An Inquiry-Based Practical Curriculum for Organic Chemistry as Preparation for Industry and Postgraduate Research

Abstract

This paper describes the development of a new practical curriculum for third-year organic chemistry to replace the recipe-based approach typically used in undergraduate teaching laboratories. The new curriculum consists of an inquiry-based project set in a simulated industrial context preceded by two scaffolding experiments to prepare students for the task. The industrial project requires students to evaluate experimentally three multi-step synthetic routes to a given target based on cost, technical challenge and environmental impact in order to make a recommendation as to which route the ‘company’ should use to synthesize the compound. The project equips students with technical skills suitable for both postgraduate research and industry, and develops metacognition and understanding through the use of the jig-saw cooperative learning strategy and reflection. The students were found to engage with the practical work at a deep intellectual level, demonstrating that contextualized inquiry-based laboratory teaching afforded an improved quality of learning. In addition, the reported practical curriculum made a difficult subject accessible and even popular, to some measure grew the students’ ability in all desired graduate attributes and resulted in the establishment of a professional identity for individual students.

Full text

An Inquiry-Based Practical Curriculum for Organic
Chemistry as Preparation for Industry and
Postgraduate Research
Lynne A. Pilchera,*, Darren L. Rileya, Kgadi C. Mathabatheband Marietjie Potgietera
aDepartment of Chemistry, University of Pretoria, South Africa.
bDepartment of Science, Mathematics and Technology Education, University of Pretoria, South Africa.
Received 15 June 2015, revised 27 August 2015, accepted 31 August 2015.
ABSTRACT
This paper describes the development of a new practical curriculum for third-year organic chemistry to replace the recipe-based
approach typically used in undergraduate teaching laboratories. The new curriculum consists of an inquiry-based project set in a
simulated industrial context preceded by two scaffolding experiments to prepare students for the task. The industrial project
requires students to evaluate experimentally three multi-step synthetic routes to a given target based on cost, technical challenge
and environmental impact in order to make a recommendation as to which route the ‘company’ should use to synthesize the
compound. The project equips students with technical skills suitable for both postgraduate research and industry, and develops
metacognition and understanding through the use of the jig-saw cooperative learning strategy and reflection. The students were
found to engage with the practical work at a deep intellectual level, demonstrating that contextualized inquiry-based laboratory
teaching afforded an improved quality of learning. In addition, the reported practical curriculum made a difficult subject
accessible and even popular, to some measure grew the students’ ability in all desired graduate attributes and resulted in the
establishment of a professional identity for individual students.
KEYWORDS
Inquiry-based, organic chemistry practical training, professional identity, industry-based, metacognition.
1. Introduction
Industry today commonly expects graduates to be able to
apply theoretical knowledge to practical situations. The truth of
the matter is, however, that industry is often faced with the
problem of academically strong graduates who are poorly
prepared for the practical situations in which they have to
perform. As a result new graduates typically find themselves
frustrated and struggle to make the transition from university to
industry.Thebiggest shortfallthat wehave identifiedin thefield
of synthetic chemistry is that students are not well equipped to
use the available literature and to translate that literature into
practice.
Teachingat tertiar y level is designed to facilitate preparation of
professionals and the laboratory is one of the places where a
chemist must operate as a professional person. The aim of
laboratory training at university level should be to increase
students’ ability to act like scientists in the way they solve
problems, design investigations, interpret data, troubleshoot
methods and set up equipment.1,2 Gunstone and Champagne
stated that meaningful learning will occur in the laboratory if
students are given enough time and are afforded opportunities
for inter-personal interactions and reflection.3Domin identified
four distinct categories in his taxonomy of laboratory instruction
styles,namely exposition,inquiry,discovery andproblem-based
instruction.1In contrast to the expository style, the other
approaches give students more responsibility for and owner-
ship of the activity in which they engage.
