATIONAL LEVEL

Undergraduate lower division

  

FORMAT

PDF

   

TOPICAL AREAS

N/A

   

LANGUAGE

English

   

TYPE/METHODS

Directed

 

 

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