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 |
| 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 |
| 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. |
|---|---|
| ISSN: | 0021-9584 |
| DOI: | 10.1021/acs.jchemed.1c00661 |
