Chemistry 121(01) Winter 2014
Introduction to Organic Chemistry and Biochemistry
Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
E-mail: upali@latech.edu
Office: 311 Carson Taylor Hall ; Phone: 318-257-4941;
Office Hours: MTW 9:00 am - 11:00 am;
TR 9:00 - 10:00 am & 1:00-2:00 pm.
December 20, Test 1 (Chapters 12-13)
January 27 Test 2 (Chapters 14-16)
February 14 Test 3 (Chapters 17-19)
February 26, Test 4 (Chapters 20-22)
February 27, 2014, Make Up Exam:
Bring Scantron Sheet 882-E
Chapter 17: Amines and Amides
17.1 Bonding Characteristics of Nitrogen Atoms in Organic Compounds, 547
17.2 Structure and Classification of Amines, 548
17.3 Nomenclature for Amines, 549
17.4 Isomerism for Amines, 551
17.5 Physical Properties of Amines, 552
17.6 Basicity of Amines, 553
17.7 Reaction of Amines with Acids, 554
17.8 Alkylation of Ammonia and Amines, 557
17.9 Heterocyclic Amines, 558
17.10 Selected Biochemically Important Amines, 560
17.11 Alkaloids, 565
17.12 Structure and Classification of Amides, 568
17.13 Nomenclature for Amides, 570
17.14 Selected Amides and Their Uses, 571
17.15 Basicity of Amides, 572
17.16 Physical Properties of Amides, 573
17.17 Preparation of Amides, 574
17.18 Hydrolysis of Amides, 576
17.19 Polyamides and Polyurethanes, 578
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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. .
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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)
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30.1
point (°C) -88.6
31.1
-6.3
CH3 OH
32.0
65.0
4
Physical Properties of Amines
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Hydrogen bonding in Amides
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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.
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Common Names of Amines
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IUPAC Nomenclature of Amines
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Common/IUPAC Nomenclature of Amides
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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:__________________
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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:__________________
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i)
Type:___________________
Name:__________________
l)
Type:___________________
Name:__________________
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Cyclic Amines
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1. Identify the amines and amides from the following
and give their common and/or IUPAC names.
m)
n)
Type:___________________ Type:___________________
Name:__________________ Name:__________________
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o)
Type:___________________
Name:__________________
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Basicity: Amine Salt formation
Amines
have
a basic
PH
PH> 7
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2. Classify each of the following as either 1', 2', or 3'
amines and quaternary amine :
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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?
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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
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Preparation of Amines
a) Reaction of ammonia with alkyl halides
b) Reduction of amides
c) Reduction of Nitro Groups
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Preparation of Amines
a) Reaction of ammonia with alkyl halides
b) Reduction of amides
c) Reduction of Nitro Groups
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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
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Chemical Reactions of Amides
a) Hydrolysis reaction amides (Acid/base hydrolysis)
O
O
NH2 +
Ph
2-Phenylbutan amide
H2 O + HCl
H2 O
heat
+
-
OH + NH4 Cl
Ph
2-Phen ylb utanoic acid
b) Reduction of amides to amines
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5) Name and complete the following
preparations/reactions of amines and amides:
a)
b)
c)
d)
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5) Name and complete the following
preparations/reactions of amines amides:
e)
f)
g)
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5) Name and complete the following
preparations/reactions of amines amides:
h)
i)
j)
k)
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5) Name and complete the following
preparations/reactions of amines amides:
l)
m)
n)
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Drugs & Narcotics
the penicillins differ
in the group bonded
to the acyl carbon
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)
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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]
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Heterocyclic Amines and Alkaloids
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Cocaines
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Chlorophyll and Hemoglobin
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Purines and Pyrimidines: DNA Bases
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