Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

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Currents in Pharmacy Teaching and Learning

journal homepage: www.elsevier.com/locate/cptl

Experiences in Teaching and Learning

Learning organic chemistry day by day: The best choice of the best
pharmacy students
⁎
Guido Angelini, Carla Gasbarri
Department of Pharmacy, University “G. d'Annunzio” of Chieti-Pescara, Chieti 66100, Italy

A R T IC LE I N F O ABS TRA CT

Keywords: Background and purpose: During over ten years of experience in teaching organic chemistry at the
Teaching experience Department of Pharmacy we have tried to answer the following question: why do most students
Organic chemistry tend to take the exam one, two, or more years after the end of the course they have attended?
Second-year undergraduate Several reasons could justify this delay, but three seem to be the most common drawbacks for our
Exam score
students: a) time needed for the comprehension of the arguments; b) the number of mandatory
exams to pass before organic chemistry; c) lack of a self-evaluation method.
Educational activity and setting: To increase the number of students in the exam sessions of the
semester just after the course we have proposed two strategies: 1) a systematic, but stressless,
approach by which homework and everyday life examples concerning organic chemistry are used
to increase the sense of responsibility in studying; 2) the modification of the number of man-
datory exams required for organic chemistry.
Findings: The rate of successful students in the exam sessions at the end of the course increased
from 38.3 up to 61.3%. Interestingly, the highest scores tend to be obtained by students in the
first session available just after the conclusion of the course.
Discussion and summary: The combined effect of Strategy 1 and Strategy 2 seems to be effective in
promoting the learning of organic chemistry and points out that the best performances tend to be
associated with students which follow organized studying.

Background and purpose

Organic chemistry is all around us: this is the most common way to introduce the course in textbooks.1–9 Although some methods
have been proposed to improve learning, this discipline still represents one of the most dreaded courses for undergraduate stu-
dents.10–13 During our experiences in teaching we have tried to change this perception by increasing the numbers of examples and
exercises discussed in class showing how organic chemistry follows logical steps predicted by specific rules. Extensive time in the
classroom allowed us to obtain good feedback from our students in order to understand their difficulties in learning. We use class
break time to talk about the arguments just explained and to encourage questions students may consider too silly to be asked in front
of the class or during office hours.
Our students are introduced to organic chemistry in the first semester of the second year. They are divided into two groups
following alphabetic order and are equally distributed into two classrooms with the same syllabus and timetable. Each group is
assigned to one teacher for the entire course. Lessons take place three times a week from October to January. Course attendance is
compulsory and different sessions for the qualifying exam can be selected by students at the conclusion of the semester: the early

⁎
Corresponding author.
E-mail addresses: guido.angelini@unich.it (G. Angelini), carla.gasbarri@unich.it (C. Gasbarri).

https://doi.org/10.1016/j.cptl.2018.03.003
Received 13 June 2017; Received in revised form 31 October 2017; Accepted 2 March 2018
1877-1297/ © 2018 Elsevier Inc. All rights reserved.

Please cite this article as: Angelini, G., Currents in Pharmacy Teaching and Learning (2018),
https://doi.org/10.1016/j.cptl.2018.03.003
G. Angelini, C. Gasbarri Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

