Carboxylic Acids

Carboxylic Acids

  • Carboxylic acids are organic compounds containing a carboxyl group (-COOH).
  • The carboxyl group consists of a carbonyl group (C=O) and a hydroxyl group (O-H) attached to the same carbon atom.
  • Carboxylic acids are named by replacing the -e at the end of the parent alkane with -oic acid e.g., ethane turns to ethanoic acid.
  • They are usually found as colourless liquids or white solids.
  • They have distinctive sour odours and are responsible for the smell of vinegar (ethanoic acid) and rancid butter (butanoic acid).

Physical Properties of Carboxylic Acids

  • Carboxylic acids can form hydrogen bonds due to the presence of hydrogen atoms in the -OH group, which gives them higher boiling points than similar-sized alkanes or alcohols.
  • The entire carboxyl group is polar due to the electronegative oxygen atoms which gives carboxylic acids the ability to dissolve in water.
  • Solubility in water decreases with increasing chain length beyond four carbon atoms as the non-polar hydrocarbon chain style dominates.

Chemical Properties of Carboxylic Acids

  • Carboxylic acids can undergo a variety of chemical reactions, including neutralisation, esterification and oxidation.
  • During neutralisation reactions, carboxylic acids react with bases to produce a salt and water.
  • In an esterification reaction, a carboxylic acid reacts with an alcohol in the presence of a strong acid catalyst to form an ester. This is commonly used in the production of artificial flavours and scents.
  • The carboxyl group can be further oxidised to form carbon dioxide, however, it typically requires strong oxidising agents.

Safety and Handling

  • Carboxylic acids can be corrosive and cause skin and eye irritation.
  • Proper safety precautions including the use of lab coats, gloves, and safety glasses should be followed whenever handling these substances.
  • They should always be handled by using a fume hood, as the vapours can be harmful if inhaled.

Everyday Applications

  • Carboxylic acids are found in a multitude of everyday substances, including vinegar (contains ethanoic acid) and citrus fruits (contains citric acid).
  • They are used in the production of plasticisers, detergents, pharmaceuticals and industrial chemicals.