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and Esters
Lecture Outline
1. Carboxylic Acids
2. Nomenclature and Sources of Aliphatic
Carboxylic Acids
3. Physical Properties of Carboxylic Acids
4. Classification of Carboxylic Acids
5. Preparation of Carboxylic Acids
6. Chemical Properties of Carboxylic Acids
2
Chapter Outline
7. Nomenclature of Esters
8. Occurrence and Physical Properties of Esters
9. Polyesters: Condensation Polymers
10. Chemical Properties of Esters
11. Glycerol Esters
12. Soaps and Synthetic Detergents
13. Esters and Anhydrides of Phosphoric Acid
3
Carboxylic Acids
4
Carboxylic acids are organic compounds that contain the
carboxyl functional group as shown here.
5
Carboxylic acids are either aliphatic or aromatic.
This This
is theisgeneral
the general formula
formula benzoic acid
benzoic acid carboxylic acid)
for an aromatic carboxylic acid. (an aromatic
for an aromatic carboxylic acid. (an aromatic carboxylic acid)
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Nomenclature and Sources of
Aliphatic Carboxylic Acids
7
IUPAC Rules for Naming Carboxylic Acids
8
IUPAC Rules for Naming Carboxylic Acids
9
Common Names of Carboxylic Acids
Several carboxylic acids are known by common names as
shown in the table below.
Natural Source
Formula Name Reference
HCOOH formic acid ants
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Naming Substituents of Carboxylic Acids
The substituents of carboxylic acids can also be named using
the Greek alphabet.
.
14
Solubility of Carboxylic Acids
The solubility of carboxylic acids is determined by which
of the two groups (i.e. the nonpolar R group or the polar
–COOH group ) of the molecule is the most dominant
in the chemical structure.
16
Acid-Base Properties of RCOOH
17
Occurrence of Carboxylic Acids
in Biochemistry
Carboxylic acids are released in the blood by the liver in
an excessive amount during ketoacidosis which is a
condition associated with uncontrolled diabetes.
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Classification of
Carboxylic Acids
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Types of Carboxylic Acids
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Types of Carboxylic Acids
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Unsaturated Carboxylic Acids
An unsaturated acid contains one or more C=C bonds.
The C=C bond affects the physical and chemical properties
of the acid.
23
Dicarboxylic Acids
Dicarboxylic acids have two carboxyl (COOH) groups.
These acids undergo a decarboxylation reaction ( i.e.loss of
CO2 ) to form a monocarboxylic acid or an anhydride
as shown below.
24
Citric acid is a hydroxytricarboxylic acid. It is 5-8% of
lemon juice and widely distributed in plant and animal
tissues.
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Hydroxy Acids
Hydroxy acids have the functional groups of an alcohol and
a carboxylic acid. Two important -hydroxy acids are lactic
acid and salicylic acid.
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Hydroxy Acids
Lactic acid is found in sour milk as well as in muscle tissue
as result of exercise.
28
Hydroxy Acids
Malic acid and tartaric acid are two other common
-hydroxy acids found in apples and grapes respectively.
29
Amino Acids
Amino acids have a carboxyl group(– COOH) and an
amino group (– NH2). The –COOH group acts as an acid
while the – NH2 acts as a base.
30
Amino Acids
Amino acid units are the building blocks of proteins.
31
Preparation of
Carboxylic Acids
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Preparation of Carboxylic Acids
33
Oxidation of an Alcohol
Primary alcohols are oxidized to carboxylic acids
(general reaction)
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Oxidation of an Alcohol
Primary alcohols like benzyl alcohol can also be oxidized
to a carboxylic acid.
35
Oxidation of an Aldehyde
Aldehydes are oxidized to carboxylic acids
( general reaction)
36
Oxidation of Alkyl Groups Attached to an
Aromatic Ring
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Hydrolysis of a Nitrile
Nitriles are prepared by reacting an alkyl halide and a
cyanide salt.
The nitrile is then hydrolyzed to a carboxylic acid.
39
Reactions of Carboxylic Acids
Carboxylic acids undergo two broad classes of reactions
which are acid-base reactions and substitution reactions.
40
Acid –Base Reactions
Low molar-mass carboxylic acids release H+ ions in
solution and as a result have the following properties
unique to acids in general.
a. Sour taste
b. Blue litmus paper changes to red in an acidic solution
c. Forms solutions with a pH < 7
d. Reacts with bases in neutralization reaction
41
Acid –Base Reactions
The characteristics listed in the previous slide are not true
of higher molar-mass carboxylic acids because the
dominant nonpolar R group makes these higher molar-
mass carboxylic acids insoluble in water.
42
There are four major types of substitution reactions
of carboxylic acids.
(anhydride formation)
(ester formation)
(amide formation) 43
Acid Chloride Formation
Acid chlorides are prepared by reacting thionyl chloride
(SOCl2) and a carboxylic acid.
