Chemistry 30

Unit C Organic Chemistry

Chapter 9 and 10
Lab Safety Rap
 Chapter 9

Hydrocarbons from Petroleum

 Introduction
• Organic Chemistry is the study of carbon
compounds, on which living (organic) matter is
based.
• The carbon cycle shows the interrelationship of
all living things with the environment and with
technologies that refine fossil fuels.
 9.1 Fossil Fuels
• Organic Chemistry deals with compounds of
carbon, excluding oxides (e.g., CO(g)) & ionic
compounds of carbon based ions such as
carbonate.
 9.1 Fossil Fuels
• The major source of
carbon compounds is still
living or previously living
things, such as plants,
animals and all types of
fossil fuels.

• Fossil fuels are chemical

potential energy. The
original source of this
energy is the sun.
 Hydrocarbons
• These are molecules containing only carbon
& hydrogen that are covalently bonded
together.
 Hydrocarbons
• Coal, oil and natural gas
are all non-renewable
sources of fossil fuels
& the primary source of
hydrocarbons.

• Hydrocarbons are the

starting point in the
synthesis of thousands
of products, including
fuels, plastics &
synthetic fibers.
Refining
• Is the technology
that includes
chemical & physical
processes for
separating complex
mixtures in simpler
mixtures.

• Physical processes
can separate coal &
natural gas.
Refining
• Coal may be crushed,
whereas components of
natural gas are separated
by solvent extraction or
by condensation &
distillation.

• Crude oil & oil sands

refining is more complex,
but yields a greater
variety of products.
Table 1 Refining of Fossil Fuels
 9.2 Alkanes from Natural Gas
• Geologists predict where oil
&/or gas is to be found & then
drill into the ground to recover
it.

• The separation of oil & gas can

be explained by solubility theory.
 Oil (nonpolar) will not dissolve in
water (polar), & limestone (ionic)
are slightly soluble in water, but
not soluble in oil.
 Naming Alkanes
• Alkanes are hydrocarbons
containing only single
covalent bonds.

• They have the general

formula CnH2n + 2

• The simplest example is

methane, CH4
 Naming Alkanes
• A methane molecule consists of one carbon
atom covalently bonded to four hydrogen
atoms by the simultaneous sharing of their
unpaired (bonding) valence electrons.
 Structure of Methane
H
I
H-C-H
I
H

• Carbon always forms four covalent bonds, since it

has four available bonding electrons.

• This is the basis of the structure of organic

molecules.
 Carbon Chains
• Carbon can also make stable carbon to carbon
bonds.
• This means that chains of carbon atoms can be
produced of increasing size & complexity by adding
more carbon atoms & allowing branching.
 Carbon Chains
• Ethane (C2H6) is the simplest hydrocarbon
with a C - C bond:
 Continuous Chain Alkanes
• Contain any number of C
atoms in a straight chain.

• Alkanes are classified as

saturated hydrocarbons -
compounds of carbon &
hydrogen containing only
carbon-carbon single
bonds with the maximum
number of hydrogen atoms
bound to each carbon.
 Continuous Chain Alkanes
• The table on the next slide shows the first
10 continuous chain alkanes.

• Note the increasing boiling point of these

alkanes, indicated by the state of the
molecule, as the molecular weight
increases.
• These molecules form a homologous series,
showing constant increment of change in the
molecular structure.

• In alkanes this increment of change is

- CH2 -
 Molecular Formula
• Molecular formula of organic molecules
provide the number of each type of atom in
the molecule.

• For example, propane: C3H8(g)

 Complete Structural Formula
• Structural formula of organic molecules
show the arrangement of the atoms in the
molecule.

• For example, propane: (C3H8(g))

H H H
I I I
H-C-C–C-H
I I I
H H H
 Condensed Structural formula
• Condensed structural formula can be drawn for
hydrocarbons by leaving out some bonds &/or
atoms from the full structural formula, for
example:
H H H
• C3H8(g) I I I
H-C-C–C-H
I I I
H H H

• becomes CH3 - CH2 - CH3

 Condensed Structural formula
• The bond lines indicate the bond between carbon
atoms, they can even be left out altogether,
i.e. CH3CH2CH3

• Or can be reduced even further by placing brackets

around the units forming an homologous series:

CH3CH2CH2CH2CH3 may become CH3(CH2)3CH3

 Line Structural Formula
• Chemists further simplify structural formula
by leaving out the symbols for atoms.

• This leaves only the bond lines to represent the

structure of the molecule:

• e.g., octane, C8H18(l) The “kinks” in the line are due to

H3C the bond angles between
adjacent carbon atoms.

CH3
• For example, a branched chain alkane:

CH3 - CH2 - CH - CH3

I
this is a branch

CH3
 Branched Chain Alkanes
• Atoms or groups of atoms may take the place
of a hydrogen atom on the parent
hydrocarbon chain. These are called
substituents.
• The substituents may be other hydrocarbons,
halogens, oxygen, sulfur, phosphorus etc.
• For example, a branched chain alkane:

CH3 - CH2 - CH - CH3

I
CH3 this is a branch
• This could also be drawn as a line structural
formula as follows:

CH3

H3C CH3
• When the branch is another hydrocarbon,
as above, the branch is called an alkyl
group.

