Organic Compounds

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Organic Compounds

• Chapter 24

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Organic Compounds

• Section 1- Simple Organic Compounds slides 3-20
• Section 2- Other Organic Compounds slides 21-32
• Section 3- Petroleum- A Source of Carbon
  Compounds slides 33-44
• Section 4- Biological Compounds slides 45-62

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Section 1 Simple Organic Compounds

• What Youll Learn
• About organic and inorganic carbon compounds
• Difference between saturated and unsaturated
  hydrocarbons
• Identify isomers

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1 Simple Organic Compounds

• Most compounds that contain the element carbon
  are organic compounds made by living organisms or
  synthesized in laboratories.
• More than 90 of carbon compounds are organic.
• Others like carbon dioxide and carbonates are
  inorganic compounds.

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Why does carbon form so many organic compounds?

• With 4 electrons in its outer energy level,
  carbon can form one covalent bond with each of
  these electrons.
• There are many C compounds because C can form so
  many bonds.
• Some are small like the ones used as fuel while
  some are complex like those in medicine and
  plastics.

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How can C atoms arrange themselves?

• C atoms can bond together as chains, branched
  chains, rings.

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How can C atoms arrange themselves?

• The first structure shows carbon bonded in a
  straight chain as heptane, an organic compound in
  gasoline.
• The second structure, a branched chain, shows
  isoprene, an organic compound in natural rubber.
• The third structure, a cyclic ring or chain, is
  vanillin from vanilla flavoring.
• Also forms single, double or triple covalent
  bonds.

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Hydrocarbons

• A compound that is made of only carbon and
  hydrogen is called a hydrocarbon.
• Natural gas contains the hydrocarbon methane or
  CH4.

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Single Bonds

• Hydrocarbons with only single-bonded C atoms are
  called saturated hydrocarbons. It is saturated
  because each C is bonded to as many H as possible.

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Boiling Points of Hydrocarbons
butane
pentane
propane
ethane
methane
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Boiling Points of Hydrocarbons

• Did you see a pattern?
• The boiling points of saturated hydrocarbons
  increase as the number of carbon atoms in the
  chain increases.

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Can different hydrocarbons have the same formula?

• Image
• File history
• Links
•                                                 
                                                    

• Butane is C4H10 and so is isobutane. Butane is a
  straight chain molecule but isobutane has a
  branched chain.

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What are isomers?

• Isomers are compounds that have the same chemical
  formula, but have different molecular structures
  shapes.
• Thousands of hydrocarbons are isomers.
• Butane isobutane are two of them.

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Properties of Butane Isomers
Property Butane Isobutane
Description Colorless gas Colorless gas
Density 0.60 kg/L 0.603 kg/L
Melting Point -135C -145C
Boiling Point -0.5C -10.2C
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Are there other kinds of isomers?

• Some isomers differ only slightly in the way
  their atoms are arranged. Some form what are
  called right-handed left-handed molecules.
  These have nearly identical physical and chemical
  properties.

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Multiple Bonds

• Ethene or ethlylene gas is what makes fruit
  ripen.
• You can see ethene has one double bond.
• The two C atoms share two pairs of electrons.

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Multiple Bonds

• The ethyne molecule has a triple bond with two
  carbon atoms sharing three pairs of electrons.
  Also called acetylene, its used in welding
  torches. Ethene and ethyne are unsaturated
  hydrocarbons.

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Multiple Bonds

• An unsaturated hydrocarbon is one that has at
  least one double bond or triple bond. The
  compounds are unsaturated because each carbon
  atom is not bonded to as many hydrogens as
  possible.
• The last three letters tell what type of bond is
  in the molecule. Compounds ending in ane have
  only single bonds. Those with ene have at least
  one double bond and yne signifies at least one
  triple bond.

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Flow Chart
Organic compounds
Straight chains
Contain only C H are called
________ chains
_________ chains
Bond as
Single bonds
_____ bonds
______ bonds
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Flow Chart
Organic compounds
Straight chains
Contain only C H are called
Branched chains
hydrocarbons
Cyclic chains
Bond as
Single bonds
Double bonds
Triple bonds
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Section 2 Other Organic Compounds

• What Youll Learn
• What aromatic compounds are
• What alcohols and acids are
• Some organic compounds you use everyday

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2 Other Organic Compounds

• Organic compounds produce tastes and smells such
  as wintergreen, cloves, cinnamon, and vanilla.
• This is wintergreen or methyl salicylate used in
  chewing gum.

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Aromatic Compounds

• Other organic compounds have unpleasant tastes or
  smells.
• This figure shows the structural formula for
  acetyl salicylic acid or aspirin which has a sour
  taste.
• An aromatic compound contains a benzene structure
  having a ring made of six C atoms.

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Why is benzene stable?

• The chemical structure for benzene is C6H6.
• The benzene ring is made of six C atoms bonded
  together by three double bonds three single
  bonds alternating around the ring.

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Why is benzene stable?

