JOURNAL OF RESEARCH IN SCIENCE TEACHING

VOL. 51, NO. 6, PP. 694713 (2014)

Research Article
Culturing Reality: How Organic Chemistry Graduate Students
Develop Into Practitioners
1

Gautam Bhattacharyya and George M. Bodner

1

Department of Chemistry, Clemson University, 363 Hunter Labs, Clemson,

South Carolina 29634-0973
2
Department of Chemistry, Purdue University, West Lafayette, Indiana
Received 21 January 2014; Accepted 8 June 2014

Abstract: Although one of the presumed aims of graduate training programs is to help students
develop into practitioners of their chosen fields, very little is known about how this transition occurs. In
the course of studying how graduate students learn to solve organic synthesis problems, we were able to
identify some of the key factors in the epistemic development from student to practitioner. Semistructured interviews were conducted with four first-year organic chemistry graduate students enrolled in
a course on organic synthesis and two third-year organic chemistry graduate students who were in the
process of preparing an original research proposal in organic synthesis as a component of their Ph.D. oral
qualifying exams. Three interconnected factors that fostered the students development into practicing
organic chemists were identified: (1) the students needed to perceive the material they were asked to learn
in the course lectures and in other interactions with the professor as real; (2) they needed to work on
authentic activities that provided concrete instruments for knowledge construction; and (3) the students
needed scaffolding with a more-knowledgeable other in the form of feedback on the authentic activity. #
2014 Wiley Periodicals, Inc. J Res Sci Teach 51: 694713, 2014
Keywords: communities of practice (CoP); constructivism; ethnomethodology; graduate education;
organic chemistry; organic synthesis; qualitative research; situated cognition

Recently, a commission appointed by the President of the American Chemical Society (ACS)
called for all doctoral programs to consider making substantive changes in their graduate and postdoctoral training programs ostensibly because there has been little change in these programs over
the past several decades (American Chemical Society, 2012). The structure of the research
experiences required of graduate students on their way toward a Ph.D. in chemistry is consistent
with a constructivist perspectiveknowledge is constructed in the mind of the learner (Bodner,
1986)and has been consistent with this perspective ever since graduate programs were created
more than 100 years ago. But the graduate-level courses that provide the foundation upon which the
Ph.D. program is built still involve a professor, serving as a content expert, delivering lectures to
students who sit and listen passively, doing no more than acting as the recipients of information. As
such, it is not surprising that the individuals who enroll in graduate courses approach the tasks
placed before them in these courses by behaving as students, rather than
The present address of Gautam Bhattacharyya is Department of Chemistry, Missouri State University,
Springfield, Missouri, 65897.
Correspondence to: G. Bhattacharyya; E-mail:
gautamb@missouristate.edu DOI 10.1002/tea.21157
Published online 3 July 2014 in Wiley Online Library (wileyonlinelibrary.com).
#
2014 Wiley
Periodicals, Inc.

DEVELOPING PRACTITIONERS OF CHEMISTRY

practicing chemists (Bhattacharyya & Bodner, 2005); they focus on what they believe will be
important for their exams and do what they believe is necessary to earn a good grade in the
course. The difference between the way graduate students tend to behave toward their
academic coursework and the way they approach their dissertation research interferes with
their development as practitioners who are capable of independently functioning in their
chosen field (Bhattacharyya & Bodner, 2005).
In order to gain insight into the process by which individuals enrolled in a graduate program
develop from behaving as students to acting as members of the community of practice (CoP) of
chemists, we carried out a study of organic chemistry graduate students specializing in the domain
of organic synthesis, the process by which organic chemists propose and then carry out the step-bystep sequence of chemical reactions necessary to synthesize complex organic compounds, such as
the compound in Figure 1, from simpler, readily available starting materials. Our use of the concept
of community of practice is consistent with Wengers definition of a CoP as a group of people who
share a concern, a set of problems, or a passion about a practice and who deepen their knowledge
and expertise by interacting on an ongoing basis (Wenger, 1998, 2000). Additionally, we will use
Wengers definition of practitioner as a member of a CoP, who, thereby, develops (1) [a] sense of
joint enterprise, or a commitment to competence in a specific domain; (2) relationships of
mutuality, or interacting with each other to produce a set of normative customs for group
membership; and (3) shared repertoire of resources, or tools that the entire community may use
(Wenger, 2000, p. 229).

Figure 1.

Spongistatin is a macrocyclic lactone with broad antifungal activity that was the subject of a total synthesis

proposed by a graduate student during the original proposal (O.P.) component of the Ph.D. program at Purdue.

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Becoming a synthetic organic chemist requires the development of two fundamentally

different but complementary skills: the ability to envision the step-by-step conversions
necessary to synthesize a target compound and the dexterity needed to carry out the
corresponding reactions in the laboratory. Proposing the synthesis of an organic compound
requires the chemist to employ a variety of problem-solving skills in a non-linear and recursive
fashion. Included among these skills are the ability to visualize the three-dimensional
structures of molecules from the two-dimensional line drawings used to represent these
structures, knowledge of the reactivity of each of the various functional groups present in the
molecular structure, knowledge of the various reactions of a given functional group that can be
used in a synthetic scheme, and the ability to predict the mechanismon the molecular scale
of the reactions being proposed in the synthetic scheme. Each of these skills, in turn, requires
the understanding of a variety of fundamental chemical principles. Thus, it is not surprising
that certain solutions to organic synthesis problems are described as elegant (Berson, 1999),
a term that has also been used to describe solutions to problems in mathematics, engineering,
and programming (May & Roberts, 2007).
This paper focuses on the results of a study of graduate students working within the
domain of organic synthesis that provided insight into both the process by which these students
began to evolve into practicing organic chemists and the factors that promoted this
development. As such, the study addresses some of the needs expressed in the recentlypublished report by the ACS Presidential Commission (2012) calling for the reform of graduate
student education in the chemical sciences.
Guiding Research Question
This study was done within the context of research on how graduate students pursuing a
Ph.D. in organic chemistry learn to solve organic synthesis problems. As such, it focused on
one particular research question:
How does the acculturation of graduate students into the CoP of practicing organic
chemists affect their approaches to solving organic synthesis problems?

