An organic compound which possesses a carboxyl group connected to an alkyl group is called a carboxylic acid. The carboxylic group is -COOH, and the general formula of carboxylic acid is RCOOH. The carboxylic acids participate in hydrogen bonding, as they can accept as well as donate hydrogen bonds. They undergo self-association and exist as dimers. As the length of the alkyl group increases, the carboxylic acid tends to become more hydrophobic, and its solubility in water decreases. The lower carboxylic acids are soluble in water, and the higher ones are soluble in ethers and alcohols. They have high values of boiling points due to extensive hydrogen bonding. Due to their proton donating nature, carboxylic acids behave as BrÃ³nsted acids. Carboxylic acids undergo a variety of reactions. Being acidic in nature, they react with bases or basic salts to form carboxylate salts. For example, carboxylic acids react with sodium hydrogen carbonate to form sodium salts of carboxylic acid, along with the release of carbon dioxide gas. They also undergo an esterification reaction by reacting with alcohols in the presence of mineral acid. The derivatives of carboxylic acids, such as acid anhydride and acid chlorides, also undergo a variety of reactions. Carboxylic acids can be aliphatic, like acetic acid, and aromatic, like benzoic acid.
Reduction of carboxylic acids to aldehydes
The electrophilicity of the carbonyl carbon of carboxylic acid is more than that of carbonyl carbon in carbonyl compounds, like aldehydes and ketones. The acidic proton present on the carboxylic acid is capable of reacting with the hydride reagents. Because of this, a carboxylic acid cannot be reduced by sodium borohydride. For the reduction of carboxylic acids to aldehydes, the former can be first reacted with an alcohol to form a carboxylic ester, which can be further reduced to an aldehyde using DIBAL-H, which is diisobutylaluminium hydride. The reagent selectively reduces esters into aldehyde. In this reaction, the carboxylic acid reacts with the alcohol to form an intermediate, in which rearrangement takes place to form the ester. Then the attack of the hydride on the electrophilic carbonyl carbon takes place to form an intermediate. This tetrahedral intermediate undergoes rearrangement to form the aldehyde, and the leaving group is removed.
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