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org/jchemeduc Activity

An Exploration-Based Activity to Facilitate Students’ Construction of

Molecular Symmetry Concepts
Narapat Rattanapirun and Parames Laosinchai*
Cite This: J. Chem. Educ. 2021, 98, 2333−2340 Read Online

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ABSTRACT: Molecular symmetry is a topic that requires mental manipulation of molecules when searching for symmetry elements
and their corresponding symmetry operations. Such mental activities are difficult for students in a traditional classroom where only
definitions and demonstrations are provided. Therefore, an exploration-based activity was developed to help university chemistry
students construct molecular symmetry concepts. Since symmetry is a mathematical concept, Pirie and Kieren’s model of growth of
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mathematical understanding was used as the framework to design the activity. Each task allowed students to self-construct the
meaning of symmetry by performing an operation on 2D figures and/or 3D manipulatives. The activity was designed for students
without a background in molecular symmetry and conducted at two public universities. In class, the students went through stages of
understanding that were consistent with those in the model. The results from the conceptual test confirmed that they were able to
apply the learned concepts to identify the symmetry elements and symmetry operations of the given molecules.
KEYWORDS: Second-Year Undergraduate, Inorganic Chemistry, Hands-On Learning/Manipulatives, Group Theory/Symmetry

■ INTRODUCTION
Molecular symmetry is a topic that requires the ability to
visualize molecular structures in three dimensions (spatial
visualization); identify symmetry elements such as axes, planes,
or points; and describe the molecular structures after
performing the corresponding operations (spatial orientation
skills).1 Students need to recognize 3D structures from 2D
drawings and mentally manipulate molecules while searching
for symmetry operations in order to successfully identify
symmetry elements. However, most students find it difficult
during their first encounters with symmetry due to the need to
think three-dimensionally, and the difficulty escalates as the
number of neighboring atoms increases.
Numerous resources were developed to help students
visualize symmetry operations and symmetry elements in
three dimensions. These included common objects,2−4
collections of everyday objects,5,6 physical models,5,7−11
computer programs,12,13 web applications,14−18 and mobile
applications.19,20 Physical objects were useful for demonstrat-
ing specific symmetry of molecules and helping students
visualize 3D molecular structures. However, reflection, and
thus improper rotation, could not be performed on these
objects due to their rigidity.8 Computer programs, web
applications, and mobile applications could overcome this
limitation. They could facilitate better visualization of
symmetry elements and symmetry operations. Students could
choose a molecule and a symmetry element, and they watched
the effect of the corresponding symmetry operation. Although
students could explore symmetry elements and operations,
they did not have to find symmetry elements by themselves.21
In conclusion, these physical and virtual learning media were
designed to facilitate students’ visualization of symmetry
elements rather than their construction of symmetry concepts.
© 2021 American Chemical Society and
Division of Chemical Education, Inc.
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Besides the aforementioned learning media, inquiry activities
were used to teach molecular symmetry.22,23 These activities
began by showing a molecule before and after a symmetry
operation and asked students to identify the corresponding
symmetry operation. Nevertheless, students needed to know
how to perform single-step symmetry operations before
participating in the activities, which meant that the activities
did not address how to facilitate students’ self-construction of
these concepts.
In an attempt to rectify this shortcoming, we developed a
novel exploration-based activity using 2D and 3D manipu-
latives, things that can be manipulated, for students to explore
and investigate with the purpose of constructing symmetry
concepts by themselves. The activity allowed students to
construct mental images of the operations. Through thought-
provoking questions, they could distinguish between objects
with symmetry and those without and identify the elements
that produced symmetry operations. The terms in molecular
symmetry, e.g., principal axis and horizontal plane, were
introduced by allowing them to apply symmetry concepts to an
object of high symmetry.
