Introducing Complex NMR Mixtures at the Undergraduate Level: Analysis of the Diels-Alder Reaction Between Methylcyclopentadiene and Maleic Anhydride (Part I)

Peer reviewed: 
Yes, item is peer reviewed.
Scholarly level: 
Faculty/Staff
Final version published as: 

Oleg Sannikov, Samuel Hanson, Paul Saunders, Kaitlin L. Branch, Nabyl Merbouh, Introducing Complex NMR Mixtures at the Undergraduate Level: Analysis of the Diels-Alder Reaction between Methylcyclopentadiene and Maleic Anhydride (Part I), Journal of Laboratory Chemical Education, Vol. 7 No. 1, 2019, pp. 8-18. DOI: 10.5923.j.jlce.20190701.02

 

Date created: 
2019
Keywords: 
Methylcyclopentadiene
Diels-alder reaction
Complex mixtures
Nuclear magnetic resonance analysis
Abstract: 

Analysis of a simple NMR spectrum is fairly easy and straight forward for undergraduate students but analyzing a fairly complex NMR can be very daunting and requires a methodical approach. This work uses the ubiquitous Diels-Alder reaction of methylcyclopentadiene and maleic anhydride to introduce students to an NMR spectrum that consist of inseparable mixtures of isomers and their analysis using advanced NMR spectroscopic techniques. This laboratory experiment further outlines the use of derivatization techniques for the separation of isomeric mixtures by preparing diastereomers and using NMR spectroscopy for their identification.

Language: 
English
Document type: 
Article
File(s): 
Statistics: