Cart
Article
The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
Discovery-based experiments are excellent tools for promoting substantive interaction among students and between students and instructors. Three related synthetic puzzles are described. In each case an ester is produced via oxidation of a primary alcohol by calcium hypochlorite and acetic acid. Students are placed in teams of three and a different alcohol is assigned to each member of the group. Each person in the group is responsible for synthesizing, purifying, and spectroscopically analyzing his or her unknown product. As a group, the students are asked to determine the structure of their three nonobvious products and to provide a mechanistic rationale for the transformations.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
Oxidation / ReductionCiting Articles
Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.
This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Ring-Closing Metathesis: An Advanced Guided-Inquiry Experiment for the Organic Laboratory
Hala G. Schepmann and Michelle MynderseJournal of Chemical Education2010 87 (7), 721-723Ring-Closing Metathesis: An Advanced Guided-Inquiry Experiment for the Organic Laboratory
Hala G. Schepmann and Michelle MynderseJournal of Chemical Education2010 87 (7), 721-723The design and implementation of an advanced guided-inquiry experiment for the organic laboratory is described. Grubbs’s second-generation catalyst is used to effect the ring-closing metathesis of diethyl diallylmalonate. The reaction is carried out under ...
A Two-Step Synthesis of Virstatin, A Virulence Inhibitor of Vibrio cholerae
Chriss E. McDonaldJournal of Chemical Education2009 86 (4), 482A Two-Step Synthesis of Virstatin, A Virulence Inhibitor of Vibrio cholerae
Chriss E. McDonaldJournal of Chemical Education2009 86 (4), 482Virstatin, an N-butanoic acid substituted naphthalimide, inhibits the ability of Vibrio cholerae to cause disease. A three-week experiment involving synthesis, purification, and spectral characterization of this compound is described. This experiment is ...
The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346The State of Organic Teaching Laboratories
Gail HorowitzJournal of Chemical Education2007 84 (2), 346This review explores the dramatic changes that have taken place in the organic chemistry laboratory course over the last two to three decades. The most significant changes have been in the areas of pedagogy and technology. Significant inroads have been ...
Use of Optical Rotation and NMR Signal Counting To Identify Common Aldoses
John AlmyJournal of Chemical Education2004 81 (5), 708Use of Optical Rotation and NMR Signal Counting To Identify Common Aldoses
John AlmyJournal of Chemical Education2004 81 (5), 708An inexpensive, small scale experiment for second semester organic students describes the unambiguous identification of a common aldose "unknown" from five possible candidates: glucose, mannose, galactose, arabinose, or xylose. The aldose is first reduced ...
The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving
Holly D. Bendorf and Chriss E. McDonaldJournal of Chemical Education2003 80 (10), 1185The Base-Induced Reaction of Salicylaldehyde with 1-Bromobutane in Acetone: Two Related Examples of Chemical Problem Solving
Holly D. Bendorf and Chriss E. McDonaldJournal of Chemical Education2003 80 (10), 1185This investigational laboratory experiment emphasizes structure determination using modern spectroscopic techniques. The experiment examines the base-induced reaction of salicylaldehyde with 1-bromobutane in acetone. The product obtained from the reaction ...
Full Text HTMLTools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Received: August 03, 2009
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
