Alkanes

Introduction
Contain only carbon and hydrogen
atoms.
Alkanes are not considered a
functional group

as they are relatively unreactive and do

not undergo many chemical reactions.

All bonds between carbon atoms and

between carbon and hydrogen atoms
in alkanes are single bonds.
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 Liquid petroleum, also called

crude oil, is the main source of
alkanes
The primary use of alkanes is as a
fuel for heating, generating
electricity, and transportation
(internal combustion engines).
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Acyclic and Cyclic

Alkanes
Most alkanes are acyclic
(noncyclic or not in a ring).

Acyclic materials are classified

into two subgroups:
straight or linear chains and
branched chains
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 Branched chain alkanes have side

groups.
groups are called by various names:
substituents,
side chains,
pendent groups,
or just branches.
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 Alkanes may also be cyclic; that is,

the carbon atoms are connected to
form a ring.
Alkanes are occasionally called
aliphatic compounds or paraffins
Alkanes come in all shapes and sizes
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Shapes of
alkanes
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 Nomenclature
Alkanes containing
5 to 19 carbon atoms have Greek
prefixes
they all end in ane
Formulas:
The general formula for an acyclic
alkane is CnH2n+2.
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 Each successive molecular formula

contains one additional carbon atom
and two additional hydrogen atoms, a
CH2 unit.

Formulas of
alkanes

This list is known as a homologous series and the individual

molecules are called homologs.

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 Structures
Alkanes are called saturated
compounds because they contain the
maximum number of hydrogen atoms
that can be attached to the carbon
atoms in a given compound.

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 Constitutional Isomers
Constitutional isomers (also) called
structural isomers) are non-identical
compounds with the same molecular
formula.
They have the same number and kind
of atoms but the atoms of each
isomer are connected in a different
order.
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 The atoms in methane, CH4, ethane, CH3CH3,

and propane, CH3CH2CH3, can only be
connected one way.
Each has only one constitutional isomer.
Butane,C4H10, can exist as two constitutional
isomers.

Different representations of constitutional

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 The two isomers are two different

compounds, with different chemical
and physical properties.

As the number of carbon atoms in

an alkane increases, the number of
constitutional isomers increases
exponentially
If the methyl groups are on opposite
sides of the ring. This is the trans
form.
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 CIS AND TRANS ISOMERS

Cis and trans isomers are different
compounds.
If the methyl groups are on the
same side of the molecule (the
groups are said to be cis to each
other.
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Cis and trans isomers

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Alkyl Groups
Removing the hydrogen atom from an alkane
gives an alkyl group
The substituent derived from methane
(CH4) by removing one hydrogen atom is a
methyl group.
Similarly, removing one hydrogen atom
from either carbon atom in ethane, CH3CH3,
would give an ethyl group, CH3CH2 .

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 For propane removing a hydrogen atom

from either end of the molecule would give
an n-propyl group (usually just called a
propyl group).
Removing a hydrogen atom from the central
carbon atom gives a different alkyl group,
an isopropyl group.
Alkyl groups are not compounds

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Classification of carbon
atoms
A carbon atom is often
classified by the number
of other carbon atoms bonded to it.

Primary (1) carbon atoms are bonded to one other

carbon atom,
Secondary (2) carbon atoms are bonded to two

other carbon atoms,

tertiary (3) carbon atoms have three other
carbon atoms bonded to them.
quaternary (4) carbon atoms are bonded to
four other carbon atoms.
Primary hydrogen atoms are bonded to a primary
carbon atom, etc

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Physical Properties
All bonds in alkanes and cycloalkanes are
C-C or C-H bonds.
The C-C bond is nonpolar.
The C-H bond is essentially nonpolar,

Thus all bonds are nonpolar and therefore

the molecules are nonpolar.
Using the generalization like dissolves
like, these materials are soluble in
nonpolar solvents, such as carbon
tetrachloride and other alkanes.
They are immiscible (not soluble) in polar
solvents like water.
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 DENSITIES
The density of alkanes is about 0.7 g/mL while
the density of water is about 1.0 g/mL at room
temperature.
Since alkanes are less dense and immiscible
with water, a mixture of the two materials
forms two layers, with alkanes being the less
dense upper layer.
The most common example is oil floating on
water.
Alkanes are hydrophobic (water-fearing).

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INTERMOLECULAR
FORCES

The physical state of a compound

depends upon the attraction between
molecules.
Since alkanes are nonpolar,
intermolecular attraction between
molecules results from London
dispersion (LD) forces.

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The total effect of LD force interactions

increases as the size of the molecule
increases.
The total intermolecular attraction forces of
the lower molecular weight linear alkanes
e.g., methane, propane, and butane, are
small and these materials are gases at room
temperature

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 Larger molecules have a greater

summation of LD forces, sufficiently
strong to make them liquids.
Pentane to heptadecane have sufficient LD
forces to make them liquids at room
temperature.
Higher molecular weight alkanes have even
greater total LD forces. As a result they are
solids at room temperature.

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 Increasing LD force interactions

results in increasing boiling and
melting point temperatures as the
molecular weight increases in these
linear molecules
Generally, branched molecules boil
and melt at lower temperatures owing
to decreased LD force interactions
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QUESTIONS
Draw a line-bond structure for
hexane.
Draw all the isomers for pentane,
C5H12
Draw a structure that contains a
quaternary hydrogen atom

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