Trout et al. refer to inquiry as ‘the evidence-based process that
scientists engage in to study and propose explanations about
aspects of the natural world’.4It involves formulating research
questions, proposing methods and strategies for investigation
and forming and communicating conclusions. According to
Minner et al., for instruction to be classified as inquiry-based it
needs to have three aspects: firstly, the presence of science
content, secondly, student engagement with science content;
and thirdly students must take responsibility for at least one
component of the investigation, i.e. question, design, data,
conclusion or communication.5Inquiry instruction as a peda-
gogical approach can be characterized into different categories
depending on varying degrees of educator involvement. Buck
and co-workers characterized inquiry in the undergraduate
laboratory according to the level of student independence, rang-
ing from the confirmation laboratory (level 0) where everything
is provided to authentic inquiry (level 3) where the problem,
procedures, analysis, communication and conclusions are
designed by the student.6In guided inquiry (level 1) students
look for patterns in data collected via given experimental proce-
dures and in open inquiry (level 2) students design their own
experiments to address some general topic. A number of studies
have reported the positive impact of some level of inquiry in
science instruction on content learning and retention.5Hofstein
et al. found that ‘students in the inquiry group who had experi-
ence in asking questions in the chemistry laboratory outper-
formed the control grouping in their ability to ask more and
better questions’.7Krystyniak and Heikkinen reported that
during an inquiry activity students were less reliant on the
instructor than in non-inquiry activities; instead they sought
support and guidance regarding experimental procedures from
their peers. Furthermore students became confident in their
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 236
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
* To whom correspondence should be addressed. E-mail: lynne.pilcher@up.ac.za
ISSN 0379-4350 Online / ©2015 South African Chemical Institute / http://saci.co.za/journal
DOI: http://dx.doi.org/10.17159/0379-4350/2015/v68a32

understanding of the part for which they were responsible and
therefore took on a more active role in the discussions concern-
ing that part of the task.8
Metacognition has been defined as exercising control over,
being in touch with or reflecting on one’s own thinking.9
Metacognition is embedded in scientific inquiry because suc-
cessful inquiry requires a scientist to constantly reflect on and di-
rect his/her thinking towards the desired outcome. The develop-
ment of metacognitive competencies is a prized outcome of sci-
enceeducation becauseit promotesmeaningful learning, auton-
omy and self-regulation.10 The short-term goal for developing
thinking and metacognitive skills is to enable students to carry
out experiments with understanding.11–12 The long-term goal is
to develop their problem solving skills in preparation for the
world of work. Thus, metacognition is a desired attribute for grad-
uates.13 Kipnis and Hofstein arrived at the conclusion that an in-
quiry-type laboratory assignment that is properly planned and
performed carries the potential to provide students with an
opportunity to practise and develop metacognitive skills.10
The combination of cooperative learning, inquiry instruction
and metacognitive instruction creates an environment condu-
cive to encouraging discourse and building of a joint under-
standing among students.14 Given the constraints of time and
cost we identified guided inquiry-based instruction with elements
of discovery and problem-based learning as the most promising
way to develop the problem-solving and planning skills that
graduates were lacking.
2. Context
This paper reports on the reconceptualization of the practical
curriculum for the CMY 384 organic chemistry module at the
University of Pretoria. This module is presented to 3rd year
students who are enrolled in a Bachelor of Science (BSc)
programme with chemistry as a major subject. The BSc
programme is run over a three-year period with one quarter (7
weeks, 28 lectures) of each year allocated to organic chemistry
lectures. The third year organic syllabus focuses on aromatic and
carbonyl chemistry exclusively; the practical curriculum, how-
ever, draws on organic chemistry knowledge developed across
the entire programme. The practical component of the module
comprises6×6hlaboratory sessions run overa six-week period,
with one practical session per week.
3. Aims
The aim of this project was to replace the existing practical
component of the CMY 384 module with a curriculum that is
holistically designed to prepare students to meet the expecta-
tions of their first industrial job or research projects at Honours
level. The design specifications for the new curriculum were to
include a project in synthetic chemistry that spans several
sessions, is inquiry-based, links theory to practice and simulates
an industrial context. In addition, it should develop technical
skills as well as metacognitive ability.
4. Design
The new practical curriculum consists of two preparatory
experiments performed in sessions 1 and 2, and an inquiry-
based industrial project executed during sessions 3 to 6. The first
two sessions (Fig. 1) were used as ‘scaffolding’ sessions to pre-
pare the students to successfully tackle an inquiry-based project.
Students need practice to be able to carry out inquiry-based
experiments and should be offered activities that build up to
increasingly open and complex levels of inquiry.15 Such an
approach is not widely implemented in undergraduate laboratory
instruction. Since students in the third year organic chemistry
module would likely not have experienced an inquiry-based
environment, they needed to be systematically equipped with
the skills necessary to cope in such an environment. Scaffolding
was therefore employed with the first two experiments being
dedicated to developing the necessary skills and gradually
increasingthe levelof opennessof inquiry with each experiment.
Sessions 3 to 6 comprised a multistep synthetic organic assign-
ment and involved a planning session, two experimental
sessions and a presentation session. The project mimics a typical
industrial scenario that new graduates might experience when
starting out in the workplace. Students are given three different,
three-step synthetic routes to the same target molecule to
perform, assess and report on.
The first scaffolding experiment (P1) involves the develop-
ment of extrapolation skills in which students are given a
detailed recipe-based procedure in the style of a laboratory note-
book record and are then required to extrapolate the reported
method and quantities to work with different but related
reagents as well as different quantities of reagents. The reaction
used is a simple aldol condensation between an aldehyde and a
ketone. Four aldehydes and four ketones are provided allowing
for up to 16 unique compounds to be prepared. Individual
students are each given a different starting reagent combination
and have to extrapolate the procedure for their given combina-
tion of reagents. They immediately apply this extrapolated
procedureas theyperformthe experimentusing their calculated
values for the quantities to be used in their experiments.
