Saturated

Hydrocarbons
Word
Organic
Wall
Hydrocarbon Saturated Unsaturated
Compound Hydrocarbon Hydrocarbon
Fractional Cracking Alkane Homologous
Distillation Series
Parent Chain Substituent Cyclic Cycloalkane
Group Hydrocarbon

Chemists in the early nineteenth century knew that living things, such as the plants,
produce an immense variety of carbon compounds. Chemists referred to these
compounds as organic compounds because they were produced by living
organisms.

Today, organic compounds are applied to all carbon- containing compounds with
the primary exceptions of carbon oxides, carbides, and carbonates, which are
considered inorganic.

Organic chemistry is the field of chemistry that studies carbon- based

compounds.

Recall that carbon is an element in group 14 of the periodic table, with an electron
configuration of 1s2 2s2 2p2. A carbon atom has four valence electrons, so it can
form four covalent bonds to other atoms.

In organic compounds, carbon atoms are bonded to hydrogen atoms or atoms of

other elements that are near carbon in the periodic table; especially nitrogen,
oxygen, sulfur, phosphorus, and the halogens. Carbon atoms also bond to other
carbon atoms and form chains from two to thousands of carbon atoms in length, as
well as, complex, branched chain structures, and ring structures.

Hydrocarbons
The simplest organic compounds are hydrocarbons, which contain only the
elements carbon and hydrogen. Thousands of hydrocarbons are known, each
containing only the elements carbon and hydrogen.
The simplest hydrocarbon molecule, methane, CH4, consist of a carbon atom
bonded to four hydrogen atoms.

Models and Hydrocarbons

Chemists use four different models to represent organic molecules in a variety of

ways; molecular formulas, structural formulas, ball and stick models, and space
filling models.
 Multiple carbon- carbon bonds

Carbon atoms can bond to each other not only by single covalent bonds but also by
double and triple bonds.
Chemists classified hydrocarbons containing double and triple bonds according to
a chemical test in which they mixed each hydrocarbon with bromine and then
measured how much reacted with the hydrocarbon. Some hydrocarbons would
react with a small amount of bromine, some would react with more, and some
would not react with any amount of bromine.
Chemists called the hydrocarbons that reacted with bromine unsaturated
hydrocarbons (contain double or triple covalent bonds). Hydrocarbons that did not
react with bromine were said to be saturated (contain only single covalent bonds).
Saturated hydrocarbons are hydrocarbons having only single bonds, and
unsaturated hydrocarbons are hydrocarbons that have at least one double or
triple bond between carbon atoms.
 Refining Hydrocarbons

Crude oil is the term for "unprocessed" oil, the stuff that comes out of the ground.
It is also known as petroleum. Crude oil is a fossil fuel, meaning that it was made
naturally from decaying plants and animals living in ancient seas millions of years
ago. Crude oils are such a useful starting point for so many different substances
because they contain hydrocarbons. 
Petroleum is much more useful to humans when it is separated into simpler
components or fractions. Separation is carried out in a process called fractional
distillation, which involves boiling the petroleum and collecting components or
fractions as they condense at different temperatures. Fractional distillation is done
in a fractionating tower.

Petroleum chemists and engineers developed a process to help match the supply
and demand. This process in which heavier fractions are converted to gasoline by
breaking their large molecules into smaller molecules is called cracking. Cracking
is done in the absence of oxygen and the presence of a catalyst.
 Alkanes
Alkanes are hydrocarbons that contain only single bonds between carbon atoms.

Straight- Chain Alkanes

Methane is the smallest member of the alkane series. It is used as a fuel in homes
and is a product of many biological processes.
The alkanes form a series of compounds all with general formula CnH2n+2, , where n
is the number of carbon atoms, e.g. methane CH4, ethane C2H6, propane C3H8, and
butane C4H10.

Naming Straight- Chain Alkanes

All alkanes end with the suffix -ane.
Alkanes with five or more carbons in a chain have names that use a prefix derived
from the Greek or Latin word for the number of carbon atoms in each chain.
For example; pent- has 5 carbons, hex- has 6 carbons, hept- has 7 carbons, oct- has
8 carbons, non- has nine carbons, and dec- has 10 carbons.

You can see that -CH2- is a repeating unit in the chain of carbon atoms. For
example, ethane has one more -CH2- than methane.
A series of compounds that differ from one another by a repeating unit is called a
homologous series.

Branched- Chain Alkanes

Carbon atoms can bond to one, two, three, or even four other carbon atoms. This
property makes possible a variety of branched- chain alkanes.

