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Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
The Collins oxidation is an organic reaction for the oxidation of primary alcohols to aldehydes. It is distinguished from other chromium oxide-based oxidations by the use of Collins reagent, a complex of chromium(VI) oxide with pyridine in dichloromethane. [1] [2] Mechanism of the Collins oxidation [3]
The Dess–Martin oxidation is an organic reaction for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones using Dess–Martin periodinane. [1] [2] It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin who developed the periodinane reagent in 1983.
For oxidations to the aldehydes and ketones, two equivalents of chromic acid oxidize three equivalents of the alcohol: 2 HCrO 4 − + 3 RR'C(OH)H + 8 H + + 4 H 2 O → 2 [Cr(H 2 O) 6] 3+ + 3 RR'CO. For oxidation of primary alcohols to carboxylic acids, 4 equivalents of chromic acid oxidize 3 equivalents of the alcohol. The aldehyde is an ...
A remarkable feature of these reactions is the ability to conduct carbonyl allylation from the alcohol oxidation state. Due to a kinetic preference for primary alcohol dehydrogenation, diols containing both primary and secondary alcohols undergo site-selective carbonyl allylation at the primary alcohol without the need for protecting groups. [18]
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.
Another side reaction is the Tischenko reaction of aldehyde products with no α-hydrogen, but this can be prevented by use of anhydrous solvents. [4] Another general side reaction is the migration of the double bond during the oxidation of allylic alcohol substrates. [14] Oppenauer oxidation of a steroid derivative. [15]
In chemistry, an alcohol (from Arabic al-kuḥl 'the kohl'), [2] is a type of organic compound that carries at least one hydroxyl (−OH) functional group bound to a saturated carbon atom. [ 3 ] [ 4 ] Alcohols range from the simple, like methanol and ethanol , to complex, like sugar alcohols and cholesterol .