The key educational aspects at this stage are the development
of chemistry mathematical skills and the ability to work inde-
pendently in a laboratory setting. Mole calculations, introduced
in first year theory, are applied in second year practical work;
however, by third year a number of students have not mastered
these skills. This practical curriculum presents the students with
their first exposure to extrapolation and reaction scaling. As
students are given different combinations of reagents it is easy to
identify those students who are struggling with the concept
of stoichiometry and scaling solvent volumes to keep reaction
concentration consistent and who require individual instruc-
tion. In addition students are put into a situation where they
have to work as individuals within the laboratory environment
for the first time as they are all doing a different, albeit related,
reaction. The development of the ability to work as an individual
is seen as a key component of inquiry-based research. Students
are encouraged to reason their way through challenges that may
arise during execution. This experience promotes confidence
and ownership.
The second scaffolding experiment (P2) involves providing
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 237
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
Figure 1 CMY 384 practical curriculum session breakdown.

the students with a brief literature style experimental procedure
from which the students need to develop their own step-by-step
protocol for the experiment. Students are required to perform
the experiment using their own protocols after they have been
evaluated and corrected by a demonstrator. As with P1, the
students are given different combinations of starting reagents
and have to extrapolate the procedure, in addition to having to
analyse and interpret a literature style method. The educational
development at this level builds on that developed in P1;
however, it extends to the development of critical interpretation
skills. This level of interpretation is not necessarily straight-
forward as students have at first and second year level been
conditioned to expect step-by-step recipe-based synthetic
methods and have not given much thought to the rationale for
each procedural step. Literature articles typically do not include
information that is obvious to someone skilled in the art of
synthetic chemistry thus it is important to teach students to
make the link.
The inquiry-based project (P3-1 to P3-4) is set in a simulated
industrial context. The skill of applying and integrating
knowledge to evaluate options and make informed decisions in
a relevant context is poorly developed at the third year under-
graduatelevel.16 Wethoughtthat givingstudents anopportunity
to practise this skill would stimulate the development of this
competency. Students are given a brief from a hypothetical
company ‘Chem-Co Ltd’. The brief details that the company is
interested in taking a specific product, 3-phenyl propionate, to
market; and that they have identified three potential routes to
preparethe productin question.The company asks that teamsof
chemists assess each route by experimentation in a laboratory
environment in terms of three key factors: cost, technical diffi-
culty and environmental impact. Furthermore, in order to keep
costs down the company asks that in assessing the routes no
more than 2 g of the final product is produced. Ultimately
students have to report their findings as an executive summary
in which they make recommendations to the ‘board’ of
Chem-Co Ltd as to which route they feel is best.
The synthetic routes (A, B and C) each consist of a three-step
synthesistargeting 3-phenylpropionate (Fig.2). The routes have
been carefully chosen to highlight the three key issues of cost,
technical difficulty and environmental impact in such a manner
that the question is open-ended with no one clear ‘best’ route.
This project clearly illustrates the concept that there is usually
more than one valid route to any compound. The chemistry
within the routes is drawn from the organic undergraduate cur-
riculum (years 1 to 3): hydrogenation was introduced in the first
year, Grignard chemistry in the second year, and at the start of
the project students were completing the final chapter of enolate
chemistry. Students at this stage were familiar with reaction
mechanisms and could use their knowledge to interpret reac-
tions that have not been specifically taught, notably the
Knoevenagel reaction (which can be extrapolated from enolate
theory) and the particular esterification methods. The routes have
comparable time demands, but different levels of complexity.
5. The Inquiry-based Project
In this section we provide information on the implementation
of the inquiry-based project highlighting organizational and
educational aspects. ‘Cooperative learning is a student-centred,
active-learning approach that uses structured situations in
which a fixed small group interacts in a non-competitive manner
to accomplish a common goal’.17 We decided to use a cooperative
learning approach for the following reasons: working through
collaboration results in a reduction in cognitive load which facili-
tates enhanced cognitive and metacognitive activity.18 In addi-
tion, working through collaboration requires participants to
monitor their contribution to the task which obliges participants
to explain their ideas and conceptions to others.19 A laboratory is
a social environment where students work independently and
in collaboration with peers. Student–student and student–staff
interactions play an important role in how students carry out ex-
periments and how they monitor and control their thinking.
Students could pool their knowledge and skills to negotiate a
common understanding of the task and its demands. They could
then select appropriate strategies to perform the task and collec-
tively monitor their thinking and their performance.
