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Introducing Complex NMR Mixtures at the Undergraduate Level: Isomerization, Separation and Analysis of the Diels-Alder Adducts from the Reaction of Methylcyclopentadiene and Maleic Anhydride (Part II)

Resource type
Date created
2020-10-26
Authors/Contributors
Author: Ye, Eric
Abstract
This paper introduces undergraduate students to advanced NMR techniques to help elucidate the structures of endo and exo norbornene isomers formed during the Diels-Alder reaction between cyclopentadiene and methylcyclopentadiene with maleic anhydride. The microwave assisted isomerization of the norbornene derivatives resulted in a mixture of endo and exo isomers that were separated and analyzed using advanced NMR spectroscopy techniques, with a focus on the spectral interpretation and unequivocal assignment of the endo and exo stereoisomerism when possible.
Document
Identifier
DOI: 10.5923/j.jlce.20200803.01
Published as
Oleg Sannikov, Eric Ye, B. Mario Pinto, Paul Saunders, Nabyl Merbouh, Introducing Complex NMR Mixtures at the Undergraduate Level: Isomerization, Separation and Analysis of the Diels-Alder Adducts from the Reaction of Methylcyclopentadiene and Maleic Anhydride (Part II), Journal of Laboratory Chemical Education, Vol. 8 No. 3, 2020, pp. 39-80. DOI: 10.5923/j.jlce.20200803.01.
Publication title
Journal of Laboratory Chemical Education
Document title
Introducing Complex NMR Mixtures at the Undergraduate Level: Isomerization, Separation and Analysis of the Diels-Alder Adducts from the Reaction of Methylcyclopentadiene and Maleic Anhydride (Part II)
Date
2020
Volume
8
Issue
3
First page
39
Last page
80
Publisher DOI
10.5923/j.jlce.20200803.01
Copyright statement
Copyright is held by the author(s).
Scholarly level
Peer reviewed?
Yes
Language
English
Member of collection
Download file Size
10.5923.j.jlce_.20200803.01.pdf 3.22 MB

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