Chromic acid oxidation of isopropyl alcohol. Oxidation steps

Wiberg, Kenneth B.; Schaefer, H. J.

doi:10.1021/ja01032a024

Cited by 50 publications

(23 citation statements)

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“…The course of this dichromate oxidation can be followed spectrophotometrically as the yellow-orange absorption at 350 nm of the chromium VI is converted to green absorption of the chromium III ion (56). The probable mechanism of oxidation of alcohols by chromium (VI) species involves the formation of chromate esters and their subsequent decomposition to ketones (57). As a rule, in the absence of competing side reactions, the more hindered alcohols react faster than the less hindered compounds.…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Chemistry of Monohydric Alcohols

Benitez

1981

ACS Symposium Series

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Alcohols can be regarded as hydroxyl derivatives of hydrocarbons. They can be characterized by the number of hydroxyl groups (monohydric, dihydric, etc.), according to their structure (primary, secondary or tertiary), and by the structure of the hydrocarbon function to which the hydroxyl is attached (aliphatic, cyclic, saturated or unsaturated).This chapter is concerned almost exclusively with the chemistry of saturated aliphatic monohydric alcohols with particular emphasis on the reactions used in the conversion of these alcohols to other useful compounds. Manufacture of many of the alcohols is covered in other chapters. Acidity and BasicityAlcohols are amphoteric and thus can function both as weak Br^nsted acids and as bases:R-OH + HA ^ R0H 2 + (ROH acting as a base)The acidity of the hydroxyl group can be seen in the rapid proton-deuteron exchange that can take place when alcohols are dissolved in D^O (Reaction I), alkali metals (Reaction II) and organometallic reagents (Reaction III and IV). R-OH +t R-0 + ZH (ROH acting as an acid) (I) (ID (III) (IV)

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Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Chemistry of Monohydric Alcohols

Benitez

1981

ACS Symposium Series

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“…Wiberg and Schafer have summarized the possible mechanisms for the oxidation of an alcohol to a carbonyl compound (13).…”

Section: Oxidations Of Alcohols By Chromic Acidmentioning

confidence: 99%

“…Wiberg and Schâfer have found evidence that the oxidation of an alcohol by chromium(V) also proceeds through an ester intermediate (13).…”

Section: Oxidations Of Alcohols By Chromic Acidmentioning

confidence: 99%

“…If we consider the oxidation of an alcohol by a metal to proceed via a complex, as evidence indicates for both cerium(IV) (2) and chromic acid (13), the competitive oxidation of two alcohols, A^ and A^, may be represented as The concentration of free alcohol may be expressed as the substituent is even one carbon atom closer to the reaction center, the equilibrium constant ranges only from 0.64 for g-nitrobenzyl alcohol to 0.82 for ^-methylbenzyl alcohol.…”

Section: General Considerationsmentioning

confidence: 99%

“…General Considerations, this would lead to a smaller p value. Another possible explanation is that the expression for relative rates derived using the assumption that 1:1 complexes are formed may not be valid due to complications introduced by chromate diesters (13). In order to determine whether or not these complications were affecting the results, a system was chosen for oxidation in which the competition involved two modes of cleavage within the same molecule.…”

Section: Radical Trapping With Oxygenmentioning

confidence: 99%

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