Research: Science and Education

edited by

Melanie M. Cooper

Organic Chemistry Educators' Perspectives

on Fundamental Concepts and Misconceptions:
An Exploratory Study

Department of Chemistry
Clemson University
Clemson, SC 29634

Jennifer M. Duis
Department of Chemistry, Carl Wieman Science Education Initiative, University of British Columbia,
Vancouver, British Columbia V6T 1Z1, Canada

Research was conducted while at the University of Northern Colorado, Department of Chemistry and
Biochemistry, Greeley, CO 80639

In the 1970s, various subcommittees of the American Chemical

Society's (ACS) Curriculum Committee developed a comprehensive
report containing detailed topical outlines and performance objectives that covered the standard content for undergraduate
courses in each area of chemistry including general, analytical,
organic, inorganic, physical, and biochemistry (1, 2). While the
ACS still has a committee that provides chemistry curriculum
guidelines for ACS approved chemistry programs (now the
Committee on Professional Training) (3), the extensive 1970s
report has not been updated. Today short, general, topical guidelines
for each area of chemistry continue to be provided for ACSapproved chemistry programs to follow (4, 5). The conceptual
topics for organic chemistry currently include:
The understanding that our only way to molecular knowledge is
through experimentation; correlating structure with reactivity
and function through wet chemical methods, spectroscopy (notably
nuclear magnetic resonance and infrared spectroscopy and X-ray
crystallography), and use of computational methodology
Bonding and its consequences on molecular structure and
reactivity
Interplay between electronic, steric, and orbital interactions in
the behavior and properties of molecules
The dependence of structure and reactivity on context, the
environment, whether gaseous, liquid, or solid; or in solution
Lewis and Brnsted acid-base chemistry
Stereochemistry and conformational analysis
Addition, elimination, substitution, and rearrangement mechanisms, and reactive intermediates
Functional groups, with particular emphasis on the centrality of
the carbonyl group in organic reactions
Organic synthesis, including retrosynthetic analysis of target
molecules
Synthesis and behavior of macromolecular species, including
biomolecules such as proteins and polysaccharides and synthetic
polymers (4)

The ACS topical guidelines are broadly accepted in the

education community, as shown by the wide use of ACS
discipline-specific exams. While general chemistry curriculum
and topic coverage are frequently discussed in the chemical
education literature and media (6-14), there is little general
discussion of the curriculum or fundamental concepts of organic
chemistry in the recent literature (15, 16). In fact, there appears
to be a general assumption that the organic chemistry curriculum

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is either standard or open to a variety of approaches, all of which

are valid. For example, the ACS Web site recently stated, there
are many excellent organic chemistry textbooks whose contents
can provide a sound basis for organizing an introductory organic
chemistry course (5). While the majority of current undergraduate organic chemistry textbooks are quite uniform in
content, this does not mean the same holds true for current
curricula. Despite the homogeneity of modern undergraduate
textbooks, standards used by the ACS exams, and topical guidelines, appeals for debate on the curriculum were raised soon after
the 1970s curriculum report (15) and continue to be raised
sporadically (16). Thus, this exploratory study was undertaken to
assess what concepts tertiary-level organic chemistry educators
believe are important, core, or fundamental in organic chemistry,
and the misconceptions these educators observe in students.
Furthermore, these results have been used to: (i) determine whether
renewed discussion is required; and (ii) help to focus and orient
such a discussion if it is determined to be timely for the community.
Methodology
Participants and Setting
Subjects were solicited either in person or by electronic mail
to participate in this exploratory study. Twenty-three tertiarylevel organic chemistry educators participated, 6 females and
17 males, with one to 48 years of experience teaching organic
chemistry (average of 22 years, 74% with g10 years of experience)
at three colleges, one two-year state college and 17 universities
within the USA and one satellite campus on another continent.
The majority (17 of 23, 74%), were employed by ACS-accredited
institutions, all but one taught organic chemistry for majors, and
61% (14 of 23) also taught graduate organic chemistry at the time
of the study.
Data Collection and Analysis
Initially, 5 organic chemistry educators who could provide
a variety of perspectives on the teaching of organic chemistry,
based on their differing teaching styles, participated in semistructured interviews to provide a purposeful sampling (17) of
instructors. The interview protocol and preliminary results
obtained informed the conversion of the interview to a survey
protocol (administered via e-mail and contained in the supporting information) to continue data collection. Next, 18 additional
organic chemistry educators, solicited directly by the author or

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10.1021/ed1007266 Published on Web 02/08/2011

Research: Science and Education

Table 1. General Chemistry Concepts Educators Reported Reviewing
in Organic Chemistry Courses
Concepts

