JCE Online Journal of Chemical EducationDivision of Chemical Education, American Chemical SocietyAmerican Chemical Society
 | Subscriptions  | Software Orders  | Support  | Contributors  | Advertisers  | 

JCE Print

JCE Digital Library

JCE Software

Only@JCE Online

About JCE


  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > November  >
In the Laboratory
Borohydride Reduction of Estrone
Demonstration of Diastereoselectivity in the Undergraduate Organic Chemistry Laboratory
Animesh Aditya, David E. Nichols, and G. Marc Loudon
Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907
Cover
November 2008
Vol. 85 No. 11
p. 1535

Abstract
This experiment presents a guided-inquiry approach to the demonstration of diastereoselectivity in an undergraduate organic chemistry laboratory. Chiral hindered ketones such as estrone, undergo facile reduction with sodium borohydride in a highly diastereoselective manner. The diastereomeric estradiols produced in the reaction can be analyzed and differentiated by thin-layer chromatography and melting point.
Supplement
Student handouts; Instructor notes
*
Download
Contents
More Information
*
Citation
Aditya, Animesh; Nichols, David E.; Loudon, G. Marc. J. Chem. Educ. 2008, 85, 1535.
*
Keywords
Aldehydes / Ketones; Diastereomers; IR Spectroscopy; Laboratory Instruction; Microscale Lab; Organic Chemistry; Problem Solving / Decision Making; Second-Year Undergraduate; Stereochemistry; Steroids; Thin Layer Chromatography
*
History
Created:
Last Updated:
9/19/2008
9/26/2008
 Caution! 
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > November  > Page 1535


Subscriptions

JCE HS CLIC

Our Secondary School editors work hard to distill all the JCE materials to produce a fraction of particular interest to high school teachers. We call it CLIC.


Contributions Welcome
JCE welcomes your submission

Advertisers
In recent years we have worked hard to better match our advertisers with our readers. When shopping for chemistry education materials, visit our advertisers' WWW sites first.

Be An Ambassador
Take JCE along on your outreach missions. Copies of the Journal, guest access to JCE Online, our publications catalog, and more are available for your participants.