An Analysis of Ozonolysis for Classroom Instruction

The number of triple bonds, double bonds, rings, and rings cleaved on ozonolysis (reductive workup) are determined directly from the molecular formulas of a hydrocarbon reactant and its organic reaction products. The equations for the analysis are derived and exemplified, starting with two equations...

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Bibliographic Details
Published in:Journal of chemical education 1996-11, Vol.73 (11), p.1019
Main Author: Gross, Ray A
Format: Article
Language:English
Subjects:
Basic Skills
Chemical reactions
Classroom Communication
Concept Teaching
Organic chemistry
Oxidation
Ozone
Teaching Methods
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Summary:The number of triple bonds, double bonds, rings, and rings cleaved on ozonolysis (reductive workup) are determined directly from the molecular formulas of a hydrocarbon reactant and its organic reaction products. The equations for the analysis are derived and exemplified, starting with two equations that express the sum of pi bonds and rings (SOPAR) in a hydrocarbon: s = pi + r and s = n + 1 - h/2. The increase in the number of hydrogen (Deltah) and oxygen (Deltao) atoms in the organic products are a function of the number of double and triple bonds in the reactant hydrocarbon. When all of the organic products are included, the change in the number of carbon atoms (Deltan) is zero and the number of triple bonds equals Deltah/2, the number of double bonds equals Deltao/2 - Deltah, the number of rings equals s - Deltao/2, and the number of rings cleaved equals Deltao/2 - Deltah - Deltas.
ISSN:0021-9584
1938-1328
DOI:10.1021/ed073p1019