1. Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
13.1
Carboxylic Acids
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

2. Carboxylic Acids O A carboxylic acid contains a carboxyl group, which
is a carbonyl group (C=O) attached to a hydroxyl group (—OH).
is found on carbon 1 in carboxylic acids. O 
CH3 — C—OH hydroxyl group or CH3COOH
carbonyl group

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

4. IUPAC Names The IUPAC names of carboxylic acids:
Replace the -e in the alkane name with -oic acid.
CH methane HCOOH methanoic acid
CH3—CH3 ethane CH3—COOH ethanoic acid
Number substituents from the carboxyl carbon 1.
CH O
| ║
CH3—CH—CH2—C—OH
3-methylbutanoic acid

5. Names and Sources of Some Carboxylic Acids

6. Common Carboxylic Acids
Methanoic acid (formic acid) O ║
H─C─OH
ethanoic acid (acetic acid)
CH3─C─OH

7. Aromatic Carboxylic Acids
Benzoic acid
is the aromatic carboxylic acid.
locates substituents by numbering the ring from carbon 1 in the carboxyl group.
benzoic acid
3-chlorobenzoic acid aminobenzoic acid

8. Learning Check Give the IUPAC names of each compound. A. CH3─CH2─COOH|
B. CH3─CH─CH2─COOH C.

9. Solution A. CH3─CH2─COOH propanoic acid CH3 |
B. CH3─CH─CH2─COOH 3-methylbutanoic acid
C bromobenzoic acid

10. Chapter 13 Carboxylic Acids, Esters, Amines and Amides
13.2
Properties of Carboxylic Acids
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

11. Polarity of Carboxylic Acids
are strongly polar.
have two polar groups:
hydroxyl (−OH) and
carbonyl (C=O).

12. Polarity of Carboxylic Acids
form dimers in which hydrogen bonds form between two carboxyl groups.
O H—O
|| |
CH3—C C—CH3
| ||
O—H O
A dimer of acetic acid
have higher boiling points than alcohols, ketones, and aldehydes of similar mass.

13. Comparison of Boiling Points
Compound Molar Mass Boiling Point O ║
CH3−CH2−C−H °C
CH3−CH2−CH2−OH °C
CH3−C−OH °C

14. Solubility in Water Carboxylic acids:
form hydrogen bonds with many water molecules.
with 1-4 carbon atoms are very soluble in water.
Water molecules

15. Boiling Points and Solubility

16. Acidity of Carboxylic Acids
are weak acids.
ionize in water to produce carboxylate ions
and hydronium ions.
O O
║ ║
CH3−C−OH + H2O CH3−C−O– + H3O+

17. Neutralization of Carboxylic Acids
Carboxylic acid salts
are a product of the neutralization of a carboxylic acid with a strong base.
CH3—COOH + NaOH CH3—COO– Na+ + H2O
acetic acid sodium acetate
(carboxylic acid salt)
are used as preservatives and flavor enhancers.

18. Learning Check
Write the equation for the reaction of propanoic acid with
A. water
B. KOH

19. Solution Write the equation for the reaction of propanoic acid with
A. water
CH3—CH2—COOH + H2O CH3—CH2—COO– + H3O+
B. KOH
CH3—CH2—COOH + KOH CH3—CH2—COO– K+ + H2O

20. Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
13.3
Esters
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

21. Esters In an ester, the H in the carboxyl group is replaced
with an alkyl group. O 
CH3 — C—O —CH3
ester group

22. Esterification
Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. O
 H+
CH3—C—OH + H—O—CH2—CH3 
CH3—C—O—CH2—CH H2O
ethyl acetate (an ester)

23. Learning Check
Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst.

24. Solution O  H+ CH3—CH2—C—OH + H—O—CH3 propanoic acid methanol 
Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst. O
 H+
CH3—CH2—C—OH + H—O—CH3
propanoic acid methanol 
CH3—CH2—C—O—CH H2O

25. Ester Products Aspirin
is used to relieve pain and reduce inflammation.
is an ester of salicylic acid and acetic acid.
Oil of wintergreen
is used to soothe sore muscles.
is an ester of salicylic acid and methanol.

