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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.
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 ...
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]
The reaction uses a hypervalent iodine reagent [2] similar to 2-iodoxybenzoic acid to selectively and mildly oxidize alcohols to aldehydes or ketones. The reaction is commonly conducted in chlorinated solvents such as dichloromethane or chloroform. [2] The reaction can be done at room temperature and is quickly complete.
The reaction rate equals the rate of the propagation steps which form the main reaction ... An example is the oxidation of an alcohol to a ketone by ...
The Albright–Goldman oxidation is a name reaction of organic chemistry, first described by the American chemists J. Donald Albright and Leon Goldman in 1965. [1] The reaction is particularly suitable for the synthesis of aldehydes from primary alcohols. Analogously, secondary alcohols can be oxidized to form ketones.
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.
Dess–Martin periodinane (DMP) is a chemical reagent used in the Dess–Martin oxidation, oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. [1] [2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity ...