Birchall, Lee T., Shehata, Sara, Serpell, Christopher J. ORCID: https://orcid.org/0000-0002-2848-9077, Clark, Ewan R. ORCID: https://orcid.org/0000-0001-7287-2631 and Biagini, Stefano C. G. ORCID: https://orcid.org/0000-0002-4713-5127 (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 (Print), 1938-1328 (Online) (doi:10.1021/acs.jchemed.1c00661)

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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
Additional Information:	The authors are grateful to the students on the CH620 module for their contributions in refining the structure of this lab. This work was supported by the School of Physical Sciences, University of Kent Graduate Training Scheme (LTB), and by the EPSRC Doctoral Training Programme (SS). We gratefully acknowledge Andrew Morrell and Helena Shepherd for advice and help with GC analyses and crystallographic interpretations, respectively.
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 > Q Science (General)
Faculty / School / Research Centre / Research Group:	Faculty of Engineering & Science Faculty of Engineering & Science > School of Science (SCI)
Last Modified:	02 Apr 2026 16:01
URI:	https://gala.gre.ac.uk/id/eprint/52715

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