Unit 18
Organic Chemistry
Organic Chemistry : Carbon Chemistry
1.
Carbon is different from all other elements because it
forms chains, branches, and rings. Carbon can combine
with many different elements such as H, O, N, S, Cl.
2.
Over 6 million carbon compounds are known. A new
compound is discovered every 10 minutes.
3.
Some of the most valuable carbon compounds come from
coal, oil, and gas. Other carbon compounds are made into
plastics, clothing, food additives, drugs, etc.
4.
Most organic compounds DO NOT dissolve in H2O.
Organic chemical reactions proceed at slower rates.
5.
Over 90% of carbon compounds are synthetic. The rest
come from living organisms.
Carbon by itself can take on several forms.
Graphite is carbon bonded in sheets. Pencils have
graphite in them. As you write, the sheets peel off.
Diamond is carbon bonded in 4 directions, tetrahedral.
Carbon can also be
used to create
“bucky balls” or
“bucky tubes”.
Bucky balls have
been used to shrink
wrap drugs.
Bucky tubes
although very small
(nm range) are
stronger than steel.
Important classes of Organic Compounds
Used for fuel, cosmetics.
Antifreeze, drinks
Aromas, flavorings,
preservatives, sugars
Aromas, flavorings,
solvents, sugars
Ways to show a molecule:
1. Chemical formula
C4H10
2. Structural formula
3. Condensed structural formula
Using the Molecule Model Kits
Atoms : Colors
Hydrogen: yellow
Oxygen: red
Carbon: black
Nitrogen: blue
Chlorine: green
Bonds
Single
- one pair of e
-
Use one wooden peg
Double = two pair of eUse 2 springs
Triple
three pair of eUse 3 springs
Isomers: Molecules with the same chemical
formula, but different arrangement of atoms.
With different arrangement of atoms, the
properties of the chemicals are different.
Small molecules only have one arrangement possible.
CH4 Methane
C2H6 Ethane
Propane, C3H8
has only 1 isomer
As molecules get bigger, isomers are
possible. C4H10 has 2 isomers.
C5H12 has 3 isomers
Assignment
Find all 9 Isomers of
C7H16
Extra credit
Find all 18 Isomers of
C8H18
Naming Organic Molecules
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Name root name according to the number
of carbons in the longest continuous chain.
Name the suffix according to the bonding,
carbon to carbon.
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Single bond C – C
Double bond C = C
Triple bond C C
end with -ane
end with -ene
end with -yne
Name substitutions on the main chain
before the root name, giving the lowest
possible number.
Hydrocarbon
Name: the following:
CH3CH2CH2CH3
Butane
CH3CH2CH3
Propane
CH3CH2CH2CH2CH2CH2CH3
Heptane
Substitute Naming
Group Names
Methyl -CH3
Ethyl -CH2CH3
Propyl -CH2CH2CH3
Butyl
-CH2CH2CH2CH3
Halides
Chloro -Cl
Bromo -Br
Iodo -I
Fluoro -F
Prefixes used when
more than one group
of the same kind is
attached
ditritetrapentahexa-
two substitutes
three
four
five
six
Identify the longest
continuous chain of
carbons. That is the
main chain, the root
name comes from
that.
Identify all
substitutes that are
present on the main
chain.
Number the carbons to give all substitutes
the lowest possible numbers.
2,3-dimethylpentane
Name the following:
1. Count the number of carbons in the main chain
2. Number the carbons to give the substitutes
the lowest number possible
3. Identify the substitutes and how many
2-methyl-hexane
Name substitutes in
alphabetical order.
2-methyl
Root name 5 carbons: pentane
3-ethyl
3-ethyl-2-methylpentane
Draw the following molecule:
3,4-diethyl-5-iodo-4-propyl-2,6,7,7tetramethyldecane
Naming organic molecules containing
functional groups
Drop the e, add
Functional Group
ending
-OH
Group Name
Alcohol
Carboxylic Acid
Ketone
Name
- ol
- oic Acid
- one
Functional Group
Group Name
Aldehyde
Name ending
- al
Drop –ane, add
Double bond
Triple bond
- ene
- yne
Name the following Organic molecules
Name the
carbon number
that the
alcohol is
attached to.
Name the
carbon number
that the ketone
is attached to.
Carboxylic acids
will always be on
carbon 1.
