Download Carbon, because of its valence electrons, can form four bonds and

Organic Compounds
Organic compounds—covalently bonded compounds usually containing the element carbon.
EXCEPTION: carbonates and oxides are inorganic compounds.
Carbon can form a wide variety of compounds with many unique and distinct properties because:
A. carbon-carbon bonding—carbon readily bonds to itself to form long chains or rings. Carbon
also forms single, double, or triple bonds readily.
B. Carbon bonding to other elements—carbon readily bonds to elements with similar
electronegativities (O, N, S, and the halogens).
C. Arrangement of atoms—groups of atoms containing carbon arranged in different ways will
produce compounds with different properties.
Structural formula—indicates the number and types of atoms present in a molecule and also shows the
bonding arrangement of the atoms.
Carbon, because of its valence electrons, can form four bonds and hydrogen can form only one bond. The
names of methane, ethane, propane, butane, and pentane are used for alkanes containing one, two, three,
four, and five carbon atoms, respectively.
methane
ethane
propane
butane
Isomers
Different compounds that have the same molecular formula are called isomers. They contain the same
numbers of the same kinds of atoms, but the atoms are attached to one another in different ways. Isomers
are different compounds because they have different molecular structures. For instance, the two isomers of
C4H10 are:
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2-methyl propane
butane
As you can see, structural formulas can take up a lot of space when drawn out. In order to save space, a
condensed structural formulas will often be written in a smaller space.
The examples of butane and 2-methyl propane shown above both have the chemical formula C4H10.
However the are different compounds with different names because the atoms are arranged differently.
These are examples of structural isomers.
Structural Isomers—also called constitutional isomers—isomers in which the atoms are bonded together in
different ways.
Although structural isomers have the same chemical formula, because the atoms are arranged differently,
the compounds are named differently and have different properties.
Geometric Isomers—isomers in which the order of atom bonding is the same but the arrangement of atoms
in space is different.
2 Types of Geometric Isomers
1. cis-atoms in question are on the same side
2. trans-atoms in question are on opposite sides
Hydrocarbons—organic compounds containing the elements hydrogen and carbon.
Hydrocarbons are the simplest group of organic compounds. These compounds are groups by the types of
bonding between carbon atoms (single, double, or triple)
Saturated Hydrocarbons—hydrocarbons in which each carbon atom in the molecule forms four single
covalent bonds with other atoms
Alkanes—hydrocarbons that contain only single bonds.
General Formula: CnH2n+2
Cycloalkanes—alkanes in which the carbon atoms are arranged in a ring, or cyclic, structure.
General Formula: CnH2n
Naming Alkanes
1. Count number of carbon atoms and apply prefix
2. suffix –ane
Carbon Atom Prefixes
# of C atoms
1
2
3
4
Prefixes
methethpropbut-
2
5
6
7
8
9
10
penthexheptoctnondec-
Naming Branched-Chain Alkanes
Alkyl group—groups of atoms formed with one hydrogen atom is removed from an alkane molecule
(sometimes called branches)
-named using suffix –yl
1.
2.
3.
4.
5.
Name parent hydrocarbon (find longest chain of carbons and add suffix –ane)
add names of alkyl groups (branches) and numerical prefix if needed. If there is more than one
branch then they are listed alphabetically.
number carbon atoms so branches have the lowest number possible
insert position numbers
punctuate name
Properties and Uses of Alkanes
-can be solids, liquids, or gases at room temperature
Natural gas—fossil fuel composed primarily of alkanes containing 1-4 C atoms.
-very small molecules
-weak intermolecular forces
5-20 carbons—liquids at room temperature
20+ carbons—solids at room temperature (waxes-26-30 C atoms)
As the number of carbon atoms increase, boiling points increase
Petroleum—complex mixture of different hydrocarbons that varies greatly in composition. This mixture is
often separated in a process called fractional distillation.
Fractional distillation—process used to separate components of a mixture on the basis of boiling point.
Unsaturated Hydrocarbons—hydrocarbons in which not all carbon atoms have 4 single covalent bonds
(contain 1 or more double or triple bonds).
Alkenes—hydrocarbons that contain one or more double bonds.
