Activity

pubs.acs.org/jchemeduc

An Inquiry Experience with High School Students To Develop an

Understanding of Intermolecular Forces by Relating Boiling Point
Trends and Molecular Structure
Melinda Ogden*
Atlantic Community High School, Delray Beach, Florida 33445, United States
*
S Supporting Information

ABSTRACT: Knowledge of intermolecular forces (IMFs) is fundamental to comprehending chemical

and biological systems and their transformations at a particulate level. Including instruction on IMFs in
the high school curriculum allows for students to develop a conceptual understanding of the material
presented in chemistry class as opposed to simply restating facts. Herein, a student-centered activity
developed for high school students to discern relationships between molecular structure and boiling
point as an introduction to IMFs is described. The lesson was developed in such a way that students
must use data to support their conclusions, and the data employed were chosen specifically to prevent
misconceptions or incomplete conceptions from forming. Details regarding the interactions between
students and the teacher are provided to help those looking to employ this activity in their own class
successfully. This activity and follow-up lesson were implemented with over 250 high school students,
many of whom, even a year later, were able to apply their deep understanding of particulate level
electrostatic interactions to new chemical systems, including solubility of molecular compounds.
KEYWORDS: High School/Introductory Chemistry, First-Year Undergraduate/General, Collaborative/Cooperative Learning,
Inquiry-Based/Discovery Learning, Hydrogen Bonding, Noncovalent Interactions, Student-Centered Learning

■ INTRODUCTION
Intermolecular forces (IMFs) are crucial to understanding
This approach allows the teacher to interact with each
student at their current level of understanding and bring all
many aspects of chemistry and biology, yet their abstract nature students to the same level of knowledge by providing different
amounts of assistance. By having students develop the ideas
can pose problems for the concrete-operational students in a
themselves, they are able to truly understand IMFs and what
tenth grade chemistry course. There have been many studies
governs their strength instead of memorizing a set of rules to
showing students have deep misconceptions about IMFs and
follow to answer questions. The students also gain valuable
their role in phase changes1−5 and that having students draw
practice using data to generate explanations,9 and grounding
the molecules and indicate the IMFs helps to resolve those
the activity with data prevents the students from making too
misconceptions.6,7 Graphs of boiling points or boiling point
broad of generalizations.
trends have been described as instructional tools for IMFs8 and
This activity was implemented with tenth grade students in
as a method to probe students’ understanding of the types
their first of two semesters of honors chemistry in an urban
of IMFs for different molecules.2 Here, I explain how these
public high school with approximately 2500 total students. This
approaches were combined in an inquiry setting with high
experience was incorporated after students learned to draw
school students in a manner that avoids the ubiquitous miscon-
Lewis dot structures and VSEPR shapes for covalent compounds
ceptions students have regarding IMFs.
but before any experience with IMFs. This complete lesson, from
Using an inquiry approach maximizes student understanding,
data gathering to teacher wrap-up, takes approximately 200 min
and this approach was thus chosen as the method to introduce on a block schedule in which a class period is 100 min and
students to IMFs. Students first measure boiling points of students meet every other day. On a traditional 50 min period
several compounds and are then provided with boiling points for schedule, I estimate the experience to take 150 min total.

■
additional compounds making up a homologous series of
alkanes, ethers, alcohols, and several other molecules included LABORATORY EXPERIMENT
to prevent formation of misconceptions. Students work to group
the molecules into categories based on structure and boiling The first component of this experience is for the students to
point until all molecules have a group with an explanation. Mean- measure the boiling point of several compounds. In my imple-
while, the teacher ensures the students are developing appro- mentations, students measured the boiling points for water,
priate ideas by challenging the students’ molecular groupings if
too broad. Once complete, the class shares their ideas and the Received: September 11, 2016
teacher provides scientific terminology, organizes their ideas, and Revised: April 30, 2017
explains the relationships between structure and boiling points.
© XXXX American Chemical Society and
Division of Chemical Education, Inc. A DOI: 10.1021/acs.jchemed.6b00697
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Activity

