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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 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 ...
The reaction mechanism of Corey–Kim oxidation. Under Corey–Kim conditions allylic and benzylic alcohols have a tendency to evolve to the corresponding allyl and benzyl chlorides unless the alcohol activation is very quickly followed by addition of triethylamine. In fact, Corey–Kim conditions —with no addition of triethylamine— are ...
The Luche reduction can be conducted chemoselectively toward ketone in the presence of aldehydes or towards α,β-unsaturated ketones in the presence of a non-conjugated ketone. [ 5 ] An enone forms an allylic alcohol in a 1,2-addition, and the competing conjugate 1,4-addition is suppressed.
The Corey–Itsuno reduction, also known as the Corey–Bakshi–Shibata (CBS) reduction, is a chemical reaction in which a prochiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol.
In organic chemistry, a hemiacetal is a functional group the general formula R 1 R 2 C(OH)OR, where R 1, R 2 is a hydrogen atom or an organic substituent. They generally result from the nucleophilic addition of an alcohol (a compound with at least one hydroxy group) to an aldehyde (R−CH=O) or a ketone (R 2 C=O) under acidic conditions.
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.