Received: February 25, 2021
Revised: May 18, 2021
Published: June 7, 2021
https://doi.org/10.1021/acs.jchemed.1c00191
J. Chem. Educ. 2021, 98, 2333−2340
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Table 1. Framework for Symmetry Understanding Levels Adapted from Pirie and Kieren’s Model of Growth of Mathematical
Understandinga
Level of
Understanding Pirie and Kieren’s Description of These Levels Example in the Activity
Primitive Prior knowledge used to perform an activity. It is fundamental to one’s growth of understanding of Experience with reflection in daily life and
knowing a certain topic. mathematics.
(PK)
Image making What one sees while performing an activity and the mental image that one tries to construct. How given figures are reflected across given
(IM) lines. The methods vary among students.
Image having One’s constructed mental image of the physical actions performed in the activity. It eliminates the Ability to instantly draw reflected images
(IH) need to perform physical actions. without going through any physical
processes.
Property Attribute(s) of the mental image(s) noticed from reflection upon the actions. They include Some reflected images coincide with the
noticing similarities, distinctions, combinations, or connections between multiple mental images. preimage while others do not.
(PN)
Formalizing The underlying concept or formal method discovered from the activity. It can be applied to a more Find a formal method for reflecting any figure
(F) general class of similar activities. across any line of reflection.
Observing Attribute(s) of the concept(s) or method(s) derived from reflection upon one’s formal thinking. Not observed in class.
(O) They result from one’s abilities to observe, structure, and organize personal thought processes.
Structuring Explanations of the interrelationships among all the observations and related concepts. They Not observed in class.
(S) indicate complete understanding of the topic.
Inventizing (I) Ability to break free of the structured knowledge and ask questions that lead to a new concept. Not observed in class.
a
See refs 24 and 25.

■ CONSIDERATION IN DESIGNING ACTIVITY

Order of Symmetry Concepts
The exploration-based activity started with the concept of
reflection (σ), with which all students were familiar, followed
by inversion (i), proper rotation (Cn), improper rotation (Sn),
and identity (E). Identity was placed as the last concept so that
it would emerge as the result of a sequence of other operations.
Choices of Terms
Learning symmetry usually begins with the introduction of new
terminologies and symbols, most of which are not familiar to
students. In order to simplify symmetry learning, worksheets
were written in simple language. For example, the word
“inversion” was replaced by the phrase “reflection through the
center point”, and the term “improper rotation” was replaced
by “rotation followed by reflection”. These simplifications
benefited students by making the terms easier to read,
understand, and communicate.
■ METHOD
Ethical Considerations
IRB approval was acquired before starting any data collection.
All of the prospective participants from two public universities
were informed about the research project in order to provide
equal opportunities to participate in this study. After receiving
the information, 14 students from each university were willing
to participate. Each participant signed an informed consent
form prior to participating in the activity. They could stop
participating anytime for any reason. They had the freedom to
express their views freely in all the matters affecting them. The
research activity did not disturb their routine study. The
participants’ information was kept confidential, and their
anonymity was maintained.
Participants
The study was conducted at two public universities located in
central Thailand in the second semester of the academic year
2019. The participants from university 1 were second-year

■
THEORETICAL PERSPECTIVE
Molecular symmetry is classified by the type of mathematical
transformation performed on a molecule. Being able to
visualize the result of such a transformation is fundamental
to understanding molecular symmetry. Among mathematical
learning theories, Pirie and Kieren’s model of growth of
mathematical understanding24,25 is the most explicit in terms
of explaining how a student acquires this ability. According to
the model, the growth of mathematical understanding is
dynamic, leveled but nonlinear, and entails the continual
organization of students’ knowledge structures while perform-
ing given tasks. The framework contains eight levels, namely,
primitive knowing (PK), image making (IM), image having
(IH), property noticing (PN), formalizing (F), observing (O),
structuring (S), and inventizing (I). A short description of each
level together with an example in the activity is provided in
Table 1.