Number of Responses

Acid-Base Chemistry

18

Orbital Hybridization

11

Bonding

Lewis Dot Structures

3-D Structures

Polarity

Intermolecular Forces

Resonance Structures

Thermodynamics and Kinetics

who responded to online invitations to participate (18, 19),

completed the aforementioned surveys. Purposeful sampling was
continued through direct e-mail solicitation followed by participant self-selection via invitations posted on the Web site (18)
and listserv (19). Data were collected, after obtaining informed
consent from each participant, in the form of transcriptions of
semistructured interviews (20) and written responses to openended survey questions. Participants were asked to identify what
general chemistry concepts they review or reteach in undergraduate organic chemistry, the concepts they believe are fundamental to organic chemistry, organic chemistry topics students
find difficult, and the misconceptions they observe in students.
In solicitation and informed consent documents, Nakhleh's
definition of the term misconception, any concept that differs
from the commonly accepted scientific understanding (21), was
given as the interpretation intended for the study. Categorical or
thematic analysis was applied to the interview transcripts and
survey responses under the tradition of a basic or generic qualitative
study, to identify recurrent patterns in the form of themes or
categories (20). The identified themes related to the fundamental concepts of organic chemistry are additionally compared
to the two most recent ACS topical guides for undergraduate
organic chemistry.
Results
Most undergraduate organic chemistry courses have a general
chemistry prerequisite. Thus, organic chemistry educators expect
students to enter the course with an understanding of a number
of general chemistry concepts. However, the participants find
that they must review or reteach some of the general chemistry concepts they feel students will need in order to understand organic chemistry. On average, participants noted five
general chemistry concepts they typically review in organic
chemistry. Concepts noted by five or more participants
(g22%) are summarized in Table 1. Additional general chemistry concepts noted by more than one participant include:
electronegativity, equilibrium, mechanisms, and reaction coordinate diagrams.
All participants named concepts they considered fundamental to organic chemistry (five concepts on average). These
concepts overlapped between participants and with the ACS
guidelines (4, 5); however, the responses varied considerably.
Surprisingly, only one concept area, reaction mechanisms, was
cited by more than half (16 of 23, 70%) of the participants.
Additionally, only four concept areas were noted by more than

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one-third of the organic chemistry educator participants: correlation

between structure and properties (10 of 23, 43%), acid-base
chemistry (9 of 23, 39%), structure and bonding (9 of 23, 39%),
and functional group chemistry and properties (9 of 23, 39%).
Finally, two of the topic areas delineated by the ACS guidelines
for undergraduate organic chemistry at the time of this study
(Detailed Consideration of Polyfunctional Substances and Concepts in Molecular Recognition) were not mentioned by any of
the participants (5). The concepts noted by five or more
participants (g22%) as fundamental to organic chemistry are
summarized in Table 2. Additionally, fundamental concepts
noted by more than one participant include: equilibrium and
its effects, electronegativity, reaction coordinate and energy
diagrams, nucleophilicity and electrophilicity, synthesis, molecular orbital theory and its consequences, and kinetics versus
thermodynamics. More than one-third (35%, 8 of 23) of the
participants noted supplementary factors other than ACS-recommended fundamental organic chemistry concepts, such as
independent thought and formal operational thinking, the
language of chemistry, the real-world relevance of organic
chemistry, and focusing on understanding, not memorization.
Every participant also named organic chemistry topics that
consistently cause students difficulty. Difficult organic chemistry
concepts noted by five or more participants (g22%) are summarized in Table 3.
While one of the main goals of this project had been to learn
more about student misconceptions in organic chemistry, 9 of
the 23 participants (39%) were unable to provide any specific
misconceptions that they had seen in their students, and several
placed comments in the misconception area of the survey that
might be more accurately categorized as a difficult organic
chemistry concept. Several participants did not seem to believe
that their students held true misconceptions and instead noted
common student errors or just a particular point that a
particular student didn't master. However, more than 30 different student misconceptions were noted by 14 of the 23 (61%)
organic chemistry educators who participated. Misconceptions
noted by more than one participant include: carbon atoms
have more-than or less-than four bonds, electrons flow toward
negative or uncharged sites, resonance is a fast exchange of
electrons, resonance is an equilibrium, resonance states are
compounds that exist in real time, and hydroxide or alkoxide
ions can be present in reaction mechanisms carried out in
acidic solution (also noted in ref 22). Additionally, several
misconceptions noted by these 14 instructors have previously
been reported in the literature, including: bond breaking is
exothermic (23-25), hydrogen bonding is any bond involving
hydrogen (22, 26, 27), and methanol dissociates into CH3
and OH- (22).
Finally, the participants were asked to list which organic
chemistry concepts they felt were particularly important
for later chemistry learning. In this case, consensus among
instructors was minimal, with only four concepts noted by
five or more participants (g22%), as summarized in Table 4.
Additional organic chemistry concepts important for later
chemistry learning noted by more than one participant
include: functional groups, structure correlations with properties, major functional group reactions, nucleophilicity
and electrophilicity, polarity, electronegativity, 3-D structure
and molecular shapes, stereochemistry; and how organic
chemistry works.

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Table 2. Fundamental Organic Chemistry Concepts Cited by Organic Chemistry Educators
Fundamental Concepts

Number of Responses

Reaction Mechanismsa,b

16

Correlation between Structure and Properties/Reactivitya

10

Acid-Base Chemistrya,b
a

Structure and Bonding ; 3-D Nature of Molecules

Functional Groupsb (Functional Group Chemistry/Properties)a

Electron Delocalizationa/Resonance

Directly correlates with points in the ACS's Organic Chemistry Topical Supplement (5). b Directly correlates with topics in the current ACS Organic Chemistry
Supplement (4).