Lewin (1948) defined acculturation as the process by which individuals adjust to the culture of
a dominant majority. Our focus on the process of acculturation agrees with the argument proposed
by Jacobson (1996) that practitioner development is linked to learning within a culture, as well as
the suggestion by Kozma, Chin, Russell, and Marx (2000) that . . . expertise is defined
dynamically as a continuing process of participation in a discourse community, rather than merely
as a particular set of problem solving skills and conceptual structures . . . (p. 40).

The nature of the research question mandated the use of a qualitative methodology
(Patton, 2002) based on a constant comparative, grounded theory approach to the data (Strauss
& Corbin, 1990). Rather than making a priori assumptions regarding the students experiences
(Marton, 1981), this approach allowed the researchers to learn from the participants about
issues that were most pertinent to them. Our research, therefore, adds to the expanding list of
qualitative studies on the learning of organic chemistry at the university level (Anderson &
Bodner, 2008; Bhattacharyya, 2006; Bhattacharyya & Bodner, 2005; Bowen, 1990; Bowen &
Bodner, 1991; Cartrette & Bodner, 2010; Cartrette & Mayo, 2011; Christian & Talanquer,
2012; Ferguson & Bodner, 2008; Grove & Bretz, 2010, 2012; Grove, Hershbarger, & Bretz,
2008; Henderleiter, Smart, Anderson, & Elian, 2001; Kraft, Strickland, & Bhattacharyya, 2010;
McClary & Talanquer, 2011; Raker & Towns, 2012a, 2012b; Rushton, Hardy, Gwaltney, &
Lewis, 2008; Strickland, Kraft, & Bhattacharyya, 2010).
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Research Frameworks
Students are rarely experts at solving organic synthesis problems by the end of their first
year of graduate work. Over the next few years in graduate school, they tend to develop into
proficient problem solvers in the absence of any explicit classroom instruction. As in many
other disciplines, the development of this expertise occurs primarily within the social learning
environment of the research group. Social learning that occurs among graduate students within
the context of their research groups may result from informal problem-solving sessions in the
research group, discussions with peers or with chemistry faculty outside of traditional
academic settings, reading and considering literature in their field of expertise, their
experiences while attending professional meetings, and the result of consulting their
predecessors laboratory notebooks and theses or dissertations. We propose, therefore, that the
development of problem-solving skills within the domain of organic synthesis is part of a
process of acculturation through social learning into the organic chemists CoP.
While acculturation is inherently a social process, it is ultimately the individual who does
the learning and who matures as a problem solver. We therefore chose a combination of
constructivism and situated cognition as the theoretical framework for this study and
ethnomethodology as the methodological framework that guided the collection and analysis of
the data. These frameworks allowed us to probe the individuals growth in a social context,
thereby accounting for the differences that arise among individuals in a common environment.
The choice of the constructivist theory of knowledge as part of the theoretical framework
was influenced by our interest in studying the meaning-making that occurs within individuals.
More precisely, we adopted a radical constructivist orientation in which learners construct
knowledge based on their perceptions of reality (von Glasersfeld, 1989). Learning, as such, is
presumed not to involve finding the truth; rather, it is about creating knowledge that is viable
in the world (Bodner, Klobuchar, & Geelan, 2001). von Glasersfeld (1989) argued that it is
during the process of establishing viability that social interactions become critical:
Then, if a particular prediction we have made concerning an action or reaction of
another turns out to be corroborated by what the other does, this adds a second level of
viability to our scheme; and this second level of viability strengthens the experiential
reality we have constructed (p. 131).

Not only is learning in the context of a social setting compatible with radical constructivism,
von Glaserfelds quote suggests that is a significant part of the knowledge construction process.

Brown, Collins, and Duguid (1989) introduced the term situated cognition by arguing that
learning is indexed, or inextricably linked, to the situation in which it is constructed. Thus, the
development of knowledge intrinsically implies the ability to use it in relevant situations. This
view of the learning process implies that concepts are dynamic entities in a state of constant
evolution, developing alongside new situations encountered by the learner. As such, situated
cognition assumes that knowledge, even conceptual knowledge, should be viewed as a tool
rather than as an abstract object. Furthermore, learning is considered to be a process that
acculturates the learner into a community of practice.
Framing a study in a social learning setting from a radical constructivist perspective may
appear, on the surface, to be a perplexing choice. However, Cobb (1994) provided a link between
constructivism and situated cognition by noting that situated cognition explains the circumstances
under which learning may occur, whereas constructivism explains the process by which the learning
occurs in that situation. The result of combining constructivism and situated cognition is a
theoretical framework that emphasizes the importance of having individuals actively engaged in
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authentic activities in order to develop knowledge that can be transferred from an academic
context to real-world situations that arise after the individual leaves the classroom.
Methodological Framework
The research paradigm that guided this study was ethnomethodology, which provides a
lens for understanding how members of a group make sense of their routine activities (Patton,
2002). Ethnomethodology is based on the notion that the members of a group or culture the
so-called actors. . . organize and render observable the features of society and social
settings through descriptive accounts (Leiter, 1980, p. 161). These descriptive accounts are
the backbone of ethnomethodology because they define the boundaries of membership as
members of a group exchange accounts, or communicate, under the auspices of the et cetera
principle. The et cetera principle is a recognition that people never can say explicitly and
completely what they mean but can rely on each other to do any ordinary filling in (Brandt,
1992, p. 321). An actor attains membership in the group when they are able to do the filling in.
Ethnomethodology was an appropriate lens for this study because synthetic organic
chemists represent a CoP (Wenger, 1998, 2000) that routinely uses language and tools that are
unique to this domain of chemistry. These aspects are specialized enough that a content expert
from another sub-discipline of chemistry would find it difficult to participate in a discussion
among synthetic chemists. One aspect of the specialist language of synthetic chemistry is the
existence of named reactions, such as Michael addition, DielsAlder cycloaddition, or Wittig
reaction. The specificity of this language can be illustrated by noting that a frequently cited
index (ONeil, Heckelman, Koch, & Roman, 2006) lists 450 named reactions that denote ideas
and concepts that only a practitioner of the field could appreciate. The simple phrase Wittig
reaction, for example, would evoke images in the mind of a practicing organic chemist of
typical starting materials and the products obtained from the reaction, the mechanism of the
reaction, the conditions by which a specific olefin stereochemistry might be obtained, as well
as a set of congener reactions such as the Horner or WadsworthEmmons reactions.
Another specialized aspect of organic chemistry that leads practitioners of this field to
constitute a CoP is a pair of problem-solving techniques whose use is exclusive to the field:
retrosynthetic analysis and the arrow-pushing formalism. Retrosynthesis (Corey & Cheng, 1989) is
an analysis technique organic chemists use when solving synthesis problems that involves working
backwards, often step-by-step, from a target molecule into simpler precursors from which it can be
made. The arrow-pushing formalism is a convention used by organic chemists to describe the stepby-step mechanism at the molecular level by which reactions occur.