5.1. Session P3-1
At the start of this session (P3-1), the lecturer in charge gave a
ten-minute explanation of the brief and how the project would
be run. In order to facilitate cooperative learning and to allow
experimental data to be collected for three different routes, i.e. to
make the task posed in the brief more manageable, students
were divided into teams of chemists using a jigsaw learning
group approach. The jigsaw method is a research-based learn-
ing technique which was originally developed in 1971 by Elliot
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 238
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
Figure 2 The three multi-step routes (A, B and C) to synthesize methyl 3-phenylpropionate.

Aronson.20 Thiscooperative learningtechnique hasbeen studied
and used by many researchers and educators in different
subjects and at different academic levels.21–23 The technique was
found effective in increasing positive educational outcomes and
cooperation. Similar to a jigsaw puzzle each piece (a student’s
allocated role) is important for successful completion and full
understandingof thetask.20 Skills suchas listening,engagement,
empathy, communication and problem-solving are encouraged
amongst students. The jigsaw approach involved dividing the
students into home groups, each home group comprised three
students who were each tasked with assessing one of the
synthetic routes (A, B and C) outlined in the brief (Fig. 3).
The group assignments and allocation of routes were only
made available to the students upon their arrival for the P3-1
planning session to discourage sourcing of information from
students from previous years. The allocation of students was not
random but was based on the assessment of the students’ abili-
ties during the scaffolding practical sessions (P1 and P2) as well
as on peer–friend relationships within the student body. We
attempted to place students in groups where they had at least
one of: friendship, race or gender in common with the rest of the
group members. As far as possible, students were grouped with
their friends in home groups to facilitate out of hours prepara-
tion of the final report. When this was logistically impossible,
students were grouped with a friend in their specialist group to
minimize potential discomfort with group work. Within the
context of the home group students initially met and were given
10 minutes to discuss their understanding of the brief, their
individual roles and expectations of each member of the group,
what information they would need to answer the key questions
posedin thebrief andhow they would answer thesequestions.
The staff member in charge answered any questions that had
arisen and the home groups were dissolved. The students were
then reassigned to specialist groups. Each specialist group com-
prised 3-4 students who were all assigned the same synthetic
route (Fig. 4). At this stage each specialist group was provided
with journal procedures covering the three steps for their
synthetic route A, B or C, price lists for the chemicals, MSDS
data and a document detailing the twelve principles of green
chemistry. The specialist groups were given three hours to trans-
late and extrapolate the journal procedures provided to develop
a synthetic strategy that they would use in sessions P3-2 and
P3-3. Key aspects that the specialist groups investigated in-
cluded:reagent quantities to produce approximately 2 g of
3-phenyl propionate, glassware and equipment, experimental
set-up, work-up and purification, costing of chemicals, safety
assessment and a time-management plan. In an attempt to add
variability and limit copying of results and calculations from
year to year or group to group the students are not given the
actual reported yield for any of the steps, instead they are
provided with suggested yields. The suggested yields are lower
than the actual yields reported in the literature which makes
them attainable. The use of suggested yields allows the practical
coordinator the option to vary the suggestions from year to year
or even group to group, adding year-to-year variability in the
required calculations. As the specialist groups completed each
task, a staff member or demonstrator would check the work to
make sure that each group could proceed safely. Thus the
specialist group planning session ended with all students
having a safe working procedure and correct calculation of
quantities of reagents.
The specialist groups were dissolved and students re-formed
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 239
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
Figure 3 Home group composition and tasks.
Figure 4 Specialist group composition and tasks.

their home groups. The individual members of the home group
were then given 15 minutes to report back on their findings. At
this stage, having assessed the routes, students were tasked with
making predictions of how they thought each route would fare
against the criteria laid out in the brief. In order for a home group
to make a motivated prediction the group needed each member
to have processed in full the information particular to his/her
route to the extent that it could be evaluated against that of the
two other routes. Students were given the remaining time (1 to
2 h) in session P3-1 to go to the laboratory and prepare their
glassware for their first experiment.
5.2. Sessions P3-2 and P3-3
The wet laboratory sessions (P3-2 and P3-3) were each 6 hours
in length, and it was during this time that the individual
students had to assess experimentally their allocated synthetic
route. Activities undertaken were those typical of an undergrad-
uate laboratory and included setting up of reactions, reaction
monitoring, reaction work-up and purification. Educational
aspects that were focused on in addition to development of
practical laboratory skills were the development of trouble
shooting skills as well as the development of an inquiry-based
approach to research. Students were expected to critically examine
what they were doing in the laboratory and to formulate their
own ideas on how to tackle problems. Academic staff members
and demonstrators facilitated this way of thinking through the
use of pertinent probing questions in response to students’
questions, the objective being that the student should be able to
formulate their own answers without the demonstrator having
to resort to simply giving an answer. As an additional challenge
the students had to fit three synthetic steps into two laboratory
sessions one week apart. This required careful time management
and that consideration should be given to possible degradation
of intermediate products.