General Formula: C2H2n
Naming Alkenes
1. Find longest chain of carbons that contains the double bond and apply prefix.
2. add suffix –ene
3. add position numbers for double bond location
Examples:
ethene
3
propene
2-butene
1-butene
Indicate by numbers the positions of the alkyl groups attached to the parent chain.
4-methyl-2-pentene
3,3-dimethyl-1-butene
Properties of alkenes are similar to alkanes. In addition, alkenes, like alkanes have many commercial uses.
Alkynes—hydrocarbons with one or more triple bonds.
General formula: CnH2n-2
Naming Alkynes
1. Name parent compound by applying prefix
2. add suffix –yne
3. add location of triple bond
Examples:
propyne
2-butyne
1-butyne
4-methyl-2-pentyne
Alkynes are also nonpolar and exhibit the same trends in physical properties as other hydrocarbons.
Aromatic Hydrocarbons—hydrocarbons that have 6-membered carbon rings and delocalized electrons.
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Benzene—primary aromatic hydrocarbon with molecular formula C6H6
All aromatic hydrocarbons are derived from benzene rings
Naming Simple Aromatic Hydrocarbons
1. name the parent hydrocarbon (benzene)
2. Add the names of the alkyl groups
3. number the carbon atoms (give lowest # possible)
4. Insert position numbers
5. punctuate the name
Functional Group—an atom or group of atoms that is responsible for the specific properties of an organic
compound.
Substituted Hydrocarbons—groups of compounds containing a functional group.
Hydrocarbons that are substituted with groups other than the alkyl groups are named in the same way.
Other groups that are often substituted are the halogens (bromo-, chloro-, iodo-) as well as nitro (-NO2) and
amine (-NH2).
2-bromopropane
1-chloro-2-butene
2,4-dinitro-2-pentene
5-bromo-2-methyl-2-propene
The following table contains a summary of functional groups that substitute in hydrocarbons:
Alcohol
Aldehyde
Amine
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A Carboxylic Acid
(Organic Acid)
An Ester
An Ether
A Halide (Alkyl
Halide)
A Ketone
Naming Organic Compounds with Functional Groups
Functional Group—an atom or group of atoms that is responsible for the specific properties of an organic
compound.
Alcohols—organic compounds that contain one or more hydroxyl groups (-OH).
Alcohol Nomenclature
1. Name the parent compound. Locate largest chain containing functional group. Add suffix –ol.
2. # the carbon atoms.
3. insert position numbers
4. punctuate the name.
Alkyl halides—organic compounds in which one or more halogen atoms—fluorine, chlorine, bromine, or
iodine—are substituted for one or more hydrogen atoms in a hydrocarbon.
Halide Nomenclature
1. Name parent compound
2 # C atom in parent chain
3. insert prefixes to represent halide elements
4. Insert position numbers
5. punctuate the name
Ethers—organic compounds in which 2 hydrocarbon groups are bonded to the same atom of oxygen.
Ether Nomenclature
1. Name the parent compound. Ether comes at the end of the name.
2. Add the names of the alkyl groups (alphabetically); add prefix if 2 groups are same (di)
Aldehydes and Ketones
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Aldehydes—organic compounds in which the carboxyl group is attached to a carbon atom at the end of a
carbon atom chain.
Aldehyde Nomenclature
1. Name the parent compound.
2. add suffix -al
Ketones—organic compounds in which the carboxyl group is attached to carbon atoms within the chain.
Ketone Nomenclature
1. name parent chain and add suffix –one.
2. # C atoms in parent chain
3. insert position numbers
4. punctuate the name
Carboxylic acids—organic compounds that contain the carboxyl functional group (also called organic
acids).
Carboxylic Acid Nomenclature
1. Name parent compound
2. add suffix –oic acid.
Esters—organic compounds with carboxylic acid groups in which the hydrogen of the hydroxyl group has
been replaced by an alkyl group.
Ester Nomenclature
1. Name parent compound.
2. Change –oic acid ending to –oate.
3. add name of alkyl group
4. leave appropriate spaced between names.
Amines—organic compounds that can be considered derivatives of ammonia, NH 3.
Amine Nomenclature
1. name the parent compound.
2. add names of the alkyl groups (alphabetically)
3. combine names of alkyl groups
4. add suffix –amine
3 Types of Amines
Primary amine—one hydrogen replaced
Secondary amine—two hydrogens replaced
Tertiary amine—three hydrogens replaced.