Less familiar features that are unique to organic synthesis include the role that the
chemistry literature plays, the manner in which molecules are represented, and the aspects of a
reaction that are given importance. The tendency for organic chemists to focus on only certain
components of the reaction might be illustrated by noting that it is rare for them to write a
balanced equation to represent a reaction; only the important components of the reaction would
traditionally be indicated. As another example, it is common for synthetic organic chemists to
use laboratory protocols found in the scholarly literature as much as seven or eight decades
ago. This use of older literature for experimental set-ups is far less common in most of the
other sub-disciplines of chemistry. Additionally, consider the differences in commonly-used
databases. Organic chemists, particularly those in the synthesis field, rely heavily on Beilstein,
whereas inorganic chemists use Gmelin (It is only since 2010 that these two have been
packaged together as an online database called Reaxys, http://www.elsevier.com/online-tools/
reaxys).
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Methods
Participants and Setting
Purposeful sampling (Patton, 2002) was used to select participants for this study. Since we
were trying to understand how the synthetic problem-solving skills of graduate students
develop as they become progressively more immersed in the organic chemistry CoP, we
recruited participants from graduate students working in research groups in the organic
division of the Department of Chemistry at Purdue University whose primary focus was
synthetic chemistry. These research groups could be considered typical synthetic organic
groups in that they all had a combination of students working on reaction methodologythat
is, the development of single reaction stepsor total synthesis which was described earlier.
Two groups of participants were recruited: first-year graduate students enrolled in a graduatelevel course on organic synthesis and third-year graduate students from organic synthesis research
groups working on a multi-step synthesis upon which to base their Original Proposal (O.P.), a
requirement for Ph.D. candidacy in the Department of Chemistry. The students voluntarily agreed to
participate and received no tangible compensation for their participation. To protect the participants
confidentiality, they are referred to by the pseudonyms Quincy, Victor, William, and Zachary for the
first-year participants, and Andrew and Benjamin for the third-year participants. All of the
participants in this study were male. This was not a result of any explicit decisions made by the
researchers, but a reflection of the pool of graduate students available at the time of the recruitment.
The specific reasons are discussed in the respective sub-sections below.
First-Year Students. All 15 first-year students in a graduate-level course on organic synthesis
were solicited to participate in this study during the second semester of the 20022003 academic
year. Of this groupwhich represented the entire organic chemistry cohort for that years entering
classonly two were women. One could not join the study due to a conflict of interest (she was
also a member of the Bodner research group) and the other was foreign-trained. Students from
foreign countries were excluded from the sample population because we wanted to study the
problem-solving performance of graduate students with minimal prior exposure to the culture of
organic chemistry and the foreign-educated students enrolled in the organic synthesis course all had
an M.S. degree in organic chemistry. The four first-year graduate students who enrolled were all
recent graduates of B.S. programs in chemistry from an American college or university.