session (February), the first summer session (April), the second summer session (June–July) and the autumnal session (September).
Students can choose which exam to take but not necessarily in the semester at the end of the course they have attended. In the case of
failure they can repeat the exam in the next session. The exam is divided into two parts. Each part must be passed in the same session
and is mainly based on the knowledge and comprehension of functional groups and their reactivity, systematic and common no-
menclature, stereochemistry, and acidity/basicity of the organic molecules. The first part consists of a two-hour test in which students
have to write the correct solutions to six problems (drawing molecular structures from the IUPAC names and vice versa; completing
reaction mechanisms with particular attention to the stereochemistry of the products; discussing the strength of given compounds as
acid or base by comparing pKa values).
Only students graded with a positive score (from a minimum of 18/30 to a maximum of 30/30) can access the second part: an oral
exam in which they have to show their level of mastery by writing on a board in front of all of the other students by using appropriate
symbols and formulae to describe transition states, intermediates, tautomerism, and acid-base equilibria. Finally, they are graded
with a single score. Laude is added to 30/30 score if high reasoning capability is shown during the examination. Until the 2014–2015
academic year three qualifying exams in mathematics, physics, and general inorganic chemistry were mandatory prior to taking the
organic chemistry exam.
During our experiences in teaching we have tried to facilitate the comprehension of this discipline by adopting several methods
from known learning theories.
Generally, four theories are employed to describe the mechanism by which the acquisition of information becomes knowledge in
the learning process: behaviorism, cognitivism, constructivism, and connectivism. In the first theory, studying is planned and or-
ganized by the teacher, while students write notes, memorize concepts and answer the teacher's questions after the principle of
stimulus-response.14,15 In the second theory, learning comes from problem solving: the teacher assists students in memorization and
storing information by using existing schemes or concept maps to formulate cognitive associations.16 In particular, concept map
assignments seem to help pharmacy students to reinforce and enhance the topics presented in class. Moreover, the best scores from
the graphic response, rather than oral assessment, tend to be obtained from the same student.17
Both behaviorism and cognitivism are acquisition theories in which learning is a passive process based on the central role of the
teacher. In the pharmacy education context, instructional strategies based on the acquisition of learning by using known facts in
everyday life seem to be more efficient in developing student cognitive abilities and skills in application to practice.18
A drastic inversion of the roles is observed in constructivism and connectivism.19,20 Both are participation theories based on the
concept of learning as an active process centered on the direct involvement of students, while the teacher becomes a facilitator, able
to provide guidelines and encourage students to become thinkers. In constructivism, the teacher supports students in working to-
gether to ask and answer questions and promoting discussions. In connectivism, the role of technology in the social context of the
digital age is emphasized: learning comes from networks with databases and digital platforms in which students find materials, follow
online course and make self-evaluation tests.21 Recently, it has been pointed out that pharmacy students strongly improve their
engagement in learning by using social media, such as Facebook and Twitter.22,23
Previous papers have shown how a combination of the mentioned theories should be employed to reach effective results in the
light of the large variety of problems and difficulties which could affect students during the learning process.24–26 Moreover, despite
the adopted teaching theory, students decide for themselves how much to be involved in learning.27
Our approach has always been based on both the key role of the teacher and the active role of the student. The teacher has to
make organic chemistry reasonable explaining logical rules to understand properties and reactivity of the functional groups. The
student has to take in the explained concepts and apply them to recognize or predict the behavior of a given organic molecule, but
above all she/he must be willing to learn organic chemistry. After explanations of a given argument, we solve exercises previously
assigned in the exam sessions and available online on the web page of the department to demonstrate the level of difficulty of the
exam. Participation of students, alone or in groups, is promoted by quick questions prior to showing how to write or think clearly to
solve the exercise.
Since the beginning of our experiences in teaching, our teaching method has been centered on the classification of the compounds
as electrophiles or nucleophiles, acids or bases with the aim to minimize memorization and maximize understanding as described by
the following examples:
Example 1. The definition of Brønsted acidity is repeated, as well as the main factors affecting the strength of a generic acid, before
introducing a functional group having acid behavior. In this way, the higher acidity of phenols in comparison to aliphatic alcohols
becomes reasonable and the pKa values are the only information students have to memorize.
Example 2. The definitions of nucleophile and electrophile, as well as the main factors affecting their strength, are repeated to
identify the chemical behavior of a given class of compounds. In this way, the reactivity of the Grignard reagents as strong
nucleophiles or strong bases, becomes reasonable. Consequently, students have to recognize what electrophile or acid is present in a
given reaction involving Grignard reagents.
Example 3. The definition of basicity is repeated, as well as the main factors affecting the strength of a generic base, before
introducing a functional group having basic behavior. In this way, the higher basicity of cyclohexylamine in comparison to aniline
and pyridine becomes a consequence of their structures and the pKa values of the relative ammonium ions are the only information
students have to memorize.