• The General formula for an alkyl group is

CnH2n + 1

• The alkyl group is named for the parent

alkane from which it is derived by changing
the ending from -ane to –yl.

• The branch on the example before is called

methyl (from methane, the name for a
hydrocarbon with only one carbon in it).
• Other examples:
CH3 – CH2 – is ethyl
CH3 – CH2 – CH2 – is propyl

• Alkyl groups are also sometimes referred

to as radicals.

• The physical & chemical properties of a

branched chain alkane will be different
than those of a continuous chain alkane.

• So it is important to be able to recognize &

name these different compounds.
 Rules for Naming Branched
Chain Alkanes
• Naming of organic compounds follows IUPAC
rules.

• This is a precise, internationally recognized

system allowing for the systematic naming of all
organic compounds.
 The Rules
1. Find the longest continuous chain of C atoms and
name it.

2. Locate the branches on the chain.

3. Number the C atoms in the continuous chain

starting at the end closest to the branching which
will give the carbon atoms to which the branches
are attached the lowest possible numbers.

4. Name the branches.

 The Rules (Continued)
5. Show the location of the branches by the number
of the C atom to which it is attached on the
continuous chain.

6. Use the prefixes di-, tri-, etc. to indicate the

appearance of the same alkyl group more than
once.

7. List the names of the alkyl groups alphabetically

(ignore di-, tri-, etc.).

8. Use commas to separate numbers & hyphens to

separate numbers & words. There are to be no
spaces within the name of the alkane.
 Example 1:
CH3 – CH2 - CH2 - CH - CH3
I
CH3
 Example 2:

CH3 – CH2 - CH2 – CH2 – CH

I
CH3
 Example 3:

CH3
CH2 CH3
| |
CH3 – CH2 - CH - CH – CH2 – CH2- CH – CH2 -
CH3

I
CH3
Alkanes Worksheet
Alkanes worksheet
Alkanes Worksheet
Alkanes Worksheet
 Structural Isomers

Consider the following two molecules:

CH3 - CH - CH3
CH3 - CH2 - CH2 - CH3 and
I

CH3

This is butane This is methylpropane

 CH3 - CH2 - CH2 - CH3 CH3 - CH - CH3
I
CH3

• Both have the molecular formula, C4H10, but different

structural formula.

• One is a straight chain alkane, the other is a branched

alkane.

• They are different compounds & have different

properties.

• These two molecules demonstrate a phenomenon that

occurs constantly in organic chemistry called
isomerization.
 CH3 - CH2 - CH2 - CH3 CH3 - CH - CH3
I
CH3

• Since there are many possible combinations of

the atoms that go to make up organic molecules,
especially as the molecules increase in size, there
are often two or more possible structures for
the same combination of atoms.

• The type of isomerization seen above is

structural isomerization.

• These two molecules are structural isomers.

• They differ in chemical and physical properties, for
example boiling point.

• These two isomers have very similar chemical

properties. They both burn in the presence of
oxygen to form carbon dioxide and water vapour.

• They are used as precursors for the manufacture

of other organic compounds and as additives in
gasoline.

• Both are colourless gases.

• The boiling point of butane is –0.5ºC while that of

methylpropane is –11.7ºC.
• The number of structural isomers increases
with the number of carbon atoms, ie. 5 for
C6H14, 75 for C10H22 and over 4 million for C30H62
!!!
Isomers of C6H14
 Properties of Alkanes
• Alkanes are non-polar, since electrons are
equally shared by the nuclei of the carbon
atoms in the chain.

• Alkanes are gases or low boiling point liquids,

since only very weak forces hold the
molecules together.

• Larger molecular weight alkanes (>16 C) form

waxy solids.
• Due to the fact that
they are non-polar,
alkanes are not misable
with water.

• Remember the rule

that “like dissolves
like”, so alkanes do not
dissolve in water, but
liquid alkanes are very
good solvents for other
hydrocarbons.
 Cyclic Hydrocarbons
• So far we have been concerned
with straight chain hydrocarbons.

• However, it is possible for the two

ends of a carbon chain to become
attached to form a ring structure
called a cyclic compound
(hydrocarbon).

• These ring structures contain

between 3 and 30 carbons when
found in nature. The most common
are 5 and 6 membered rings.
 Cycloalkanes
• Saturated cyclic hydrocarbons are called
cycloalkanes.
• They have the general formula CnH2n
• This is the same general formula as for alkenes.
• In fact they are structural isomers of alkenes.
• An example of a cycloalkane is cyclopentane:

• If a branch is present treat the cycloalkane

as the parent chain and identify the
branches (Use the lowest numbers possible).
 Example
• What is the name of the following
branched cycloalkane?

• 1,2-dimethylcyclopentane
 Properties of cycloalkanes
• They have higher boiling points than the
corresponding alkane.

• The smaller compounds are more reactive

than the corresponding alkane, since they
have a strained structure.