The graduate-level course from which first-year graduate students were recruited is
described as an advanced treatment of methods for preparing major types of organic
functionalities and bonds, stressing stereochemical control and involving mechanisms for
understanding the reactions employed. The course was designed for first-year graduate
students pursuing Ph.D. degrees in organic chemistry and was taught by the departments
leading authority on organic synthesis.
The course met three times a week for 50-min lectures delivered by the professor. The students
were given a set of printed lecture notes before they started any major topic. These notes contained
reaction schemes and structures reproduced from articles from the primary literature in the area of
organic synthesis. There was no textbook for the course, although the professor strongly
recommended Bogers (1999) notes on organic synthesis. The students were required to read all
synthetically-related communications in the Journal of the American Chemical Society and all of
the articles in Organic Letters that appeared during the semester in which they were enrolled in the
course. The students were given a handout that included 25 of the most commonly used named
reactions that built on the traditional reactions introduced in the undergraduate organic chemistry
course with which students were assumed to be familiar. This handout included examples of
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typical starting materials, reagents, and products for each reaction as well as the mechanism of
the reaction.
The students were evaluated through two homework assignments, three exams, and one
semester-long project. The homework assignments contained four problems, at least one of
which was a short synthesis task and represented a total of one-sixth of the course grade. The
three exams, which represented half of the total points in the course, included questions in
which the students were given the name of a reaction and expected to provide appropriate
starting materials, reagents, and products, as well as questions based on reactions from the
required journal reading for which the students were expected to generate a mechanism.
A third of the total course grade was based on a semester-long project that involved
proposing a total synthesis of one of the twenty compounds shown in Figure 2 whose synthesis
had not been reported in the literature. The students were required to submit a first draft of
their total synthesis at the beginning of the ninth week of class and the final draft 6 weeks later.
The submitted work was to be clearly presented using a structure-drawing program such as
ChemDraw and all commentary was to be written with a word-processing program. Although
the first draft was not graded by the professor, he provided annotated feedback on potential
problems in the synthetic route being proposed.
Third-Year Students. Two third-year graduate students were recruited for the second phase
of this study during the Fall semester of 2003. These participants were in the process of
producing an original research proposal (O.P.) based on a total synthesis of an organic
compound that would be defended in the oral component of their Ph.D. candidacy exams. Both
students were in organic synthesis research groups and had successfully completed the organic
synthesis course in which the first-year students were enrolled. We cannot show the target
molecules chosen by the participants in this phase of the study because participant
confidentially would immediately be lost. To illustrate the complexity of the tasks these
students faced, an example of the target molecule proposed for a total synthesis O.P. by a
graduate student who was not a participant in this study is shown in Figure 1.
Although there were about a dozen other third-year students who were also working on
their O.P.s during this time, Andrew and Benjamin were the only two preparing total synthesis
proposals. The choice made by the other students was a reflection of their ultimate career
interests of applying their skills in organic synthesis to solving problems in the biomedical
and/or material sciences. Once again, only males were available for this study.
Data Collection
The data for this study included transcripts of audio-taped interviews with the students, the
written artifactsincluding scratch workgenerated by the participants as they worked on the
project outside of interview sessions, and the interviewers field notes taken during the interviews.
Each first-year participant was interviewed between eight and ten times. Each third-year participant
was interviewed between six and eight times, which reflected the time each third-year student spent
from the initial conception of the idea for the O.P. to post-examination debriefing after the O.P. was
defended. The slight variation in total number of interviews among the first-year participants
resulted from cancellations by them due to illness or other personal matters.
First-Year Students. Since the essence of ethnomethodology is to uncover how members make
sense of their routine activities, the interviews were built around the students activities in the
course. During the first 6 weeks of the course, the students focused their efforts on studying for the
class and on selecting potential target molecules from the compounds shown in Figure 2.
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DEVELOPING PRACTITIONERS OF CHEMISTRY

Figure 2. Possible target molecules for the semester-long project.

Early interviews therefore focused on how the participants studied for the course and what they
felt they gained from the course. As the semester progressed, the focus of the interviews shifted
to the participants work on their total synthesis projects. Keeping in line with the accounting
for aspect of ethnomethodology, the participants were told they would be asked to explain
and/or justify each maneuver in their problem solving processes. The final interviewat the
end of the semester, after the total synthesis projects had been returned by the professor and the
final course grades had been assignedwas used to solicit the participants reflections on the
course, the total synthesis project, and the professors feedback on their projects. It also
provided an opportunity for member checking (Ely, 1991; Lincoln & Guba, 1985; Seale,
1998).
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Third-Year Students. The third-year students were asked to contact the interviewer once they
had begun the process of selecting the target molecule for their original proposal, but before they
started any other work on their O.P. The first interview with the third-year students consisted of
background questions that probed the participants experience with organic synthesis and project
questions that probed the molecule they chose; why they chose it; the process by which they
selected that particular molecule; the resources they used to find a target molecule; the role that
other members of the graduate program might have played in their selection of a target molecule;
and the synthetic challenges they perceived they would face in proposing a synthetic pathway that
would produce the target molecule. The interviewer then met weekly with each participant until
they submitted their O.P.s to elicit the thought processes they used while working on their
syntheses. The last interview was conducted after the participants had defended their O.P. to get the
participants reflections on the process and reactions to feedback they received from their examining
committees, and to allow them, during a member-checking phase, to comment on our preliminary
analysis of their earlier interviews.

Data Analysis
Because the goal of this work was to understand the meaning-making processes of
individuals in a culturally-embedded situation, the unit of analysis for this study was the
individual. The three sources of datatranscripts, researcher notes, and artifactsfor each
participant were repeatedly examined to establish a chronology of events for each individual.
Chronology was deemed important because the analysis of when an individual acts can be as
important as the act itself in an ethnomethodological approach (Brandt, 1992). These
chronologies provided the basis for writing case records for each participant.
The case records were then examined to generate emergent themes for each of the sample
populationsthe first-year and third-year studentsand these themes were then compared to
find similarities and differences in the problem-solving approaches of the two groups. An
overarching theme emerged from the comparison of the two data sets that summarized the
experiences of all participants and led to the final conclusions of the study. Although making
comparisons between such small groups may appear unusual, in their case study of two
middle-school students, Rose and Calabrese Barton (2012) noted:
. . . we use these findings to build claims about how and why framing matters, and the
tools others may use to conduct similar kind of work. Thus, as case study, we intend for
these results to yield the kind of context-dependent knowledge necessary for
understanding the nuanced ways in which individuals make sense of and make decisions
about socioscientific issues (p.547).