Reactions of Organic Compounds
Substitution Reaction—one or more atoms replaces another atom or group of atoms in a molecule.
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Addition Reaction—an atom or molecule is added to an unsaturated molecule and increases the saturation
of the molecule.
Hydrogenation—one or more hydrogen atoms are added to an unsaturated molecule.
Elimination Reaction—a simple molecule is removed from adjacent carbon atoms of a larger molecule.
Four Reaction Classes
Addition
Elimination
Substitution
Rearrangement
Condensation Reaction—two molecules or parts of the same molecule combine.
Often water is removed during this reaction.
Polymers—large molecules made up of many small units joined to each other through organic reactions.
Monomers—small units that make up polymers.
2 Types of Polymers
Thermoplastic polymer—melts when heated and can be reshaped many times.
Thermosetting polymer—does not melt when heated, but keeps its original shape.
Addition Polymers—formed by addition reactions between monomers that contain a double bond.
Types of Addition Polymers
polypropylene (plastic bottles)
polyvinyl chloride (PVC) (pipe)
polyacrylonitrile (fabrics)
polystyrene (Styrofoam)
polyvinyl acetate (latex paint)
natural and synthetic rubber
Condensation Polymers—polymer formed by condensation reactions.
Types of Condensation Polymers
Nylon
Polyester
Biological Chemistry
Biochemistry—the study of the chemicals and reactions that occur in living things.
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Carbohydrates—molecules composed of carbon, hydrogen, and oxygen atoms in a 1:2:1 ratio, and provide
nutrients to the cells of living things.
-can be produced by plants through photosynthesis
-examples: sugars, starches, and cellulose
Types of carbohydrates:
Monosaccharides—a simple sugar that is the basic subunit of a carbohydrate (glucose)
Disaccharide—a sugar consisting of two monosaccharide units joined together (sucrose)
Polysaccharide—a carbohydrate made up of a long chain of simple sugars (cellulose)
Carbohydrate Reactions:
Condensation Reaction—a reaction in which two molecules or parts of the same molecule combine and a
molecule of water is produced.
Hydrolysis Reaction—a reaction between water and another substance to form one or more new substances
(opposite of condensation reaction)
Lipids—a type of biological chemical that does not dissolve in water, has a high percentage of C and H
atoms, and is soluble in nonpolar solvents.
-examples: long-chain fatty acids, phospholipids, steroids, and cholesterol
Fatty acids—type of lipid consisting of a long, nonpolar hydrocarbon “tail” and a polar carboxylic acid
functional group as the “head.” These are the simplest lipid molecules
Saturated fatty acids—no carbon-carbon double bonds in the hydrogen chain
Unsaturated fatty acids—one or more double bonds in the hydrocarbon chain
Saponification—type of chemical reaction that occurs when a fat combines with NaOH forming a salt and
water. This is the chemical process by which soap is formed.
Saponifiable lipids—lipids that react with a base to form soap (including fats, oils, and fatty acids).
Nonsaponifiable lipids—nonpolar compounds that do not form soap (steroids, vitamins, bile acids)
Amino Acids—basic building blocks of proteins. Amino acids combine together to form proteins. There
are 20 types of amino acids found in the human body and more than 700 that exist in nature.
Essential Amino acids—nine of the 20 amino acids needed by the body that are not produced by the body.
These 9 amino acids must come from the food we eat.
Amino acids—organic molecules that contain two functional groups: a basic –NH2 amino group and an
acidic –COOH carboxylic acid group.
Peptide bonds—chemical bonds that hold amino acids together to form proteins.
Protein—an organic biological polymer that is made up of polypeptide chains of 50 or more amino acids
and is an important building block of all cells.
Common types of protein found in the human body:
A. Keratin—the main component of hair and fingernails
B. Enzymes—used to speed up chemical reactions (biological catalysts)
C. Hemoglobin—protein used to carry oxygen in the blood
D. Insulin—protein used to regulate glucose levels in the blood (diabetics do not produce this
hormone)
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E. Antibodies—protect the body from foreign substances (part of your immune system)
Nucleic Acids—an organic compound whose molecules carry genetic information and is made up of one or
two chains of monomer units called nucleotides.
Two types of Nucleic Acids:
A. Deoxyribonucleic acid (DNA)
B. Ribonucleic acid (RNA)
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