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Himic Anhydride: A Retro Diels-Alder Reaction for the Organic Laboratory and an Accompanying NMR Study

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Title: Himic Anhydride: A Retro Diels-Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
Language: English
Authors: Birchall, Lee T., Shehata, Sara, Serpell, Christopher J. (ORCID 0000-0002-2848-9077), Clark, Ewan R. (ORCID 0000-0001-7287-2631), Biagini, Stefano C. G. (ORCID 0000-0002-4713-5127)
Source: Journal of Chemical Education. Dec 2021 98(12):4013-4016.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 4
Publication Date: 2021
Document Type: Journal Articles
Reports - Research
Education Level: Higher Education
Postsecondary Education
Descriptors: Organic Chemistry, Scientific Concepts, Undergraduate Students, Laboratory Experiments, Laboratory Equipment
DOI: 10.1021/acs.jchemed.1c00661
ISSN: 0021-9584
Abstract: The thermal equilibration of himic anhydride [IUPAC (2-"endo,"3-"endo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-"exo,"3-"exo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the "exo"-product can be performed as a standard undergraduate laboratory experiment requiring minimal equipment. The interpretation of the [superscript 1]H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants.
Abstractor: As Provided
Entry Date: 2021
Accession Number: EJ1319371
Database: ERIC
FullText Text:
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  Data: Himic Anhydride: A Retro Diels-Alder Reaction for the Organic Laboratory and an Accompanying NMR Study
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  Data: <searchLink fieldCode="AR" term="%22Birchall%2C+Lee+T%2E%22">Birchall, Lee T.</searchLink><br /><searchLink fieldCode="AR" term="%22Shehata%2C+Sara%22">Shehata, Sara</searchLink><br /><searchLink fieldCode="AR" term="%22Serpell%2C+Christopher+J%2E%22">Serpell, Christopher J.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-2848-9077">0000-0002-2848-9077</externalLink>)<br /><searchLink fieldCode="AR" term="%22Clark%2C+Ewan+R%2E%22">Clark, Ewan R.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0001-7287-2631">0000-0001-7287-2631</externalLink>)<br /><searchLink fieldCode="AR" term="%22Biagini%2C+Stefano+C%2E+G%2E%22">Biagini, Stefano C. G.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-4713-5127">0000-0002-4713-5127</externalLink>)
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  Data: <searchLink fieldCode="SO" term="%22Journal+of+Chemical+Education%22"><i>Journal of Chemical Education</i></searchLink>. Dec 2021 98(12):4013-4016.
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  Data: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
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  Data: 10.1021/acs.jchemed.1c00661
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  Data: 0021-9584
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  Data: The thermal equilibration of himic anhydride [IUPAC (2-"endo,"3-"endo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride] to (2-"exo,"3-"exo")-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride and subsequent recrystallization of the "exo"-product can be performed as a standard undergraduate laboratory experiment requiring minimal equipment. The interpretation of the [superscript 1]H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants.
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