English (United States)
Electrochemistry is the scientific study of the electrical aspects of chemical reactions. The Fry group has discovered an electrochemical reaction by which the anodic oxidation of 1, 1-diphenylacetaldehyde in the presence of alcohols produces the corresponding benzhydryl alkyl ether with the loss of the acetyl group. Oxidation of the ketone occurs in two stages with the loss of two electrons. Loss of the first electron leads to the formation of a benzhydryl radical and the loss of the second electron forms the benzhydryl cation intermediate that reacts with the alcohol. The goal of this research was to investigate the rate at which the radical is converted into the cation by alkylating the benzylic carbon with a 5 carbon chain. Upon oxidation, a hexenyl radical would be formed which generally cyclizes to form cyclopentylmethyl products. If the radical is oxidized before this ring can be formed, a hexenyl cation would be produced which cyclizes to form a cyclohexyl product. The rates of cyclization to form such ring structures have been measured previously. Thus we will obtain important information on the rate of cyclization of the radical intermediate relative to the rate of oxidation of the radical, based on the structure of the cyclized product. Brominating the benzhydryl carbon of 1,1-diphenylacetaldehye and then alkylating it using 4-penten-1-ol, resulted in an aldehyde ether at very low yields. An alternate route was investigated by creating 2,2-diphenyloxirane and then opening it to create beta - alkoxy alcohol. This resulted in two closely related products that were difficult to separate with column chromatography. Once better separation techniques are identified, we will be able to confirm their structure.
Webley, Ann-Dorie Romania, "Synthesis of ß-Alkoxy Alcohols to Investigate the Rate of Anodic Oxidation of 1,1-Diphenylacetaldehyde" (2018). Honors Theses - All. 2031.
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