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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 ...
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
The reaction process begins with deprotonation at the halogenated position. In a related reaction, α-halo carboxylic esters can be reduced by lithium aluminium hydride to the α-halo alcohols, which can be converted to the α-epoxides. [5] α-Halo-esters can be converted to vinyl halides. upon reaction with ketones and chromous chloride. [6]
The Wolff rearrangement has been used in many total syntheses; the most common use is trapping the ketene intermediate with nucleophiles to form carboxylic acid derivatives. The Arndt-Eistert homologation is a specific example of this use, wherein a carboxylic acid may be elongated by a methylene unit.
Acid halides hydrolyze in the presence of water to produce carboxylic acids, but this type of reaction is rarely useful, since carboxylic acids are typically used to synthesize acid halides. Most reactions with acid halides are carried out in the presence of a non-nucleophilic base, such as pyridine, to neutralize the hydrohalic acid that is ...
He labeled carboxylic acid derivatives with oxygen isotope O18 and reacted these derivatives with water to make labeled carboxylic acids. At the end of the reaction he found that the remaining starting material had a decreased proportion of labeled oxygen, which is consistent with the existence of the tetrahedral intermediate.
In organic chemistry, the Schmidt reaction is an organic reaction in which an azide reacts with a carbonyl derivative, usually an aldehyde, ketone, or carboxylic acid, under acidic conditions to give an amine or amide, with expulsion of nitrogen.
The Kulinkovich reaction describes the organic synthesis of substituted ... O. G. (2004). "Alkylation of carboxylic acid derivatives with dialkoxytitanacyclopropane ...