Cart
Article
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
Despite the prevalence of epoxide chemistry in the chemical literature and in all modern undergraduate organic textbooks, neither their reactions nor their preparation are common subjects of undergraduate organic lab experiments. This paper describes an operationally straightforward, two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" which probe the stereoselectivity of two important reactions: (i) halohydrin formation from alkenes and (ii) epoxide formation via intramolecular nucleophilic substitution. It complements the increasing number of puzzle-oriented undergraduate experiments combining synthesis and mechanistic discovery which continue to appear in this Journal.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
StereochemistryCiting 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 4 ACS Journal articles (4 most recent appear below).
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 ...
Simple Epoxide Formation for the Organic Laboratory Using Oxone
William C. Broshears , John J. Esteb , Jeremy Richter and Anne M. WilsonJournal of Chemical Education2004 81 (7), 1018Simple Epoxide Formation for the Organic Laboratory Using Oxone
William C. Broshears , John J. Esteb , Jeremy Richter and Anne M. WilsonJournal of Chemical Education2004 81 (7), 1018We present an epoxide formation experiment for a second-semester organic chemistry laboratory. This oxidation utilizes Oxone, a commercially available oxidizing agent, in the industrially relevant process of epoxide formation. The oxidant performing the ...
Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate
Gayle J. Pageau , Rodwell Mabaera , Kathryn M. Kosuda , Tamara A. Sebelius , Ali H. Ghaffari , Kenneth A. Kearns , Jean P. McIntyre , Tina M. Beachy and Dasan M. ThamattoorJournal of Chemical Education2002 79 (1), 96Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trand-beta-Methylcinnamate
Gayle J. Pageau , Rodwell Mabaera , Kathryn M. Kosuda , Tamara A. Sebelius , Ali H. Ghaffari , Kenneth A. Kearns , Jean P. McIntyre , Tina M. Beachy and Dasan M. ThamattoorJournal of Chemical Education2002 79 (1), 96The diastereoselective synthesis of ethyl (E)-3-methyl-3-phenylglycidate, a strawberry flavoring agent, is carried out by epoxidizing ethyl trans-β-methylcinnamate with m-chloroperbenzoic acid. This epoxidation is appropriate for the introductory organic ...
Grignard Reaction of an Epoxide: A Mechanistic Study
James A. Ciaccio , Sabrina Volpi and Ransford ClarkeJournal of Chemical Education1996 73 (12), 1196Grignard Reaction of an Epoxide: A Mechanistic Study
James A. Ciaccio , Sabrina Volpi and Ransford ClarkeJournal of Chemical Education1996 73 (12), 1196Addition of PhMgBr to styrene oxide (1) affords a mixture of 2,2-diphenylethanol (3) and 1,2-diphenylethanol (6) (3:6 = 1:3); reversing the order of addition inverts the ratio of 3 to 6 formed (3:6 = 2:1). Students identify 3 and 6 by TLC comparison with ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
SciFinder Links
Explore by:
History
- Received: August 03, 2009
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
