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Chemistry LibreTexts

Reactivity of Carboxylic Acids

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  • Conversion of a Carboxylic Acid to an Amide
    The direct reaction of a carboxylic acid with an amine would be expected to be difficult because the basic amine would deprotonate the carboxylic acid to form a highly unreactive carboxylate.  However when the ammonium carboxylate salt is heated to a temperature above 100 o C water is driven off and an amide is formed.
  • Conversion of carboxylic acids to acid chlorides
    Carboxylic acids react with Thionyl Chloride to form acid chlorides. During the reaction the hydroxyl group of the carboxylic acid is converted to a chlorosulfite intermediate making it a better leaving group. The chloride anion produced during the reaction acts a nucleophile.
  • Conversion of carboxylic acids to alcohols using LiAlH4
    Carboxylic acids can be converted to 1o alcohols using Lithium aluminum hydride (LiAlH4). Note that NaBH4 is not strong enough to convert carboxylic acids or esters to alcohols. An aldehyde is produced as an intermediate during this reaction, but it cannot be isolated because it is more reactive than the original carboxylic acid.
  • Conversion of Carboxylic acids to amides using DCC as an activating agent
    The direct conversion of a carboxylic acid to an amide is difficult because amines are basic and tend to convert carboxylic acids to their highly unreactive carboxylates. In this reaction the carboxylic acid adds to the DCC molecule to form a good leaving group which can then be displaced by an amine during nucleophilic substitution. DCC induced coupling to form an amide linkage is an important reaction in the synthesis of peptides.
  • Fischer Esterification
    Fischer esterification is the esterification of a Carboxylic acid by heating it with an alcohol in the presence of a strong acid as the catalyst.
  • Hell-Volhard-Zelinskii Reaction
    Carboxylic acids can be brominated in the alpha position with a mixture of Br2 and PBr3 in a reaction called the Hell-Volhard-Zelinskii reaction.
  • Making Acyl Chlorides (Acid Chlorides)
    This page looks at ways of swapping the -OH group in the -COOH group of a carboxylic acid for a chlorine atom. This produces useful compounds called acyl chlorides (acid chlorides). It covers the use of phosphorus(V) chloride and phosphorus(III) chloride as well as sulfur dichloride oxide (thionyl chloride).
  • Making Esters From Carboxylic Acids
    Esterification is the reaction between alcohols and carboxylic acids to make esters. Esters have a hydrocarbon group of some sort replacing the hydrogen in the -COOH group of a carboxylic acid.
  • Reactions of Carboxylic Acids
    Because of their enhanced acidity, carboxylic acids react with bases to form ionic salts. 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.
  • Reduction of Carboxylic Acids with \(LiAlH_4\)
    This page looks at the reduction of carboxylic acids to primary alcohols using lithium tetrahydridoaluminate(III) (lithium aluminium hydride), LiAlH4. The "(III)" is the oxidation state of the aluminium. Since aluminium only ever shows the +3 oxidation state in its compounds, the "(III)" is actually unnecessary.
  • Simple Reactions of Carboxylic Acids as Acids
    This page looks at the simple reactions of carboxylic acids as acids, including their reactions with metals, metal hydroxides, carbonates and hydrogencarbonates, ammonia and amines.
  • The Decarboxylation of Carboxylic Acids and Their Salts
    This page looks at the formation of hydrocarbons by the decarboxylation of the salts of carboxylic acids (and of certain acids themselves) by heating them with soda lime. It does NOT cover the decarboxylation of some acids by simply heating them.


Reactivity of Carboxylic Acids is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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