The structure on the left represents butane, and the structure on the right represents
a branched- chain alkane known as isobutane; a substance whose chemical and
physical property are different from those of butane.
Carbon atoms can bond to one, two, three, or even four other carbon atoms. This
property makes possible a variety of branched- chain alkanes.

Naming Branched- Chain Alkanes

When naming branched- chain alkanes, the longest continuous chain of carbon
atoms is called the parent chain. All side branches are called substituent groups
because they appear to substitute for a hydrogen atom in the straight chain.
If one of the hydrogen atoms is removed what is left is known as an alkyl group
(R-). Each alkyl group branching from the parent chain is named for the straight-
chain alkane that has the same number of carbon atoms as the alky group. The
ending -ane is replaced with the letters -yl.
Steps for naming branched-chain alkanes
– Count the number of carbon atoms in the longest continuous chain.
– Number each carbon in the parent chain, starting with the carbon
closest to the substituent group. This gives all the substituent groups
the lowest position numbers possible.
– Name each alkyl group substituent.
– If the same alkyl group appears more than once as a branch on the
parent structure, use a prefix to indicate how many times it appears.
– When different alkyl groups are attached to the same parent chain,
place their names in alphabetical order.
– Write the entire name, using hyphens to separate numbers from words
and commas to separate numbers.
 Example
Problem
Name the alkane shown.

Step 1. Count the number of carbon atoms in the longest continuous chain.
Because structural formulas can be written with chains oriented in various ways,
you need to be careful in finding the longest continuous carbon chain. In this case,
it is easy. The longest chain has eight carbon atoms, so the parent name is octane.
Step 2. Number each carbon in the parent chain. Number the chain in both
directions, as shown below. Numbering from the left puts the alkyl groups at
Positions 4, 5, and 6. Numbering from the right puts alkyl groups at Positions 3, 4,
and 5. Because 3, 4, and 5 are the lowest position numbers, they will be used in the
name.

Step 3. Name each alkyl group substituent. Identify and name the alkyl groups
branching from the parent chain. There are one-carbon methyl groups at Positions
3 and 5, and a two-carbon ethyl group at Position 4.
Step 4. If the same alkyl group occurs more than once as a branch on the parent
structure, use a prefix (di-, tri-, tetra-, and so on) before its name to indicate how
many times it appears. Look for and count the alkyl groups that occur more than
once. Determine the prefix to use to show the number of times each group appears.
In this example, the prefix di- will be added to the name methyl because two
methyl groups are present. No prefix is needed for the one ethyl group. Then show
the position of each group with the appropriate number.

Step 5. Whenever different alkyl groups are attached to the same parent structure,
place their names in alphabetical order. Place the names of the alkyl branches in
alphabetical order, ignoring the prefixes. Alphabetical order puts the name ethyl
before dimethyl.
Step 6. Write the entire name, using hyphens to separate numbers from words and
commas to separate numbers. Write the name of the structure, using hyphens and
commas as needed. The name should be written as 4-ethyl-3,5-dimethyloctane.
 Cycloalkanes
A variety of organic compounds exist as carbon atoms can form ring structures. An
organic compound that contains a hydrocarbon ring is called a cyclic
hydrocarbon.
To indicate that a hydrocarbon has a ring structure, the prefix -cyclo is used with
the hydrocarbon name.
Cyclic hydrocarbons that contain only single bonds are called cycloalkanes.
The relationship between numbers of carbon and hydrogen atoms in cycloalkanes
can be expressed as: CnH2n.

Naming substituted cycloalkanes is the same as straight-

chains but with a few exceptions.
– The ring is always considered the parent chain.
– Numbering starts on the carbon that is bonded to the substituent.
– When more than one carbon has a substituent, number in the direction
that gives the lowest possible numbers for the substituents.

Example
Problem
Name the cycloalkane shown.

Step 1. Count the carbons in the ring and use the name of the parent cyclic
hydrocarbon. In this case, the ring has six carbons, so the parent name is
cyclohexane.
Step 2. Number the ring, starting from one of the CH3– branches. Find the
numbering that gives the lowest possible set of numbers for the branches. Here are
two ways of numbering the ring.

Numbering from the carbon atom at the bottom of the ring puts the CH3– groups at
Positions 1, 3, and 4 in Structure A.
Step 3. Name the substituents. All three are the same–carbon methyl groups.
Step 4. Add the prefix to show the number of groups present. Three methyl groups
are present, so you add the prefix tri- to the name methyl to make trimethyl.
Step 5. Alphabetical order can be ignored because only one type of group is
present.
Step 6. Put the name together using the name of the parent cycloalkane. Use
commas between separate numbers, and hyphens between numbers and words.
Write the name as 1,2,4-trimethylcyclohexane.