5.3. Session P3-4
The culmination of the project involved a presentation session
(P3-4) where students within their previously allocated home
groups were tasked with compiling and presenting their results
in a mock board meeting with Chem-Co. Ltd. The home groups
were given no indication of how they should structure or
present their findings except that it should take the form of a
PowerPoint presentation and that every group member should
make a contribution. Due to the open-ended nature of the
synthetic routes A, B and C, different home groups typically
came to different conclusions depending on how much emphasis
they put on each of the criteria in the brief as well as their experi-
mental outcomes. As the project is designed to have no one
correct answer students were then invited to participate in an
open discussion amongst the home groups during which time
they could critique each other’s recommendations and findings.
Finally the session ended with industry-focused feedback from
the staff members in charge, highlighting the areas that were not
adequately covered or perhaps were not considered by students
in the presentations.
5.4. Development of Metacognitive Skills
Throughout the inquiry project metacognition was stimulated
by way of four questionnaires with reflection prompts which
students had to complete before and during the laboratory
activity. The questionnaires served as a reminder to students to
activate their metacognitive abilities of planning, monitoring,
control and evaluation while carrying out the task. Each ques-
tionnaire consisted of reflection prompts relevant to different
stages of the activity, i.e. during the planning session or during
the wet lab activity. The reflection prompts were adapted from
Schraw’s regulatory checklist which was designed to provide an
overarching heuristic that facilitates the regulation of cogni-
tion.24 Fig. 5 is a diagrammatic representation of when the ques-
tionnaires were introduced. It is important to note that these
questionnaires, called Reflective Learning Strategy Question-
naires (RLSQs, available as supplementary material), were not
designed for assessment purposes but for eliciting productive
metacognitive activity.
The Pre-laboratory individual RLSQ encouraged the students
to monitor their understanding of the task and to activate prior
knowledge after reading the brief which detailed the scope of
the task. The students were expected to complete this question-
naire prior to attending planning session P3-1. The pre-laboratory
home group questionnaire was divided into two sections: the
first was answered before dispersing to specialist groups and
prompted them to define what information they needed to
bring back from specialist groups; the second was answered
after returning from the specialist groups and required an evalu-
ation of information obtained during the specialist group sessions
to predict the best route. It also prompted the home group to
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 240
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
Figure 5 An overview of the four sessions indicating when the four RLSQs were completed.

plan for the final presentation in session P3-4. The pre-laboratory
specialist group questionnaire questions were designed to help
the group use their planning time optimally and to evaluate
whether the experimental plan and procedure they had just
produced during the planning session was complete.
The final RLSQ, the post-laboratory day one RLSQ, was given
tothe studentsto completeindividually betweenthe twoexperi-
mental days to help them to evaluate what they would have
done differently and how their plans had to change based on
their results thus far. Questions like ‘Do you have a clear under-
standing of what you have done and what you still have to do?’
and ‘If you could repeat today’s work, how would you do things
differently?’ encouraged students to reflect on the events of the
day and to evaluate their understanding and progress.
5.5. Description of Synthetic Routes
In order to facilitate an open-ended nature to the inquiry-
based project (P-3) the three routes where designed in such a
manner that each route highlighted one of the key aspects raised
in the brief (environmental impact, technical difficulty, and
cost). A discussion of our evaluation of each route against the
three criteria will be made available to bona fida instructors on
request.
Route A (Fig. 2) involved the in situ preparation of Grignard
reagent 2from 4-ethylbromobenzene 3, the subsequent
carboxylic acid 4was accessed by condensation of 2with carbon
dioxide in the form of dry ice followed by an acidic work-up.
Finally the acid was converted into 3-phenyl propionate 1
through treatment with dimethylcarbonate.
RouteB involvesan Arbuzovreaction oftriethylphosphite and
a-bromo ester 5followed by a Horner-Wadsworth-Emmons
olefination of the resulting phosphonate ester 6with benzalde-
hyde. Finally catalytic hydrogenation of alkene 7affords the
desired 3-phenyl propionate 1.
Route C involves a Knoevenagel type condensation with
benzaldehyde and malonic acid followed by simultaneous
b-decarboxylation to afford acid 8. Esterification using thionyl
chloride gives alkene 7which is hydrogenated under the same
conditions as in route B to afford the desired 3-phenyl propio-
nate 1.
5.6. Assignment of Routes
Students were informally assessed in terms of their experi-
mental ability based upon their in-laboratory performance in
experiments 1 and 2. When the home groups were constituted
the student perceived to be weakest was assigned route C. The
reasoning behind this assignment was twofold, firstly it involves
simple experimental set-ups, secondly as the third step is the
same as that for route B it affords the student a chance to share
the results from their team mate working on route B should their
reaction fail or they work too slowly.
5.7. Assessment
Individual student assessment in the inquiry-based project
(P3)was basedon anevaluation ofthe qualityof laboratorynote-
book records submitted at the end of session 6, as well as the
quality of products of reactions and melting points where appli-
cable. The rubrics developed for the scaffolding experiments
were used for these evaluations (see Supplementary material).
