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Oxidation of benzyl alcohols by nitrous and nitric acids in strong sulfuric acid media

✍ Scribed by David S. Ross; Chee-Liang Gu; Georgina P. Hum; Ripudaman Malhotra

Publisher
John Wiley and Sons
Year
1986
Tongue
English
Weight
505 KB
Volume
18
Category
Article
ISSN
0538-8066

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✦ Synopsis

We have studied the oxidation of benzyl alcohols by nitrous and nitric acid in sulfuric acid media. The oxidation by nitrous acid is rapid and has an activation energy of 10.6 -t 0.8 kcal mol-'. A Hammett plot of logkp vs. u -is linear with a p value of -1.4. The oxidation by nitric acid in sulfuric acid media is autocatalytic. From the kinetic and product analyses, it is concluded that a common oxidant, the nitrosonium ion is involved when either nitrous or nitric acid is used. A mechanism is proposed which involves the abstraction of hydride from the alcohols as the rate determining step. It is demonstrated that the autoxidation of the alcohols is catalyzed by nitrous acid or nitric oxide. *We use N(II1) and N(V) to stand for the added NaNOz and NaNO,, respectively

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