Table 1. Molecules in Order of Increasing Boiling Point time they have used a pure liquid other than water. The process
may also be a light bulb moment regarding instrument error
Molecule Condensed Structural Formula Boiling Point (°C)a
depending on the quality of thermometers or temperature
methane CH4 −161.4 probes being used because each group of students could have
ethane C2H6 −88
different measurements. Before beginning with the measure-
propane C3H8 −42.1
ments, it is important the students understand that if a liquid at
methoxymethane CH3OCH3 −24.82
its boiling point were to get any hotter, it would become a gas,
butane C4H10 −0.50
methoxyethane CH3OCH2CH3 10.8
and therefore the boiling point is measured once the tem-
ethoxyethane CH3CH2OCH2CH3 34.6
perature of the liquid stops increasing. A description of how to
acetone CH3COCH3 56.5 achieve this understanding with the students is included in the
methanol CH3OH 64.7 Supporting Information.
ethanol CH3CH2OH 78.5 After measurement of the boiling points, the second
isopropanol CH3CHOHCH3 82.5 component is the categorization of the molecules based on
diethyl sulfide CH3CH2SCH2CH3 92 structure and boiling point. Students are provided with the
1-butanthiol C4H9SH 98.4 condensed structural formulas and boiling points for addi-
water H2O 100 tional compounds and are asked to draw Lewis structures
butan-1-ol C4H9OH 117 for all of the molecules to visualize them. All of the com-
glycerol HOCH2CHOHCH2OH 290.0 pounds are listed in Table 1, though some of the boiling
a
Data are from ref 10. points are measured by the students. To not influence the
grouping, the molecules’ names are not provided, and the
list is randomized. Student hand-outs are available in the
ethanol, methanol, and isopropanol because they were readily
available and inexpensive. (Sources, pricing, and safety informa- Supporting Information.
tion are available in the instructor materials in the Supporting
Information. Caution should be taken while boiling alcohols
due to the flammability.) Measuring the boiling point is often
■ STUDENT ANALYSIS AND THE ROLE OF THE
TEACHER
an enlightening experience for students as it may be the first Once students have gathered their own boiling point data for
the compounds the teacher has chosen for measurement, it is
Box 1. Category Rules Students Are Expected To Develop
important to discuss how those data should be combined with
the provided data. As students inevitably share their findings
(1) Within a group, molecules with more atoms/mass/
around the room, a discussion of instrument error comes up.
electrons have a higher boiling point.
(2) Molecules with only carbon and hydrogen have the If there is a systematic error with the measured boiling points,
lowest boiling point when compared with molecules of the measured points can be adjusted to accepted values for
similar size. comparison, vice versa, or because the compounds in Table 1
(3) Molecules with atoms in the chain other than carbon have boiling points which are far enough from each other, the
have higher boiling points than those with only carbon. measured boiling points can be used as collected without
(4) Molecules with an −OH on the end have the highest affecting the categorization with the understanding that the
boiling points. students are not comparing values taken under the same
(5) The more −OH groups on a molecule, the higher the conditions. If the experiment is carried out far from sea level, a
boiling point. discussion of boiling point in terms of vapor pressure and
atmospheric pressure would also be warranted.

Table 2. Refinement of Students’ Categorizations

Molecules Which Can Help

Student Categorization/Reasoning
Molecules with negative boiling points, mole-
cules with “medium” boiling points, and
molecules with “high” boiling points as groups.
Molecules with more carbons have higher
boiling points (within a group).
Molecules with more hydrogens have higher
boiling points
Molecules with oxygen have higher boiling
points
Molecules with sulfur have boiling points higher
than those with oxygen.
Molecules with an oxygen on the end have
boiling points higher than those with the
oxygen in the middle (not addressing specialty
of hydroxyl group).
Refine
Alkanes, ethers, alcohols
Glycerol, diethylsulfide,
water
Ethane, methoxymethane,
ethanol
Diethylsulfide
Butanthiol, butan-1-ol
Diethylsulfide, butanethiol
Teacher Intervention
Students often first group solely by arbitrary boiling point cut-offs and ignore structural
characteristics. To introduce the importance of structural features in their groups, start
with the negative boiling points and ask if methoxymethane looks more like the alkanes
with negative boiling points, or more like the methoxyethane. A similar question can be
posed for an ether compared with an alcohol if needed.
Point to any/all molecules with three and four carbons and then point out glycerol, which
also has three carbons, and water. Comparing ethoxyethane and diethylsulfide can also
help students get to the concept of the number of electrons playing a role.
Each of these molecules has six hydrogens, yet they have significantly different boiling
points. This will help students in forming more specific groups based on structural
characteristics.
Point out ethoxyethane and diethylsulfide.
This conception can result from addressing the previous one; pointing out butanthiol and
butan-1-ol can alleviate the issue.
Have the students build models of diethylsulfide, butanethiol, diethyl ether, and butanol to
develop a more precise grouping statement which explains why butanol has a boiling
point higher than that of butanethiol but diethyl ether has a boiling point lower than that
of diethylsulfide. It sometimes helps to pull in water and glycerol as well.