Marks were also assigned for mechanisms proposed or researched
for all synthetic steps and for assignment of 1H and 13C NMR
spectra for all products in the student’s assigned route. In addi-
tion, an assessment of the quality of the slides used by the home
group for their final presentation in session 6 contributed a 10 %
groupmark tothe total.Marks werenot assignedto their presen-
tation skills because it was felt that students were more likely to
engage in the spirit of the exercise when they did not have the
added pressure of being assessed for their presentation skills.
6. Findings
The results of the inquiry-based industrial project can be
divided into two categories: firstly, the results of the students’
investigations as revealed by their presentations, and secondly,
the attitude and personal development of the students.
6.1. Students Evaluation of the Three Routes
Students’ communication of their findings in the presentation
session was generally of a high standard and in almost all cases
the assessment of the three routes was dealt with both critically
and logically. Students tended to break down their assessment
beyond the three criteria laid out in the brief to include other
related aspects such as time demand, waste generated, yields,
hazards and number of operations.
The best route, in terms of the criteria laid out in the ‘Chem-Co
Ltd’ brief, chosen by home groups varied. Students tended to
favourtwo routesequally overthe third†.Typicallyhome groups
more focused on environmental impact tended to favour one
route, whereas those focused more on cost favoured another.
Students regarded new procedures or those that they had had
little prior opportunity to practise as technically challenging and
unfavourable.
Assessment of the three performance criteria for the synthetic
routes was dealt with at a fairly basic level. In terms of costs
almost all students were able to price the different routes in terms
of the amount of reagents consumed relative to the amount of
final product produced. More astute students attempted to look
at broader issues which influence cost such as power consump-
tion (ambient temperature vs. refluxed reactions) and time taken
(cost of scientists per unit time). We also came across a few
students who were breaking the cost assessment down further
to include the number of operational steps in the process, and
management of by-products and waste. The cost assessment
was performed quantitatively based on cost of starting reagents
combined with a more qualitative assessment of less easily calcu-
lated factors such as power and time consumption.
Although students were easily able to identify areas of technical
challenge, they tended to struggle to correlate whether or not
the difficulty was because of their own skill levels or because the
route and the chemistry itself posed genuine issues. Students tend
to be somewhat misled because they were equating technical
difficulty with unfamiliarity of a technique regardless of how
well the technique worked. As a general rule, groups tended to
place less emphasis on technical challenge as a reason for reject-
ing a particular route.
The final aspect of green chemistry was largely dealt with in a
qualitative manner. Students tended to focus on identifying
reagents or steps that were not considered to be green in nature,
the more observant students tended to consider the by-products
and waste produced as well. In the initial implementation of this
practical curriculum in 2013 students were mostly unaware of
the idea of atom economy and how that relates to greenness. In
2014 we provided students with a synopsis of what atom economy
is in addition to the document detailing the twelve principles of
green chemistry provided in 2013. Students in the 2014 group
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 241
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
†An explicit description of the findings is avoided in order not to compromise the inquiry
aspect and the shelf-life of this experiment for these particular reactions. A document
containing detailed analysis of the students’ evaluations of the routes will be made
available to bona fide researchers and instructors on request.

then tended to emphasize atom economy with the topic being
dealt with at some level in almost all presentations. In a few cases
students made suggestions of greener approaches that could
have been utilized.
6.2. Student Development
The scaffolding experiments (P1 and P2) were necessary to
ensure students were able to tackle the inquiry-based project
(P3). In particular it appeared important that students had
developed in two areas: firstly, the ability to work independ-
ently, which is not developed during first and second year
practical training as the entire class of students would be assigned
exactly the same experiments. Secondly, students needed to be
capable of interpreting, translating and extrapolating a journal
styled experimental procedure as opposed to using a detailed
recipe based procedure typically presented at first and second
year levels.
When presented with the brief for the inquiry-based project
many students expressed apprehension with regard to the
difficulty of the task at hand; however, once the realization set in
that they were able to successfully tackle the project, students
attitudes in almost all cases had a complete turn-around. Evidence
of this turn-around was clearly observed in students’ over-
whelmingly positive assessment of the course. Many students
cited the practical component of the module as being their
favourite section as demonstrated by the following two
comments from an anonymous survey question: What did you
like most about the course (module)?
Student 1: ‘The practicals were great, it was something different
and I learnt a few things that I wouldn’t have in a normal practical
where everyone synthesised the same compound.’
