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H. Amines are formed when one or more of the H atoms
of ammonia NH3 are replaced by an alkyl group.
Functional
group:
General
Formula:
Ammonia
structure:
Ex. methylamine:
Each H can become a
C in a hydrocarbon.
molecular: CH5N
condensed: CH3NH2
Ex. trimethylamine:
CH3
CH3
CH3
condensed: (CH3)N
Ex. 1-propanamine
H H H
H
H C C C N
H H H
H
condensed: CH3CH2CH2NH2
Ex. Amino acids contain a carboxylic group –COOH
and an amine group
amine group
propane
backbone
carboxylic
group
Urea
Urea has two amine (-NH2) groups joined by
a carbonyl (C=O) functional group.
Urea serves an important role in the
metabolism of nitrogen-containing compounds by
animals and is the main nitrogen-containing
substance in the urine of mammals.
The body uses it in many processes, most
notably nitrogen excretion. Urea is widely used in
fertilizers as a convenient source of nitrogen.
I. Amides are formed when an H of an amino group
reacts with the –OH of an organic acid
Ex:
amino group:
propanoic acid:
H
H
H
O
C
C
C —OH
H
H
Functional
group:
H2O
+
Result: An amide
called propanamide
H
H
H
O
C
C
C—
H
H
Thalidomide: Prescribed as an
antinauseant for morning sickness in
pregnant women in the late 1950s. In
1961, it was withdrawn due to toxicity.
Nazis developed
Thalidomide and
tested it on
concentration
camp prisoners,
author claims
When amides are formed from amino acids,
they are called peptide bonds in biology. Many amino
acids combine in this way to form proteins.
amino group
from one acid
--COOH
of an
organic
acid
Water is
produced,
so this is a
condensation
reaction.
peptide
bond
N,N-Diethyl-meta-toluamide, abbreviated DEET
Start with:
3-methyl
benzoic acid
react with
diethyl amine
DEET
VI. Organic Reactions – usually occur more slowly
than inorganic reactions because the covalent bonds
that get broken are relatively strong.
A. Combustion – Almost all organic compounds burn.
Case 1: With sufficient oxygen
C3H8(g) + 5__O2(g)
-->
3CO2(g)
+ 4H2O (g)
--> carbon ______
dioxide + water
Case 2: With insufficient oxygen
2C3H8(g) + 7O2(g)
-->
6CO(g)
8 2O (g)
+ ___H
monoxide + water
--> carbon _______
B. Substitution – An atom or group of atoms replaces
one or more of the H atoms in a saturated hydrocarbon.
Ex. The reaction of ethane with chlorine gas
H H
H C C H
H Cl
+ Cl-Cl
H H
C2H6
H C C H
+
H-Cl
+
HCl
H H
+
Cl2
C2H5Cl
The single C-H bond in the alkane ethane is first
broken, and the H is removed to form hydrogen chloride.
One chlorine atom Cl is then substituted into the open
bond site on ethane to form the halide chloroethane.
C. Addition – Adding one or more atoms at a
double or triple bond
Ex. In the reaction of ethene and chlorine gas, the double
bond of ethene is opened, and a Cl is added to each C:
Cl Cl
+ Cl-Cl
H C C H
H H
C2H4
+
Cl2
C2H4Cl2 = dichloroethane
Ex. H can be added to unsaturated hydrocarbons :
H H
+ H-H
C2H4
ethene-unsaturated
H C C H
H H
SATURATED!
ethane C2H6 - ____________!
D. Saponification is the process for making soap.
triglyceride
+ base
-->
alcohol
+
soap
In the example above, the base NaOH breaks the
triglyceride (a sort of triple ester) into the alcohol glycerol
and the salt of a fatty acid, which is the soap. The Na end
of the soap is polar and dissolves in water. The hydrocarbon
is nonpolar and dissolves in oil and dirt.
How do soaps clean?
http://www.edinformatics.com/interactive_molecules/soap.htm
F. Fermentation - the chemical process in which yeast
cells secrete the enzyme zymase. This breaks glucose
sugar molecules into alcohol and carbon dioxide.
Ex 1: Fermentation to produce alcohol
C6H12O6
zymase
-->
2C2H5OH
glucose
2 2
__CO
+
carbon dioxide
ethanol
2
+
2
O =C = O
Ex 2: Fermentation to produce vinegar (acetic/ethanoic acid)
H O
+ O2
ethanol
oxygen
yeast
H C C —OH
H
ethanoic acid
+
H2O
water
G. Polymerization involves smaller molecules joining
together to form one big molecule. A monomer is a
small molecule. A polymer is a big molecule.
 Monomers join together to form polymers.
monomer
Ex. amino +
acid
monomer
amino
acid
monomer
+
amino
acid
polymer
-->
protein
There are two types of polymerization:
1. Condensation polymerization - The monomers
join together by dehydration (removing water).
An OH from one unit + an H of another = H2O
Ex.
many esters
Polyester = ________
Acid + alcohol
=
water
_______
+
ester
(the monomer)
polyester
(the polymer)
Polyester is used in plastic bottles and is a
suspected endocrine disruptor.
2. Addition polymerization – the joining together of
monomers by breaking a double or triple bond.
ethene
Ex.
one monomer
(ethylene)
break the
double bond
H
H
—C—C—
H
H
To show that any number n of these
monomers can be linked together, write the
monomer in parentheses with a subscript n:
Then add n monomers to get the polymer:
polyethylene