Carboxylic Acids, Esters, and Related Compounds When the carboxyl group is attached to a ring, the ring
name remains unchanged, and the suffix "-carboxylic
Carboxylic Acids acid" is added.
1. Functional Group and Structure Example: Benzenecarboxylic acid (benzoic
acid) – C₆H₅COOH.
Carboxylic acids are organic compounds that contain a
carboxyl group (-COOH). This group consists of two For dicarboxylic acids (those with two carboxyl
subgroups: groups), the name includes "-dioic acid."
Carbonyl Group (C=O): A carbon atom Example: Butanedioic acid (succinic acid) –
double-bonded to an oxygen atom. HOOCCH₂CH₂COOH.
Hydroxyl Group (-OH): A hydroxyl group
single-bonded to the same carbon atom as the 3. Physical Properties
carbonyl.
Carboxylic acids exhibit strong intermolecular forces
The general structure of carboxylic acids is R-COOH, due to hydrogen bonding. This leads to:
where "R" represents a hydrocarbon group (e.g., alkyl
or aryl group). Higher melting and boiling points than other
similar-sized organic compounds like alcohols
2. Homologous Series and Naming or aldehydes.
Dimers: Two carboxylic acid molecules can
Carboxylic acids form a homologous series, where form dimers, connected by two hydrogen
each subsequent compound differs by a CH₂ unit from bonds. These dimers increase the boiling
the previous one. They are named by replacing the "-e" points.
in the parent alkane name with "-oic acid."
Example:
Examples:
Acetic acid boils at 118°C, while propanoic
Methanoic acid (Formic acid): HCOOH. It is acid boils at 141°C, much higher than similar-
the simplest carboxylic acid and is found in sized hydrocarbons or alcohols.
ants.
Ethanoic acid (Acetic acid): CH₃COOH. It is 4. Acidity
the main component of vinegar.
Propanoic acid: CH₃CH₂COOH. It is used as Carboxylic acids are more acidic than alcohols and
a preservative in bread to prevent mold. water, with a typical pKa of about 5. However, they
are still considered weak acids. Their acidity is due to
For compounds with other substituents, prefixes and the resonance stabilization of the carboxylate ion
numbers are used to indicate their positions on the formed when the proton is lost.
carbon chain.
Example:
When a hydroxyl group (-OH) is attached, the
prefix "hydroxy" is used. Ethanoic acid (acetic acid) has a pKa of 4.76,
o Example: 2-hydroxypropanoic acid meaning it partially ionizes in water to form
(lactic acid) – CH₃CH(OH)COOH. acetate (CH₃COO⁻) and H⁺ ions.
A 0.1 M solution of acetic acid is about 1.3%
If the molecule contains a double bond, the suffix "- ionized, making it a weak acid compared to
enoic acid" is used, and the position of the double strong acids like HCl.
bond is indicated by a number.
Example: 2-butenoic acid (crotonic acid) –
CH₃CH=CHCOOH.
5. Solubility in Water
Carboxylic acids are soluble in water due to their Example:
ability to hydrogen bond with water molecules.
However, as the length of the hydrocarbon chain Ethanol + Ethanoic acid → Ethyl ethanoate
increases, the solubility decreases. Small carboxylic (ethyl acetate).
acids like formic and acetic acids are highly soluble, Methanol + Propanoic acid → Methyl
while larger ones, like hexanoic acid, are less soluble. propanoate.
6. Important Reactions 3. Physical Properties
Esterification: Carboxylic acids react with Esters have:
alcohols in the presence of an acid catalyst
(e.g., sulfuric acid) to form esters and water. Lower boiling points compared to carboxylic
acids of similar size because they do not form
Example: hydrogen bonds.
o Acetic acid (CH₃COOH) reacts with Example:
ethanol (CH₃CH₂OH) to form ethyl
acetate (CH₃COOCH₂CH₃) and Ethyl acetate has a boiling point of 77°C,
water. which is much lower than that of acetic acid
(118°C).
Solubility: Esters are generally less soluble in
water than carboxylic acids because they
Esters cannot form hydrogen bonds as easily. Smaller
esters (e.g., methyl acetate) are more soluble,
1. Structure and Formation but as the alkyl chain length increases,
solubility decreases.
Esters are derived from carboxylic acids by replacing
the hydrogen in the hydroxyl group (-OH) with an 4. Hydrolysis
alkyl or aryl group (-OR'). Their general formula is R-
COOR', where R is the acyl group (from the Esters can be broken down into carboxylic acids and
carboxylic acid) and R' is the alkyl group (from the alcohols via hydrolysis:
alcohol).
Acidic Hydrolysis: Ester reacts with water in
Examples: the presence of an acid catalyst, reversing the
esterification process.
Ethyl ethanoate (ethyl acetate) –
CH₃COOCH₂CH₃, formed from ethanol and Example:
ethanoic acid.
Methyl butanoate – CH₃CH₂CH₂COOCH₃, oEthyl acetate can be hydrolyzed back
formed from methanol and butanoic acid. It into acetic acid and ethanol.
has a fruity odor and is found in pineapples. Basic Hydrolysis (Saponification): The ester
reacts with a base (like NaOH) to form a
2. Naming carboxylate salt and an alcohol.
The name of an ester is based on the alcohol and Example:
carboxylic acid from which it is derived:
o Ethyl acetate + NaOH → Sodium
The alkyl group (R') from the alcohol is named acetate + Ethanol.
first, followed by the acyl group (R-CO) from
the carboxylic acid with the suffix "-ate."
Related Compounds
1. Acyl Halides
Acyl halides are derivatives of carboxylic acids,
formed by replacing the hydroxyl group (-OH) with a
halogen (commonly chlorine). Their general formula is
R-COX, where X is the halogen.
Example:
Ethanoyl chloride (CH₃COCl), derived from
ethanoic acid, is commonly used in organic
synthesis.
2. Amides
Amides are derived from carboxylic acids by replacing
the hydroxyl group with an amine group (-NH₂). They
are important in the structure of proteins.
Example:
Ethanamide (acetamide) – CH₃CONH₂,
derived from acetic acid. This compound has
applications in the production of plastics and
textiles.