Student 2: ‘I enjoyed the practical components the most as I got to
build my confidence with regards to using the instruments.…’
Feedback was obtained through conversation with the
students, anonymous course evaluation surveys and through
feedback from colleagues in other departments. A number of
students reported to their biochemistry lecturer that: 1) the last
practical project was challenging and very innovative giving
exposure to industry realities: problems and corresponding
solutions, 2) the new chemistry curriculum was so interesting
that they were considering an honours in chemistry rather than
honoursin biochemistry as initially planned, and3) theCMY 384
module was the best and most enjoyable module in the BSc
degree even though it was one of the most difficult. Students
were so excited about the project that they were talking about it
outside the confines of the course. In the two years since imple-
menting this practical curriculum we have observed a sharp
increase in students’ interest in organic chemistry reflected in
the increase in the number of students applying to do organic
chemistry-based honours projects‡.
We were able to observe students’ personal development in
terms of improved self-confidence, communication skills and
troubleshooting abilities. In particular, we were pleasantly
surprised by the improvement in the quality of laboratory talk.
The interactions of students with staff and demonstrators
evolved from that of simply asking for solutions to that of seek-
ing validation for their own ideas which were presented with
confidence and were supported by sound arguments. Students
acknowledged that this project design improved their under-
standing of their experimental work:
‘I think people would get a lot better result if we actually thought
about the experiment but if we are not really forced to do that in the
way that we were in this activity we probably won’t.’ (Quote from
a post-course interview)
In their reasoning students demonstrated an improved ability
to think at three levels: molecular, macroscopic and symbolic
and to switch seamlessly between these thinking levels as indi-
catedby thisstudent commentgiven in a post-course interview:
‘…you were just given a recipe you don’t really know what you are
doing … and you don’t [know] what’s really happening molecular,
…. But now on this third year level and with this experiment you
gain an appreciation of what real life is gonna be like. So you have to
figure out for yourself.’
Another fundamental and rather exciting observation that we
made having adopted the new inquiry-based model combined
with a simulation of an industry environment is that students
began to develop a professional identity wherein they started to
believe that they were no longer simply students learning about
chemistry but actual chemists capable of doing research. This is
illustrated by the following student comment in a response to a
survey:
‘The experiments done in this course gave us as students more in-
sight in how the actual work might work in the real world and it was
very educational to develop the methods ourselves instead of just
reading a manual.’
Interactions in the laboratory between students and lecturers
became an equal exchange between professionals to formulate
ideas and critique them. This transformation was especially
evident during the presentations of the teams of chemists to the
‘board’ of Chem-Co. Students took ownership of both the
process and the outcomes. This observation was in sharp
contrast to the past where, presumably because of a limited job
market specific to chemistry, our students did not have a sense
of belonging to a professional community. Development of a
professional identity gave the students confidence and a story to
tell as they could see how their studies equipped them to func-
tion in a relevant working situation.
7. Discussion and Conclusions
It is the desire of most institutions of higher learning to produce
graduates who are critical thinkers, who are confident in the
work environment; who can function independently; who are
lifelonglearners; who can generate new ideas, resolve problems,
create products and come up with solutions that are valuable to
society.13,25 After completion of this inquiry-based industrial
project, our students had developed in each of the attributes
listed by the University of Pretoria (Fig. 6).
This programme addressed each one of the graduate attributes.
Our approach of giving students individual tasks meant that
they had to learn to work independently. As a result of inde-
pendent achievement, their self-confidence grew. We introduced
an inquiry-based approach and this stimulated the intellectual
curiosity of our students. By modelling an industrial environ-
ment the students gained understanding of economic and
industrial realities, not formally part of the syllabus. The use of
the jigsaw method required students to work in different teams.
Their role in each team and the contribution they had to make
developed interpersonal skills as well as accountability to the
group. Our students learnt to apply their theoretical knowledge
to develop experimental methods and to solve problems in the
laboratory. Requiring students to consider the environmental ef-
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 242
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
‡Whereas previously less than half our honours students chose to do organic projects, in
2014, 12 out of 13 students and in 2015 10 out of 12 students chose organic chemistry
honours projects.

fects of their synthetic routes fostered a sense of social responsi-
bility. Our students developed a sense of ownership of their
work which enabled them to communicate with clarity and
authority when presenting their findings.
In addition, the graduate attributes that industry expects from
organic chemists were also addressed. Our students’ ability to
plan and design experimental procedures based on abbreviated
journal-like descriptions and relevant theory was developed.
Students were able to estimate the initial scale of a reaction based
on the final downstream product quantity required. They
gained experience in interpreting MSDS data and all safety
aspects associated with chemicals. Manipulative skills and skills
of record keeping and data handling were practised. Our
students grew in their ability to think at the symbolic, macro-
scopic and molecular levels for interpretation of observations
and experimental results and for problem solving.
Experimental chemistry, with its associated chemical hazards
and cost of reagents§, is generally believed to be closed to the
introduction of authentic inquiry-based learning at undergrad-
uate level. The design of this project kept the inquiry aspect to an
evaluation of a pre-planned set of experimental routes. Thus the
chemistry was already tested, the safety aspects well considered,
time constraints were accounted for and the chemicals were
available. This guided-inquiry approach encompassed the bene-
fits of inquiry while being well targeted to the experience level of
our students and the level of expectation for a new graduate.