26. 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.
methyl ethanoate (acetate) O 
CH3— O—C —CH3
IUPAC: methyl ethanoate
common: methyl acetate

27. Esters in Plants
Esters give flowers and fruits their pleasant fragrances and flavors.
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Publishing as Benjamin Cummings

28. Learning Check
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears. O 
CH3 — C—O—CH2—CH2—CH3

29. Solution
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears.
from 1-propanol O 
CH3—C—O—CH2—CH2—CH3
Propyl ethanoate (IUPAC)
Propyl acetate (common)

30. Learning Check Draw the structure of the following compounds.
A. 3-bromobutanoic acid
B. ethyl propionoate

31. Solution A. 3-bromobutanoic acid Br | CH3—CH—CH2—COOH
B. ethyl propionoate O 
CH3—CH2 —C—O—CH2—CH3

32. 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+
H—C—O—CH2—CH H2O 
H—C—OH + H—O—CH2—CH3

33. Base Hydrolysis (Saponification)
Base hydrolysis or saponification,
is the reaction of an ester with a strong base.
produces the salt of the carboxylic acid and an alcohol. O ||
CH3—C—O—CH2—CH NaOH
 CH3—C—O– Na+ + HO—CH2—CH3
salt of carboxylic acid alcohol

34. Base Hydrolysis of Fatty Acids Produces Soaps

35. 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.

36. Learning Check A. water and an acid catalyst. B. KOH.
Write the organic products when methyl acetate reacts with
A. water and an acid catalyst.
B. KOH.

37. Solution A. water and an acid catalyst. O  CH3—C—OH + HO—CH3 B. KOH.
Write the organic products when methyl acetate reacts with
A. water and an acid catalyst. O 
CH3—C—OH HO—CH3
B. KOH.
CH3—C—O– K HO—CH3

38. Chapter 13 Carboxylic Acids, Ester, Amines, and Amides
13.4
Amines

39. Amines Amines are derivatives of ammonia, NH3.
contain N attached to one or more alkyl or aromatic groups.
CH3 CH3
 
CH3—NH2 CH3—NH CH3—N—CH3 N H 2

40. Classification of Amines
Amines are classified as primary, secondary, or tertiary.
In a primary (1°) amine, one carbon group is bonded to the nitrogen atom.
A secondary (2°) amine has two carbon groups bonded to the nitrogen atom.
A tertiary (3°) amine has three carbon groups bonded to the nitrogen atom.
H CH CH3
| | |
CH3—N—H CH3—N—H CH3—N—CH3
1° ° °

41. Models of Amines
The three-dimensional models show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom.
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

42. Naming Amines Simple amines are named as alkylamines.
List the names of the alkyl groups bonded to the N atom in alphabetical order in front of amine.
CH3—CH2—NH2 ethylamine
CH3—NH—CH3 dimethylamine
CH3 |
CH3—N—CH2—CH3 ethyldimethylamine

43. Learning Check Give the common name and classify as
primary, secondary, or tertiary.
A. CH3—CH2—CH2—NH2
CH3 |
B. CH3—CH2—N—CH3

44. Solution A. CH3—CH2—CH2—NH2 propylamine, 1° CH3 | B. CH3—CH2—N—CH3
ethyldimethylamine, 3°

45. Aromatic Amines The amine of benzene is named aniline.
Alkyl groups on the N use the prefix N- with alkyl name.
aniline chloroaniline N-methylaniline

46. Learning Check Give the common name of each compound.
A. CH3—NH—CH2—CH3
CH3 |
B. CH3—CH2—N—CH2—CH3 C.

47. Solution A. CH3—NH—CH2—CH3 ethylmethylamine CH3 |
B. CH3—CH2—N—CH2—CH3 diethylmethylamine C.
aniline

48. Hydrogen Bonding for Amines
The N−H bond
provides hydrogen bonding in 1°and 2° amines, but not in 3° amines.
is not as polar as the O-H bonds in alcohols.

49. Solubility in Water Amines with 1-5 carbon atoms are soluble in water.
form hydrogen bonds with the polar O-H bond in water.

50. Learning Check Consider the following compounds. 1) CH3—CH2—CH2—NH2
2) CH3—CH2—NH—CH3
3) CH3—CH2—CH2—CH3
A. Which compound has the highest boiling point?
B. Which compound is soluble in water?

51. Solution Consider the following compounds. 1) CH3—CH2—CH2—NH2
2) CH3—CH2—NH—CH3
3) CH3—CH2—CH2—CH3
A. Which compound has the highest boiling point?
1) CH3—CH2—CH2—NH2
B. Which compound is soluble in water?

52. Amines React as Bases Like ammonia, amines are weak bases in water.
NH H2O NH OH–
ammonium hydroxide
CH3—NH H2O CH3—NH OH–
methylammonium hydroxide

53. Neutralization forms Amine Salts
An amine salt
forms when an amine is neutralized by acid.
is named by replacing the amine part of the name with ammonium followed by the name of the negative ion.
CH3—NH2 + HCl CH3—NH3+ Cl–
methylamine methylammonium chloride

54. Properties of Amine Salts
Amine salts are
solids at room temperature.
soluble in water and body fluids.
the form used for drugs.

