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Organic Chemistry - Carboxylic Acids

Carboxylic acids are called so because the OH group has a tendency to give up a hydrogen ion. When it does, it is called a carboxylate ion. The carboxylate ion is a resonant structure and since resonance creates stability carboxylic acids are more acidic than alcohols, phenols, aldehydes, and ketones. 

One of the important reasons that carboxylic acids are so acidic is that the carboxylate ion is stabilized by resonance. Because carboxylic acids have twice the hydrogen bonding, their boiling points are higher than the boiling points of alcohols. 

When it comes to solubility, carboxylic acids are more or less like alcohols. Small sized carboxylic acids with carbon chains of four carbons or fewer are soluble in water. 

Halogenation makes a carboxylic acid even more acidic. You should know that carboxylic acid can gain a halogen on the alpha carbon. When we have got a carboxylic acid and we put a chlorine on the alpha carbon, we get a stronger acid than we had before, and it is now called an acid chloride. This happens in the presence of SOCl2. 

A carboxylic acid can be turned into an alcohol. This happens in the presence of LiAlH4.