Low Molecular Weight Acids
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General methods of preparation of carboxylic acids
➢ Hydrolysis of Nitriles
The C≡N triple bond undergoes nucleophilic additions in a similar way to a C=O. As with the carbonyl group, so often protonation is needed in order to activate it for the addition of weak nucleophiles such as water. As expected, when nitriles are hydrolyzed (by nucleophilic addition of water followed by nucleophile elimination), they form either carboxylic acids or amides, depending on the conditions.
Fig. 1 Hydrolysis of nitriles
➢ Hydrolysis of Esters and Amides
In typical reactions, the alkoxy (OR') group of an ester is replaced by another group. One such reaction is hydrolysis, literally "splitting with water." The hydrolysis of esters is catalyzed by either an acid or a base, and the reaction is reversible and does not go to completion.
Fig. 2 Hydrolysis of ester
Amides can be hydrolyzed in either acidic or basic solution, and hydrolysis of amides to carboxylic acids is an industrially important reaction. The mechanisms are much like those of ester hydrolysis, but the reactions are very much slower.
Fig. 3 Hydrolysis of amide
➢ Carbonation of Grignard Reagents
Grignard reagents react with carbon dioxide in two stages. i) Dry carbon dioxide is bubbled through a solution of the Grignard reagent. ii) The product is then hydrolyzed (reacted with water) in the presence of a dilute acid. Typically, we would add dilute sulphuric acid or dilute hydrochloric acid to the solution formed by the reaction with the CO2.
Fig. 4 Carbonation of Grignard reagent
➢ Malonic Ester Synthesis
Malonic ester is a reagent specifically used in a reaction which converts alkyl halides to carboxylic acids called the malonic ester synthesis. Malonic ester synthesis is a synthetic procedure used to convert a compound that has the general structural formula 1 into a carboxylic acid.
Fig. 5 Malonic Ester Synthesis
➢ Ardnt-Eistert Synthesis
The Arndt-Eistert synthesis allows the formation of homologated carboxylic acids or their derivatives by reaction of the activated carboxylic acids with diazomethane and subsequent Wolff-Rearrangement of the intermediate diazoketones in the presence of nucleophiles such as water, alcohols, or amines.
Fig. 6 Arndt-Eistert synthesis
➢ Oxidation of Primary Alcohols and Aldehydes
Primary alcohols can be oxidized to either aldehydes or carboxylic acids, depending on the reaction conditions. In the case of the formation of carboxylic acids, the alcohol is first oxidized to an aldehyde, which is then oxidized further to the acid.
Fig. 7 Oxidation of primary alcohol and aldehyde
➢ Others
In addition to the synthesis methods listed above, carboxylic acids can also be prepared by these methods: oxidation of alkenes, oxidation of methyl ketones, Cannizzaro reaction, Baeyer-Villiger oxidation of ketones with peracids, etc.
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