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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 carboxylic acid Schmidt reaction starts with acylium ion 1 obtained from protonation and loss of water. Reaction with hydrazoic acid forms the protonated azido ketone 2 , which goes through a rearrangement reaction with the alkyl group R, migrating over the C-N bond with expulsion of nitrogen.
If the compound is a natural product or a carboxylic acid, the prefix oxo-may be used to indicate which carbon atom is part of the aldehyde group; for example, CHOCH 2 COOH is named 2-oxoethanoic acid. If replacing the aldehyde group with a carboxyl group (−COOH) would yield a carboxylic acid with a trivial name, the aldehyde may be named by ...
Depending on the reaction conditions, the aldehydes may then be converted to carboxylic acids. 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 ...
Ketones, aldehydes, carboxylic acids, esters, amides, and acid halides - some of the most pervasive functional groups, -comprise carbonyl compounds. Carboxylic acids, esters, and acid halides can be reduced to either aldehydes or a step further to primary alcohols , depending on the strength of the reducing agent.
The Pinnick oxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite (NaClO 2) under mild acidic conditions. It was originally developed by Lindgren and Nilsson. [1] The typical reaction conditions used today were developed by G. A. Kraus.
The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R−CH(OH) 2) by reaction with water before it can be further oxidized to the carboxylic acid. Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates
Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic acid (it takes two aldehydes to produce one acid and one alcohol). [5] This can be economically viable if the products can be separated and both have a value; the commercial conversion of furfural into furfuryl alcohol and 2-furoic acid is an example of this ...