Chem 220a

Problem Set 8

Chapter 9

Due: Monday, October 31, 2005

Ozone

Christian Friedrich Schönbein (1799-1868) discovered ozone (Gr.; odorant), the sharp odor from electrical discharges. In 1847, he observed that ozone will oxidize organic compounds but not to their ultimate products of oxidation, carbon dioxide and water. [Two years prior, he had spilled nitric and sulfuric acid on his Frau's apron in her kitchen. The apron, made of cotton, combusted and thus was discovered gun cotton, nitrocellulose. Schönbein also observed that hydrogen peroxide (Threnard; 1818) is oxidized to oxygen gas in thepresense of hemoglobin. ] In the period 1903-1916, Carl Dietrich Harries (1866-1923), an assistant to both Hofmann and Fischer at Berlin, published some 80 papers on the reactions of ozone with organic compounds. His interest was stimulated by the reaction of ozone with rubber, which causes the rubber to become hard and brittle. These studies led to the analytical and synthetic uses of ozonolysis. From 1904-1916 he was a professor at Kiel. Disenchanted with academic life, he became Director of Research for Siemens and Halske, the German company co-founded by the electrical pioneer, Werner von Siemens, his father-in-law. Not surprisingly, Siemens went into the business of producing ozone generators. The studies of Rudolf Criegee (1902-1975; Karlsruhe) that produced a unified mechanism for the process of ozonolysis.

 

The alkyne module in ORGO gives a good review of acetylene chemistry.