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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.
Under acidic conditions, the hemiacetal and the alcohol can further react to form an acetal and water. Simple hemiacetals are usually unstable, although cyclic ones such as glucose can be stable. Acetals are stable, but revert to the aldehyde in the presence of acid. Aldehydes can react with water to form hydrates, R−CH(OH) 2.
Ketones are trigonal planar around the ketonic carbon, with C–C–O and C–C–C bond angles of approximately 120°. Ketones differ from aldehydes in that the carbonyl group (C=O) is bonded to two carbons within a carbon skeleton. In aldehydes, the carbonyl is bonded to one carbon and one hydrogen and are located at the ends of carbon chains.
Hemiacetals form in the reaction between alcohols and aldehydes or ketones. Using an acid catalyst, the reaction proceeds via nucleophilic attack of the carbonyl group by the alcohol. [4] A subsequent nucleophilic attack of the hemiacetal by the alcohol results in an acetal. [2] Solutions of simple aldehydes in alcohols mainly consist of the ...
Aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol group can be further reduced and removed altogether by replacement with H. Two broad strategies exist for carbonyl reduction. One method, which is favored in industry, uses hydrogen as the reductant.
Reducing form of glucose (the aldehyde group is on the far right) A reducing sugar is any sugar that is capable of acting as a reducing agent. [1] In an alkaline solution, a reducing sugar forms some aldehyde or ketone, which allows it to act as a reducing agent, for example in Benedict's reagent. In such a reaction, the sugar becomes a ...
The reaction is particularly suitable for the synthesis of aldehydes from primary alcohols. Analogously, secondary alcohols can be oxidized to form ketones. Dimethyl sulfoxide/acetic anhydride serves as oxidizing agent. Albright-Goldman-Oxidation (Aldehyd) The reaction does not proceed further to the carboxylic acid.
The alcohol dehydrogenases comprise a group of several isozymes that catalyse the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, and also can catalyse the reverse reaction. [19] In mammals this is a redox (reduction/oxidation) reaction involving the coenzyme nicotinamide adenine dinucleotide (NAD ...