Cart
Article
Looking beyond the endo Rule in a Diels-Alder Discovery Lab
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
The commonly described reaction of maleic anhydride and cyclopentadiene generates a Diels-Alder product in accord with the endo rule. Replacing the dienophile with maleic acid or fumaric acid (with modified reaction conditions) allows students to discover or verify that the Diels-Alder reaction is stereospecific with respect to the stereochemistry of the alkene. The recording of NMR spectra is a particularly useful means of establishing cis-trans stereochemistry (symmetry) of the products.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Inquiry-Based / Discovery LearningKeywords (Subject):
NMR SpectroscopyCiting 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 13 ACS Journal articles (5 most recent appear below).
Greener Solutions for the Organic Chemistry Teaching Lab: Exploring the Advantages of Alternative Reaction Media
Lallie C. McKenzie , Lauren M. Huffman and James E. Hutchison , Courtney E. Rogers and Thomas E. Goodwin , Gary O. SpessardJournal of Chemical Education2009 86 (4), 488Greener Solutions for the Organic Chemistry Teaching Lab: Exploring the Advantages of Alternative Reaction Media
Lallie C. McKenzie , Lauren M. Huffman and James E. Hutchison , Courtney E. Rogers and Thomas E. Goodwin , Gary O. SpessardJournal of Chemical Education2009 86 (4), 488A major approach for implementing green chemistry is the discovery and development of synthetic strategies that reduce the quantity of solvent needed, eliminate it altogether, or rely on new reaction media. An increasing number of examples have ...
A Computational Experiment of the Endo versus Exo Preference in a Diels–Alder Reaction
Christopher N. Rowley and Tom K. Woo , Nick J. MoseyJournal of Chemical Education2009 86 (2), 199A Computational Experiment of the Endo versus Exo Preference in a Diels–Alder Reaction
Christopher N. Rowley and Tom K. Woo , Nick J. MoseyJournal of Chemical Education2009 86 (2), 199We have developed and tested a computational laboratory that investigates an endo versus exo Diels–Alder cycloaddition. This laboratory employed density functional theory (DFT) calculations to study the cycloaddition of N-phenylmaleimide to furan. The ...
The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction. An Undergraduate Project in Organic Synthesis and Structural Analysis
Xavier Sauvage and Lionel DelaudeJournal of Chemical Education2008 85 (11), 1538The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction. An Undergraduate Project in Organic Synthesis and Structural Analysis
Xavier Sauvage and Lionel DelaudeJournal of Chemical Education2008 85 (11), 1538The synthesis of N-benzyl-2-azanorbornene via aqueous hetero Diels–Alder reaction of cyclopentadiene and benzyliminium chloride formed in situ from benzylamine hydrochloride and formaldehyde is described. Characterization of the product was achieved by IR ...
Introducing Undergraduate Students to Electrochemistry: A Two-Week Discovery Chemistry Experiment
Lisa P. Nestor , Mauri A. Ditzler , Kenneth V. Mills , Richard S. Herrick and Louise W. Guilmette , Heather ShaferJournal of Chemical Education2008 85 (8), 1116Introducing Undergraduate Students to Electrochemistry: A Two-Week Discovery Chemistry Experiment
Lisa P. Nestor , Mauri A. Ditzler , Kenneth V. Mills , Richard S. Herrick and Louise W. Guilmette , Heather ShaferJournal of Chemical Education2008 85 (8), 1116Within the framework of a laboratory-focused, guided-inquiry pedagogy, students discover the Nernst equation, the spontaneity of galvanic cells, concentration cells, and the use of electrochemical data to calculate equilibrium constants. The laboratory ...
Data Pooling in a Chemical Kinetics Experiment: The Aquation of a Series of Cobalt(III) Complexes: A Discovery Chemistry Experiment
Lisa P. Nestor , Richard S. Herrick and Kenneth V. MillsJournal of Chemical Education2008 85 (8), 1120Data Pooling in a Chemical Kinetics Experiment: The Aquation of a Series of Cobalt(III) Complexes: A Discovery Chemistry Experiment
Lisa P. Nestor , Richard S. Herrick and Kenneth V. MillsJournal of Chemical Education2008 85 (8), 1120An experiment in chemical kinetics as part of our Discovery Chemistry curriculum is described. Discovery Chemistry is a pedagogical philosophy that makes the laboratory the key center of learning for students in their first two years of undergraduate ...
Tools
-
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
