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The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course
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Abstract
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session. The resulting product, which contains four new stereocenters, crystallizes upon cooling of the reaction mixture to give the pure product. Careful analysis of the 1H nuclear magnetic resonance spectrum, which contains a variety of cleanly split signals with no overlapping peaks, allows for assignment of all twelve hydrogens. A COSY spectrum of the product is also presented and interpreted.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
SynthesisCiting Articles
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
Demonstration of a Runaway Exothermic Reaction: Diels–Alder Reaction of (2E,4E)-2,4-Hexadien-1-ol and Maleic Anhydride
Brendon A. Parsons and Veljko DragojlovicJournal of Chemical Education2011 88 (11), 1553-1557Demonstration of a Runaway Exothermic Reaction: Diels–Alder Reaction of (2E,4E)-2,4-Hexadien-1-ol and Maleic Anhydride
Brendon A. Parsons and Veljko DragojlovicJournal of Chemical Education2011 88 (11), 1553-1557In a demonstration that involves a solvent-free Diels–Alder reaction of (2E,4E)-2,4-hexadien-1-ol and maleic anhydride, one can use relatively small quantities of reactants to illustrate the process of scaling up a solvent-free reaction, including ...
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Thomas E. Goodwin2009 1011 (), 37-53The Garden of Green Organic Chemistry at Hendrix College
Thomas E. Goodwin2009 1011 (), 37-53The Hendrix College organic chemistry laboratories were converted to microscale experiments in 1988 to minimize possible adverse environmental impact, increase lab safety, and decrease generation of waste and costs of waste disposal. As we became aware of ...
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A Computational Experiment of the Endo versus Exo Preference in a Diels–Alder Reaction
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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 ...
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- Received: August 03, 2009
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