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), CO
2
, CO, carbonates (CO
3
2-
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 sp
3
hybrid orbitals

The four hybrid sp
3
orbitals allow carbon to form four
bonds. When carbon is joined to four substituents (i.e.
CH
4
), 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 C
2
H
6
O. 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:



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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:

CH
3
CH
2
CH
2
CH
3
or CH
3
(CH
2
)
2
CH
3

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 (CH
4
) the primary
compound in natural gas.
Ethane (C
2
H
6
) a minor component of natural gas.
Propane (C
3
H
8
) a fuel for heating homes and cooking.
Seager & Slabaugh, 2004
More complex alkanes can be straight chained (normal) or
branched.
C C C C C

normal alkane
C
|
C C C
|
C

branched alkane
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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
Meth-
eth-
prop-
but-
pent-
hex-
hept-
oct-
non-
dec-
# 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.
Step 3: Locate and name the attached alkyl group.
Example:
CH
3

5
CH
3

CH
2
CH
2
CH CH
3
(pentane)
| |
4 3 2 1
Naming Alkanes, cont.
Step 4: Combine the longest chain and the branches into
the name.
Example:
CH
3

5
CH
3

CH
2
CH
2
CH CH
3

| |
4 3 2 1
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.
|
1
CH
3

2
CH
3
CH
4
CH
5
CH
2

6
CH
2

7
CH
3
| |
CH
3


CH

CHCH
3
CH
3
|
4-isopropyl-2, 3-dimethylheptane
Example:
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:
CH
2
CH
3

1
2
3
CH
3
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