Organic Compounds:

Alkanes 1828: Friedrich Wohler first synthesized an

organic compound from an inorganic source

Seager & Slabaugh, 2004

 Organic chemistry is the study of carbon containing

compounds except elemental carbon (diamond, graphite,
coal), CO2, CO, carbonates (CO32- group) and cyanides
(CN- group)
Inorganic chemistry studies the elements and everything
else.

Seager & Slabaugh, 2004

Bonding Characteristics
In carbon, the 2s and three 2p orbitals can mix to produce
four new sp3 hybrid orbitals

 The four hybrid sp3 orbitals allow carbon to form four

bonds. When carbon is joined to four substituents (i.e.
CH4), the resultant configuration is tetrahedral in shape.

Isomerism
Isomers: Compounds that have identical molecular
formulas, but different arrangement of atoms.
Structural isomers: A type of isomerism in which the
atoms bond in different patterns.
Ball-and-stick models of the isomers of C2H6O. Ethyl
alcohol is a liquid at room temperature and completely
soluble in water, whereas dimethyl ether is a gas at room
temperature and only partially soluble in water.

Seager & Slabaugh, 2004

 Functional Groups: Unique reactive combination of atoms

that differentiate organic compounds into classes.

Examples:

Seager & Slabaugh, 2004

 Representing Organic Compounds

Expanded structural formulas show all atoms with bonds.

Condensed structural formulas list all the atoms in order

implying how they are bound together:
CH3CH2CH2CH3 or CH3 (CH2) 2CH3

Seager & Slabaugh, 2004

Classification of Hydrocarbons
Hydrocarbons contain only carbon and hydrogen. A
hydrocarbon that contains only single bonds is a saturated
hydrocarbon or alkane.

Seager & Slabaugh, 2004

 The simplest alkane is methane (CH4) the primary

compound in natural gas.
Ethane (C2H6) a minor component of natural gas.
Propane (C3H8) a fuel for heating homes and cooking.

Seager & Slabaugh, 2004

 More complex alkanes can be straight chained (normal) or

branched.

CCCCC
normal alkane

C
|
CCC
|
C
branched alkane

Seager & Slabaugh, 2004

Conformations of Alkanes
There is free rotation around C-C bonds.

 Which of the following pairs represent structural isomers,

and which are simply the same compound?
Which are normal alkanes and which are branched
alkanes?

Naming Alkanes
The IUPAC method consists of:

Root Name
Methethpropbutpenthexheptoctnondec-

# of Carbons
1
2
3
4
5
6
7
8
9
10

Naming Alkanes, cont.

The ending ane signifies the alkane family.
Step 1: Identify and name the longest carbon chain. This
gives the root and ending.
Step 2: Number the longest carbon chain to give the
lowest number to any carbon to which a group is attached.

5 CH

CH3
|
|
Example:
CH2 CH2 CH CH3 (pentane)
3

Step 3: Locate and name the attached alkyl group.

Naming Alkanes, cont.

Step 4: Combine the longest chain and the branches into
the name.

5 CH

CH3
|
|
CH2 CH2 CH CH3
3

Example:

2-methylpentane

Naming Alkanes, cont.

Step 5:
For multiple branches, show the location of each branch
with numbers.
For multiple branches of the same type, modify the name
with di-, tri-,
List multiple branches alphabetically the di-, tri-, dont
count.

Example:

CH3 2CH 3CH 4CH 5CH2 6CH2 7CH3

|
|
|
CH3 CH
CHCH3
|
CH3
4-isopropyl-2, 3-dimethylheptane

Naming Cycloaklanes
Cycloalkanes are alkanes containing rings of carbon
atoms.
The prefix cyclo- is used before the alkane name.
When two or more substituents are attached to the
cycloalkanes, the ring numbering begins with the first
group alphabetically and proceeds to give lowest numbers
possible.

Example:

CH2CH3
1

CH3

1-ethyl-3-methylcyclopentane

The Shape of Cycloalkanes

Stereoisomers compounds with the same structural
formula but different spatial arrangements of atoms.
Geometric isomers a type of stereoisomerism that gives
cis- and trans- orientations.

 Rotation about C-C single bonds occurs in open-chain

compounds but not within rings.
Geometric isomerism can result in two geometric isomers
of 1,3-diemthylcyclopentane.
Cis-substituents on the same side.
Trans-substituents on the opposite side.

Seager & Slabaugh, 2004

Physical Properties of Alkanes

Non-polar molecules cannot hydrogen bond.

Not soluble in water (hydrophobic).
Low density (less dense than water).
Melting points increase with molecular size.
Boiling points increase with molecular size.

Alkane Reactions
Alkanes are the least reactive of all organic compounds.
The most significant reaction of alkanes is combustion
(rapid oxidation).
Many alkanes are used this way as fuels.
Methane natural gas
Propane used in gas grills
Butane lighters
Gasoline a mixture of hydrocarbons

Complete Combustion (in the presence of adequate Oxygen)

Incomplete Combustion (where there is not enough Oxygen

available)

Seager & Slabaugh, 2004