Name the following Organic molecules
Aldehydes are
always on
carbon 1
Name the
carbon before
the double bond
Functional groups are given priority. They
receive the lowest number possible. Name the
following.
Fractional Distillation: The process of
separating the components of a liquid mixture
that depends of differences in the
vaporization temperatures of the components.
Petroleum has
many components
that humans use.
Each type of
molecule will boil
off at different
temperatures,
allowing for the
separation of
them. The smaller
the molecule, the
lower the boiling
point.
Petroleum (oil) was formed by the decomposition
of vast quantities of Protista. Especially diatoms
which store oil to float.
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The US uses about 18,950,000 barrels of oil a
day.
We produce about 6,500,000 barrels a day.
The difference is imported from foreign
countries.
A barrel of crude oil is 42 gallons. It yields
about 38 gallons of fuels such as gasoline, heating
fuel, but only 2 quarts of lubricating oil for cars.
Motor Oil is designed to help engines run more
efficiently. Several ingredients are added.
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Anti-wear chemicals
Detergents to prevent dirt from building
up on moving parts
Foam inhibitors
Corrosion inhibitors
Dispersants to keep contaminants in
suspension
Friction modifiers
Oil is designed to provide the
proper viscosity.
Viscosity is the resistance to flow of a liquid.
10W oil is the thinnest, designed for use in
winter.
40W oil is the thickest, designed for use in
summer.
Multigrade oil contains both thin and thick
components for use during any season.
Polymers are chemicals made of very long chains of
carbon atoms- 1000’s of carbon atoms can be
linked together to form macromolecules.
Most of the starting molecules come from oil.
Examples of uses for polymers that are:
Man made are saran wrap, garbage bags, yarn,
garden hoses, car tires, park benches, paints, etc.
Polymers made from plants are rayon and cotton.
Polymer made from animal is silk.
Americans use a huge amount of polymers to support our
life style. On the bottom of plastic items, there is
placed a recycling code to tell you the kind of polymer.
There are 2 general reactions used
to make polymers.
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Condensation polymerization: The
molecules are added together, while a
molecule of water is removed.
Addition polymerization: The molecules
are added together at a double bond.
Condensation polymerization: The molecules
are added together, while a molecule of
water is removed.
Polymers of all the main organic molecule types,
carbohydrates, lipid, and proteins are made with
condensation polymerization.
Web page
Demonstration of a condensation
polymerization
Addition polymerization: The molecules
are added together at a double bond.
Polymerization of polyethylene requires high temperatures
and high pressures. Polyethylene is used for plastic bags,
garbage bags, etc. In 1978, enough polyethylene was
manufactured in the U. S. to supply ever person with 50
pounds of polymer.
Drug Chemistry
Drugs originate from 3 sources
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Natural products
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Chemical Derivatives from natural products
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Caffeine
Penicillin
Morphine
Ampicillin
LSD
Synthetic
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Valium
Benadryl
Drugs work on a lock and key model.
One key fits one lock
One molecule structure will fit in one
receptor site.
Anesthetics are drugs which prevent
neurons from transmitting
sensations to the brain.
Topical anesthetic numbs the skin
Local anesthetic numbs a small area of tissue
General anesthetic renders the patient
unconscious.
The first anesthetic used was diethyl ether,
CH3CH2OCH2CH3
Modern anesthetics include fluorine
containing compounds.
One of the earlier ones
used is Halothane. It is
not used much now,
because it causes liver damage.
It leaves the body too slow.
Modern drugs are designed to leave the
body faster with less side-effects.
or
Suprane
For minor surgeries,
like wisdom teeth
extraction, Sodium
pentothal may be used.
Sodium Pentothal
Patients tend to be
sleepy after pentothal,
so now they use
diprivan propofol.
Patients awake faster.
Diprivan propofol
Analgesics are drugs which enhance our
ability to tolerate pain (pain killer).
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Aspirin is acetyl salicylic acid
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Analgesic: relieves pain
Antipyratic: reduces fever
Thins blood
Hazards of using aspirin are
intestinal bleeding, allergic
reactions, and Reye syndrome.
The only difference between brands of pure
aspirin is price. So buy the cheapest!
Tylenol and Datril contain a chemical called
Acetaminophen
Advil and Motrin contain Ibuprofen,
Less irritation to stomach, acts as an
anti-inflammatory to reduce swelling.