As such, it was by using the context-dependent knowledge of our participants that we

reached the conclusions of this study.
Five major actions were taken to assure validity in this study. First, the conclusions that were
developed were grounded in the data (Patton, 2002). Second, member-checking interviews were
conducted with each participant, during which they were asked to reflect on conclusions from the
analysis of the earlier interviews. Third, the study was done in a naturalistic setting; the participants
worked on problems they chose that fulfilled certain aspects of the requirements of their Ph.D.
program, rather than artificial problems created by the researchers. Furthermore, the participants
worked at their own pace, rather than under conditions in which an arbitrary time limit was imposed
by the researchers. Fourth, because the final conclusions were drawn from comparing groups rather
than individuals, the effects of individual differences were lessened.
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DEVELOPING PRACTITIONERS OF CHEMISTRY

Fifth, after the data were analyzed by the first author, they were discussed with the second author
and colleagues in the chemical education program familiar with organic synthesis and colleagues
from the organic chemistry division to compare the extent to which the authors conclusions were
consistent with these professors experiences with Ph.D. students at that institution.
As previously noted, all of the participants of this study were male. Although it is impossible to
predict how the inclusion of women may have affected the results we can speak to one of the more
important aspects of problem solving in organic chemistryspatial ability (Bodner & Pribyl, 1987;
Carter, LaRussa, & Bodner, 1987). Despite decades of studies suggesting that women have lower
spatial ability than men, in their meta-analysis of the spatial ability literature Newcombe and Stieff
(2012) concluded that this purported superiority is a myth. As such, gender might not affect one of
the more important attributes of problem solving by organic chemists.

Results
First-Year Students
The story of the first-year students is one of remarkable evolution. When the semester began,
the participants behaved like typical students; their main goal was to get a good grade in the class.
By the end of the term these participants exhibited some of the behaviors of early-career organic
chemists. Not only had they begun using some of the problem-solving techniques of synthetic
organic chemistry, they had also begun to construct meaning behind these skills. By the end of the
semester, they were more than mere problem solvers struggling with academic problems; they had
begun to think about organic synthesis from the perspective of practicing organic chemists.

Cross-case analysis of the data collected from the first-year participants suggested that the
participants began the term accepting on faith that the subject matter covered in the synthetic
organic chemistry course was going to be useful, but they were not sure how or why. This had
an effect on what they paid attention to in class and how they studied for their course,
concentrating on what they thought would help them do well on tests. Consider the following
quote from an interview conducted with Quincy early in the semester.
When I listen to a lecture I like pick out the points that . . . I think the professor would
ask on a test. . . . So like Ill read something that I think that could be asked a question
over. And then Ill focus on that mainly.

Like Quincy, the other first-year students in this study began the course acting, as one
would expect a traditional student to act: They were concerned with earning a good grade; not
learning synthetic organic chemistry. As a result, the participants all reported that they began
by trying to memorize their way through the course. Their approach to the course on organic
synthesis was therefore similar to the approach that undergraduates, taking organic chemistry
for the first time, often take (Bodner & Weaver, 2008).
The flaws in the participants approach of trying to memorize the material in the course
became clear to them when the first drafts of their projects were returned by the professor.
Although the project served many purposes, its primary role was that of a disequilibrating tool.
Consider the effect on Victors approach to retrosynthetic analysis, for example, that resulted
from working on the semester-long project.
. . . being forced to go through a project like this kind of makes you realizewhat the important
things are . . . I mean . . . they talked about retrosynthetic analysis in sophomore organic
chemistry and I said, Great. Whatever. But . . . I found that when youre dealing with a

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complex problem, that can be very helpful. . . .and I kind of just had to come up to that
conclusion on my own, um because it just seems to work better.

The interview data suggested that the semester-long project represented the first step in
Strike and Posners (1992) model of conceptual change; it represented an event that the firstyear students could not reconcile using existing knowledge.
As they continued their work on their final projects, organic chemistry became real for
these students; it was no longer a collection of abstract principles to be memorized. Zachary,
for example, commented on the effect that reading the literature as part of his work on the
semester-long synthesis project had on his sense of being immersed in the culture of organic
chemistry for the first time.
. . . I think doing this synthesis project has forced me to, you know Im reading so much stuff,
you know. You read all the stuff that chemists are saying and all of a sudden you just start to
think how they, they write. . . . And so I think just reading their words has really helped me to,
to realize what its, what I need to do to become a good chemist. And so they always are
talking about yields and oh, you could run into this problem here, and you got to pay attention
to this and that. So, you know, keep an eye out for things. Dont just focus on one functional
group because if youre doing chemistry on that functional group, you could have something
else hanging out here that is gonna get affected by that. So I think its just the way that they
speak in these journals really has educated me a lot.

For Quincy, it was the professors lectures on examples of synthetic chemistry done at
pharmaceutical companies that made him reflect on what was necessary to succeed as a
synthetic organic chemist. For William, interactions with group members in the lab and during
group meetings helped him construct meaning for some of the problem-solving techniques
that, until then, had been merely topics of academic interest.
There was something about the overall make-up of the term-long project that made the
process of proposing syntheses seem more real to the research participants than similar
assignments in their undergraduate classes or even in this courses homework. The students
were given synthesis tasks in their homework for which they could not simply go to the library
to look up cookbook syntheses. However, those homework tasks did not have a transformative
effect as explained by Quincy
Um, Id say a little bit [referring to the syntheses tasks in the homework]. Not that much,
because for those we had such a short amount of time, and I was so busy, I was more
worried about just getting it done and getting it out. And I didnt think nearly as much
into those as I did for this.

Later in that interview, Quincy described the transformative effect of the project:
Um, I think it happened; well through this project because now Im actually thinking
about, OK what if I was actually doing a project, what would I be worrying about?
Whereas before I was more thinking about, OK, if Im reading this what would he ask
on a test? Where now this is more practical, more real life. Um, what am I going to be
doing? What do I need to worry about? Whereas before I thinking I was thinking more,
Whats he gonna ask me on tests? kind of things.

