CARBOXYLIC ACID
Carboxylic acid, any of a class of organic compounds in which a carbon (C) atom is bonded to an oxygen (O) atom by a double bond
and to a hydroxyl group (―OH) by a single bond. A fourth bond links the carbon atom to a hydrogen (H) atom or to some other
univalent combining group. The carboxyl (COOH) group is so-named because of the carbonyl group (C=O) and hydroxyl group.
properties
Carboxylic acids have high boiling points compared to other substances of comparable molar mass. Boiling points increase with
molar mass.
Carboxylic acids having one to four carbon atoms are completely miscible with water. Solubility decreases with molar mass.
Carboxylic acids are weak acids because they only partially ionise in solution. Their solutions do not contain many hydrogen
ions compared to a solution of a strong acid at the same concentration. A weak acid's pH will be higher than a strong acid's pH at
the same concentration. However, carboxylic acids are stronger in comparison to phenols and alcohols.
chemical reactions
Reaction with Metals
The reaction of carboxylic acids with metals such as K, Na, Mg, Ca leads to the formation of the corresponding salts. In the reaction
process, a proton will be released from the carboxyl group of the carboxylic acid where the metal substation will occur. The reaction
liberates H2 gas.
Reaction with Alkalies
The reaction of carboxylic acids with alkalies will lead to the formation of corresponding salts and water.
Reaction with Carbonates and Bicarbonates
Carboxylic acids undergo decomposition reaction with carbonates and bicarbonates leading to the formation of respective salts, water,
and carbon dioxide gas. This reaction can also help in testing the presence of carboxyl group. Carboxylic acids undergo reaction with a
saturated solution of sodium bicarbonate produce effervescence due to the release of CO2 gas. However, most phenols do not release
effervescence with an aqueous NaHCO3 solution. Thus the reaction of bicarbonate with carboxylic acids helps in distinguishing between
phenols and carboxylic acids.
Acid Chlorides Formation
Carboxylic Acids react with thionyl chloride (SOCl2), Phosphorus pentachloride (PCl5), or Phosphorus pentachloride to form the
respective acid chlorides. Refer below to understand the reaction.
Formation of Esters (Esterification)
Warming carboxylic acids with alcohols in the presence of a concentrated sulphuric acid or dry hydrochloric acid produces esters having
a fruity smell. In this reaction concentrated sulphuric acid act as the dehydrating agent. The reaction is an example of an equilibrium
reaction. Hence, the ester is distilled to continue shifting the reaction in the forward direction.
Formation of Amide Compounds
Treatment of carboxylic acids with ammonia thereby forming ammonium salts. Ammonium salts further upon heating lose a water
molecule leading to the formation of amides.
Decarboxylation
Distillation of soda lime (NaOH + CaO) with sodium salts of carboxylic acids result in decarboxylation reaction thereby forming alkanes.
Formation of Anhydrides
Two molecules of carboxylic Acids undergo heating with a dehydrating agent like phosphorus pentoxide leading to the formation of acid
anhydrides.
HVZ Reaction or Hell-Volhard Zelinsky Reaction
Carboxylic Acids react with chlorine molecule (Cl2) or bromine molecule (Br2) to form α-substituted carboxylic acids. The reaction takes
place in the presence of red phosphorus. This reaction refers to as the H.V.Z reaction or Hell-Volhard Zelinsky Reaction. Formic Acid
does not undergo this reaction because it does not contain an alkyl group. It is important to note that bromination will only take place at
the α-position. Moreover, the reaction will cease after the replacement of all the α-hydrogens by the bromine atoms. However,
chlorination will occur initially at the α-position and the replacement will occur in hydrogen atoms by chlorine atoms then the
replacement will move further along the chain.
Electrophilic Substitution Reactions
Aromatic carboxylic acids undergo different types of electrophilic substitution reactions like nitration, sulphonation, and halogenation.
Carboxyl group (-COOH) is an electron withdrawing group. Thus, the reaction will occur at the meta-position. The carboxyl group
deactivates. Therefore, the reaction will only occur under vigorous conditions.
Friedel Crafts Reactions
This group will not undergo Friedel-Crafts Reactions because the carboxyl group is strong electron attracting group. Thus, benzene ring
will be deactivated. Hence, it will not undergo alkylation and acylation.
uses of carboxylic acids
Carboxylic acid acts as a disinfectant.
Simplest carboxylic acid “formic acid” acts as reducing agent in textile treatments.
Acetic acid, member of the carboxylic acid group, helps in the production of esters and cellulose plastics.
Acetic acid acts as the precursor for the formation of an ester of salicylic acid which is used for aspirin production.
Palmitic acid and stearic acid finds its use in the manufacturing of soaps, pharmaceuticals, candles, cosmetics, protective coating,
etc.
Stearic acid also helps in rubber manufacturing processes.
Acrylic acid acts as an ester and helps in the production of polymers or acrylates. Similarly, methacrylic acid undergoes
polymerization to form Lucite.
Moreover, oleic acid, a type of carboxylic acids, helps in manufacturing soaps and detergents. Additionally, it is also used in
textiles.
SOURCES:
https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Basics_of_General_Organic_and_Biological_Chemistry_(Ball_et_al.)/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_De
rivatives/15.03%3A_Physical_Properties_of_Carboxylic_Acids
https://www.britannica.com/science/carboxylic-acid/Properties-of-carboxylic-acids
https://www.toppr.com/guides/chemistry/aldehydes-ketones-carboxylic-acids/chemical-reactions-uses-carboxylic-
acids/#:~:text=Carboxylic%20acids%20undergo%20decomposition%20reaction,the%20presence%20of%20carboxyl%20group.
