Article Cite This: J. Chem. Educ. XXXX, XXX, XXX−XXX
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Teaching an Undergraduate Organic Chemistry Laboratory Course with a Tailored Problem-Based Learning Approach Luca Costantino*,† and Daniela Barlocco‡ †
University of Modena and Reggio Emilia, Dipartimento di Scienze della Vita, Via Campi 103, 41125 Modena, Italy University of Milano, Dipartimento di Scienze Farmaceutiche, Via Mangiagalli 25, 20133 Milano, Italy
J. Chem. Educ. Downloaded from pubs.acs.org by UNIV OF LOUISIANA AT LAFAYETTE on 03/28/19. For personal use only.
‡
S Supporting Information *
ABSTRACT: This article presents the structure of the organic chemistry laboratory Course “Synthesis and Extraction of Drugs” that is included in Modena University (Italy) in the third year of the five-year “Chemistry and Pharmaceutical Technologies” degree program. This course is unique in its kind, and it aims to provide students with the critical-thinking skills required to face practical organic synthesis. Because the “problem-based learning” approach ensures a high level of learning, we modified this approach to reconcile the students’ knowledge, the resources available compared with the number of students, and the purpose of a deep learning. Accordingly, tailored academic materials have been prepared (a textbook, a laboratory notebook, and a selection of primary literature), appropriate in-class and laboratory activities have been set up, and a grading pattern that promotes the active learning process has been defined. Although the number of students is high, following this approach, very positive results with respect to both laboratory techniques and critical thinking ability have been obtained. KEYWORDS: Organic Chemistry, Laboratory Instruction, Inquiry-Based/Discovery Learning, Medicinal Chemistry, Synthesis his article outlines the “Synthesis and Extraction of Drugs” laboratory course, which has been put into practice at the University of Modena and Reggio Emilia, Italy. The course is set in the third year of the five-year degree course in Chemistry and Pharmaceutical Technologies (CTF), designed for preparing students to work within the pharmaceutical industry (see Supporting Information (SI) S1, p S2, description of the degree course). The course “Synthesis and Extraction of Drugs” is the first and only organic synthesis laboratory course in the CTF degree program. The course must provide knowledge on laboratory techniques, from both a theoretical and a practical standpoint, as well as an overall view of a compound’s lab synthesis; in addition, it must create the critical-thinking skills needed to fruitfully cope with practical organic syntheses. For the design of the course described in this article, we examined the flaws detected over the years, during which the course concerned only general organic synthesis laboratory techniques and was carried out in a traditional format (expository style).1 As a result, students were used to considering the theoretical part of the course as separate from the practical part. Moreover, for the practical part, students passively followed a protocol; as a matter of fact, students acquired very limited and superficial knowledge about the process of synthesis of a chemical compound. When structuring a course of studies, in addition to the knowledge and the specific competencies that students will have to gain, a series of issues must be considered: where the course itself is placed within the curriculum of the degree
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© XXXX American Chemical Society and Division of Chemical Education, Inc.
course, the students’ starting tools (prior knowledge and developed learning strategies), the number of attendants and the available resources, in terms of staff and lab rooms. Several articles have appeared in the literature underlying a positive outcome obtained by changing recipe-driven organic chemistry laboratory activities into an open-ended, researchbased approach, thus modifying the instruction style from the expository to an inquiry-, discovery-, or problem-based approach.1,2 Following a traditional, expository style, students tend not to develop important critical-thinking skills that are a fundamental requirement for science graduates. On the contrary, inquiry-based activities, which require an inductive approach to knowledge, are preferred in this respect. Only the learner’s active involvement appears to truly ensure the development of a meaningful, deep learning style and critical-thinking skills.2−10 Recently, a fourth-year undergraduate synthetic and medicinal chemistry laboratory course given in a problembased learning (PBL) format has been described (Scheme 1).6 Whereas the problems to be solved by the students and the associated learning objectives are similar to ours (the courses are at about the same position in the students’ curriculum), the methodological teaching approach is different. Owing to the high number of students attending the course, the number of staff with respect to the number of students, and the available Received: December 14, 2018 Revised: March 9, 2019
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Scheme 1. Course Described in the Present Article (A) and That Proposed by Flynn (B)6
filtration, liquid−liquid extraction, or melting point (mp) assessment. The course schedule counts 48 h of theoretical lessons and 48 h of lab activity for some 50 students per year. Twelve weeks of lectures are scheduled, and, after the first week of lessons, one afternoon laboratory activity per week is added, during which the 12 units are carried out (see SI S1, p S4; one unit is carried out during lecture hours) for a total of 11 weeks. During the first week of class (without laboratory activities), general procedures about the isolation of compounds, such as filtration and chromatography, are explained (see SI S1, p S67). The lessons and the 13 units are targeted to the progressive development of key concepts and techniques (Table 1). Therefore, students are guided along the learning pathway, which gradually increases in its complexity, from Unit 1 to Unit 13.
lab room, we adopted a tailored adaptation of the PBL approach (Scheme 1) suggested by Kelly and Finlayson.4 Instead of workshops, we decided to give lectures. Students are incited to revise the lesson contents and lab activity through the compilation and grading of prelab sheets and lab reports; these reports are corrected and given back to the students in the shortest time (usually within 1 day) to stimulate a focused discussion during the following lecture. A protocol is used during lab activities, but because a protocol, as detailed as possible, cannot totally describe how to perform a reaction, during Unit 5, students take awareness of this while in lab; the discussion that follows deals with how to integrate the protocol, and the possible solutions thus identified are experimented in Unit 6. The subsequent units take into account and cultivate the new acquired critical mental attitude. These activities prepare the student for the final PBL activity based on articles submitted by the lecturer (a group-written exam, then an individual oral exam follow); the student must demonstrate that he/she has acquired both the knowledge and critical thinking ability to deal with experimental organic synthesis and the ability to understand how to perform chemical syntheses described in the literature.
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LABORATORY HARDWARE The available laboratory (65 m2) is equipped with three fume hoods that have to accommodate two groups of three to four students each. Because the laboratory can accommodate about 18 students at a time, three turns are carried out, to ensure that all of the course students take part in the lab activities. The
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“SYNTHESIS AND EXTRACTION OF DRUGS” COURSE Students who attend the “Synthesis and Extraction of Drugs” laboratory course have already attended General and Inorganic Chemistry Modules, