Question

acidic properties of carboxylic acid

Answer 1

Carboxylic acids are polar. Because they are both hydrogen-bond acceptors (the carbonyl –C=O) and hydrogen-bond donors (the hydroxyl –OH), they also participate in hydrogen bonding. These longer chain acids tend to be rather soluble in less-polar solvents such as ethers and alcohols

Answer 2

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Both acid and carboxylate are resonance stabilized but stabilization but stabilization is far greater for the carboxylate ion than for the acid. Thus carboxylic acids get ionised due to gain in the stability in going from carboxylic acid to the more stable carboxylate ion. Any factor that stabilizes more the carboxylate ion would facilitate the release of protons and increase the acidity. Thus electron withdrawing substituents (Cl, No2, CN etc.) in a carboxylic acid would disperse the negative charge of the COO^- , stabilize it, and thus enhance the acid strength. On the other hand, the presence of an electron donating substituent it, and thus enhance the acid strength. On the other hand, the presence of an electron donating substituent such as alkyl group, would intensity the negative charge on the COO^- , ion and thus destabilize it, making the carboxylic acid less acidic.

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