Birchall, Lee T., Shehata, Sara, Serpell, Christopher J., Clark, Ewan R., Biagini, Stefano C. G. (2021) Himic Anhydride: A retro diels–alder reaction for the organic laboratory and an accompanying NMR study. Journal of Chemical Education, 98 (12). pp. 4013-4016. ISSN 0021-9584. E-ISSN 1938-1328. (doi:10.1021/acs.jchemed.1c00661) (KAR id:92314)
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Official URL: https://doi.org/10.1021/acs.jchemed.1c00661 |
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 1H NMR spectra for these norbornene carboxylic anhydride molecules promotes an appreciation of constrained ring systems and factors that affect chemical shifts and coupling constants.
Item Type: | Article |
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DOI/Identification number: | 10.1021/acs.jchemed.1c00661 |
Uncontrolled keywords: | Synthesis, Equilibrium, Reactions, Stereochemistry, NMR Spectroscopy, Hands-On Learning/Manipulatives, Organic Chemistry, Laboratory Instruction, Second-Year Undergraduate, Upper-Division Undergraduate |
Subjects: | Q Science |
Divisions: | Divisions > Division of Natural Sciences > Biosciences |
Depositing User: | Stefano Biagini |
Date Deposited: | 14 Dec 2021 10:15 UTC |
Last Modified: | 05 Nov 2024 12:57 UTC |
Resource URI: | https://kar.kent.ac.uk/id/eprint/92314 (The current URI for this page, for reference purposes) |
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