• All 6 C equally share the electrons making the
  molecule very stable.
• The symbol for benzene is a circle inside a
  hexagon.
• Many organic structures contain a benzene ring.

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Are there other ring structures?

• Organic compounds can contain more than one ring
  structure.
• Some moth crystals are made of naphthalene with
  two rings fused together.
• Many contain 3 or more rings fused together.

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Substituted Hydrocarbons

• Chemists change hydrocarbons into other compounds
  with different physical chemical properties.
• May add a double or triple bond
• May substitute different atoms or groups of atoms

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Substituted Hydrocarbons

• A substituted hydrocarbon is a hydrocarbon that
  has one or more of its hydrogen atoms replaced by
  atoms or groups of atoms of other elements.
• Chemists decide what kinds of properties they
  want in a new compound and then they choose atoms
  or groups of atoms or types of bonds that will
  give those properties.

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What are some substituted hydrocarbons?

• An alcohol forms when a hydroxyl group, OH,
  replaces one or more hydrogen atoms in a
  hydrocarbon.
• This is ethanol. When the sugars in grains or
  fruits ferments, it produces ethanol

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What are some substituted hydrocarbons?

• Organic acids form when a carboxyl group, -COOH,
  attaches to a C atom of a hydrocarbon.
• Acetic acid is an organic acid found in vinegar.
  Other organic acids include citric acid in citrus
  fruit lactic acid in sour milk.

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What other elements can be added to hydrocarbons?

• Chlorine can be used as well as H O.
• When 4 Cl atoms replace 4 H on ethene, they form
  tetra-chloroethene, a solvent used in dry
  cleaning.

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What other elements can be added to hydrocarbons?

• When 4 Fl atoms replace 4 H atoms, they form a
  compound that can be made into a black, shiny
  material used for nonstick cookware.
• N, Br and S are also used in substituted
  hydrocarbons.
• Compounds called thiols are formed when S
  replaces the O in the OH group of an alcohol.
• Thiols are also called mercaptans which smell
  very bad such as skunk spray.

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Section 3 Petroleum- A Source of Carbon Compounds

• What Youll Learn
• How carbon compounds are obtained from petroleum
• How carbon compounds form long chains of
  molecules
• What polymers are

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What is Petroleum?

• Plastic comes from petroleum, a dark, flammable
  liquid often called crude oil. It exists deep
  within Earth. Coal, natural gas, petroleum are
  all called fossil fuels because they come from
  fossilized material.
• Oil wells pump crude oil to Earths surface.
• Engineers separate the mixture by fractional
  distillation at refineries in metal towers called
  fractionating towers.

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What is a fractionating tower?

• As tall as 35 m, metal plates are arranged to let
  vapors pass through.
• Pipes are attached at different levels to
  separate crude oil into fractions using
  distillation.
• Depending upon their boiling point, vapors
  condense at particular levels or temps.

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What is a fractionating tower?

• Crude oil is heated to more than 350C. Most of
  the hydrocarbons turn into vapor begin to rise
  inside the tower.
• Vapors of the fractions with the highest boiling
  points only reach the lowest plates before
  condensing, draining off being collected.

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Uses for Petroleum Compounds

• Some fractions are used for fuels. Butane
  propane are some of the lightest fractions taken
  from the top of the tower. Molecules of propane
  have 3 C atoms butane has 4 C atoms.
• Molecules with 5-10 C atoms/molecule condense on
  the upper plate are used for gasoline
  solvents.
• Those that condense on lower plates have 12-18 C
  atoms like kerosene jet fuel.
• Bottom fractions are lubricating oil with
  leftovers used to make asphalt to pave roads.

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Polymers

• A polymer is a very large molecule made from
  small molecules linked together like a chain.
• A monomer is the small molecule that forms a link
  in the polymer chain.
• A polymer chain can contain as many as 10,000
  monomers.

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What are some common polymers?

• Plastic is a common polymer made from the monomer
  ethene or ethylene combined repeatedly to make
  polyethylene for shopping bags and plastic
  bottles.
• Polypropylene is used to make glues and carpets.
• Copolymers consist of two or more different
  monomers combined to make one polymer molecule.

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What are some common polymers?

• Characteristics include being light flexible.
• So strong used to make plastic pipes, boats, car
  bodies
• Used in place of wood metal in buildings.
• Some people call this the age of plastics.

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What determines the properties of polymer
materials?

• Their properties depend on which monomers are
  used to make them are they branched what shape
  are they?
• Sometimes the same polymer can take two
  completely different forms like polystyrene
• Clear CD cases are by blowing CO2 into melted
  polystyrene as it is molded
• Foam cups packing materials have bubbles
  remaining in the polymer making it a good
  insulator.

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What determines the properties of polymer
materials?

• Polymers can be spun into thread made into
  tough fabrics for suitcases backpacks or for
  bulletproof vests.
• Polymer fibers can stretch and return to their
  original shape for exercise clothing.

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What are some other petroleum products?

