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

• Published in: Journal of chemical education Vol. 74; no. 10; p. 1220
• Main Authors: Rhoads, Charlene M, Farquar, George R, Wood, William F
• Format: Journal Article
• Language: English
• Published: Division of Chemical Education 01.10.1997
• Subjects: Hands-On Learning / Manipulatives; Upper-Division Undergraduate; Mechanisms of Reactions; Organic Chemistry
• ISSN: 0021-9584; 1938-1328
• DOI: 10.1021/ed074p1220

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.