Three aspects of this curriculum design that are of paramount
importance to the chemistry educator deserve further comment,
namely the expected shelf-life of the open-endedness of the
industry-based project, the range of practical skills covered by
the curriculum and the transferability of the design to contexts
with a three-hour duration of practical sessions.
To maintain the open-ended inquiry aspect of the project, it is
important that following a number of years of implementation a
so-called ‘correct answer ’ does not become known. We antici-
pate that over time students may be informed by students from
previous years how the routes will fare against one another.
However, students will still have to perform the experiments to
compare yields and cost. Furthermore, in planning their experi-
mentsquantities canbe variedby varyingthe expectedyields for
the reactions and even the target quantity to be produced. This
inquiry-design is not specific to the chosen chemistry and could
conceivably be applied to any set of synthetic routes to a common
target molecule that were relevant to the theory curriculum.
The benefits of the allocation of four laboratory sessions to one
practical activity, with reallocation of two experimental sessions
to planning and reporting, far outweighed the loss in terms of
skills development of exposing students to a different experi-
ment in each session. As expected, providing students with
enough opportunity for interactions with peers and instructors
and opportunities for reflection and metacognitive activity,
resulted in enhanced understanding of what they were
expected to do and why they were doing it.3,12 Although a
student performed only one of the synthetic routes they were
exposed to the technical challenges associated with all three
routes in their home groups where results were discussed to
reach a joint conclusion. The combination of this cooperative
learning, inquiry instruction and metacognitive prompting
created an environment conducive to encouraging discussion
and joint building of understanding amongst students.14
While the practical slot in the timetable for the CMY 384
module is 6 hours, many institutions timetable 3 hour sessions
for their practical training with more sessions being allocated to
the practical programme. The reactions used in this project are
either complete within 2 hours or must be left overnight. It
should therefore be possible to adjust the project to work in a
3 hour context with reactions being set up and quenched in one
session or left ‘overnight’ until the next session and alternate
sessions being dedicated to reaction work up and product isola-
tion. In such a context eight 3 hour sessions would be required:
two for planning and preparation for the first reaction, five for
experimentation and one for reporting.
RESEARCH ARTICLE L.A. Pilcher, D.L. Riley, K.C. Mathabathe and M. Potgieter, 243
S. Afr. J. Chem.
, 2015, 68, 236–244,
<http://journals.sabinet.co.za/sajchem/>.
Figure 6 Statement of graduate attributes for the University of Pretoria.
§In the South African context, long waiting times for delivery after placing an order, also
represent a problem.

To conclude, we return to perhaps the most gratifying experi-
ence during the implementation of this new curriculum, namely
to witness how many of the students developed a sense of
professional identity while engaged in the industrial project.
Professional identity formation is key to success as ‘identity is an
underlying motivation for learning’.26 When students perceive
an activity to be meaningful they are intrinsically motivated to
master the required skills and concepts at a much deeper level
than when driven by external gains such as grades. Unlike
students in professional training such as health practitioners
and engineers with a clear career track following completion of
their studies, science students are slow to develop this identity.
In his study on the epistemic development of organic chemists
Bhattacharyya made three recommendations to support
students in their development of a professional identity namely,
the inclusion of professionally relevant elements in their train-
ing, opportunities to experience the roles performed by practi-
tioners, and opportunities to determine the problems of the
profession and search for solutions through feedback and reflec-
tion.26 The practical curriculum reported here meets all three of
these recommendations. Students who have benefited from this
experience are expected to transfer successfully to industry or
postgraduate research because not only have they acquired the
appropriate knowledge and skills they also see themselves as
professional chemists equipped to make a meaningful
contribution.
Supporting Information Available
In order not to compromise the inquiry aspect of the design for
this particular set of reactions, the supplementary material will
not be generally accessible on-line, but will be made available to
bonafide researchersand instructorson requestfrom theauthors.
1. Chemistry design principles for each route and detailed
student evaluations of each route.
2. ‘Chem-Co Ltd.’ Brief
3. RLSQs
4. Rubrics for evaluating laboratory notebooks and samples.
5. Documentation for specialist groups A, B and C (Literature
procedures, costs of reagents, notes on Green Chemistry, 1H
and 13C NMR spectra)
6. Laboratory manager notes
7. Demonstrator notes (provides the essence of the training the
demonstrators need to run the practical as well as tips for
anticipating reaction problems.)
8. Academic leader notes.
Acknowledgements
We thank Bonolo Moruri for testing all reactions described in
this paper prior to implementation of the curriculum. This work
was supported by an Education Innovation grant from the
University of Pretoria.
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