Cart
Article
Keep Going with Cyclooctatetraene!
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Abstract
This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene. Its heat of hydrogenation indicates no significant stabilization by delocalization of electrons, and its alternating carbon-carbon bond lengths are consistent with the presence of alternating "ordinary" single and double bonds. The nonplanar nature of cyclooctatetraene is conclusively indicated by the diastereotopic nature of the methyl groups in its dimethylcarbinyl derivative, illustrating one way that NMR can reveal subtle details of molecular structure. Finally, the Diels-Alder reaction provides a simple but elegant illustration of how reaction mechanisms can be deduced.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Subject):
Aromatic CompoundsCiting 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).
An Exploration of a Photochemical Pericyclic Reaction Using NMR Data
Sara M. HeinJournal of Chemical Education2006 83 (6), 940An Exploration of a Photochemical Pericyclic Reaction Using NMR Data
Sara M. HeinJournal of Chemical Education2006 83 (6), 940This inexpensive, small-scale experiment for advanced organic students describes the unambiguous identification of a photochemical dimerization product from eleven possible candidates. Trans-cinnamic acid is photochemically converted to a dimer product. ...
Quantitative Thermodynamic Descriptions of Aromaticity. A Computational Exercise for the Organic Chemistry Laboratory
Terrence GavinJournal of Chemical Education2005 82 (6), 953Quantitative Thermodynamic Descriptions of Aromaticity. A Computational Exercise for the Organic Chemistry Laboratory
Terrence GavinJournal of Chemical Education2005 82 (6), 953This article describes an exercise that enables students to establish a quantitative scale of aromaticity via computer-driven quantum mechanical calculations using Spartan software. The method utilizes a group of analogous isodesmic reactions from which ...
Looking beyond the endo Rule in a Diels-Alder Discovery Lab
Ronald M. Jarret , Jamie New , Rebecca Hurley and Laura GilloolyJournal of Chemical Education2001 78 (9), 1262Looking beyond the endo Rule in a Diels-Alder Discovery Lab
Ronald M. Jarret , Jamie New , Rebecca Hurley and Laura GilloolyJournal of Chemical Education2001 78 (9), 1262The 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 ...
The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure
Addison AultJournal of Chemical Education2001 78 (7), 924The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure
Addison AultJournal of Chemical Education2001 78 (7), 924In this paper I review and summarize the logical process through which Doering and Roth (Tetrahedron 1963, 19, 715) conceived of the possible existence of an isomer of molecular formula C10H10 that has a "fluxional" structure. That is, the molecule has a ...
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
