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Unit 18
Organic Chemistry
Organic Chemistry : Carbon Chemistry1. 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: yellowOxygen: red
Carbon: blackNitrogen: blueChlorine: green
Bonds
Single - one pair of e-
Use one wooden peg
Double = two pair of e-
Use 2 springs
Triple three pair of e-
Use 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
AssignmentFind all 9 Isomers of
C7H16
Extra creditFind all 18 Isomers of
C8H18
Naming Organic Molecules
Name root name according to the number of carbons in the longest continuous chain.
Name the suffix according to the bonding, carbon to carbon. Single bond C – C end with -ane Double bond C = C end with -ene Triple bond C C 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 NamesMethyl -CH3
Ethyl -CH2CH3
Propyl -CH2CH2CH3
Butyl -CH2CH2CH2CH3
HalidesChloro -Cl Iodo -IBromo -Br Fluoro -F
Prefixes used when more than one group of the same kind is attached
di- two substitutes
tri- threetetra- fourpenta- fivehexa- six
Identify all substitutes that are present on the main chain.
Identify the longest continuous chain of carbons. That is the main chain, the root name comes from that.
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
3-ethyl
Root name 5 carbons: pentane
3-ethyl-2-methylpentane
Draw the following molecule:
3,4-diethyl-5-iodo-4-propyl-2,6,7,7- tetramethyldecane
Naming organic molecules containing functional groups
Drop the e, add
Functional Group Group Name Name ending
- O H Alcohol - ol
Carboxylic Acid - oic Acid
Ketone - one
Functional Group Group Name Name ending
Aldehyde - al
Double bond - ene
Triple bond - yne
Drop –ane, add
Name the following Organic molecules
Name the carbon
number that the alcohol is attached to. Carboxylic
acids will always be on
carbon 1.Name the
carbon number that the ketone is attached to.
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.
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. 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.
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 ChemistryDrugs originate from 3 sources
Natural products Caffeine Penicillin Morphine
Chemical Derivatives from natural products Ampicillin LSD
Synthetic 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
Sodium Pentothal
For minor surgeries, like wisdom teeth extraction, Sodium pentothal may be
used.
Diprivan propofol
Patients tend to be sleepy after
pentothal, so now they use diprivan propofol. Patients
awake faster.
Analgesics are drugs which enhance our ability to tolerate pain (pain killer).
Aspirin is acetyl salicylic acid 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
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. Fertilizers have an N-P-K rating. Nitrates,
Phosphates, Potassium. New laws in Minnesota make it illegal to use fertilizers in MN near water.
MalathionCarbaryl
Herbicides are usually chlorinated hydrocarbons are used to kill unwanted plants in fields.
Agent Orange used during the Vietnam war, caused many health problems.
Insecticides are often chlorinated hydrocarbons, or organophosphorous
compounds are used to kill unwanted insects. They remain on soil for months.
Food can be classified into 3 categories:Carbohydrates: sugars CnH2nOn
monosaccharide 1 sugarglucose, galactose, fructose
disaccharides 2 sugarssucrose, lactose, maltose
polysaccharides many sugarsstarch, cellulose
Lipids: fat, oil, wax lots of C and H, little O
Proteins: polymers of amino acidsmade of C, H, O, little N, S
All food polymers are made by condensation polymerization.
Caffeine is a stimulant milligrams in various drinksBrewed coffee 135Mountain Dew 55Coca Cola 45Dr. Pepper 41Sunkist Orange Soda 40Pepsi 37
Hershey’s dark chocolate bar 31Hershey’s milk chocolate bar 107-Up 0Sprite 0
Food Additives are added to packaged and processed foods to:
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 Green 3: Sea GreenBlue 2: Royal blue Yellow 5: Lemon yellowRed 40: Orange – Red Yellow 6: Sunset orangeRed 3: Cherry red Citrus Red 2: approved for
chicken skin and oranges
Clean Up! 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
Review1. 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
SU-CHEM-DUClues 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. 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
Lewis Structures Orbital Notation/e-
Configuration Reduction Potentials (volts) Naming Organic Molecules H and Reaction Note Book Graphs:
Gas Laws
Ionization Energy
Radioactivity
Rate of Reaction