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

JCE Print
   Current Issue
 Previous Issues
 Supplements
 Search JCE Index

JCE Digital Library
   ChemInfo
 DigiDemos
 Featured Molecules
 LivTexts
 LrnCom
 QBank
 SymMath
 WebWare

JCE Software
   Latest Releases
 Software & Video
 Downloads
 Support

Only@JCE Online
   JCE Online Store
 JCE HS CLIC
 JCE Discussion Forums
   Biographical Snapshots
 ChemEd Resource Shelf
 Featured Molecules
 Hal's Picks
 Project Chemlab
 Reviewed WWW Sites
 "Web-Ed" Articles

About JCE
   Features
 Publications
 Operations
 Outreach
 Contact Us


  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > January  >
In the Laboratory
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory
David B. Ball
Department of Chemistry, California State University, Chico, Chico, CA 95929-0210
Cover
January 2006
Vol. 83 No. 1
p. 101
Abstract
We have implemented an integrated laboratory sequence that has replaced the advanced laboratories of inorganic, organic, and physical chemistry. To prepare our chemistry majors for the inquiry-based, research-like experiments in the integrated laboratories we introduced several experiments into the second-semester chemistry-major organic laboratory designed to give the students the required laboratory expertise to be successful in the integrated laboratories. A research type, inquiry-based project is described where students synthesize racemic α–hydroxyketones using umpolung, a polarity-reversal approach, investigate chelating versus non-chelating reducing agents, and finally determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Supplement
General procedures (equipment and instrumentation); student laboratory handout containing detailed experimental procedures for the preparation of 1 (R = isopropyl), 2 (R = isopropyl), 7, 10 (R = isopropyl and methyl), 11 (R = isopropyl), and Zn(BH4)2; spectral data for compounds; CAS registry numbers of chemicals; selected 1H spectra; and selected NOESY1D spectra are available.
*  Contents JCE2006p0101W.doc (Microsoft Word)
*  Download
JCE2006p0101W.pdf

JCE2006p0101W.zip
More Information
*  Citation
 Ball, David B. J. Chem. Educ. 2006 83 101.
*  Keywords
 Addition Reactions; Aldehydes / Ketones; Chirality / Optical Activity; Chromatography; Conformational Analysis; Constitutional Isomers; Enantiomers; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Stereochemistry; Synthesis; Upper-Division Undergraduate
*  History
 Created:
Last Updated:		 12/1/2005
12/7/2005
<< Previous Article Table of Contents Next Article >>
  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > January  > Page 101


Subscriptions
 Subscription Info
 Order Forms

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.
 JCE HS CLIC

Contributions Welcome
JCE welcomes your submission
 Contributors' Corner

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.
 Recent Advertisers

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.
 Outreach with JCE

Comments to
jceonline@chem.wisc.edu		 Copyright © Division of Chemical Education, Inc., American Chemical Society.
All rights reserved.