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Carboxylate formation reactions

Because of their enhanced acidity, carboxylic acids react with bases to form ionic salts, as shown in the following equations. In the case of alkali metal hydroxides and simple amines (or ammonia) the resulting salts have pronounced ionic character and are usually soluble in water. Heavy metals such as silver, mercury and lead form salts having more covalent character (3rd example), and the water solubility is reduced, especially for acids composed of four or more carbon atoms.

 

RCO2H + NaHCO3 RCO2(–) Na(+)   +   CO2   +   H2O
RCO2H + (CH3)3N: RCO2(–) (CH3)3NH(+)
RCO2H + AgOH RCO2δ(-) Agδ(+)   +   H2O

Carboxylic acids and salts having alkyl chains longer than six carbons exhibit unusual behavior in water due to the presence of both hydrophilic (CO2) and hydrophobic (alkyl) regions in the same molecule. Such molecules are termed amphiphilic (Gk. amphi = both) or amphipathic. Depending on the nature of the hydrophilic portion these compounds may form monolayers on the water surface or sphere-like clusters, called micelles, in solution.

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