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The systematic IUPAC name is not always the preferred IUPAC name, for example, lactic acid is a common, and also the preferred, name for what systematic rules call 2-hydroxypropanoic acid. This list is ordered by the number of carbon atoms in a carboxylic acid.
Although silyl enol ethers of aldehydes and ketones are the traditional substrates for the Rubottom oxidation, as mentioned above, silyl ketene acetals and bis (silyl acetals) can be oxidized to their α-hydroxy ester or carboxylic acid derivatives using lead(IV) acetate or hypofluorous acid-acetonitrile (HOF–ACN). [27]
Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4) are often very slow at reducing esters and carboxylic acids, whereas stronger reducing agents (LiAlH 4) immediately reduce the formed aldehyde to an alcohol. [10] Conversion to thioester followed by Fukuyama reduction
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group (−C(=O)−OH) [1] attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO 2 H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups ...
α-Halo carboxylic acids and esters are organic compounds with the respective formulas RCHXCO 2 H and RCHXCO 2 R' where R and R' are organic substituents. The X in these compounds is a halide, usually chloride and bromide. These compounds are often used as intermediates in the preparation of more elaborate derivatives. They are often potent ...
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.
This rearrangement takes place in the presence of a base, sometimes hydroxide, to yield a carboxylic acid, but usually either an alkoxide base or an amine to yield an ester or an amide, respectively. α,α'-Dihaloketones eliminate HX under the reaction conditions to give α,β-unsaturated carbonyl compounds.
At the oxidation level of carboxylic acid derivatives, the groups such as OR, OAr, NR 2, or Cl are conjugated with the carbonyl group, which means that addition to the carbonyl group is thermodynamically less favored than addition to corresponding aldehyde or ketone. Stable tetrahedral intermediates of carboxylic acid derivatives do exist and ...