Chapter 17 and GHW#7
Questions
Amines and Amides
Bonding Characteristics of Amines & Amides
Hydrocarbons compounds containing nitrogen are the
focus of the chapter 17 on amines and amides.
Amines are carbon-hydrogen-nitrogen compounds,
derived form ammonia
Amides contain oxygen in addition to these elements.
Amines and amides occur widely in living organisms. .
Hydrogen bonding in Amines
N-H- - - -N hydrogen bonds are weaker than
O-H- - - -O
CH3 CH3 CH3 NH2
molecu lar w eight (g/mol)
30.1
boiling point (°C) -88.6
31.1
-6.3
CH3 OH
32.0
65.0
Physical Properties of Amines
Hydrogen bonding in Amides
Odor or smell of Amines
Most other amines are liquids and have odors
resembling that of raw fish (strong, disagreeable
odors). Foul smell from dead fish and decaying flesh
is due to diamines released by the bacterial
decomposition of protein. Examples: putrescine and
cadaverine.
Common Names of Amines
IUPAC Nomenclature of Amines
Common/IUPAC Nomenclature of Amides
1. Identify the amines and amides from the following
and give their common and/or IUPAC names.
a)Type:_____________ b) Type:___________________ c)Type:___________________
Name:__________________
Name:______________ Name:__________________
d)Type:____________ e) Type:___________________ f) Type:___________________
Name:______________ Name:__________________
Name:__________________
1. Identify the amines and amides from the following
and give their common and/or IUPAC names.
g)
h)
Type:___________________ Type:___________________
Name:__________________ Name:__________________
j)
k)
Type:___________________ Type:___________________
Name:__________________ Name:__________________
i)
Type:___________________
Name:__________________
l)
Type:___________________
Name:__________________
Cyclic Amines
1. Identify the amines and amides from the following
and give their common and/or IUPAC names.
m)
n)
Type:___________________ Type:___________________
Name:__________________ Name:__________________
o)
Type:___________________
Name:__________________
Basicity: Amine Salt formation
Amines
have
a basic
PH
PH> 7
2. Classify each of the following as either 1', 2', or 3'
amines and quaternary amine :
3. Consider the following compounds:
a) CH3—CH2—CH2—NH2
b) CH3—CH2—NH—CH3
c) CH3—CH2—CH2—CH3
d) CH3—CH2—CH2—NH3+ClA. Arrange compounds in the order highest
boiling point to lowest?
B. Arrange compounds in the order of highest
solubility in water to the lowest?
4. Draw the structure of the following amines
and amides:
a) N-methyl-1butanamine:
b) N-methylaniline c) N-phenyl-3chlorobutanamide
d) N-ethyl-Ne) N-methylbenzamide
methylethanami
de
Preparation of Amines
a) Reaction of ammonia with alkyl halides
b) Reduction of amides
c) Reduction of Nitro Groups
Preparation of Amines
a) Reaction of ammonia with alkyl halides
b) Reduction of amides
c) Reduction of Nitro Groups
Preparation of Amides
a) Reaction with carboxylic acid to form amides
(described below in preparation of amides)
b) Polymerization to form polyamides
Nylon 66 – a polymer of hexanedioic acid and 1,6hexanediamine as monomers shown below
Chemical Reactions of Amides
a) Hydrolysis reaction amides (Acid/base hydrolysis)
O
O
NH2 +
Ph
2-Phenylbutan amide
H2 O + HCl
H2 O
heat
Ph
2-Phen ylb utanoic acid
b) Reduction of amides to amines
+
-
OH + NH4 Cl
5) Name and complete the following
preparations/reactions of amines and amides:
a)
b)
c)
d)
5) Name and complete the following
preparations/reactions of amines amides:
e)
f)
g)
5) Name and complete the following
preparations/reactions of amines amides:
h)
i)
j)
k)
5) Name and complete the following
preparations/reactions of amines amides:
l)
m)
n)
the penicillins differ
in the group bonded
to the acyl carbon
Drugs & Narcotics
H
CH2 C
O
Penicillin G
N
O
H H
S CH3
N
CH3
COOH
O
The cephalosporins
differ in the group
bonded to the carbonyl
carbon...
N
H
NH2
O
H H
N
S
...and the group bonded
to this carbon of the
six-membered ring
CH3
COOH
Keflex
(a -lactam antibiotic)
Heterocyclic Amines and Alkaloids
• Alkaloids are a group of naturally occurring
chemical compounds that contain mostly
basic nitrogen atoms. In addition to carbon,
hydrogen and nitrogen, alkaloids may also
contain oxygen, sulfur and more rarely other
elements such as chlorine, bromine, and
phosphorus.[5]
Heterocyclic Amines and Alkaloids
Cocaines
Chlorophyll and Hemoglobin
Purines and Pyrimidines: DNA Bases