Carboxylic Acids Esters,
Amines and Amides
Amines
Reactions of Amines
Amides
Reactions of Amides
1
Amines
• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
CH3
CH3


CH3—NH2 CH3—NH CH3—N — CH3
1°
2°
3°
2
Naming Amines
IUPAC aminoalkane
CH3CH2NH2
aminoethane
(ethylamine)
Common alkylamine
CH3—NH —CH3
N-methylaminomethane
(dimethylamine)
NH 2
NH CH3
NH2
|
CH3CHCH3
2-aminopropane
(isopropylamine)
Aniline
N-methylaniline
3
Learning Check AM1
Give the common name and classify:
A. CH3NHCH2CH3
CH3
|
B. CH3CH2NCH3
4
Solution AM1
A. CH3NHCH2CH3
ethylmethylamine, 2°
CH3
|
B. CH3CH2NCH3
ethyldimethylamine, 3°
5
Reactions of Amines
• Act as weak bases in water
CH3NH2 + H2O
CH3NH3+ + OH–
methylammonium
hydroxide
• Neutralization with acid gives ammonium salt
CH3NH2 + HCl
CH3NH3+ Cl–
methylammonium
chloride
6
Alkaloids
• Physiologically active nitrogen-containing
compounds
• Obtained from plants
• Used as anesthetics, antidepressants, and
stimulants
• Many are addictive
7
Nicotine
CH3
N
Nicotine, leaves of tobacco plant
8
Caffeine
O
CH3
O
CH3
N
N
N
N
CH3
Caf f e in e , cof f e e b e an s an d t e a
9
Procaine
CH3CH2
O
N
CH2CH2 O C
NH2
CH3CH2
Procaine (novocaine), painkiller
10
Leaning Check AM2
Write a structural formula for
A.
2-aminopentane
B.
1,3-diaminocyclohexane
11
Solution AM2
A.
B.
1-aminopentane
CH3CH2CH2CH2CH2-NH2
1,3-diaminocyclohexane
NH2
NH2
12
Amides
Derivatives of carboxylic acids where an
amino (-NH2) group replaces the –OH
group.
O
O


CH3 — C—OH
carboxylic acid
acetic acid
CH3 — C—NH2
amide
acetamide
13
Naming Amides
Alkanamide
O

HC–NH2
from acid name
methanamide (IUPAC)
formamide (common)
O

CH3CH2C–NH2
propanamide (IUPAC)
propionamide(common)
14
Naming Amides with N-Groups
O

CH3C–NHCH3
N-methylethanamide (IUPAC)
N-methylacetamide (common)
O

CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide
15
Aromatic Amides
O
O
C NH2
C NHCH3
Benzamide
N -methylbenzamide
16
Learning Check AM3
Name the following amides:
O

A.
CH3CH2CH2C–NH2
B.
O

CH3C–N(CH2CH3)2
17
Solution AM3
O

A.
CH3CH2CH2C–NH2
butanamide; butryamide (common)
O

B.
CH3C–N(CH2CH3)2
N,N-diethylethanamide;
N,N-diethylacetamide
18
Learning Check AM4
Draw the structures of
A. Pentanamide
B. N-methylbutyramide
19
Solution AM4
A.
Pentanamide
O

CH3CH2CH2CH2C–NH2
B.
N-methylbutyramide
O

CH3CH2CH2C–NHCH3
20
Reactions of Amides
Amides undergo
acid hydrolysis
base hydrolysis
carboxylic acid
ammonium salt
salt of carboxylic acid
and an amine
or ammonia
21
Reactions of Amides
acid hydrolysis
O

O
HCl + H2O
CH3COH + NH4+Cl–

CH3CNH2
O
NaOH

CH3CO– Na+ + NH3
base hydrolysis
22
Learning Check AM5
Write the products of the hydrolysis of
N- ethylpropanamide with NaOH.
23
Solution AM5
Hydrolysis of N-ethylpropanamide with NaOH
gives the following products.
O

CH3CH2CO– Na+ + CH3CH2NH2
24