Chemistry Honors Name: _________________________

Alkane boiling points – graphing activity Date: ________________ Period: ___

Introduction: In this activity, we will examine boiling point data for alkane molecules, so that
we can answer the following questions:

1. What effect does increasing molecular size have on boiling point?

2. How can intermolecular attractions (the type and strength) explain differences in
the viscosities and boiling points of alkane molecules?
3. Does branching affect an isomer’s boiling point?

Table 22.1 on page 695 of your textbook lists the boiling points of the first 10 straight-
chain alkane molecules. Reference this table as you complete the questions below.
Answer right on this worksheet.

Part 1. Graphing the Data.

1. Which molecules are gases at room temperature (25°C)?

2. Which molecules are liquids at room temperature, but boil below body temperature
(37°C)?

3. Prepare a graph of boiling point (y axis) versus number of carbon atoms in the alkane
molecule (x axis). Have your x axis scale range from 1 to 13 (even though you are only
plotting 1 to 10) and have your y-axis range from – 200 to + 250°C.

Draw a best-fit curve through the 10 points. Should it be a straight line or not? Well,
examine the data, and decide if the data best represents a linear relationship, or
another type of smooth curve.

4. Using a dashed line, extrapolate your best-fit curve to determine boiling points for alkanes
with 11, 12 and 13 carbon atoms. The accepted values are given below; compare them to
your extrapolated values and comment in the space below.

C11H24: 196°C C12H26: 216°C C13H28: 235°C

Part 2. Analysis.

1. What effect does increasing molecular size have on boiling point?

2. Which type of intermolecular attraction (IMA) holds alkane molecules together in a

sample?

3. If all alkane samples are held together by the same IMAs, then why do boiling points vary
among the first 10 alkanes?

4. Viscosity is a measurement of the resistance of a liquid to flow. A liquid with a high

viscosity flows slowly (like honey), while a liquid with a low viscosity (like rubbing alcohol)
flows easily.

(a) Relate viscosity to IMA strength.

(b) Rank octane, pentane, and decane in order of increasing viscosity.

5. How can intermolecular attractions (the type and strength) explain differences in the
viscosities and boiling points of alkane molecules? Make sure your answer reflects a
molecular-level understanding of the interactions.
Part 3. Branching and boiling point relationships.

Alkane molecules do not have to be straight-chained. Carbon atoms can “branch” off the
main chain, as shown in the table below. When molecules have the same molecular formula,
but have different structural formulas, the molecules are called isomers of each other.

Alkane Formula Boiling Point (°C)

CH3 – CH2 – CH2 – CH2 – CH3 36.1

CH3 – CH – CH2 – CH3

| 27.8
CH3
C5H12 isomers

CH3
|
CH3 – C – CH3 9.5
|
CH3

CH3 – CH2 – CH2 –CH2 – CH2 – CH2 – CH2 – CH3 125.6

CH3 – CH2 – CH2 –CH2 – CH2 – CH – CH3

| 117.7
CH3
Some C8H18 isomers

CH3
|
CH3 – CH – CH2 –C – CH3 99.2
| |
CH3 CH3

1. As the amount of branching increases, how does the boiling point change?

2. Thinking about molecular geometry, and your answer to question 5 from Part 2, how can
you explain this change in boiling point?
3. Here is the structural formula of a C8H18 isomer: CH3
|
CH3 – CH2 – CH2 –C – CH2 – CH3
|
CH3

Compare it to the other C8H18 isomers listed in the table on the previous page, and estimate
the boiling point of this isomer.

4. Below are three C7H16 isomers. Match each with the appropriate boiling point.

98.4 °C 79.2°C 92.0°C

Boiling Point

CH3 – CH2 – CH2 –CH2 – CH2 – CH2 –CH3

CH3 – CH2 – CH –CH2 – CH2 –CH3

|
CH3

CH3
|
CH3 – CH2 – CH2 –C – CH3
|
CH3