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6.1.3 Carboxylic Acids and Esters Solubility in Water The smaller carboxylic (up to C4) acids dissolve in water in all proportions but after this the solubility rapidly reduces. They dissolve because they can hydrogen bond to the water molecules. Acidity The carboxylic acid are only weak acids in water and only slightly dissociate, but they are strong enough to displace carbon dioxide from carbonates. CH3CO2H(aq) CH3CO2 - (aq)+ H+ (aq) Delocalisation The carboxylic acid salts are stabilised by delocalisation, which makes the dissociation more likely. delocalised H3C C O OH H3C C O O The delocalised ion has equal C-O bond lengths. If delocalisation did not occur, the C=O bond would be shorter than the C-O bond. H3C C O O The pi charge cloud has delocalised and spread out. The delocalisation makes the ion more stable and therefore more likely to form. Strength of carboxylic acids C C O OH H H Cl CH2 C O OH H3C CH2 C O O delocalised H3C delocalised Increasing chain length