Himic Anhydride: A retro diels–alder reaction for the organic laboratory and an accompanying NMR study

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
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:	20 Dec 2021 14:05 UTC
Resource URI:	https://kar.kent.ac.uk/id/eprint/92314 (The current URI for this page, for reference purposes)

University of Kent Author Information

Clark, Ewan R..

Creator's ORCID:	https://orcid.org/0000-0001-7287-2631
CReDIT Contributor Roles:

Biagini, Stefano C. G..

Creator's ORCID:	https://orcid.org/0000-0002-4713-5127
CReDIT Contributor Roles:

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