Aleve contains Naproxen
Food Chemistry
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The population of the Earth is 7.0 billion
people. At a growth rate of 2.2%, over
400,000 people are added each day to the
Earth. (U.S. 311,325,619)
Farming requires a large amount of
fertilizers, insecticides, and herbicides.
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Fertilizers have an N-P-K rating. Nitrates,
Phosphates, Potassium. New laws in Minnesota
make it illegal to use fertilizers in MN near
water.
Insecticides are often chlorinated hydrocarbons, or
organophosphorous compounds are used to kill
unwanted insects. They remain on soil for months.
Malathion
Carbaryl
Herbicides are usually chlorinated hydrocarbons are
used to kill unwanted plants in fields.
Agent Orange used during the Vietnam war, caused
many health problems.
Food can be classified into 3 categories:
Carbohydrates: sugars
CnH2nOn
monosaccharide 1 sugar
glucose, galactose, fructose
disaccharides 2 sugars
sucrose, lactose, maltose
polysaccharides many sugars
starch, cellulose
Lipids: fat, oil, wax lots of C and H, little O
Proteins: polymers of amino acids
made of C, H, O, little N, S
All food polymers are made by condensation polymerization.
Caffeine is a stimulant
milligrams in various drinks
Brewed coffee
Mountain Dew
Coca Cola
Dr. Pepper
Sunkist
Orange Soda
Pepsi
135
55
45
41
40
37
Hershey’s dark
chocolate bar
Hershey’s milk
chocolate bar
7-Up
Sprite
31
10
0
0
Food Additives are added to packaged and
processed foods to:
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Prevent spoilage
Enhance flavors
Enhance color
Adjust the pH
Leavening agent
Prevent bacterial growth
Emulsify (mix in fats)
Food colors: At one time there were over
100 chemicals used to color foods. Most
have been found to cause health problems.
Today, colorings are either
dyes which dissolve in water,
lakes which are insoluble in water, but do dissolve
in fats.
Blue 1: Bright blue
Blue 2: Royal blue
Red 40: Orange – Red
Red 3: Cherry red
Green 3: Sea Green
Yellow 5: Lemon yellow
Yellow 6: Sunset orange
Citrus Red 2: approved for
chicken skin and oranges
Clean Up!
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Wash all glassware
(not metal or ceramic square)
Put clean paper in the bottom of drawer
Put Classroom equipment on the cart.
(thermometers, flint lighters, etc.)
Tighten screws of handle and lock on
drawer
Wash safety glasses and put in sterilizer
Review
See drawings
9. 4 bonds
2a. 3-ethyl-2-methylpentane
10. see drawings
b. 2-fluoro-1-butene
11. 3 pairs of electrons, (6 e-)
c. 3-methyl-2-hexanol
12. to help you tolerate pain
d. 2-bromo-5-Iodo-3-heptanone
3a. Alcohol -ol
b. aldehyde -al
c. double bond -ene
4. Very large molecule made of monomers (molecules) with a carbon base that
makes a long chain of carbons
5. Condensation polymer (take out a molecule of water each time a molecule is
added on )(proteins, starch, cellulose)
Addition polymer (breaking a double bond each time an other molecule is
joined to the molecule)( polyethylene, polystyrene)
6. Multigrade oil with 2 different size molecules in it for year round use.
7. detergent, dispersant, friction modifiers, antifoam, anticorrosion, antiwear
8. The study of carbon based molecules
1.
SU-CHEM-DU
Clues to our six elements (at bottom)
5. Iodine
7. Same element as question 1
8. Same element as question 2
9. Same element as question 15
10. Sulfur
11. Same element as question 5
13. Same element as question 10
14. Same element as question 6
Table 20.5
Things that can be used on the final exam.
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Periodic Table
Mole Wheel
Formula Sheet
Calculator
Common Ions
Solubility (precipitates)
Ice Cube Family Trip
Blank Periodic Table (you
wrote on)
Element Research
Heat of Formation
Car Analogy
Le Chatelier’s Principles
Nomenclature guides
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Lewis Structures
Orbital Notation/eConfiguration
Reduction Potentials (volts)
Naming Organic Molecules
DH and Reaction
Note Book
Graphs:
Gas Laws
Ionization Energy
Radioactivity
Rate of Reaction