B DOI: 10.1021/acs.jchemed.6b00697
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Activity

As students start looking at the data, some are completely
overwhelmed, while others jump in right away. For this reason, it is
useful to group students by ability level so that more guidance can
be provided to the weaker students, enabling them to make progress
instead of just following along with stronger group members.
Groups of two or three work best so abilities can be matched.
The molecules were chosen in such a way as to help the
students sort by symmetry and size, so for groups that cannot
find a place to start, they can sort the molecules by boiling
point and then try and find structural categories. If students
draw the molecules on index cards and include their boiling
points, they can easily move molecules between categories and
see the groups more spatially than if listed on paper.
When the students are finished, the goal is for them to have
developed something similar to the sets of rules found in Box 1.
To help students develop the last two ideas, 1,4-butandiol
(boiling point 235 °C11) could be added to the molecule list
because it is less of an outlier structurally than glycerol
and water. It is critical to help the students identify when
oxygen is important as opposed to any element other than
carbon so that molecules which can form dipole−dipole forces
can be distinguished from those with hydrogen bonding
capabilities.
It is crucial that the teacher continuously question each
group of students on their progress and reasoning throughout
this portion of the experience because the students generally
make conclusions along the way that are inconsistent with some
of the other molecules that are included. (The teacher is not
providing instruction but rather is guiding students to reach
appropriate conclusions through questioning.) Some students
start sorting by whether or not the molecule contains an oxygen
atom but then realize that sorting by size within the group
that has oxygen atoms proves difficult. At this point, students
sort by molecules having oxygen in the middle or at the end. To
avoid having students come to the conclusion that oxygen is
necessarily special, diethylsulfide is included, which follows
the general trend within the ethers. To then help the most
advanced groups of students determine that the hydroxyl group
is in fact special, 1-butanthiol is included for comparison with
butan-1-ol. Also included for further delineation are glycerol
and water (for increased number of hydroxyl groups) and
acetone (for a polar molecule with an oxygen not in the main
chain), which only the most advanced students are able to
place. Table 2 lists common student statements which need
further refinement to meet the classification guidelines
described above and which set of molecules can help students
further refine their groupings and reasonings. Some example
student responses are shown in Figure 1.
Some weaker groups of students will end up placing all of the
outliers in one group and stating their reasoning as, “they did
not fit with the other ones”. Depending on how long it has
taken these students to get to the three main groups, it might
be worthwhile to try to get them to see that the number of
hydroxyl groups is important; otherwise, the teacher could just
circle back to them after going over everything as a class to
make sure they understand how each unique molecule fits into
their scheme.

Figure 1. Two sample student responses on how the molecules were categorized. Student 1 is missing some molecules but provides a typical
response. Student 1 organizes the molecules within each category by boiling point but does not explain why the boiling points increase within a
category. Student 2 categorizes only the molecules. When probed, students are able to explain why the boiling points differ for the molecules within a
category as well as between categories.

C DOI: 10.1021/acs.jchemed.6b00697
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Activity

Figure 2. Examples of three student drawings and explanations of the IMFs present within a sample of methane. The students clearly indicated
instantaneous, temporary shifts in electron clouds and the resulting electrostatic interactions. Students 2 and 3 also indicate the presence of bond
dipoles with student 2 explicitly indicating that the bond dipoles cancel making the molecule nonpolar.