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students (3 males and 11 females) from the Department of
Chemistry, while those from university 2 were first-year
students (4 males and 10 females) from the Department of
Industrial Chemistry. None of them had ever studied
molecular symmetry. Both universities attained similar
rankings among Thai universities. In addition, the participants
from both universities had similar prior knowledge regarding
mathematical transformations and wedge−dash structures.
Data Collection and Analysis
The implementation took 6 h. Throughout the activity, the
students were organized into groups of two on the basis of
their preferences. In addition to serving as guides for the
students, the worksheets were used as a formative assessment
of the group’s collective understanding of each type of
symmetry. The instructor frequently asked the students to
articulate their thoughts and provided additional help in
carrying out particular actions. The learning sessions were
video-recorded. Video recordings and students’ worksheets
were used to analyze the students’ growth of understanding
according to Pirie and Kieren’s model (see Table 1).
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The conceptual test, administered 2 days after the activity,
consisted of eight questions. The students were assigned to
draw wedge−dash structures of molecules, identify their
symmetry elements (drawn on the wedge−dash structures if
possible), and draw the molecular structures after performing
the corresponding operations. Within 10 days after the test,
one student from each group was randomly selected for the in-
depth interview, also video-recorded, in order to delve into his
or her thought while identifying the symmetry of molecules.
Activity in the Exploration-Based Learning Unit
The activity, comprising 11 tasks, is divided into six parts: part
1, reflection symmetry; part 2, point symmetry; part 3,
rotational symmetry; part 4, rotoreflection symmetry; part 5,
identity; and part 6, symmetry terms. Each task is followed by
questions, whose answers must be agreed upon by all students
before moving on to the next task. The questions are designed
to be aligned with the objectives of each task. During the
activity, students are allowed to talk and share the findings with
their peers. The details of the activity and questions are
provided in the Supporting Information.
Parts 1−3 begin by requiring students to describe how to
draw the reflected and rotated images of 2D figures for given
lines of reflection, points of reflection, and points of rotation,
both inside and outside the figures. They are asked to observe
the characteristics of these images, define the meaning of each
symmetry for a 2D figure, and name the symmetry element for
the corresponding 3D operation. After exploring and
conceptualizing 2D symmetry, they are then asked to
manipulate 3D objects in order to extend the concept to
three dimensions. In part 4, armed with the general meaning of
a symmetry operation, they are asked to find combinations of
rotation and reflection operations whose results are symmetry
operations, starting with combinations of symmetry operations,
followed by those of asymmetric operations, on 2D figures and
then 3D objects. Part 5 requires them to explore and observe
the results of repeating each symmetry operation on a square
until the orientation of the image is the same as that of the
preimage. At the end of each part, the instructor informs them
about the symbol for each type of symmetry.
In part 6, students are asked to identify symmetry elements
of a certain object. The purpose of this task is to introduce
terms in molecular symmetry. The symmetry elements of the
object are employed to define the meaning of a principal axis
and characterize the corresponding horizontal (σh), vertical
(σv), and dihedral (σd) planes. Due to the complexity of
defining σv and σd planes, the same number of prime symbol(s)
is used to signify the planes with the same characteristics.
■
IN-CLASS LEARNING OUTCOMES
Part 1: Reflection Symmetry
Task 1. Most of the students were able to draw the reflected
images across the given vertical lines of reflection but failed to
do so for the oblique lines. Transparencies were given to the
students in order to help them draw the reflections. After
drawing several times, they made images by constructing the
animation of the figure going through the reflection. Those
who used the transparency to draw the images could see the
animations together with the preimage. A few students were
able to draw them without using the transparency, suggesting
that they started at the formalizing level. They said that “The
distance from the line of reflection to a point in the preimage
equals that to the equivalent point in the reflected image.”
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Task 2. The majority of the students could move to the
image having level. They were able to reflect the equilateral
triangle without having to go through any physical processes.
