CARBOXYLIC ACID

 
 Carboxylic Acid
Contains a carboxyl group, which is a carbonyl group
(C=O) attached to a hydroxyl group (—OH).
carbonyl group
O

— C—OH hydroxyl group
carboxyl group
 General Formula
The general formula of a carboxylic acid
is:
RCOOH
 Models of Carboxylic Acids
The three-dimensional models show the geometry of
atoms in carboxylic acid molecules.
 Carboxylic Acid
Carboxylic acids are abundant and widely
distributed in nature.
Many have common names derived from a Greek
or Latin word describing their natural sources.
o For example: the common name for ethanoic acid
is acetic acid. Acetic acid is produced when wine
turns sour and becomes vinegar.
Like alcohols, carboxylic acids can form
intermolecular hydrogen bonds. Because of this,
carboxylic acids are higher boiling and higher
melting than other compounds of similar formula
mass.
All aromatic carboxylic acids are crystalline
solids at room temperature.
The carboxyl group in carboxylic acid is polar,
and it readily forms hydrogen-bonds with water
molecules
Formic, Acetic, Propionic and Butyric acids are
completely miscible with water.
The solubility of carboxylic acids of higher
formula mass drops off sharply. Most carboxylic
acids dissolve in organic solvents like ethanol or
acetone.
 IUPAC Names
In the IUPAC system for naming Carboxylic Acids, the –
e ending of the parent alkane is replaced by the ending –
oic acid. The parent alkane is the hydrocarbon with the
longest continuous carbon chain containing the carboxyl
group.
Example:
CH4 - methane HCOOH methanoic acid
C2H6 - ethane CH3COOH ethanoic acid
 Formula No. of Carbon IUPAC name Common name
atoms
HCOOH 1 Methanoic Acid Formic Acid

CH3COOH 2 Ethanoic Acid Acetic Acid

CH3CH2COOH 3 Propanoic Acid Propionic Acid

CH3(CH2)2COOH 4 Butanoic Acid Butyric Acid

CH3(CH2)3COOH 5 Pentanoic Acid Valeric acid

CH3(CH2)4COOH 6 Hexanoic Acid Caproic Acid

CH3(CH2)5COOH 7 Heptanoic Acid Enanthic acid

CH3(CH2)6COOH 8 Octanoic Acid Caprylic Acid

 No. of Carbon
Formula IUPAC name Common name
atoms
CH3(CH2)7COOH 9 Nonanoic Acid Pelargonic acid

CH3(CH2)8COOH 10 Decanoic Acid Capric Acid

CH3(CH2)9COOH 11 Undecanoic Acid

CH3(CH2)10COOH 12 Dodecanoic Acid Lauric Acid

CH3(CH2)11COOH 13 Tridecanoic Acid

CH3(CH2)12COOH Tetradecanoic
14 Myristic Acid
Acid
CH3(CH2)13COOH 15 Pentadoic Acid
NOMENCLATURE
 
Identify the longest chain containing the
carboxylic acid.
 The -e ending of the parent alkane name
is replaced by the suffix -oic acid.
The carboxyl carbon is always numbered
“1” but the number is not included in the
name.
The carboxyl group takes priority over
any other functional groups previously
discussed.
Name the substituents attached to the
chain in the usual way
Unsaturated acids are named using the name of
the alkene with -e replaced with -oic acid.
The chain is numbered starting with the carboxyl
group, and a number designates the location of
the multiple bond (and may include Z or E).
The systematic name of a carboxylic acid in
which the COOH group is attached directly to a
ring is derived by adding a suffix – carboxylic
acid to the name of the attached cycloalkane or
cycloalkene or arene
Typically aromatic acids of the form Ar-CO2H
are named as derivatives of benzoic acids, with
ortho, meta and para indicating the location
relative to the carboxyl group. (Recall that this is
non-IUPAC).
 Dicarboxylic Acids
First identifying the parent chain that contains the two
carboxylic acid groups and then adding a suffix -dioic
acid to the name of the parent hydrocarbon.
The parent chain is numbered from the end that gives
the substituents in the chain the lowest possible address
number.
The substituents are arranged in alphabetical order in
the full name of the dicarboxylic acid.
The systematic name of a cyclic aliphatic or
aromatic dicarboxylic acid is derived by adding a
suffix -dicarboxylic acid to the name of the
parent cycloalkane or arene i.e.
cycloalkanedicarboxylic acid or
arenedicarboxylic acid.