Table 3. Difficult Organic Chemistry Concepts Reported by Organic

Chemistry Educators
Concepts

Number of Responses

Reaction Mechanisms

15

Acid-Base Chemistry

12

Synthesis

Stereochemistry

Resonance (Electron Delocalization)

Molecular Orbital Theory

Spectroscopy

Polarity

SN1, SN2, E1, E2 Reactions

Curved-Arrow Formalism

Table 4. Organic Chemistry Concepts Cited as Important for Later

Chemistry Learning
Concepts

Number of Responses

Acid-Base Chemistry

Reaction Mechanisms

Structure-Reactivity

Kinetics

Discussion and Conclusions

This exploratory study of 23 tertiary-level organic chemistry
educators revealed instructor opinion in:
General chemistry concepts important for learning organic
chemistry
Which concepts the participants find fundamental or important
to undergraduate organic chemistry
Other factors that are important for success in organic chemistry
Which organic chemistry concepts students find difficult
What chemistry misconceptions undergraduate organic chemistry students have
Which organic chemistry concepts are important for later
chemistry learning

Interestingly, more consistency appeared across participants'

responses to which general chemistry concepts need to be
retaught than for any other question asked of the sampled
organic chemistry educators. In particular, 78% (18 of 23), the
largest number of participants who identified the same concept
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area for any question in the exploratory study, noted acid-base

chemistry as a typically reviewed topic from general chemistry. As
for concepts fundamental to organic chemistry, while some
overlap occurred with the participants' views and the guidelines
set forth by the ACS (4, 5), it is interesting that each participant
had quite different perspectives. No topic area was noted by all
participants as fundamental to undergraduate organic chemistry
and ultimately the participants' responses showed more variations than similarities. In addition, of the topic areas from the
ACS topical supplement to organic chemistry, only two participants noted the correlation of physical properties with molecular
structure and chemical kinetics, while the detailed consideration
of polyfunctional substances and concepts in molecular recognition were not mentioned by any of the participants. Furthermore, experimental techniques were absent from all but two
participants' responses, even though organic chemistry courses
are habitually accompanied by a mandatory organic laboratory
course. However, it is possible that the participants may not
have found the laboratory relevant to the questions being
asked.
The results of this study suggest that the ACS Organic
Subcommittee of the Curriculum Committee's assessment that
on the whole teachers of organic chemistry clearly agree on what
is important in the discipline may not hold true today (2). There
may be considerably more differences between individual instructors' presentation of undergraduate organic chemistry than
previously thought.
All participants noted multiple organic chemistry topics
that students consistently find difficult, but only 61% (14 of 23)
noted specific examples of chemistry misconceptions. While
more than 30 chemistry misconceptions were noted, some of
which have also been observed by researchers studying students
in other areas of chemistry, it was apparent that not all of the
study participants were necessarily aware of or actively seeking
out misconceptions in their students. It is possible that chemistry
educators fail to look for their students' misconceptions, as
students' misunderstandings may appear to be highly individualized on the surface. However, the results of ongoing research
with organic chemistry students (28), and phenomenographical
studies in a variety of content areas (for example, work referenced
in 29, 30), suggest that there may be a limited number of qualitatively different ways to understand a particular concept or
phenomenon. Thus, it is reasonable to suggest that the limited
number of different conceptions students have about organic
chemistry concepts not only can be discovered but they can also
be used to improve chemistry education. Knowledge of students'
conceptions and misconceptions is especially important from the
constructivist viewpoint, as students' conceptions and misconceptions

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Research: Science and Education

must be engaged during instruction in order for deep and correct

understanding to be achieved (31-43). Additionally, these
results suggest that new assessments need to be designed to elicit
students' explanations or descriptions of their conceptions.
Typical assessment approaches may not reveal students' underlying conceptions.
Finally, in contrast to general chemistry concepts important
for organic chemistry, the concepts the organic chemistry
educator participants considered important for later chemistry
learning had very little overlap. This result may be related to a
lack of consensus in the desired learning outcomes of introductory organic chemistry courses. The results presented here
provide a foundation for a more targeted discussion of the topic.
Overall, only one topic area, acid-base chemistry, consistently
appeared in the top three topics noted by participants. This
topic is indeed important, as acid-base chemistry is a fundamental concept for understanding organic chemistry at all
levels (4, 5, 44-46). Because this topic is clearly identified as a
critical learning outcome of undergraduate organic chemistry,
ongoing research has built upon this finding and the results from
a current study of undergraduate organic chemistry students'
conceptions of acid-base chemistry will be reported in due
course (28).
Acknowledgment
Qualitative research guidance from Maria Lahman, valuable
guidance and manuscript comments from Loretta Jones and
Laurel Schafer, and participants' contributions are gratefully
acknowledged.
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Supporting Information Available

Survey questions developed from the initial interview protocol.
This material is available via the Internet at http://pubs.acs.org.

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