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Alkanes vs.

Boiling Point
What

Happens

as it Gets

Bigger?

Objective:
Create a graph of the data for Boiling Point vs. Number of Carbons for the Alkanes.
Background:
Chemists often gather data regarding physical and chemical properties of substances. Although these
data can be organized in many ways, the most useful ways uncover trends or patterns among the
values. These patterns often trigger attempts to explain regularities.
The development of the periodic table is a good example of this approach. Recall that you predicted a
property of one element from values of that property for neighboring elements on the periodic table.
In a similar vein, we seek patterns among boiling point data for some hydrocarbons. During
evaporation and boiling, individual molecules in the liquid state gain enough energy to overcome
intermolecular forces and enter the gaseous state.
BOILING POINT PRINCIPLE:
Molecules which strongly interact or bond with each other through a variety of intermolecular forces
cannot move easily or rapidly and therefore, do not achieve the kinetic energy necessary to escape the
liquid state. Therefore, molecules with strong intermolecular forces will have higher boiling points.
This is a consequence of the increased kinetic energy needed to break the intermolecular bonds so that
individual molecules may escape the liquid as gases.
Procedure:
Create a graph of the data for Boiling
Point vs. Number of Carbons for the
Alkanes.
1) Label x-axis number of carbon
atoms.
2) Create a scale.
3) Label y-axis boiling point in C.
Remember the data chart also
shows the values for melting point
make sure you use the right data.
4) Create a scale.
5) Plot points label each point with
its molecular formula.
6) Connect with best fit curve.
7) Room temperature is 20C.
Any substance with a
melting point below 20 C
is liquid at room
temperature. Any
substance with a boiling
point below 20C is a gas at room temperature. Fill in the phase column with
each substance proper phase at room temperature.
Questions:

1)

State the relationship between number of carbons and boiling point.

2)
3)

State the relationship between the mass of an alkane and its boiling point.
State, in terms of intermolecular forces, why the boiling point of hexane at 1 atmosphere is higher
than the boiling point of butane at 1 atmosphere.

You have already observed the boiling points of straight chain alkanes are related to the number of
carbon atoms in their molecules. Lets now look at some branched alkanes.

4)

Describe why the 3 molecules list for C5H12 are isomers of each other.

5)

Which of the 3 isomers of C5H12 have the weakest intermolecuar forces of attraction. Explain.

6)

In terms of boiling points discuss if molecules which are isomers of each other, have the same
exact properties.

7)

Describe the relationship between the number of carbon side branches and the boiling point.

8)

The molecule to the right is an isomer of C8H18. Give a possible boiling point in and explain
your value.

9)

What is the name for the 3rd isomer of C8H18 with a boiling point of 99.2 ?

10) In the space below draw and name an isomer of the 2nd isomer of C8H18 with a boiling point of

117.7 which you think would have a very similar boiling point. Explain.

Distillation of crude oil


Crude oil is the term used to describe oil when it is removed from the ground. It is not a pure substance, but
is made up of many different substances, or fractions (petrol, petroleum jelly, bitumen, etc.). These fractions
can be separated out, or refined, using a special method of distillation called fractional distillation.
The crude oil is heated to between 400C and 500C, which changes all the components into gases. The mixture
of gases is pumped through a fractionating column (about 30 m high) and the various substances condense
back to a liquid at different temperatures. As the top of the column is cooler than the bottom, and because the
fractions have different boiling points, they can be pumped out at different heights.
11) Based on the alkane boiling point chart, determine where each of the alkanes will be fractioned off. The
last fraction has been filled in for you. The products are from C 1 to C4 because they all have boiling points
below 20.

Products
Methane, Ethane, Propane, and Butane.

Reflection:

Describe how the number of carbons, the boiling point and the strength of intermolecular forces are all
related. You must use all three terms in your answer.
Going Further: Use an outside resource to determine which type of products are produced from each
fraction of crude oil.