ACID CHLORIDES,

ACID ANHYDRIDES and ESTERS

 ACID CHLORIDE
• An acid chloride is a carboxylic acid derivative in
which the —OH portion of the carboxyl group,
• Has been replaced with a —Cl atom.
• Thus, acid chlorides have the general formula:
• Acid chlorides are named in either of two
ways:
• Rule 1: Replace the -ic acid ending of the
common name of the parent carboxylic
acid with -yl chloride.
• Rule 2: Replace the -oic acid ending of
the IUPAC name of the parent
carboxylic acid with -oyl chloride.
 PREPARATION OF ACID
CHLORIDE
• Preparation of an acid chloride from its
parent carboxylic acid involves reacting
the acid with one of several inorganic
chlorides (PCl3, PCl5, or SOCl2).
• The general reaction is:
• Acid chlorides react rapidly with water,
in a hydrolysis reaction, to regenerate
the parent carboxylic acid.
• Acid chlorides are useful starting
materials for the synthesis of other
carboxylic acid derivatives, particularly
esters and amides.
• Synthesis of esters and amides using
acid chlorides is a more efficient
process than ester and amide synthesis
using a carboxylic acid.
ACID ANHYDRIDES
• Structurally, acid anhydrides can be
visualized as two carboxylic acid
molecules bonded together after
removal of a water molecule from the
acid molecules.
• Symmetrical acid anhydrides both R groups
are the same) are named by replacing the
acid ending of the parent carboxylic acid
name with the word anhydride.
• Mixed acid anhydrides (different R groups
present) are named by using the names of
the individual parent carboxylic acids (in
alphabetic order) followed by the word
anhydride.
• In general, acid anhydrides cannot be formed by
directly reacting the parent carboxylic acids together.
• Instead, an acid chloride is reacted with a
carboxylate ion to produce the acid anhydride.
• Like acid chlorides, they cannot exist in
biological systems, as they undergo
hydrolysis to regenerate the parent
carboxylic acids.
• Reaction of an alcohol with an acid
anhydride is a useful method for
synthesizing esters.
 ESTERS
and
ANHYDRIDES
OF
INORGANIC ACIDS
• Inorganic acids such as:
• Sulfuric, phosphoric, and nitric acids
react with alcohols to form esters in a
manner similar to that for carboxylic
acids.
• A phosphate ester is an organic
compound formed by reaction of an
alcohol with phosphoric acid.
 PHOSPORIC ACID ANHYDRIDES
• Three biologically important phosphoric acids exist:
• Phosphoric acid, diphosphoric acid, and triphosphoric
acid.
• Phosphoric acid, the simplest of the three acids,
undergoes intermolecular dehydration to produce
diphosphoric acid.
• All three phosphoric acids undergo
esterification reactions with alcohols,
producing species such as:
• Structural similarities between a
carboxylic acid anhydride and
diphosphoric acid.