There were at least three significant differences in the homework synthesis problems when
compared to that of the term-long project. First, the complexity of the target molecules of the termJournal of Research in
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DEVELOPING PRACTITIONERS OF CHEMISTRY

long project (shown in Figure 2) approached that of molecules whose syntheses were reported
in the chemical literature. Second, each student had his own unique target and, thus, ownership
over the project. Third, the length of time on which they worked on the project more closely
resembled the authenticity of problems faced in the research lab setting.
The interview transcripts clearly indicated that the perception of realness transformed
the students into more active learners, who began to construct meaning regarding the problemsolving techniques commonly used by practicing synthetic organic chemists. Consider
retrosynthetic analysis (Corey & Cheng, 1989), for example, which is fundamental to
practicing synthetic chemists as they plan a synthesis. This technique depends on the ability to
perceive structural features in a target molecule that can be manipulated in a reverse-synthetic
senseworking backward from the final answerto deduce the optimum starting materials
for a synthetic scheme. Because the semester-long synthesis project was viewed as being
real, rather than just another end-of-chapter textbook exercise, William adopted a far more
sophisticated method of retrosynthetic analysis than he had previously used. He also
recognized that his use of this technique brought him closer to the thought process of a
practicing organic chemist.
It was just hard for me to see the retrosynthesis. And its kinda, at first I didnt really
think they were that useful. I, I didnt really spend enough time to really think about what
I could get out of it. And then, and then I just tried making the molecule without really
thinking about it chemically.

Continued exposure to the culture of organic chemistry provided by the environment of

the research group helped catalyzed the students construction of knowledge within the field of
organic chemistry. Consider the following comment by Zachary about a weekly group meeting
with his research advisor and other members of the research group:
Like the other night in . . . Thursday night group meetings, um there was a mechanism
that had a Swern oxidation and then a Corey-Fuchs reaction, so I went, Wow, I know
those things. I can kind offigure that stuff out.

The Swern oxidation and the Corey-Fuchs reactions were two of the 25 commonly used
named reactions the students were explicitly required to learn in the synthetic organic course.
An important feature of the epistemic development of the students in this study was the fact
that the professor chose reactions for them to learn that were so widely used that the students
were likely to encounter them in their out-of-class activities.
In addition to serving as a vehicle for disequilibration, the semester-long synthesis project
also served as a vehicle for meaning construction, which occurred by two, linked, aspects.
Consider Zacharys experiences, for example. In Zacharys first draft he had a step in which he
wanted to use a b-hydroxyaldehyde as a reactant, as shown in Figure 3a. In his feedback, the
professor wrote hemiacetal formation above the arrow that described this step in Zacharys
synthesis, indicating that the reaction Zachary had proposed would produce the undesired
hemiacetal by-product shown in Figure 3b.
It was apparent from the interview transcript that this simple suggestion had a transforming
effect on Zacharys approach to project. Not only did he change his route for this part of the project,
he began noting the possibility of unwanted side-reactions while analyzing other sections of his
project. One aspect of this interaction that helped Zachary in his meaning construction was learning
about intramolecular hemiacetal formation in the concrete framework of a molecule whose reaction
chemistry was important to him, rather than in the abstract context of a classroom
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Figure 3. (A) The intended reaction drawn by Zachary in the first draft of his synthetic proposal. (B) A possible side-reaction
the compound could undergo suggested in feedback from the professor.

or textbook exercise. Another aspect of this interaction revolved around Zacharys need for the
professors feedback to realize that a potential problem existed, let alone that it needed to be
solved. This feedback was an example of a scaffolding interaction with a more knowledgeable
other (Vygotsky, 1978) that provided Zachary with the framework upon which he could learn
about the intramolecular reactivity of polyfunctional compounds.
Third-Year Students. The third-year students demonstrated the epistemic development and
increased sophistication in their work that one might expect. This evolution was apparent in
their ability to use the problem-solving techniques of organic chemistry. Whereas the first-year
students based their attempts at retrosynthetic analysis on surface-level features in the structure
of the molecule, the third-year students conducted an extensive retrosynthetic analysis of their
target molecules in which they examined multiple routes to the product.
There were notable aspects of the experiences of the third-year students that deserve
attention. First, the interview data clearly indicated that the Ph.D. dissertation projects in which
these students were involved had an effect on their perspective of what it means to be a
practicing chemist that was analogous to the role the semester-long synthesis project had on the
first-year students enrolled in the organic synthesis course. Consider Benjamins explanation of
the way his dissertation research dictated what he read in the literature and what he paid
attention to in the world of chemistry.
. . . when I search the literature . . . I dont usually read the full articles. Ill just go to the
communications. And its nice now cause they have pictures. And so you can, you dont
actually have to read the title. You can just look at the reactions. And then . . . if its a total
synthesis I might look at it and see if theres any kind of interesting reactions that they did.

. . . Usually Im looking for stuff related to my [research] project . . . Make sure

somebodys not doing the same thing that I am. Or just something that looks generally
interesting that hasnt been done before.

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The interview data indicated that scaffolding interactions were still an important feature of the
problem-solving process among the third-year participants. As Andrew suggested, these interactions
helped him overcome his bias toward using a particular reaction to achieve a transformation along
the route between the starting material and the product. His ability to consider multiple paths in a
synthesis was a result of discussions with his peers, who had ideas about other ways of getting
around a particular step in the synthesis that was giving him trouble.

The difference between the first-year and third-year students in their development as
practicing chemists was the result of a change in the individuals with whom scaffolding
interactions occurred. For the third-year students, these interactions occurred primarily among
their peers, rather than authority figures such as their professors. This shift is indicative of
practitioner-like behavior that results from immersion in the culture because it puts a member
of the CoP in touch with other individuals who may be more knowledgeable about certain
aspects of the field.
First-Year Versus Third-Year Students
As would be expected, the third-year students use of the problem-solving techniques of
organic chemistry was more developed than that of the first-year students. There were three
major changes that had occurred in their approach to solving organic synthesis problems that
reflected the greater practitioner-like behavior of the third-year students.
In earlier work with first-year graduate students we noted that organic synthesis seemed to
be a paper-and-pencil exercise, with little (if any) consideration of the students experiences
carrying out reactions in the lab (Bhattacharyya & Bodner, 2005; Bowen & Bodner, 1991). The
data collected from interviews with the third-year students in this study clearly indicated that
the synthetic route being outlined on paper by these students was inextricably linked to their
understanding of the processes that would have to be carried out in the lab. Consider the
following comment made by Benjamin:
Fewer steps with the best yield. Less work, basically, in the lab sense. . . . I mean on
paper, the difference between thirty or forty steps is only like two pages. But in reality
thats probably over a month to 2 months worth of work, if not more than that, especially
if its near the end of the synthesis.