Although all of them knew how to draw the reflected images, a
handful still used the transparency especially to reflect across
oblique lines. Upon being asked to differentiate among the
reflected images, the majority mentioned that “These images
can be classified into two groups: those that coincide with the
preimage and those that do not” while the rest classified them
according to the types of the lines of reflection: vertical,
horizontal, and oblique. After being urged to emphasize the
reflected images instead of the lines of reflection, the latter
came to see eye to eye with the former. Here, the students
noticed the symmetric property of reflecting the equilateral
triangle across certain lines.
When prompted to define a line of symmetry, they came up
with “A line of symmetry passes through the center of a figure
and divides it into two equal halves or reflects a figure onto
itself”. Regarding the meaning of reflection symmetry for 2D
figures, they mentioned that “A figure in a plane has reflection
symmetry if, after reflecting the figure across a line, the
resulting image coincides with the preimage.” Interestingly,
they were able to form definitions of a line of symmetry and
reflection symmetry after merely reflecting an equilateral
triangle across several lines.
Task 3. All the students could easily identify all the lines of
symmetry for the given figures and realized that a circle had
infinite lines of symmetry. It seemed that they were ready to
use their understanding of 2D reflection symmetry as primitive
knowledge for further exploration, as evidenced by their ability
to name the corresponding 3D symmetry element and identify
the plane of symmetry for the given 3D object. In fact, most
could leap to the formalizing level for 3D reflection symmetry
and said that “A plane of symmetry is the plane bisecting an
object” or “... reflecting an object onto itself”. After the group
work, class discussion led them to define reflection symmetry
for 3D objects as “An object has reflection symmetry or a plane
of symmetry if the reflected image coincides with the
preimage.”
Part 2: Point Symmetry
By now, the students were competent in reflecting 2D figures
and 3D objects. This competency served as primitive
knowledge in the exploration of point symmetry.
Task 4. More than half were able to mentally reflect an
equilateral triangle through the given points of reflection. For
them, reflection through a point was similar to reflection across
a line or a plane. Thus, this exercise was just an application of
their formalized understanding.
Those who could not reflect the triangle had insufficient
primitive knowledge to make proper images. Using the
transparency allowed them to reorganize the primitive
knowledge in order to develop new and appropriate images.
However, this method was not applicable in three dimensions.
Therefore, the instructor employed the help of those who
achieved formalized understanding to ensure that this group of
students attained the same level of understanding.
Task 5. For the figures with point symmetry, all the
students could specify without taking any actions that “The
resulting images of these figures coincide with their preimages.”
For the other figures, most could come up with good
estimations of their reflections without having to follow the
procedure step by step while a few still had to do so.
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Figure 1. Molecules in the conceptual test: (a) CHBrClF, (b) meso-(CHBrCl)2, (c) C2H2BrCl, (d) Mn(CO)5Cl, (e) PF5, (f) C6H6, (g) CO2, and
(h) CH4.
Nonetheless, all of them noticed that “The reflections [of the
figures with point symmetry] coincide with their respective
preimages because each vertex has an opposite counterpart
that is equally far from the respective center point.” They were
able to define point symmetry as “A figure in a plane has point
symmetry if the reflected image coincides with the preimage
after reflection through the center point.” They could easily
extend their understanding to three dimensions due to the fact
that point symmetry was the same in two and three
dimensions.
Part 3: Rotational Symmetry
Task 6. The students were all able to draw the rotated
images of an equilateral triangle around the center point, the
point on the vertex, and the point aligned with a vertex of the
triangle by just looking at the figures. For the other point of
rotation, most could draw on their experiences from previous
tasks to come up with a formal way to rotate a figure. A few
could not figure out how to rotate the triangle without using
the transparency. They still had to rely on their friends for the
formal procedure.
When the center of rotation was at the center of the triangle,
all of them noticed that the rotated images coincided with the
preimage three times. They realized that this was a kind of
symmetry. That is, they started generalizing the definition of
symmetry. They noticed that “An object has symmetry if it
looks the same after a transformation.”