• Other products are made by separating individual
  compounds from the petroleum fractions then
  changed into substituted hydrocarbons to make
• Aspirin
• Insecticides
• Printing ink
• Flavorings
• Dyes

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Are there some problems with polymers?

• Disposing of things made with polymers is a
  problem because they do not decompose.
• Recycling reuses clean plastics to make new
  products.
• Depolymerization uses heat or chemicals to break
  long polymer chains into monomer fragments which
  then can be used to make other polymers. Too
  expensive to be practical now due to different
  process for each polymer.

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Section 4 Biological Compounds

• What Youll Learn
• About proteins, nucleic acids, carbohydrates, and
  lipids
• Polymers in food
• Biological polymers

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Biological Polymers

• Many important biological compounds in your body
  are biological polymers
• Huge molecules made of monomers
• Larger than monomers of other polymers
• Examples include proteins, nucleic acids,
  carbohydrates, lipids.

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Proteins

• Proteins are large organic polymers formed from
  organic monomers called amino acids.
• Only 20 amino acids can make millions of
  different proteins for various tissues of your
  body like muscles, tendons, hair, fingernails,
  etc.
• Cell parts are pictured.

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What are amino acids?

• Amino acids are the monomers that combine to form
  proteins.
• The figure shows the structures of the amino
  acids.
• Each amino acid has an amine group, -NH2 a
  carboxyl group, -COOH.

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What are amino acids?

• The amine group of one amino acid can combine
  with the carboxyl group of another amino acid.
• This compound is a peptide with a peptide bond
  joining them.
• A molecule containing 50 or more amino acids is
  called a protein.

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What do proteins look like?

• Because proteins are such a long chain, it twists
  around itself can be identified by the way it
  twists.
• Many foods contain proteins which your body
  breaks into monomers to make new proteins for
  blood muscles, etc.

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Nucleic Acids

• Nucleic acids are another group of organic
  polymers that are essential for life.
• They control cell activities reproduction.
• DNA or deoxyribonucleic acid codes stores
  genetic information (genetic code) in the nuclei
  of cells.

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What is DNA made of?

• Monomers called nucleotides make up DNA.
• Nucleotides contain an organic base, a sugar, a
  phosphoric acid unit.
• Two chains of nucleotides twist around each other
  like a twisted ladder or a double helix
  (spiral).

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What is DNA made of?

• Human DNA has 4 base pairs which forms millions
  of combinations.
• The figure shows how bases on one side of the
  ladder link with the other side to form a base
  pair.
• The genetic code of DNA gives instructions for
  making other nucleotides proteins needed by the
  body.

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What is DNA fingerprinting?

• Each molecule of DNA in your body has more than 5
  million base pairs.
• Your DNA is unique unless you have an identical
  twin.
• DNA can be used to solve crimes by removing the
  DNA from hair, blood, or saliva left at a crime
  scene.
• By breaking the polymer into monomers comparing
  the pattern to a suspects DNA, they can link the
  suspect to the crime scene.

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Carbohydrates

• Carbohydrates are organic compounds made of C, H
  O with twice as many H atoms as O atoms.
• Carbohydrates include sugars starches.
• Foods like bread pasta contain carbohydrates.

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What are sugars?

• Sucrose is table sugar which the body breaks
  down into fructose glucose or more simple
  sugars.
• Fruit contains fructose.
• Glucose is found in your blood in fruit
  honey.
• Eating sugar-rich food gives you a quick boost of
  energy.

Sucrose C12H22O11
Glucose C6H12O6
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What is a starch?

• Starch is a polymer carbohydrate made of monomers
  of glucose.
• Your body breaks it into sugars which release
  energy into your cells.
• Athletes use starches for long lasting energy
  stored in the liver muscle cells as glycogen
  for a fresh burst of power.

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Lipids

• Lipids are organic compounds like fats and oils
  such as butter and corn oil.
• Lipids are made of C, H O but with fewer O
  atoms than carbohydrates.
• Another difference is that lipids contain
  carboxyl groups, -COOH while carbohydrates do not.

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What are some lipids in your diet?

• Fats oils are similar in structure to
  hydrocarbons.
• If they only have single bonds between C atoms,
  they are saturated fats.
• Unsaturated fat that has only one double bond is
  monounsaturated.
• An unsaturated fat that has two or more double
  bonds is polyunsaturated

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What are some lipids in your diet?

• Fats are lipids that come from animals.
• Usually saturated solid at room temperature.
• Oils are unsaturated usually liquid at room
  temperature.
• Sometimes H is added to vegetable oil to saturate
  the C make it solid.

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Cholesterol

• Found in meats, eggs, butter, cheese, fish,
  your body also produces cholesterol uses it to
  build cell membranes.
• Found in the digestive fluid bile.
• Can cause damage to the heart blood vessels.

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Cholesterol

• Eating too many foods with high amounts of
  saturated fats cholesterol may cause heart
  disease.
• Some unsaturated fats may protect the heart from
  disease.
• A balanced diet contains some fats as well as
  proteins carbohydrates.