Although Benjamin was more likely to explicitly articulate the connection between the
synthesis as written on paper and its execution in the laboratory, Andrews quest for an
elegant and therefore efficient synthetic scheme was indicative of a similar association. In
trying to develop a one-pot reaction that would achieve several transformations, for example,
Andrew was attempting to shorten his synthetic route by several steps.
The third-year students also exhibited evidence of significant epistemological development
within the context of synthetic chemistry. Whereas the first-year students seemed unable to critically
evaluate data in papers from the primary literature when they began the organic synthesis course,
the third-year students demonstrated an ability to appraise the quality of the data in a journal article
without trusting the authors on faith. These students had come to realize that the quality of the
science reported in a given publication was a reflection of the community that had approved it.
Thus, articles in better journals were deemed more trustworthy because a more qualified group of
individuals had participated in their social construction.

Additionally, the third-year students considered reactions from a mechanistic standpoint.

This aspect became evident as they spoke about evaluating the synthetic steps in their schemes.
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Andrew noted that just seeing the results of the retrosynthetic analysis did not enable him to
decide whether the anticipated transformations could occur in the synthetic direction; he could
only make that assessment by envisioning the reactions mechanisms. Furthermore, Andrew
used extensive computer-based molecular modeling techniques to ensure that each
intermediate would be in a conformation that would preferentially produce his desired product.
Similarly, Benjamin went through the mechanisms of all of the key steps in his proposed
synthesis in a step-wise manner. Together, these data suggest that the third-year students were
in the leastattempting to conceptualize reactions on a molecular level. This is significant
because it is one of the key characteristics of in the development of practicing organic chemists
The first-year students, in contrast, did little or no overall analysis of their synthetic proposals;
they seemed content to just have one.
Discussion
The first-year participants in our study were successful graduate students enrolled in a course
that was central to their field of study. Yet, they began the semester by trying to memorize their way
through the course on organic synthesis; behaving in much the same way as undergraduates in the
traditional sophomore-level course rather than as practitioners-in-training. This can be understood
by noting that these individuals possessed no overarching framework for meaning-making in the
field they were studying. As a result, they did not know what to study, or how to study for this
course. They resorted to memorization as a defense mechanisma strategy that may have served
them well in their first exposure to organic chemistryto help them survive their graduate course.
Not knowing how to study or what to study is a constant problem that students face when they
undertake coursework at all levels of the educational system. The traditional approach to curriculum
development (Schwab, 1969), in general, and/or the design of classroom instruction in a particular
course has been based on the assumption that the epistemological development of learners does not
depend on the domain in which the learning occurs. This assumption can be seen, for example, in
Perrys (1970) seminal treatise on the intellectual development of college-aged males. Subsequent
studies (Carey & Smith, 1993; Duschl & Grandy, 2013), however, suggest the need for the
reinterpretation of epistemological development from a domain-specific model.

The research reported in this paper supports a model of domain-specific epistemological

development (Samarapungavan, Westby, & Bodner, 2006). The first-year students in this study
had read vast volumes of textbook material by the time they began graduate school. In the first
half of the organic synthesis course, however, it was apparent that they did not know how to
read a journal article in their field of specialization, synthetic organic chemistry. They paid no
attention to factors such as yield and stereoselectivity, for example, because they were unaware
that they were supposed to pay attention to such items.
The epistemic development of the first-year students that occurred as a result of their
enrollment in the organic synthesis course was the result of three aspects of the course. First,
course materials such as lectures on reactions from the current literature and synthesis research
in the pharmaceutical industry helped the participants connect with the subject outside of the
classroom setting; thereby making it real in their minds. Second, they encountered a task,
namely the term-long project, which made organic chemistry real because the target
molecules approached the complexity of those in the literature. Additionally, each student
worked on a unique molecule, creating a sense of ownership not felt towards the target
molecules in the homework assignments. Third, the feedback they received on the first draft of
their term project that helped them recognize that problem-solving activities, when applied to a
real problem, required them to attend to the prospect of what might occur when their
synthesis was actually carried out in the laboratory.
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The perception of realness eventually helped the participants in this study to cease
behaving like students of organic chemistry and begin behaving like practicing organic
chemists because, for the first time, they could see themselves in that role. Their attitude
toward studying changed radically because the material had suddenly become useful. Rather
than studying for an exam, they viewed the material as something that needed to be learned as
part of their pursuit of a career as practicing organic chemists. During the course of the
semester, the participants in this study began to realize that the material in this course would be
useful in their careers; the course was not just a way to fulfill one of the requirements for their
doctoral degree. We propose that the first-year graduate students view of the utility of the
course content by the end of the semester played an important role in the first steps toward
their evolution into practicing organic chemists in much the same way that Strike and Posners
(1992) analysis of the role of fruitfulness plays in their theory of conceptual change.
Once the first-year participants changed their perception of the task involved in learning
organic chemistry, they became more active learners. They did not simply apply some of the
key problem-solving techniques of synthetic organic chemistry in a random, algorithmic sense;
they constructed meaning around the framework of these techniques that allowed them to
begin the process of constructing robust and transferable knowledge within the domain of
synthetic organic chemistry.
Working on the course project was critical for the first-year participants for two reasons.
First, they were working on a task that held meaning for them because their choice of a target
molecule sparked an element of intellectual interest in the task upon which they were working.
Second, the project provided a scaffold for knowledge construction. They were no longer
learning chemistry in an arbitrary or abstract context; they were learning it in a context that
was relevant to their immediate and future career goals.
Finally, the professors feedbackespecially on the term-long projectwas an integral
component of the students knowledge construction and was an archetypal example of a
Vygotskian scaffolding with a more-knowledgeable other (Vygotsky, 1978). One of the
significant difficulties with learning to propose syntheses is that there are few, if any,
indications from ones completed reaction sequence to suggest potential mistakes. Not only
was the professors feedback pivotal in helping students identify errors, but it was equally
important in bringing new, relevant content to the students awareness. The latter was
expressed by Quincy in the following quote:
Just looking at the stuff and he would say, I, I would ask him questions like, you know,
Do you think this would work? or Im looking for a synthesis that would do this. and
then hed, he would give feedback on, Yeah I think Ive heard of this but you have to
watch out for such and such. Like I was looking at converting a diol to, the primary one
to an aldehyde but not the secondary. He said it can be done but, you have to look for
reagents that cleave off the diol completely. Um, so I think that helped.