Task 7. All the students could immediately specify the
number of times that the rotated images coincided with the
preimages of the right triangle, square, rectangle, and trapezoid
after one full turn. They mentioned that “The rotated image of
the right triangle and trapezoid coincides with the preimage
one time. It is like doing nothing, which means that these
figures have no rotational symmetry.” Furthermore, they were
able to define rotational symmetry of 2D figures by stating that
“A figure in the plane has rotational symmetry if the rotated
image coincides with the preimage after rotating by less than
one full turn.” In order to simplify further discussion, the
instructor introduced the term “the order of rotational
symmetry”.
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When asked to find the relationship between the order of
rotational symmetry and the angle at which the image
coincides with the preimage for the first time, they could
formalize that “the angle equals to 360 deg divided by the
order of rotational symmetry.” After that, they explored and
identified the axis of rotational symmetry of 3D objects. They
shared and discussed the meaning of rotational symmetry for
3D objects. They could extend the definition of rotational
symmetry from two dimensions to three dimensions as follows:
“An object has rotational symmetry or an axis of symmetry if
the rotated image coincides with the preimage after rotating by
less than one full turn.”
Part 4: Rotoreflection Symmetry
Primitive knowing of this part entailed the internal
representations that the students had constructed about
reflection and rotation.
Task 8. From the activities in parts 1 and 3, all the students
realized that any combination of symmetric rotation and
reflection produced an image coinciding with the preimage.
Task 9. So far, the students had exclusively dealt with
symmetry operations. Hence, an example of a combination of
asymmetric operations whose result was a symmetric one was
provided. (Rotate an equilateral triangle 60° and reflect across
the line bisecting the angle of rotation.) In effect, the instructor
tried to equip them with necessary primitive knowing for the
new kind of symmetry operation. They were then challenged
to find rotation−reflection operations whose components were
not symmetry operations. This was the first time they
encountered this symmetry. Therefore, all of them had to
physically adapt the steps in the example to the square and
rectangle in order to find the required operations. Even though
they successfully found such operations, most could not
mentally perform the operations.
After that, they were asked to explore and identify the
rotation−reflection symmetry operation of each 3D object,
with the additional restriction that the reflection plane had to
be perpendicular to the axis of rotation. Physical objects were
provided to help them identify symmetry elements and
symmetry operations. A 3D model of allene was the first
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Table 2. Evaluation Results for Students’ Identification of Symmetry Elements of Molecules in Figure 1
Students Correctly Identifying the Symmetry Elements by Molecule, % (N = 28)
Symmetry Element meso-(CHBrCl)2 C2H2BrCl Mn(CO)5Cl PF5 C6H6 CO2 CH4
Reflection Symmetry
Horizontal plane 67.86 85.71 96.43 96.43
Vertical plane 89.29 (2σv) 85.71 (3σv) 100.00 (3σv) 28.57 (∞σv)
Dihedral plane 71.43 (2σd) 85.71 (3σd) 7.14 (6σd)
Point Symmetry
Inversion center 75.00 92.85 100.00
Rotational Symmetry
Principal axis 96.63 (C4) 85.71 (C3) 78.57 (C6) 10.71 (C∞) 60.71 (4C3)
Cn axis 89.29 (C2) 60.71 (C2) 10.71 (3C2)
67.86 (C3)
Perpendicular C2 axis 71.43 (3C2) 64.29 (6C2) 0.00 (∞C2)
Rotoreflection Symmetry
Sn axis 60.71 (S3) 39.29 (S3) 0.00 (S∞) 0.00 (3S4)
50.00 (S6)

object being explored. At first, they tried to rotate the model by
half a turn (a symmetric rotation), only to find out that the
subsequent reflection did not yield the required image. From
their experience with the 2D rotoreflection that they had just
performed, they realized that they should try a quarter-turn
rotation. Most were able to find the required rotoreflection
operation in one of two ways: either rotating the whole model
or twisting one end of the model by a quarter of a turn. Either
way, they could see that the subsequent reflection would send
each H atom to the original position of another H atom at the
other end. A few needed a detailed demonstration by the
instructor to help construct the correct image. The other two
objects represented octahedral molecules: one with three pairs
of identical opposite atoms and the other with two groups of
three identical atoms arranged in the meridional configuration.