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G. Angelini, C. Gasbarri Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Example 4. The stereochemistry of a molecule is connected to the hybridation of the carbon directly involved in the formation of the
new chiral center. The molecule having a chiral center obtained from a sp2 carbon, as in the case of a carbocation, carbonyl group or
alkene is always present in racemic mixtures.
Students must identify the hybridization of the carbon before drawing the mechanism of a given reaction in order to predict the
stereochemistry of the products should it be converted into a chiral center.
Despite our efforts to instill the importance of dedication and perseverance in studying organic chemistry, we have noticed the
tendency of students to take this exam one or two years after the end of the course. To justify this delay most of them indicate that
they need more time to comprehend the content discussed in the class. Other students report that they still have to pass one of the
three mandatory qualifying exams from the first year. Another common student response is that there are only few exercises solved in
the text books, so they do not have enough practice to know if they are able to solve them correctly. Moreover, during the ex-
amination we have noticed that the successful students showing the highest level of understanding had more recently attended the
course. In light of the above considerations, we started an instructional study to improve the number of students in the exam sessions
within the semester just after the course utilizing two strategies: 1) a systematic approach to organic chemistry based on the or-
ganization of study lead by the teacher; 2) modification of the number of mandatory qualifying exams required for organic chemistry.
The level of difficulty has been kept constant in the investigated exam sessions, as well as the same parameters have been adopted to
assign the scores by both teachers involved (Guido Angelini, PhD and Carla Gasbarri, PhD), for example correct language and
symbols, as well as capability of connections between the different topics.

Educational activity and setting

The first strategy was adopted starting in the 2014–15 academic year and consists of increasing the self-confidence of students as
they successfully move from relatively simple exercises solved by the teacher to more difficult ones assigned as homework and solved
by the teacher the next day or at the end of the week.
It is well known that increasing student time-on-task enhances learning and successfully improves their achievement, especially
by using online homework systems.28–30 Generally, assigning homework without grading or grading only randomized exercises are
common methods in the case of classrooms with a large number of students. Our strategy is essentially based on an approach by
which students have enough time to spend on homework, without being stressed by the idea of being graded or receiving a partial
score as in itinere tests (periodic exams on a single discipline during the semester in which only selected topics are included and
which scores are taken into account for the final qualifying exam) but keeping control over learning. After discussing a specific topic,
several exercises are solved by the teacher on the dashboard, then one or two exercises of the same level of difficulty are administered
to the class as homework. Each student can decide to solve them, working in a team or by her/himself or to leave the exercises
without a solution.
Before starting a new topic, during the next lesson the teacher provides the guidelines to solve the previously assigned problems,
asking the class for suggestions or comments.
Feedback between the students and teacher directly offers a response as to the level of comprehension of organic chemistry: the
former understand what they have to study more deeply, the latter can go over hard-to-learn concepts and topics again, before
introducing new concepts. Sometimes, right answers coming from the personal effort of the involved students are rewarded by a
symbolic award, like a three-dimensional model of an organic molecule. To avoid anxiety and competition in the class, as previously
observed in pharmacy education, and promote student collaboration, we do not assign any scores.31
Although we encourage students to follow this systematic studying, each student has to decide whether or not to adopt this
strategy. This approach contributes to increasing the level of responsibility and awareness in studying. Examples of homework are
reported below:

