Chapter 16 Carboxylic Acids and

Esters
16.1
Carboxylic Acids

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1
Carboxylic Acids

A carboxylic acid
Contains a carboxyl group, which is a carbonyl group
(C=O) attached to a hydroxyl group (OH).
Has the carboxyl group on carbon 1.
carbonyl group
O

CH3 COH hydroxyl group or CH3COOH
carboxyl group

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Models of Carboxylic Acids
The three-dimensional models show the geometry
of atoms in carboxylic acid molecules.

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3
 IUPAC Names
The IUPAC names of carboxylic acids
Replace the -e in the alkane name with -oic acid.
CH4 methane HCOOH methanoic acid
CH3CH3 ethane CH3COOH ethanoic acid
Number substituents from the carboxyl carbon 1.
CH3 O
|
CH3CHCH2COH
4 3 2 1

3-methylbutanoic acid
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Common Names

The common names of simple carboxylic acids

Are formic acid (1C), acetic acid (2C), propionic acid
(3C), and butyric acid (4C).
HCOOH formic acid
CH3COOH acetic acid
Locate substituents using , , for the carbon atoms
adjacent to the carboxyl carbon.
CH3
|
CH3CHCH2COOH
3-methylbutanoic acid (-methylbutyric acid)
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Alpha Hydroxy Acids
Alpha hydroxy acids
(AHAs)
Occur naturally in
fruit, milk, and
sugarcane.
Are used in skin
care products.

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Names and Sources of Some
Carboxylic Acids
TABLE 16.1

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Common Carboxylic Acids

Methanoic acid (formic acid)

O

HCOH

ethanoic acid (acetic acid)

O

CH3COH
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Aromatic Carboxylic Acids

Benzoic acid
Is the aromatic carboxylic acid.
Locates substituents by assigning 1 to the carbon
attached to the carboxyl group.
Has common names that assign prefixes ortho,
meta, and para for 2 substituents.
ortho 1, 2 location
meta 1, 3 location
para 1, 4 location
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Aromatic Carboxylic Acids
O
O O
C OH
C OH C OH

Cl
NH2

benzoic acid 3-chlorobenzoic acid 4-aminobenzoic acid

m-chlorobenzoic acid p-aminobenzoic acid

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Learning Check

Give the IUPAC and common names:

A. CH3COOH

CH3
|
B. CH3CHCOOH

COOH
C.
Br

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Solution

A. CH3COOH ethanoic acid (acetic acid)

CH3
|
B. CH3CHCOOH 2-methylpropanoic acid
(-methylpropionic acid)
COOH
C. 2-bromobenzoic acid
Br
(o-bromobenzoic acid)

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Learning Check
Give the IUPAC and common names for the following:
A. CH3CH2COOH
CH3
|
B. CH
O 3CHCH2COOH
C.
C OH

Br
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Solution
A. CH3CH2COOH propanoic acid
(propionic acid)
CH3
|
O
B. CH3CHCH2COOH 3-methylbutanoic acid
(-methylbutyric acid)
C OH

C. 3-bromobenzoic acid
(m-bromobenzoic acid)

Br

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Chapter 16 Carboxylic Acids and
Esters

16.2
Properties of Carboxylic Acids

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Polarity of Carboxylic Acids
Carboxylic acids
Are strongly polar.
Have two polar groups:
hydroxyl (OH) and carbonyl (C=O).

-
O
+ - +
CH3 C O H

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Boiling Points of Carboxylic Acids

The boiling points of carboxylic acids

Are higher than alcohols, ketones, and aldehydes of similar
mass.

Are high because they form dimers in which hydrogen bonds

form between the polar groups in the two carboxyl groups.

O HO
|| |
CH3C CCH3
| ||
OH O
A dimer of acetic acid

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Comparison of Boiling Points
Compound Molar Mass Boiling Point
O

CH3CH2CH 58 49C

CH3CH2CH2OH 60 97C

O

CH3COH 60 118C
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Solubility in Water
Carboxylic acids Water molecules
Form hydrogen
bonds with many
water molecules.

With 1-4 carbon

atoms are very
soluble in water.

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Boiling Points and Solubility

TABLE 16.2

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 Acidity of Carboxylic Acids
Carboxylic acids
Are weak acids.
Ionize in water to produce carboxylate ions
and hydronium ions.
O O

CH3COH + H2O CH3CO + H3O+

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Acid Dissociation Constants

TABLE 16.3
Carboxylic acids
Have small Ka values.
Exist mostly as molecules
and a few ions in aqueous
solutions.

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Chapter 16 Carboxylic Acids and
Esters
16.3 Esters
16.4 Naming Esters

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Esters
In an ester,
The H in the carboxyl group is replaced
with an alkyl group.

O

CH3 COCH3
ester group

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Esterification

Esterification is
The reaction of a carboxylic acid and alcohol in the
presence of an acid catalyst to produce an ester.
O
H+
CH3COH + HOCH2CH3

O

CH3COCH2CH3 + H2O
ethyl acetate (an ester)
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Naming Esters
The name of an ester contains the names of
The alkyl group from the alcohol.
The carbon chain from the acid with ate ending.
from alcohol from acid
O
methyl
CH3 OC CH3
ethanoate (acetate)
IUPAC: methyl ethanoate
common: methyl acetate

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Ester Products
O
Aspirin
C OH
Is used to relieve pain and
O
reduce inflammation.
Is an ester of salicylic acid O C CH3
and acetic acid.

O
Oil of wintergreen
Is used to soothe sore C O CH3
muscles.
Is an ester of salicylic acid OH
and methanol.
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Esters in Plants
TABLE 16.4
Esters give
flowers and
fruits their
pleasant
fragrances and
flavors.

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Learning Check

Give the IUPAC and common names of the following

compound, which is responsible for the flavor and odor
of pears.

O

CH3COCH2CH2CH3

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Solution
Give the IUPAC and common names of the following
compound, which is responsible for the flavor and odor
of pears.

O

CH3COCH2CH2CH3

Propyl ethanoate (IUPAC)

Propyl acetate (common)

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Learning Check

Name the following esters:

O

A. CH3CH2CH2COCH3

O

B. CH3CH2 COCH2CH3

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Solution

A. Methyl butanoate (methyl butyrate)

B. Ethyl propanoate (methyl propionate)

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Learning Check

Write the structure of the following esters:

A. Ethyl pentanoate

B. Propyl butyrate

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Solution

A. Ethyl pentanoate
O

CH3CH2CH2CH2COCH2CH3

B. Propyl butyrate
O

CH3CH2CH2COCH2CH2CH3

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Chapter 16 Carboxylic Acids and
Esters
16.5
Properties of Esters

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Acid Hydrolysis of Esters

In acid hydrolysis
An ester reacts with water to produce a carboxylic
acid and an alcohol.
An acid catalyst is required.
O
H+
HCOCH2CH3 + H2O

O

HCOH + HOCH2CH3

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Base Hydrolysis (Saponification)
Base hydrolysis (also called saponification)
Is the reaction of an ester with a strong base.
Produces the salt of the carboxylic acid and an
alcohol.
O
||
CH3COCH2CH3 + NaOH
O

CH3CO Na+ + HOCH2CH3
salt of carboxylic acid alcohol

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Soaps
The base hydrolysis of long chain fatty acids
produces acid salts called soaps.

40

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Cleaning Action of Soap
A soap
Contains a nonpolar
end that dissolves in
nonpolar fats and
oils, and a polar end
that dissolves in
water.
Forms groups of
soap molecules
called micelles that
dissolve in water and
are washed away.

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