Because they had spent a relatively long time exploring the
more complex model of allene, they could now identify the
rotoreflection symmetry operation (or the lack thereof) with
ease. They concluded that “An object has rotoreflection
symmetry if the combination of rotation about an axis and
reflection across a plane perpendicular to that axis results in the
object that coincides with the original object.”
Part 5: Identity
After exploring and observing the results of repeatedly applying
symmetry operations, all the students noticed that, after a
certain number of times, the image always had the same
orientation as the preimage. They realized that this had to be
another kind of symmetry possessed by every figure/object.
After being informed about the name of the symmetry, they
concluded that “Identity is an operation that does nothing and
can be found in all objects.”
Part 6: Symmetry Terms
All the students could draw every symmetry element on the
picture of the given object (maybe with additional guidance on
how to draw a plane) and specify the positions of the atoms
after performing the corresponding operation, confirming that
they could apply all the symmetry concepts to this highly
symmetric object.
operations of the molecules (Figure 1) after participating in the
activity. Table 2 shows the percentage of the students who
correctly identified each symmetry element of each molecule.
All the quotes in this section came from the interview.
Reflection Symmetry
Horizontal Plane. Most of the students were able to
identify the horizontal plane of PF5 (Figure 1e). Those who
could not find this plane incorrectly drew its wedge−dash
structure (Figure 2). They might think that the three
equatorial F atoms were not in the same plane. Hence, they
could not identify other symmetry elements of PF5 as well.
Figure 2. Incorrect drawings of PF5.
C2H2BrCl (Figure 1c) and C6H6 (Figure 1f) have the
horizontal planes that contain all atoms. Nearly all the students
were able to identify the σh plane of C6H6, and two-thirds were
able to identify the σh plane of C2H2BrCl. Those who could
not find these planes incorrectly visualized the shape of each
molecule. Most of them thought that each molecule was two-
dimensional and therefore would have trouble identifying the
σh plane. They did not realize that every planar molecule
necessarily had a plane of symmetry. They mentioned that
“[They] forgot about it.” On the other hand, CO2 (Figure 1g)
has a horizontal plane that does not contain all atoms. Nearly
all the students were able to identify this plane, but they did
not realize that it was the horizontal plane because they could
not identify the principal axis (C∞).
Vertical and Dihedral Planes. Most of the students were
able to identify the vertical planes of Mn(CO)5Cl (Figure 1d)

■
and PF5. The shape of C6H6 is like a regular hexagon with
which they were familiar because task 3 asked them to identify
STUDENTS’ ABILITY TO IDENTIFY SYMMETRY all the lines of reflection of a square, a fellow regular polygon.
ELEMENTS AND OPERATIONS Thus, all of them were able to identify the 3σv planes. They
The conceptual test served as a means of evaluating the explained that “They can identify the planes of symmetry by
students’ ability to identify symmetry elements and symmetry drawing the lines that divide the molecule into two congruent
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Figure 3. Incorrect drawings of CH4.
parts.” Some could not identify the σd planes of Mn(CO)5Cl
and C6H6 even though they could identify the σv planes.
However, in the interview, when asked to reconsider, they
could easily do so.
For CO2, those who were able to identify the ∞σv planes
thought that this molecule resembled a cylinder or a capsule
whose cross-section was a circle. From task 3, they knew that a
circle had infinite lines of symmetry. Thus, they could infer
that CO2 should have an infinite number of planes of
symmetry. Those unable to identify the symmetry planes
thought that this molecule resembled a straight line which had
one dimension. Therefore, they could not imagine the
existence of any σv planes.
Methane. Methane is a highly symmetric molecule and
belongs to a special group. It is therefore natural that most of
the students could not find all the symmetry elements.
