What is Carboxylic Acid?
Carboxylic acids are compounds containing the carboxyl functional group in their molecules. The carboxyl group is made up of carbonyl and hydroxyl groups and therefore, the name carboxyl is derived from carbo (from carbonyl) and oxyl from the hydroxyl group. The carboxylic acids may be aliphatic or aromatic depending upon whether the -COOH group is attached to the aliphatic alkyl chain or aryl group respectively.
The functional groups that consist of a Carbonyl Group (C=O) along with a hydroxyl group (O-H) which is attached to the same carbon atom are known as carboxyl groups. The formula for Carboxyl Groups is-
-C(=O)OH
Acids with the presence of one carboxyl group are termed carboxylic acids and since they are proton-donors, they are also known as Bronsted-Lowry acids. Acids with the presence of two carboxyl groups are known as dicarboxylic acids and the ones with the presence of three carboxyl groups are known as tricarboxylic acids.
Salts and esters of carboxylic acids are known as carboxylates.
Though the IUPAC nomenclature of carboxylic acids is ‘oic acids’ in the suffix, ‘ic acids’ is used more commonly.
Qualitative Test for Carboxylic Acid
The following tests are performed for the identification of carboxylic acid.
1. Action with Blue Litmus
All carboxylic acids turn blue litmus red.
Procedure-
Place the droplet of the liquid, solid or crystal on a moist blue litmus paper and observe the colour change.
If the red colour changes to blue, it indicates the presence of a carboxylic group.
2. Action with Carbonates and Bicarbonates
Carboxylic acids decompose carbonates and bicarbonates evolving carbon dioxide with brisk effervescence.
Carboxyl groups react with sodium hydrogen carbonate releasing carbon dioxide gas which can be identified by the effervescence produced. To distinguish carboxylic acids from phenols, this test can be used.
\[RCOOH + NAHCO_3 \rightarrow RCOONa + Co_2 \uparrow + H_20\]
Procedure-
Take one ml of organic liquid in a test tube and add a pinch of sodium bicarbonate \[(NaHCO_{3} )\] to it.
If carboxylic acid is present in the organic compound, a brisk effervescence is observed.
3. Carboxylic Acid NaHCO3 Mechanism
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The reaction of carboxylic acids with aqueous sodium carbonate solution leads to the evolution of carbon dioxide producing brisk effervescence. However, most phenols do not produce effervescence with an aqueous solution of sodium bicarbonate. Therefore, this reaction may be used to distinguish between carboxylic acids with sodium bicarbonate or sodium carbonate, the carbon dioxide evolved comes from Na2CO3 or NaHCO3 and does not form a carboxyl group.
4. Formation of Ester
When carboxylic acids are heated with alcohols in the presence of concentrated sulphuric acid and hydrochloric acid, esters are formed. The reaction is reversible and is called esterification.
Carboxylic acids react with alcohol when there is a presence of sulphuric acid to form an ester that has a fruity smell.
Procedure-
To 0.1 g of the organic compound add 1 ml ethyl alcohol and one or two drops of concentrated sulphuric acid in a test tube. After heating the mixture in a water bath for about five minutes, pour it into a beaker that has water. If a fruity smell is observed, it indicates the presence of the carboxyl group in the organic compound.
\[RCOOH + C_2H_5OH \rightarrow COOC_2H_5 + H_2O\]
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5. Fluorescein Test
This test is used for the identification of the dicarboxylic group. When the dicarboxylic compound is heated, it produces acid anhydride. This anhydride reacts with resorcinol in the presence of Conc. H2SO4 and produces a fluorescent dye.
Procedure-
Take a small amount of organic compound and heat it with resorcinol and one or two drops of concentrated sulphuric acid in a clean and dry test tube.
After a few minutes, the solution turns dark-brown and a liquid is formed.
Add a few drops of this solution to a dilute NaOH solution.
If the solution turns red with green fluorescence, it indicates the presence of dicarboxylic acid.
6. Reaction with FeCl3
Some carboxylic acids give precipitates when they react with iron trichloride. For example, acetic acid gives puff coloured precipitate.
Did You know?
Methanoic acid is used in leather tanning
Methanoic acid is used as an antiseptic.
Benzoic acid and some of its salts are used as urinary antiseptics.
Carboxylic acid esters are used in perfumery.
1. How can you identify carboxylic acids?
Carboxylic acids are commonly known by their trivial names such as formic acid, acetic acid, etc. Carboxylic acids have the suffix ‘ic acids’ in their names. By the guidelines of IUPAC, the carboxyl group has ‘oic acids’ in their names. For example- Butyric acid is known as butanoic acid according to the guidelines of IUPAC.
The carboxylate anions are usually named with the suffix ‘ate’. For a conjugate acid, names have the suffix ‘-ic acid’ and the names for conjugate bases have ‘-ate’. For example- For acetic acid, the conjugate base is acetate.
2. What are the properties of carboxylic acids?
The properties of carboxylic acids are-
Carboxylic acids are hydrogen-bond acceptors as well as hydrogen bond donors, because of which they are polar and participate in hydrogen bonding.
The boiling point of carboxylic acids are higher than that of water as their surface areas are great.
Carboxylic acids are proton donors (H+). They are also known as Bronsted Lowry acids.
Carboxylic acids are considered to be weak acids.
The esters of carboxylic acids have very pleasant odours which are commonly used in perfumes.
3. Mention some of the applications of carboxylic acids.
Carboxylic acids have a wide and significant role in society as-
Carboxylic acids and the derivatives of carboxylic acids are often used in the production of biopolymers, polymers, adhesives, coatings, pharmaceutical drugs, etc.
Carboxylic acids are also used as food additives, food solvents, flavourings, antimicrobials, etc.
The esters of carboxylic acids can be used in the production of perfumes since their smell is very pleasant.
Carboxylic acids play an important role in the field of medicine as well.
4. How are carboxylic acids used in the pharmaceutical industry?
The carboxylic acids have a very important role in the pharmaceutical industry because-
They act as a solubilizer that acts in modulating solubility and permeation of cells.
Bio Precursors and prodrug compounds that are not biologically active can be converted into active ones under specific conditions. (Examples are- Drugs from antithrombotic, antiviral and anti-hypertensive classes)
Pharmacophore provides specific interactions with enzymes by triggering and blocking their biological response.
Carboxylic acids have a wide variety of applications in the cosmetic industry as well.
5. Mention some carboxylic acids that one encounters in daily life.
Some of the carboxylic acids that we encounter in our daily lives are-
Salicylic Acids- Salicylic acids are most commonly used in skin care products to exfoliate dead skin cells.
Lactic Acid- Lactic acid is accumulated in muscles in the body while doing anaerobic exercises.
Citric Acid- Citric acid is highly acidic and therefore is used in industrial applications.
Acetylsalicylic Acids- Acetylsalicylic acid is most commonly used in aspirin and is extracted from willow barks.
6. Write the Tests that Can Show the Difference Between Alcohol and Carboxylic Acid.
Acetic acid gives effervescence with NaHCO3 due to the libration of carbon dioxide.
Ethanol does not give effervescence with NaHCO3.
Ethanol gives a yellow precipitate with an alkaline solution of iodine while acetic acid does not give this test.
7. What is Carboxylic Acid?
Carboxylic acids are compounds containing the carboxyl functional group in their molecules. The carboxylic acids may be aliphatic or aromatic depending upon whether the -COOH group is attached to the aliphatic alkyl chain or aryl group respectively.