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Mechanism of the oxidation of para-substituted 1-phenylethanols with sodium hypochlorite in acetic acid

✍ Scribed by Ayano Sakai; David G. Hendrickson; William H. Hendrickson

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 143 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00296-3

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✦ Synopsis

The ρ-value of -1.8 for the oxidation of para-substituted 1-phenylethanols by sodium hypochlorite in acetic acid suggests that ketone is formed directly from alcohol by loss of a hydride. The kinetic isotope effect is 3.0. When the disappearance of oxidant is followed by iodometric titration, 5-nonanol is oxidized about 20 times faster than 1-butylpentyl hypochlorite decomposes. However, when NaCl is added to the alkyl hypochlorite, the reaction rates are about the same.

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