Epoxidation with Possibilities: Discovering Stereochemistry in Organic Chemistry via Coupling Constants

A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an “unknown” stereoisomer of 3-hexen-1-ol, and use 1H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereoche...

Full description

Saved in:
Bibliographic Details
Published in:Journal of chemical education 2017-05, Vol.94 (5), p.640-643
Main Authors: Treadwell, Edward M, Yan, Zhiqing, Xiao, Xiao
Format: Article
Language:English
Subjects:
Alkenes
College Science
Coupling
Epoxidation
Experiments
Hands on Science
Hydrocarbons
Inquiry
Laboratory Experiments
NMR
Nuclear magnetic resonance
Organic Chemistry
Oxidation
Science Experiments
Science Instruction
Science Laboratories
Spectroscopy
Stereochemistry
Teaching Methods
Undergraduate Study
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A one-day laboratory epoxidation experiment, requiring no purification, is described, wherein the students are given an “unknown” stereoisomer of 3-hexen-1-ol, and use 1H NMR coupling constants to determine the stereochemistry of their product. From this they work backward to determine the stereochemistry of their starting alkene.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.6b00587