Bond Analysis as a Tool in the Solution of Ozonolysis Problems

A new way to find all of the carbon-carbon double and triple bonds in an unknown analyte is described. The procedure works for compounds containing small numbers of carbon-carbon multiple bonds. These results are obtainable from the bond change occurring in organic compounds during ozonolysis by a reductive workup. Double bonds invariably produce two new bonds and triple bonds five. Knowledge of the number and kinds of carbon-carbon multiple bonds and the number of products their cleavages produce allows the structures of many analytes to be elucidated, given only molecular formulas. One-hundred student unknowns with solutions are available as supporting materials.