44
Reactivity of Acid Chlorides
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Reactivity of Acid Chlorides
Acid chlorides can use to prepare esters like methyl
acetate or amides like acetamide as shown the example
below.
46
Acid Anhydride Formation
Acid anhydrides are prepared by reacting two molecules
of a carboxylic acid.
47
Ester Formation
Esters are prepared by a reacting a carboxylic acid and an
alcohol in the presence of a strong acid catalyst.
48
Nomenclature of Esters
49
IUPAC Rules for Naming Esters
1. Name the alkoxy alkyl group.
2. Name the carboxylic acid parent and change the -ic
ending to –ate.
50
The ester formed by the reaction of propanoic acid
and methanol is methyl propanoate.
Table 24.3 in the next slide lists the IUPAC and common
names of other esters.
51
52
Occurrence and Physical
Properties of Esters
53
Properties of Low-Molar Mass Esters
Low molar- mass esters are volatile nonpolar liquids at room
temperature. They are good solvents. Ethyl acetate for example is
used in paints and varnishes.
These esters also have a characteristic fragrant or fruity odor compared
to the parent carboxylic acid as shown below.
54
Properties of High Molar Mass Esters
High molar mass esters are nonpolar solids at room temperature.
Many of these esters are waxes.
Carnauba wax for example is an ester that can have a 28-carbon fatty
acid chain and a 34-carbon alcohol chain.
56
Polyesters: Condensation Polymers
A polyester is a polymer formed between an alcohol
monomer and a carboxylic acid monomer.
57
Polyesters: Condensation Polymers
This is a polymerization reaction that produces the
polyethylene terephthalate (PETE) polyester.
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Polyesters: Condensation Polymers
Polyethylene terephthalate is a common polyester found in
Mylar films and the 2-L soft drink bottle.
Glycerol is a trifunctional
molecule with three –OH o-Phthalic acid would
groups. form a cross-linked polyester
if reacted with glycerol.
60
Chemical Properties of Esters
61
Reactions of Esters
The principal reaction of esters is hydrolysis.
62
Acid Hydrolysis
(general reaction)
63
Specific examples of acid-catalyzed ester hydrolysis
64
Alkaline Hydrolysis (Saponification)
66
Glycerol Esters
67
Triacylglycerols
Esters of glycerol (i.e. glycerol esters) are known as
triacylglycerols ( also called triglycerides).
69
Fats and Oils
Some common unsaturated fatty acid derivatives found
in oils include the corresponding parent fatty acids oleic
acid, linoleic acid, and linolenic acid as shown here.
Hydrogenation of Glycerides
Oils are partially hydrogenated using a metal catalyst
and hydrogen gas to obtain a solid like the shortening
found in a consumer product like Crisco.
72
During partial hydrogenation some of the cis bonds change
to trans bonds which is the basis for the term ‘trans fat”.
Hydrogenolysis
Long chain alcohols are prepared by reducing triacylglycerols
with hydrogen gas and a copper chromite catalyst.
73
Hydrolysis
Fatty acids are prepared by hydrolyzing triacylglycerols
with either enzymes or mineral acid catalysts.
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Saponification
Soap ( i.e. carboxylate salts) is prepared by the alkaline
hydrolysis of triacylglycerols.
75
Soaps and Synthetic
Detergents
76
Soaps
Soaps are salts of long-chain fatty acids that are prepared by
the general reaction shown here.
Figure 24.1 shows the action of the hydrocarbon tails and the
polar heads of the carboxylate ions. 78
Figure 24. 1 The cleansing action of soap.
79
The Cleansing Action of Soaps in Hard Water
(insoluble in water)
80
The Cleansing Action of Soaps
in Acidic Solutions
(insoluble in water)
81
Synthetic Detergents
Synthetic detergents ( i.e syndets) are synthetic organic
products that act as cleansing agents.
These synthetic detergents are effective in soft water and
hard water.
82
Ionic Synthetic Detergents
Synthetic detergents can be ionic ( either anionic or cationic)
or nonionic.
Anionic detergent
Cationic detergent
83
Nonionic Synthetic Detergents
A nonionic detergent molecule contains a grease-soluble
component and a water soluble component as shown below.
84
Biodegradability
Biodegradable organic substances are those that can be
readily decomposed by microorganisms in the environment.
85
Biodegradability
However detergents with branched-chain alkyl benzenes
are not biodegradable.
86
Esters and Anhydrides of
Phosphoric Acid
87
Esterification of Phosphoric Acid (H3PO4)
88
Example of a Esterification Reaction with H3PO4
Both fats and oils are triacylglycerols with the difference being fats
are solids from animal sources while oils are liquids from plant
sources. 91
Summary
Triacylglycerols can be hydrolyzed to form soap in an alkaline
hydrolysis reaction called saponification.