CARBOXYLIC ACIDS

Organic acids were known long before inorganic acids were isolated. The sting of a
red ant’s bite is due to an organic acid which the ant injects into the wound. The
crisp, tart flavour of citrus fruits is produced by an organic acid, appropriately
called citric acid. When fermentation reaction goes wrong, it produces vinegar
instead of alcohol. The formic acid of ants, the citric acid of fruits and the acetic
acid of vinegar all belong to the same family of compounds, the carboxylic acids.
Carboxylic acids therefore occur widely in nature, and serve important roles in
organic synthesis.
Carboxylic acids are considered to be oxidation products of aldehydes, with the
functional group being the Carboxyl –COOH. It can be considered to be a
combination of the carbonyl (CO) and the hydroxyl (OH) groups, but it has
characteristic properties of its own. In general carboxylic acids can be represented
by the formula

R-COOH R = alkyl, or aryl

Importance of some Carboxylic acids

- Formic acid, HCOOH, one of the strongest organic acids, is found in the sting of
bees and ants, causing the characteristic pain and swelling when it is injected into
the tissue.
- Acetic acid, CH3COOH, is usually found as a 4 to 5 % solution in vinegar. It is very
important in metabolic reactions.
- Citric acid, HOOC-CH2-C(OH)(COOH)-CH2-COOH, an example of a tricarboxylic
acid, is found in citrus fruits. Magnesium citrate, a salt of citric acid, is used as a
medication for stimulating the evacuation of bowels. Sodium citrate, another salt, is
used as a blood anticoagulant.

Citric acid Lactic acid Pyruvic acid Tartaric acid

- Lactic acid, CH3CH(OH)COOH, is formed in the fermentation of milk sugar lactose.

It is also both an alcohol and an acid formed whenever the body produces energy
anaerobically.
- Oxalic, pyruvic and tartaric acids are all naturally occurring organic acids with
different uses.
- Stearic acid, C17H35COOH, is a solid greaselike acid, whose sodium salt is
commonly used as soap.

Stearic acid ASA

- Benzoic acid is used medicinally as an antifungal agent. The sodium salt of

benzoic acid is used as a preservative.
- The acetyl derivative of salicylic acid, commonly known as Aspirin ASA, is used as
an analgesic and antipyretic in the treatment of colds, headaches, minor aches and
pains, and as a mild blood thinner.

30
NOMENCLATURE
Most of the carboxylic acid we consider are derived from natural sources. They are
most frequently known by their common names, many of which are based upon
Latin and Greek names, and are related to the source of the acid. These common
names are often formed by adding the suffix “ic” + acid to the common names for
aldehydes and ketones.

Formic acid Acetic acid Butyric acid

Distilled from ants From aerobic fermentation Formed when good
of cider and honey bacteria in gut breakdown
dietary fibre

Below is a list of members of the carboxylic acid family and the derivations of their
common names.

Condensed IUPAC Name Common Derivation of Common

Formula Name Name
HCOOH Methanoic acid Formic acid Latin formica, ant
CH3COOH Ethanoic acid Acetic acid Latin acetum, vinegar
CH3CH2COOH Propanoic acid Propionic Greek protos, first, and
acid pion, fat
CH3CH2CH2COOH Butanoic acid Butyric acid Latin butyrum, butter
CH3(CH2)3COOH Pentanoic acid Valeric acid Latin valere, powerful
CH3(CH2)4COOH Hexanoic acid Caproic acid Latin caper, goat
CH3(CH2)6COOH Octanoic acid Caprylic acid
CH3(CH2)8COOH Decanoic acid Capric acid
CH3(CH2)10COOH Dodecanoic acid Lauric acid Laurel tree
CH3(CH2)12COOH Tetradecanoic acid Myristic acid Myristica fragrans (nutmeg)
CH3(CH2)14COOH Hexadecanoic acid Palmitic acid Palm tree
CH3(CH2)16COOH Octadecanoic acid Stearic acid Greek stear, tallow

Organic acids containing two carboxylic groups are called dicarboxylic acids, those
containing three are tricarboxylic acids. Examples are

HOOC-COOH HOOC-CH2-COOH HOOC-CH2-CH2-COOH

Oxalic acid Malonic acid Succinic acid

Question: What is the IUPAC name of the three dicarboxylic acids above?

When common names are used, substituted acids are named by locating the
position of the substituent group by means of the Greek letters , β, γ, , etc, rather
than numbers. These letters refer to the position of the carbon atom in relation to
the carboxyl carbon.

31