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Isomers

and Other
Good Stuff
Tutorial

Definition
Isomers are substances that
have the same molecular
formula but a different
structural formula.
Changing the arrangement of atoms
gives a compound totally new
properties. Even moving a
double bond from one carbon
to another will make an
isomer. This is one reason that
nature chose carbons.

I realize that you are a teenager and


therefore, you know everything,
but I will make some suggestions
for you.
1. Always begin with the n-form
(this means normal or straight
chain).
2. Number your carbons.
3. Always remove the end carbon
and move it to A NON END
CARBON.
4. KISS: Keep It Simple, Stupid.
Most kids try to make elaborate
isomers and end up making

The Rules
Remember the following:
I. Carbon must have 4 bonds.
II. Oxygen must have 2 bonds.
III. Hydrogen must have 1 bond.

Problem 1

Make an isomer
for
Propane.

See, you dont know everything. If


you tried to make one then you
were not paying attention. You
cannot make an isomer for
propane, it was a trick problem.
The reason is because you are to
remove an end carbon and then
replace it on a non end carbon. If
you remove a carbon then you have
two end carbons, therefore, you
cannot make an isomer.

Problem 2

Make all of the


possible isomers for
pentane.

First start out with the molecular formula.


Pentane is C5H12. Draw n-pentane.

Now number the carbons.

Remove the end carbon and move it to a non


end carbon.

Note: It would still be the same isomer if the


carbon were written below the number 3
carbon. It would also be the same isomer if the
carbon were placed on the number 2 carbon.

What would be two names, essentially


the same, for this compound?

The answer is either 2 methyl butane or 3


methyl butane. They are the same since
carbons number both ways. Technically,
the 2 methyl is more correct. This
compound is an ISOMER for pentane.

Problem 2

Give the possible


isomers for C3H8O.

It will be easier to make isomers


now that you have an oxygen to
play with. The rule is that
Carbon must have 4 bonds,
oxygen 2 bonds, and hydrogen 1
bond.
Some of your possible answers are
below and on the next slide.

Problem 3

Give the possible


isomers for BUTENE.

Problem 4

Draw 2,3 n-pentene.

The name tells you several things:


1. First, pent tells you that it has 5
carbons.
2. The ene ending tells you that
this substance is an ALKENE, so it
has one carbon to carbon double
bond.
3. The 2,3 tells you specifically
that the double bond is between
carbons 2 and 3.
4. The n tells you that this is a
straight chained carbon
compound.

Problem 5
Draw the structural formula
for a hydrocarbon with the
molecular formula of C6H12.
This substance is not
an alkene.

The fact that it has the formula of an


alkene tells you that two hydrogen
atoms have somehow been lost.
Since you did not lose them with the
forming of a double bond, they had to be
lost another way. The only possible
solution is that a ring structure was
made. Here are two possibilities:

Problem 6
Study the substance below. How
many hydrogens would be
needed to convert it into an
alkene?
How many to fully saturate it?

What is shown is a polyunsaturated


hydrocarbon. To change it into an
alkene you will eliminate all the
double bonds, except 1. This
means that you will need two
hydrogens for every bond
eliminated. You need to eliminate
two bonds, so 2 x 2 is 4 hydrogen
atoms needed.
To saturate it you need to eliminate
the last double bond. You need 2
more hydrogens for a total of 6 H
to completely saturate the

Problem 7

Could molecular weight


of a molecule be used to
determine whether or
not the substances are
isomers?

Molecular weight is the sum of the


individual atoms of a molecule.
Since isomers have the same
chemical formula they would also
have the same molecular weight,
so the answer is no.
You could use chemical tests to
identify isomers. Isomers have
different chemical properties.

Problem 8

What is the word used


for long, repeating
organic substances?

Polymer is the word to


represent long repeating
chains of organic material.
Poly means many and
mer refers to the individual
unit that is repeated. Most
plastics are polymers. For
example, polyethylene is
made from ethene molecules.

Problem 9

Using a two carbon


alcohol, create a
polymer.
What is the mer?

14 1 1 0 1 (!@- c- I I

A two carbon alcohol would have


the formula C2H3OH. This is
referred to as a substituted
hydrocarbon since a H atom was
replaced by the OH functional
group. The mer would be

The actual polymer would be

Why not 5 hydrogens?


The reason that there are not more
hydrogen atoms is this, if you
were making a two carbon
alcohol, period, it would be
C2H7OH
However, I asked for the mer or
unit that combines. That means
that you would lose the end
carbons and they would combine

Problem 10
Give a possible structural formula
for
2, 5 dimethyl hexene

Problem 10
Give a possible structural formula for
2, 5 dimethyl hexene
Your answer should have a methyl
group
-CH3 on carbons 2 and 5. Your carbon
chain should be six carbons long with
ONE double bond somewhere in the
compound.
See next slide.

Problem 11
What exactly is
2, 5 dimethyl hexene ?
Answer next slide.

Problem 11
What exactly is
2, 5 dimethyl hexene ?
It is an ISOMER of OCTENE. Can
you explain why?