Additionally, about a quarter of them had misconceptions
about its molecular structure as shown in Figure 3. Three
students who were able to identify all the planes of symmetry
stated that “Fitting this molecule inside a cube makes seeing all
the planes possible.” The majority could identify the following
three planes in descending order of correct identification: the
planes containing H(1)−C−H(2), H(3)−C−H(4), and
H(1)−C−H(4), respectively. The first plane was in the
plane of the paper. The second was perpendicular to the first.
The last was easier to see than any of the remaining planes.
Point Symmetry
Although this kind of symmetry was easy to identify, a quarter
of the students could not identify the point of symmetry of
meso-(CHBrCl)2 (Figure 1b) due to their misunderstanding of
its position. They thought that the point had to be at one of
the C atoms. This might be because when it came to point
symmetry, they predominantly encountered molecules con-
taining a single atom at their centers.
Conversely, nearly all the students were able to identify the
point of symmetry of C6H6, although it does not have the
center atom. They had identified the symmetry point of a
square (which is also a regular polygon) in task 5, enabling
them to see that C6H6 should also have point symmetry. Those
who were unable to identify the symmetry point thought that
the carbon−carbon single bonds were longer than their
double-bond counterparts. The hexagon in their minds was
irregular (Figure 4) and thus contained no point symmetry.
Finally, all could easily see the point of symmetry of CO2 due
to its simplicity.
Rotational Symmetry
Principal Axis. Most of the students could identify the
principal axis of each given molecule. In descending order of
the numbers of correct answers, the molecules were Mn-
(CO)5Cl, PF5, and C6H6 (excluding CO2 and CH4). They
stated that “The principal axis is quite easy to find. A molecule
whose equatorial atoms around the center are the same tends
to have the principal axis with the order of rotational symmetry
equal to the number of equatorial atoms.” They also noticed
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Figure 4. Distorted hexagonal shape.
that “If the order of the principal axis is divisible by two or
three, the axis also have other order of rotational symmetry.”
For PF5 and C6H6, those who could not find the principal axis
had misconceptions about the shape of each molecule.
Conversely, a few could find the C∞ axis of CO2. They
mentioned that “The axis that passes through the two carbon−
oxygen double bonds can have any order of rotational
symmetry. Hence, if this molecule has infinite planes of
symmetry, it should have an infinite-order axis.” Some were
unable to identify the infinite-order axis because there were
neither tasks nor questions in the activity related to an infinite-
order axis. Others thought that the molecule was a line.
Perpendicular C2 Axis. It was slightly more difficult for
the students to identify C2 axes perpendicular to a principal
axis. The majority could find the 3C2 axes of PF5 and the 6C2
axes of C6H6. Besides those who had misconceptions about the
molecular structures of PF5 and C6H6, only a few could not
identify all the perpendicular C2 axes. For the former molecule,
the 3C2 axes passed through a P−F bond on one side but
bisected two P−F bonds on the other, slightly complicating the
identification process. For the latter, the two C2 axes passing
between carbon atoms were neither horizontal nor vertical
relative to the plane of paper, causing a few to be able to
identify only four C2 axes, those passing through the carbon
atoms and the one in the horizontal position. On the other
hand, all thought that CO2 contained only one C2 axis, instead
of infinitely many, regardless of whether they could identify its
principal axis.
Methane. Methane contains more than one axis with the
highest order of rotational symmetry. Slightly less than two-
thirds were able to identify the 4C3 axes. They found these
elements by viewing the molecule in the directions of the C−
H(1) and C−H(2) bonds. Upon seeing the two C3 axes
passing through these bonds, they realized that there were two
more C3 axes passing through the remaining bonds.
Two of the three students who could find all the 3C2 axes
also found all the σd planes while about half could not identify
any C2 axes. For the other students, the vertical C2 axis
(relative to the given figure) was always found while the one
bisecting the H(1)−C−H(4) angle was never found.
Rotoreflection Symmetry
This kind of symmetry was difficult to identify because the
corresponding operation had to be performed in two steps.