The epistemic development exhibited by the third-year students was a consequence of their
continued immersion in the culture of organic chemistry. Unlike the results of prior work with firstyear graduate students (Bhattacharyya & Bodner, 2005; Bowen & Bodner, 1991), these students
were able to connect what they wrote on paper to experimental procedures carried out in the lab. As
Benjamin suggested, attempts to repeat published work provided a clear lesson that what one finds
in the primary literature of the field is not necessarily immutable truth. Furthermore, the arduous
nature of the synthetic lab had also impressed upon the third-year students the knowledge that each
arrow in a multi-step synthetic pathway can represent weeks of work. These
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results, therefore, indicate how further engagement in the CoP helped the third-year
participants maintain their practitioner behaviors instead of regressing to student-like ones.
The source of the observed difference in the abilities of members of the two groups to
conceptualize reactions on a molecular level, using the traditional mechanistic thought process
characteristic of the work of practicing organic chemists, was less clear. One possibility is that
thinking mechanistically on the molecular level requires a deeper understanding of the
fundamental principles and concepts upon which the reactions are based than is held by firstyear students. For the first-year students, most of these principles were examples of a
phenomenon that Vygotsky (1997) called verbalismsa parrot-like repetition of words
simulating knowledge of the corresponding concepts but actually covering up a vacuum (p.
150). This result is consistent with previous research with a comparable group of participants
for whom the fundamental concepts of organic chemistry were, indeed, verbalisms
(Bhattacharyya & Bodner, 2005).
Implications
Although the research described in this paper focused on a group of graduate students in a
specific sub-discipline of chemistry, the three factors that helped the participants evolve from
student-like behaviors to practitioner-like ones may be considered as generalizable guidelines
to help students similarly develop in other disciplines. Additionally, there are applications to
undergraduate instruction, which are discussed in the following paragraphs.
Well-meaning educators often use real-world examples of scientific concepts to engage
students in content of the courses they teach. The instructors goals for using real-world
examples include motivating students to learn the material better, and consequently perform
better in the course. The results of our study are consistent with the assumption that the
perception of realness and the consequent motivation to learn are personal constructions of
the learners, that is, others cannot transfer either to learners. The circumstances that triggered
the first-year graduate students to perceive the course material as real were the result of
completely different events. Quincy, for example, was particularly drawn to the lectures on
pharmaceutical design and synthesis because he had decided prior to instruction that he wanted
to be a chemist in the pharmaceutical industry. For William, this shift occurred while working
on a class assignment, whereas for Zachary it was the result of activities in the research group
that brought meaning to organic synthesis. In each case, however, the perception of realness
occurred when the situation had some personal relevance. Our results suggest, therefore, that
the perception of realness, like knowledge, is a personal construction based on the learners
prior experiences and future goals. Real world, therefore, does not necessarily equate with
relevance; the learnerand only the learneris the agent of that change (Bhattacharyya, 2010;
Bhattacharyya, Mayorga, & Melloy, 2012).
The professor of the synthesis course tried to connect with the studentssense of realness
in a multitude of ways. Chief among them were choosing lecture topics and materials that the
students were likely to encounter outside of class. While it may not be reasonable to expect
that students in a sophomore-level organic chemistry course would readily come across the
material in their out-of-class life, it is possible to use practitioner-level examples. An effective
example of this at the undergraduate level is Kleins (2013) organic chemistry text in which he
has problems at the end of each chapter derived from the primary literature (He also provides
the citations in those problems).
A second implication of our study regards the types of tasks students may be given during
homework or in-class problem solving. A characteristic of the term-long project that promoted the
perception of realness for the students was that each student had ownership over a unique target
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DEVELOPING PRACTITIONERS OF CHEMISTRY

molecule. One way to help create this sense of ownership in a larger course setting is by using
design tasks, which are inherently open-ended and do not have unique correct answers or a
single, prescribed method for solving them. Both of these characteristics could help students
develop a sense of ownership over their solutions, thereby promoting a sense of realness
with the students. Furthermore, Schon (1987) demonstrated that design activities are excellent
vehicles for inducing reflection in learners. A basic characteristic of design tasks is that they
are ill-defined to the degree that one does not initially know the nature of the problem(s) that
need to be solved. Schon observed that the process of defining the problem(s) facilitates
reflection on many, if not all, of the concepts related to the task.
Finally, the cycle of feedback and revision provided by the term-long synthesis project
also merits attention. The professors comments on the first draft of the synthetic proposals had
a transformative effect on the students. Although instructors tend to provide feedback on
homework and/or exams, students are seldom asked to submit revised versions of the
assignments. While this cycle of revision and resubmission may not be practicable in large,
introductory-level courses, our data indicate that they can be significant learning experiences
that should be considered as a part of smaller courses.
The authors would like to express their immense gratitude to all of the research
participants for their time and insights and to the professor of the organic synthesis
course from which the first-year participants were recruited.

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