55. Alkaloids Alkaloids are
physiologically active nitrogen-containing compounds.
obtained from plants.
used as anesthetics, antidepressants, and in stimulants such as caffeine.
often addictive.

56. Cocaine Cocaine is sold illegally as the amine salt.
reacted with NaOH to produce the free amine form known as “crack.”

57. Caffeine Caffeine is a stimulant of the central nervous system.
is found in coffee beans, tea, chocolate, and soft drinks.

58. Nicotine Nicotine increases the adrenaline level in the blood.
causes addiction to tobacco. N C H 3

59. Morphine and Codeine Morphine and codeine are alkaloids.
obtained from the oriental poppy plant.
used as painkillers.
modified to make heroin.

60. Learning Check Write the structural formula for A methylpropylamine
B chloroaniline

61. Solution
A. methylpropylamine CH3–CH2–CH2–NH–CH3
B chloroaniline

62. Chapter 13 Carboxylic Acids, Esters, Amines, and Amides
13.5
Amides
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

63. Amides
In amides,
an amino group(–NH2) replaces the –OH group of carboxylic acids.
O O
|| ||
CH3—C—OH CH3—C—NH2
Copyright © by Pearson Education, Inc.
Publishing as Benjamin Cummings

64. Aromatic Amide
The aromatic amine is benzamide.
benzamide

65. Preparation of Amides Amides are produced
by reacting a carboxylic acid with ammonia
or an amine (1° or 2°).
using heat.
O O
 Heat 
CH3—C—OH + NH CH3—C—NH2 + H2O
O O
 Heat 
CH3—C—OH + CH3—NH CH3—C—NH—CH3 + H2O

66. Naming Amides Amides are named as alkanamides.
IUPAC replaces –oic acid ending with –amide.
Common names replace -ic acid ending with –amide. O
 Methanamide (IUPAC)
H—C—NH2 Formamide (common)
 Propanamide (IUPAC)
CH3—CH2—C—NH2 Propionamide (common)

67. Naming Amides with N Groups
An alkyl group bonded to the N atom is named as
N-alkyl in front of the amide name.
O H
 │
CH3 —C—N—CH N-methylethanamide (IUPAC)
N-methylacetamide (common)
CH3—CH2 —C—N—CH2—CH3
N-ethylpropanamide (IUPAC)
N-ethylpropionamide (common)

68. Learning Check Give the IUPAC and common names for the following. O 
A. CH3–CH2–CH2–C–NH2
O H
 │
B. CH3–C–N–CH2–CH3

69. Solution O  A. CH3–CH2–CH2–C–NH2 butanamide; butryamide O H  │
 │
B. CH3–C–N–CH2–CH3
N-ethylethanamide; N-ethylacetamide

70. Learning Check Draw the structures of A. pentanamide.
B. N-methylbutyramide.

71. Solution O  CH3–CH2–CH2–CH2–C–NH2 B. N-methylbutyramide
A. pentanamide O 
CH3–CH2–CH2–CH2–C–NH2
B. N-methylbutyramide
CH3–CH2–CH2–C–NH–CH3

72. Some Amides in Health and Medicine
Urea is the end product of protein metabolism.
Saccharin is an artificial sweetener.
Some amides such as phenobarbital, Nembutal and Seconal are barbiturates.
Acetaminophen is used to reduce fever and pain.

73. Some Amides in Health and Medicine

74. Physical Properties of Amides
that are primary (−NH2) or secondary (−NH−) form hydrogen bonds.
that are primary have higher melting points than secondary.
that are tertiary (no H on N) do not form hydrogen bonds and have lower melting points.
all form hydrogen bonds with water.
with 1-5 carbon atoms are soluble in water.

75. Hydrogen Bonding of Amides||
CH3—C—N—H |
H Hydrogen bonding occurs
between primary amides. H

76. Hydrolysis of Amides Amides undergo
Acid hydrolysis to produce a carboxylic acid and an ammonium salt.
Base hydrolysis to produce the salt of a carboxylic acid and an amine or ammonia.

77. Hydrolysis Reactions O || O CH3—C—OH + NH4+Cl– || HCl + H2O CH3—C—NH2
acid hydrolysis O ||
O CH3—C—OH + NH4+Cl–
|| HCl + H2O
CH3—C—NH2
NaOH O
CH3—C—O– Na+ + NH3
base hydrolysis

78. Learning Check N-ethylpropanamide with NaOH.
Write the products of the hydrolysis of
N-ethylpropanamide with NaOH.

79. Solution Write the products of the hydrolysis of
N-ethylpropanamide with NaOH. O 
CH3—CH2—C—O– Na+ + CH3—CH2—NH2