Figure 3. Student responses to why ethanol is a liquid at room temperature while iodine is a solid. Students show understanding of the relative
strengths of different types of IMFs and are able to convey that London dispersion forces can be stronger than the other types for a molecule with a
large enough electron cloud. Students are also able to relate boiling points to state of matter at a given temperature. It should be noted that Student
3 states “break it’s molecules up”, which may signal the misconception that the bonds within a molecule break during phase changes. However, in
responses to other questions, Student 3 clearly drew IMFs between molecules breaking during phase changes, similar to those seen in Figure 4.
Formalizing and Applying the Knowledge each category are listed by increasing boiling point as well,
Once each group of students has finalized their molecule corresponding to rule 1. The extra molecules are then placed in
categories. Here, the stronger students lead the discussion and,
categories and reasonings, the class reconvenes to formalize
as some of the molecules are placed, weaker students are able to
knowledge together. First, three main categories of molecules categorize some of the other molecules as a bigger scheme
are generated and drawn on the board in increasing order of unfolds. Diethylsulfide, butanthiol, and acetone are placed in
boiling point: the alkanes, ethers, and alcohols corresponding the same category as the ethers because they are asymmetric.
to rules 2, 3, and 4 described above. The molecules within Glycerol and water are included in the category with the
D DOI: 10.1021/acs.jchemed.6b00697
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Activity

Figure 4. Student drawings and explanations of what happens when water boils. Students indicate in words and with drawings that phase changes
involve breaking IMFs, not molecular bonds.

Figure 5. Student responses to why glucose is soluble in water but cyclohexane is not. Structures of both molecules were provided. Students had not
previously discussed solubility or solutions in any way prior to this question which was posed on a unit exam. Students 1 and 3 include the idea that
in order for one substance to be soluble with another, the attraction between the two must be stronger than the attraction between molecules within
each substance. These three typical responses to the question show a deep understanding of interparticle attractions and ability to apply that
understanding to a completely new situation. An extension to this activity could evaluate solubility and its relation to IMFs, possibly using the
experiment described by Montes et al.14

alcohols. A schematic and notes are available in the instructors
materials in the Supporting Information.
After all molecules have been placed (or almost all in a weak
class), the concept of IMFs is introduced, and the appropriate
scientific terminology is provided. The introduction to IMFs is
most easily started with dipole−dipole forces. Here, the con-
cept of bond dipoles and dipole moments are brought in.
Students quickly see the interaction between partial positive
and partial negative charges on adjacent molecules. London
dispersion forces are then explained as instantaneous dipole−
dipole forces and hydrogen bonding as a special case of dipole−
dipole which is stronger due to the large dipole moments.
E DOI: 10.1021/acs.jchemed.6b00697
Included in the set of molecules are instances where a molecule
with a weaker type of IMF has a boiling point higher than that
of a molecule with a stronger type of IMF. It is important to
show the students that the relative strength of IMFs holds for
molecules of similar sizes; otherwise, the strength of LDFs
dominates.12
If the class of students overall had trouble placing all of the
molecules, they can be categorized at the end of the discussion.
The relationship between the electrostatic interactions and
boiling point is easily identified by the students given their
extensive training on the differences between liquids and
gases in terms of particle spacing throughout their schooling.
J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education Activity

Having an understanding of the phase changes at a particulate
level helps to avoid the misconception of molecules break-
ing apart into constituent atoms upon boiling. Examples of
student drawings and responses showing their understanding
of IMFs (Figure 2), their relative strengths (Figure 3), and
relation to physical properties (Figures 4 and 5) can be seen in
Figures 2−5. Although these representative responses show
thorough understanding, it would be useful to further analyze
them, as described by Becker et al.13
(5) Peterson, R. F.; Treagust, D. F. Grade-12 Students’
Misconceptions of Covalent Bonding and Structure. J. Chem. Educ.
1989, 66 (6), 459−460.
(6) Cooper, M. M.; Williams, L. C.; Underwood, S. M. Student
Understanding of Intermolecular Forces: A Multimodal Study. J.
Chem. Educ. 2015, 92, 1288−1298.
(7) Williams, L. C.; Underwood, S. M.; Klymkowsky, M. W.; Cooper,
M. M. Are Noncovalent Interactions an Achilles Heel in Chemistry
Education? A Comparison of Instructional Approaches. J. Chem. Educ.
2015, 92, 1979−1987.