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Nonetheless, the majority of the students were able to find the
S3 axis of PF5 because both steps were symmetry operations.
Those who were able to find the C3 axis and σh plane
mentioned that “If I can find a Cn axis and a symmetry plane
perpendicular to it, that molecule should have an Sn axis with n
as the order of the symmetry.” It can be seen that the students
who could see the relationship between Cn and σh would be
able to identify Sn. In this case, about three-quarters of those
who could find the C3 axis and σh plane also found the S3 axis.
Fewer students could find the S6 and S3 axes of C6H6
although both steps were symmetry operations. Those who
were able to find the C3/C6 axis tended to find the S3/S6 axis
whereas those who were able to identify the S3/S6 axis must
have already found the C3/C6 axis. Interestingly, those who
found S3/S6 for C6H6 also found S3 for PF5. For all three
rotoreflection symmetries, about two-thirds of those who
found the rotation axes could find their rotoreflection
counterparts.
The rotoreflection axes of methane (3S4) were the most
difficult to identify. A quarter of them were able to identify the
axis bisecting the H(1)−C−H(2) and H(3)−C−H(4) angles.
Those who were able to identify this S4 axis could imagine that
collapsing the two carbon−carbon double bonds of allene
would result in methane. The other S4 axes were never found.
Identity
All the students could identify the only symmetry element of
CHBrClF (Figure 1a) which was identity. Some identified the
element as C1. From task 7, they concluded that “If a figure has
only C1, it is an asymmetric figure.” The activity made them
realize that this molecule was an asymmetric molecule, and C1
was for this reason also the identity operation.
■
CONCLUSION
The primary goal of this study was to create the exploration-
based activity that can be used to help students construct
symmetry concepts and to improve students’ spatial ability
through the use of 2D and 3D manipulatives. Each task started
with questions for students to explore, observe, and draw
conclusions through student-centered learning rather than
lecturing. The crucial step in the learning process involved
performing operations on 2D and 3D tangible models to create
the meaning of each type of symmetry rather than passively
listening to a lecture and memorizing new terms and
definitions. Through this process, the students were able to
mentally reflect and rotate 2D figures and 3D objects across/
around the center (point, line, plane) of operation. These
abilities enabled them to synthesize the concepts of symmetry
and identify the overwhelming majority of symmetry elements
and the corresponding symmetry operations of the given
molecules. Moreover, we came to the realization that students’
misconceptions about molecular structures could hinder the
learning of symmetry concepts and made it difficult for them to
form correct mental images while identifying symmetry
elements and the corresponding symmetry operations.
Instructors should therefore investigate students’ prior knowl-
edge before beginning a new concept and incorporate the
findings into a lesson plan. Learning symmetry this way
contributes to a deep understanding of the basic concepts of
symmetry, as can be seen from the results of the conceptual
test which not only required the students to identify symmetry
elements and symmetry operations of molecules but also called
upon them to specify the positions of the atoms after
2339
pubs.acs.org/jchemeduc Activity
performing the operations. This activity can serve as a model
for teaching and learning molecular symmetry.
■ ASSOCIATED CONTENT
* Supporting Information
sı
The Supporting Information is available at https://pubs.ac-
s.org/doi/10.1021/acs.jchemed.1c00191.
Details of activity and questions (PDF, DOC)
■ AUTHOR INFORMATION
Corresponding Author
Parames Laosinchai − Institute for Innovative Learning,
Mahidol University, Nakhon Pathom, Nakhon Pathom
73170, Thailand; Email: parames.lao@mahidol.edu
Author
Narapat Rattanapirun − Institute for Innovative Learning,
Mahidol University, Nakhon Pathom, Nakhon Pathom
73170, Thailand; orcid.org/0000-0001-8114-5591
Complete contact information is available at:
https://pubs.acs.org/10.1021/acs.jchemed.1c00191
Notes
The authors declare no competing financial interest.
■
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