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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 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

Assignment Find all 9 Isomers of

C7H16

Extra credit Find 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 Names

Methyl -CH3

Ethyl -CH2CH3

Propyl -CH2CH2CH3

Butyl -CH2CH2CH2CH3

Halides

Chloro -Cl Iodo -I

Bromo -Br Fluoro -F

Prefixes used when more than one group of the same kind is attached

di- two substitutes

tri- three

tetra- four

penta- five

hexa- 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 Chemistry Drugs 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.

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.

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 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 135

Mountain Dew 55

Coca Cola 45

Dr. Pepper 41

Sunkist

Orange Soda 40

Pepsi 37

Hershey’s dark

chocolate bar 31

Hershey’s milk

chocolate bar 10

7-Up 0

Sprite 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 Green

Blue 2: Royal blue Yellow 5: Lemon yellow

Red 40: Orange – Red Yellow 6: Sunset orange

Red 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

Review

1. 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-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. 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

DH and Reaction

Note Book

Graphs:

Gas Laws

Ionization Energy

Radioactivity

Rate of Reaction