Birchall, Lee T;
Shehata, Sara;
Serpell, Christopher J;
Clark, Ewan R;
Biagini, Stefano CG;
(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.
10.1021/acs.jchemed.1c00661.
Preview |
Text
Himic Anhydride A Retro Diels-Alder Reaction for the Organic Laboratory and an Accompanying NMR Study.pdf - Published Version Download (1MB) | Preview |
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.
| Type: | Article |
|---|---|
| Title: | Himic Anhydride: A Retro Diels–Alder Reaction for the Organic Laboratory and an Accompanying NMR Study |
| Location: | United States |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/acs.jchemed.1c00661 |
| Publisher version: | https://doi.org/10.1021/acs.jchemed.1c00661 |
| Language: | English |
| Additional information: | © The Author(s), 2021. This is an Open Access article distributed under the terms of the Creative Commons Attribution Licence (CC BY 4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0 |
| Keywords: | Synthesis, Equilibrium, Reactions, Stereochemistry, NMR Spectroscopy, Hands-On Learning/Manipulatives, Organic Chemistry, Laboratory Instruction, Second-Year Undergraduate, Upper-Division Undergraduate |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10204802 |
Archive Staff Only
 |
View Item |