■ SUMMARY
In 4 years, this experience has been completed with 10 classes,
totaling approximately 250 students. Students are easily able to
explain the relationship in boiling or freezing point between any
set of compounds. Students can also easily explain the states of
matter under standard conditions for any set of compounds.
The students’ understanding of IMFs and how they arise is
thorough and consistent across all levels of students after
this experience. The students were also able to apply their
knowledge of IMFs to explain solubility of covalent compounds
without guidance. Additionally, many of the same students were
in 11th grade Advanced Placement chemistry the following year
and were able to recall all of the details of IMFs without
prompting and to accurately draw instances of IMFs of all
types. Understanding the forces governing interparticle inter-
actions is key to having a particulate level comprehension of a
chemical system. With this experience, I found that students
both understand IMFs and can apply their knowledge even a
year later.
(8) Glazier, S.; Marano, N.; Eisen, L. A Closer Look at Trends in
Boiling Points of Hydrides: Using and Inquiry-Based Approach to
Teach Intermolecular Forces of Attraction. J. Chem. Educ. 2010, 87
(12), 1336−1341.
(9) Nichol, C. A.; Szymczyk, A. J.; Hutchinson, J. S. Data First:
Building Scientific Reasoning in AP Chemistry via the Concept
Development Study Approach. J. Chem. Educ. 2014, 91 (9), 1318−
1325.
(10) The Merck Index; O’Neil, M. J., Heckelman, P. E., Koch, C. B.,
Roman, K. J., Eds; Merck & Co, Inc.: Whitehouse Station, NJ, 2006.
(11) Lide, D. R. CRC Handbook of Chemistry and Physics; CRC
Press/Taylor & Francis: Boca Raton, FL, 2005.
(12) Earles, T. T. Can London Dispersion Forces Be Stronger than
Dipole-Dipole Forces, including Hydrogen Bonds? J. Chem. Educ.
1995, 72 (8), 727.
(13) Becker, N.; Noyes, K.; Cooper, M. Characterizing Students’
Mechanistic Reasoning about London Dispersion Forces. J. Chem.
Educ. 2016, 93 (10), 1713−1724.
(14) Montes, I.; Lai, C.; Sanabria, D. Like Dissolves Like: A
Classroom Demonstration and a Guided-Inquiry Experiment for
Organic Chemistry. J. Chem. Educ. 2003, 80 (4), 447−449.

■
*
ASSOCIATED CONTENT
S Supporting Information

Student handout. (PDF) Student handout. (DOCX) The

Supporting Information is available on the ACS Publications
website at DOI: 10.1021/acs.jchemed.6b00697.
Instructor information (PDF; DOCX)
Student handout (PDF; DOCX)

■ AUTHOR INFORMATION
Corresponding Author
*E-mail: melinda.ogden@palmbeachschools.org.
ORCID
Melinda Ogden: 0000-0003-0916-6480
Notes
The author declares no competing financial interest.

■ REFERENCES
(1) Luxford, C. J.; Bretz, S. L. Development of the Bonding
Representations Inventory to Identify Student Misconceptions about
Covalent and Ionic Bonding Representations. J. Chem. Educ. 2014, 91,
312−320.
(2) Jasien, P. G. Helping Students Assess the Relative Importance of
Different Intermolecular Interactions. J. Chem. Educ. 2008, 85 (9),
1222−1225.
(3) Kind, V. Beyond Appearances: Students’ Misconceptions About
Basic Chemical Ideas. http://www.rsc.org/learn-chemistry/resource/
res00002202/beyond-appearances?cmpid=CMP00007478 (accessed
April 2017).
(4) Nakhleh, M. B. Why Some Students Don’t Learn Chemistry. J.
Chem. Educ. 1992, 69 (3), 191−196.

F DOI: 10.1021/acs.jchemed.6b00697
J. Chem. Educ. XXXX, XXX, XXX−XXX