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Ozonolysis Experiments Using Gas Chromatography-Mass Spectrometry: An Undergraduate Organic Chemistry Laboratory Experiment

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Charlene M. Rhoads , George R. Farquar and William F. Wood

Humboldt State University, Department of Chemistry, Arcata, CA 95521-4957

J. Chem. Educ., 1997, 74 (10), p 1220

DOI: 10.1021/ed074p1220

Publication Date (Web): October 1, 1997

Section:

History, Education, and Documentation

Abstract

Ozonolysis can be used to locate the position of double bonds in compounds by fragmentation of the molecule at the double bond. A general method was developed for undergraduate laboratory instruction using ozonolysis at room temperature followed by gas chromatography-mass spectrometry (GC-MS). The simple ozonolysis apparatus described can be constructed from material found in most chemistry laboratories. Ozonolysis experiments were performed on methyl oleate, stilbene, a-methylstilbene, 4-methylstyrene and a-methylstyrene. The products of the ozonolysis were identified by comparison of gas chromatographic retention times with authentic samples of possible fragments and analysis of mass spectra of starting materials and products. Mass spectral data of these chemicals are included.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Mechanisms of Reactions

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Mass Spectral Fragmentation Patterns of Deuterated Butyl and Ethyl Acetates: An Easy Microscale Isotopic Labeling Experiment
Hengameh Zahedkargaran and Leverett R. Smith
Journal of Chemical Education2001 78 (10), 1379
- Mass Spectral Fragmentation Patterns of Deuterated Butyl and Ethyl Acetates: An Easy Microscale Isotopic Labeling Experiment
  Hengameh Zahedkargaran and Leverett R. Smith
  Journal of Chemical Education2001 78 (10), 1379
  We have developed an experimentally uncomplicated microscale second-semester organic lab exercise that illustrates the use of isotopic labeling, in this case deuteration, to help confirm and interpret mass spectral fragmentation patterns in butyl acetate ...
  Abstract | Hi-Res PDF | PDF w/ Links
A Simple and Efficient Ozone Generator
Debra J. Sponholtz , Michael A. Walters , Jimmy Tung and Joseph J. BelBruno
Journal of Chemical Education1999 76 (12), 1712
- A Simple and Efficient Ozone Generator
  Debra J. Sponholtz , Michael A. Walters , Jimmy Tung and Joseph J. BelBruno
  Journal of Chemical Education1999 76 (12), 1712
  We report on the construction of an inexpensive, efficient, and compact ozonolysis apparatus, suitable for use in oxidation chemistry, which is a convenient alternative to the more expensive generators currently on the market. The details, operating ...
  Abstract | Hi-Res PDF | PDF w/ Links