ALKANES2

ALKANES
INTRODUCING
ALKANES
AND
CYCLOALKANES
Alkanes are the simplest
family of hydrocarbons -
compounds containing
carbon and hydrogen only.
They only contain carbon-
hydrogen bonds and
carbon-carbon single
bonds. The first six are:
methane CH4
ethane C2H6
propane C3H8
butane C4H10
pentane C5H12
hexane C6H14
You can work out the formula of any of
them using:
CnH2n+2
Isomerism
All the alkanes with 4 or more carbon

atoms in them show structural
isomerism. This means that there are
two or more different structural formulae
that you can draw for each molecular
formula.
For example, C4H10 could be either of
these two different molecules:
butane 2-methylpropane
NAMING OF ORGANIC COMPOUNDS
A modern organic name is simply a

code.
Each part of the name gives you some
useful
information about the compound.
Example, to understand the name
2-methylpropan-1-ol you need to take
the name to pieces.

The prop in the middle tells you how
many
carbon atoms there are in the longest
chain (in this case, 3). The an which
follows
the "prop" tells you that there aren't
any
carbon-carbon double bonds.
2-methylpropan-1-ol
The other two parts of the name tell
you about interesting things which are
happening on the first and second
carbon atom in the chain. Any name you
are likely to come across can be broken
up in this same way.

Counting the carbon atoms
You will need to remember the codes

for the number of carbon atoms in a
chain up to 6 carbons. There is no easy
way around this - you have got to learn
them. If you don't do this properly, you
won't be able to name anything!
code no of carbons
meth 1
eth 2
prop 3
but 4
pent 5
hex 6
Types of carbon-carbon bonds
Whether or not the compound contains
a carbon-carbon double bond is shown
by the two letters immediately after the
code for the chain length.
Code means an ~ carbon-carbon single

Bonds en ~contains a carbon-carbon
double bond
For example, butane means four
carbons in a chain with no double
bond.
Propene means three carbons in a

chain with a double bond between
two of the carbons.
Alkyl groups
Compounds like methane CH4,

and ethane CH3CH3 are
members of a family of
compounds called alkanes. If
you remove a hydrogen atom
from one of these you get an
alkyl group.
For example:
A methyl group is CH3.

An ethyl group is CH3CH2.
These groups must, of course,
always be attached to
something else.
Types of compounds
The alkanes
Example 1: Write the structural

formula for 2-methylpentane.
Start decoding the name from the

bit that counts the number of
carbon atoms in the longest chain
- pent counts 5 carbons.
Are there any carbon-carbon
double bonds? No - an tells us
there aren't any!
Now draw this carbon skeleton:
C–C–C–C–C
Put a methyl group on the number 2
carbon atom:
C–C–C–C–C
I
CH3
Does it matter which end you
start counting from? No - if you
counted from the other end, you
would draw the next structure.
That's exactly the same as the
first one, except that it has been
flipped over.
Finally, all you have to do is
to put in the correct number
of hydrogen atoms on each
carbon so that each carbon
is forming four bonds.
Example 2: Write the structural formula
for 2,3-dimethylbutane.
• Start with the carbon backbone.

There are 4 carbons in the longest
chain (but) with no carbon-carbon
double bonds (an).
C–C–C–C
• This time there are two
methyl groups (di ) on the
number 2 and number 3
carbon atoms.
Completing the formula by
filling in the hydrogen
atoms gives:
Example 3: Write the structural
formula for 2,2-dimethylbutane.
This is exactly like the last
example, except that both
methyl groups are on the
same carbon atom. Notice
that the name shows this by
using 2,2- as well as di. The
structure is worked out as
before:
C–C–C–C
Cycloalkanes
Cycloalkanes again only contain
carbon-hydrogen bonds and carbon-
carbon single bonds, but this time
the carbon atoms are joined up in a
ring. The smallest cycloalkane is
cyclopropane.
If you count the CYCLOALKANES
carbons and
hydrogens, you
will see that they
no longer fit the
general formula
CnH2n+2. By
joining the carbon
atoms in a ring,
you have had to
lose two
hydrogen atoms.
Cyclohexane, for example, has a
ring structure which looks like this:
This is known as the "chair" form

of cyclohexane - from its shape
which vaguely resembles a chair.
Chemical Reactivity
Alkanes
Alkanes contain strong carbon-
carbon single bonds and strong
carbon-hydrogen bonds. The
carbon-hydrogen bonds are only
very slightly polar and so there
aren't any bits of the molecules
which carry any significant
amount of positive or negative
charge which other things might
be attracted to.
The net effect is that alkanes have
a fairly restricted set of reactions.
You can
burn them - destroying the whole
molecule;
react them with some of the
halogens, breaking carbon-
hydrogen bonds;
crack them, breaking carbon-
carbon bonds.
Cycloalkanes
With the electron pairs this close
• Cycloalkanes are very together, there is a lot of repulsion
similar to the alkanes between the bonding pairs joining
in reactivity, except for the carbon atoms. That makes the
the very small ones - bonds easier to break.
especially
cyclopropane.
Cyclopropane is much
more reactive than you
would expect.
• The reason has to do
with the bond angles in
the ring. Normally,
when carbon forms
four single bonds, the
bond angles are about
109.5°. In
cyclopropane, they are
60°.
Physical Properties
Boiling Points
The boiling points shown are all for
the "straight chain" isomers where
there are more than one.
Notice that the first four alkanes are

gases at room temperature. Solids
don't start to appear until about
C17H36.
You can't be more precise than that

because each isomer has a
different melting and boiling point.
By the time you get 17 carbons
into an alkane, there are
unbelievable numbers of isomers!
Cycloalkanes have boiling points

which are about 10 - 20 K higher
than the corresponding straight
chain alkane.
Explanations
There isn't much

electronegativity difference
between carbon and
hydrogen, so there is hardly
any bond polarity. The
molecules themselves also
have very little polarity. A
totally symmetrical molecule
like methane is completely
non-polar.

ALKANES2

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ALKANES2

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ALKANES

All the alkanes with 4 or more carbon

A modern organic name is simply a

2-methylpropan-1-ol you need to take

the name to pieces.

you about interesting things which are

happening on the first and second

carbon atom in the chain. Any name you

are likely to come across can be broken

up in this same way.

You will need to remember the codes

Code means an ~ carbon-carbon single

Propene means three carbons in a

Compounds like methane CH4,

A methyl group is CH3.

Example 1: Write the structural

Start decoding the name from the

Now draw this carbon skeleton:

• Start with the carbon backbone.

This is known as the "chair" form

Notice that the first four alkanes are

You can't be more precise than that

Cycloalkanes have boiling points

There isn't much

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