Prev. Article Next Article Table of Contents

Article

Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Marsha R. Baar and Kristin Wustholz

Department of Chemistry, Muhlenberg College, Allentown, PA 18104

J. Chem. Educ., 2005, 82 (9), p 1393

DOI: 10.1021/ed082p1393

Publication Date (Web): September 1, 2005

Section:

History, Education, and Documentation

Abstract

endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a Diels–Alder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride. This Diels–Alder reaction can be performed on macro- or miniscale, at room temperature for a week or under reflux for 2.5 hours to produce a 91% yield of a white solid that precipitates from solution and can be analyzed without further purification. Typical student results after 1.5 hours of reflux were 1.05 g (78%), mp 203.4–205.3 °C (lit. 204–206 °C). Results from IR and ¹H and ¹³C NMR were consistent with literature values.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Asymmetric Synthesis

View: Hi-Res PDF | PDF w/ Links

Citing 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 2 ACS Journal articles (2 most recent appear below).

Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels−Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis
Marsha R. Baar, Danielle Falcone and Christopher Gordon
Journal of Chemical Education2010 87 (1), 84-86
- Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels−Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis
  Marsha R. Baar, Danielle Falcone and Christopher Gordon
  Journal of Chemical Education2010 87 (1), 84-86
  Microwave heating enhanced the rate of three reactions typically performed in our undergraduate organic chemistry laboratory: a Diels−Alder cycloaddition, a Wittig salt formation, and a Williamson ether synthesis. Ninety-minute refluxes were shortened to ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Identification of an Unknown Compound by Combined Use of IR, 1H NMR, 13C NMR, and Mass Spectrometry: A Real-Life Experience in Structure Determination
Louis J. Liotta and Magdalena James-Pederson
Journal of Chemical Education2008 85 (6), 832
- Identification of an Unknown Compound by Combined Use of IR, 1H NMR, 13C NMR, and Mass Spectrometry: A Real-Life Experience in Structure Determination
  Louis J. Liotta and Magdalena James-Pederson
  Journal of Chemical Education2008 85 (6), 832
  In this introductory organic chemistry experiment, the students get an opportunity to analyze and identify an unknown compound as it is done in a real-laboratory setting. First, students are instructed on the proper operation of three major instruments, ...
  Abstract | Hi-Res PDF | PDF w/ Links