1) In the classroom: The Wittig reaction is discussed. Fragmentation of the alkene into two components is pointed out as the
guideline to find the starting electrophile and nucleophile. Formation of phosphonium ylide as the nucleophile of the reaction and
role of the carbonyl group as electrophile are commented on. Homework for this session: students have to prepare a given
asymmetric alkene by using the Wittig reaction, showing how to generate phosphonium ylide. The solution discussed by the
teacher is reported in Fig. 1.
2) In the classroom: Reactions of aromatic compounds are discussed. Role of the Lewis acid, resonance in the intermediate of the
reactions and the effects of the substituents are the main topics. Homework for this session: students have to synthesize the para-
nitrophenol starting from benzene, showing the formation of the intermediate of each reaction. The solution discussed by the
teacher is reported in Fig. 2.
3) In the classroom: Preparation of imines starting from a carbonyl compound and a primary amine in the presence of H3O+is
discussed. The addition-elimination mechanism and the reversibility of the reaction are commented on. Homework for this session:
students have to draw the reaction mechanism between acetone and propylamine at pH 4–5. The solution discussed by the teacher
is reported in Fig. 3.
4) In the classroom: Nucleophilic acyl substitution is discussed. The reactivity of the carboxylic acids is compared to the reactivity
of their derivatives. Intermediate formation and the experimental conditions are commented on. Homework for this session: stu-
dents have to draw the mechanism for the reaction between (R)−2-methylpentanoic acid and (R)−2-butanol. The solution
discussed by the teacher is reported in Fig. 4.

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G. Angelini, C. Gasbarri Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Fig. 1. Example of homework solution discussed in the class by the teacher: preparation of an alkene by Wittig reaction.

Fig. 2. Example of homework solution discussed in the class by the teacher: synthesis of para-nitrophenol.

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G. Angelini, C. Gasbarri Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Fig. 3. Example of homework solution discussed in the class by the teacher: formation of an imine.

Fig. 4. Example of homework solution discussed in the class by the teacher: Fischer esterification.

Links to websites in which exercises, problems and questions are available with solutions are also suggested to promote regular
practice.
Motivation plays a fundamental role in learning.32,33 Recently, it has been pointed out that autonomy and scaffolding represent
the main components in promoting intrinsic motivation in learning pharmaceutical sciences, beside competence and relatedness.34,35
During the course we point out the connection between organic chemistry and everyday life to increase the awareness of students in
what they eat, drink, breathe, wear, etc. trying to instill a sense of responsibility in the acquisition of their own scientific culture,
independently from their professional future plans. We share information, news and curiosities. Sometimes we talk about our re-
search activities mainly focused on carbon nanotubes, azobenzenes spectral properties, surfactant and polymeric aggregations, de-
livery systems and non-conventional solvents to highlight the involvement of organic chemistry and its crucial role in a large variety
of fields.36–47 Moreover, we show the connections between organic chemistry and the other disciplines of the pharmacy course,
especially medicinal chemistry, biochemistry, and pharmaceutical technology to highlight the basis of the pharmacy student for-
mation.
The second strategy mentioned above has been adopted starting with the 2015–16 academic year (in association with the first
strategy) and consists of the modification of the number of mandatory qualifying exams required before organic chemistry. We have
proposed to retain only general inorganic chemistry rather than mathematics and physics because of its similarity with organic
chemistry. Students take general inorganic chemistry in the second semester of the first year, while they take organic chemistry in the

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Table 1
Distribution of the successful students of the investigated academic years into the exam sessions.
(%) (%) (%) (%) (%)
Investigated academic year Number of studentsa Successful studentsb Early session 1st summer session 2nd summer session Autumnal session

2013–14 (reference) 167 38.3 16.2 7.8 8.9 5.4

2014–15 Strategy (1) 130 49.2 32.3 9.9 6.2 0.8
2015–16 Strategies (1) + (2) 143 53.1 25.1 11.3 12.5 4.2
2016–17 Strategies (1) + (2) 80 61.3 41.2 8.8 8.8 2.5

a
Referred to the students of the second year attending the course for the first time.
b
Referred to the students of the second year.

first semester of the second year, as previously described.

Due to this proximity students still have in mind the fundamental concepts learned in the general inorganic chemistry course and
can easily recognize the connections to organic chemistry. Our request has been accepted by the Department of Pharmacy starting
with the 2015–2016 academic year. In this way students can decide for themselves whether to pass mathematics and physics before
taking organic chemistry or not, planning their exams as they prefer.
To observe the results of these two strategies, a comparison was made in the 2013–14 academic year in which the exercises were
regularly solved by the teacher without homework for the students, while mathematics and physics, together with general inorganic
chemistry, were mandatory exams to pass before organic chemistry.

