9/18/2009
Amines and
Amides
Amines
• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
CH3
CH3


CH3—NH2 CH3—NH CH3—N — CH3
1.8
1°
2°
3°
1
Naming Amines
IUPAC aminoalkane
Learning Check
(Common alkylamine)
CH3—NH —CH3
N-methylaminomethane
(dimethylamine)
CH3CH2NH2
aminoethane
(ethylamine)
NH2
Give the IUPAC name and classify:
A. CH3NHCH2CH3
CH3
|
B. CH3CH2NCH3
NH CH3
NH2
|
CH3CHCH3
2-aminopropane
(isopropylamine)
2
Aniline
N-methylaniline
3
Reactions of Amines
4
Alkaloids
• Act as weak bases in water
CH3NH2 + H2O
CH3NH3+ + OH–
methylammonium
hydroxide
• Physiologically active nitrogen-containing
compounds
• Obtained from plants
• Used as anesthetics, antidepressants, and
stimulants
• Many are addictive
• Neutralization with acid gives ammonium salt
CH3NH2 + HCl
CH3NH3+ Cl–
methylammonium
chloride
6
7
1
9/18/2009
Nicotine
Caffeine
O
CH3
CH3
O
N
CH3
N
N
N
N
CH3
Caf f e in e , cof f e e b e an s an d t e a
Nicotine, leaves of tobacco plant
8
9
Procaine
CH3CH2
Learning Check
O
N
CH2CH2 O C
Write a structural formula for
NH2
CH3CH2
A.
1-aminopentane
B.
1,3-diaminocyclohexane
Procaine (novocaine), painkiller
10
Amides
11
Naming 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
Alkanamide
O

HC–NH2
from acid name
methanamide (IUPAC)
formamide (common)
O

CH3CH2C–NH2
propanamide (IUPAC)
propionamide(common)
14
2
9/18/2009
Naming Amides with N-Groups
O

CH3C–NHCH3
Aromatic Amides
N-methylethanamide (IUPAC)
N-methylacetamide (common)
O
O
C NH 2
C NHCH 3
O

CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide
Benzamide
N -methylbenzamide
15
16
Learning Check
Learning Check
Name the following amides:
O

A.
CH3CH2CH2C–NH2
B.
Draw the structures of
A. Pentanamide
B. N-methylbutanamide
O

CH3C–N(CH2CH3)2
17
19
Reactions of Amides
Reactions of Amides
acid hydrolysis
Amides undergo
O

acid hydrolysis
O
base hydrolysis
HCl + H2O
CH3COH + NH4+Cl–

CH3CNH2
carboxylic acid
ammonium salt
salt of carboxylic acid
and an amine
or ammonia
O
NaOH

CH3CO– Na+ + NH3
base hydrolysis
21
22
3
9/18/2009
Learning Check
Write the products of the hydrolysis of
N- ethylpropanamide with NaOH.
23
4