Findings

To verify the efficacy of the first strategy (“Strategy 1”), alone or in combination with the second strategy (“Strategy 2″), we have
compared the percentage of successful students passing the exam during the sessions available in the semester at the end of the
course. The data are reported in Table 1.
A significant increase in the number of successful students in the exam sessions in the semester at the end of the course can be
observed by adopting Strategy 1 and 2 in comparison to reference: the percentage of students increases from 38.3% (2013–14) to
49.2% (2014–15) up to 61.3% (2016–17), as reported in Table 1. Moreover, for all the investigated academic years, most students
pass the exam during the early sessions. This tendency is improved from 16.2 to 32.3% in the presence of Strategy 1 and can be
improved up to 41.2% in combination with Strategy 2, suggesting that our approach encourages the studying and learning of organic
chemistry. The distribution of the scores in the range 18–22, 23–26 and 27–30 for the investigated academic years has been reported
in Fig. 5. The percentage of 30 cum Laude of the total successful students has been shown in Fig. 6.
Interestingly, it has been observed that in the presence of Strategy 1 alone or with Strategy 2 the best performances take place in
the early session in which the rate of 30 cum Laude falls in the range 63–75%.

Discussion

The introduction of Strategy 1 from the 2014–15 academic year strongly increases the number of students in the exam session
from 38.3 to 49.2% (Table 1), slightly increases the number of students having a score in the range 27–30 in comparison to reference
(Fig. 5), but strongly improves the number of 30 cum Laude (Fig. 6).
The introduction of Strategy 2 from the 2015–16 academic year seems to be negligible on the score distribution in comparison to

Fig. 5. Distribution of the exam scores for the successful students in the investigated academic years.

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G. Angelini, C. Gasbarri Currents in Pharmacy Teaching and Learning xxx (xxxx) xxx–xxx

Fig. 6. Percentage of 30 cum Laude / total successful students assigned in the investigated academic years.

Strategy 1, as pointed out by the data reported in Fig. 5, but contributes to an increase in the number of students in the exam session
from 49.2 to 53.1% (Table 1) and the number of 30 cum Laude from 14% to 18%, as pointed out by the data reported in Fig. 6. The
strong increase in the number of successful students from 53.1% to 61.3% (Table 1) and level of performances pointed out in Figs 5
and 6 obtained by the 2016–17 academic year indicate that the benefit of the introduction of Strategy 2 needs more time to be
relevant in comparison to Strategy 1. We have attributed this to the fact that, differently from Strategy 1, the benefits associated with
Strategy 2 are not immediately understood by most students probably because of their difficulty in making changes in their planning
organization.

Summary

Strategy 1 seems to be effective in promoting the studying and learning of organic chemistry, as demonstrated by the obtained
results starting with the 2014–15 academic year. The high scores associated with student performances reflect our efforts to improve
their self-confidence with organic chemistry, confirming the importance of motivational approaches.48 Strategy 2 contributes to an
increase in the percentage of students able to take the exam at the end of the course, suggesting a preference in passing organic
chemistry just after the exam of general inorganic chemistry.
Differently from Strategy 1, the importance of Strategy 2 for the pharmacy course needs more time to be comprehended and
accepted by students.
The results presented herein highlight a general trend by which the best performances are associated with students able to follow
a systematic and organized course of study.
Although our study was limited to a single institution in an Italian educational context, the results point out that this behavior still
remains an individual decision of each student that we, as teachers, can only encourage.

Conflicts of interest

Authors declare no conflicts of interest.

Financial disclosures

Authors have no financial disclosures.

Acknowledgments

We wish to thank the Department of Pharmacy, University “G. d'Annunzio” of Chieti-Pescara, in which we work as Assistant
Professors of Organic Chemistry.

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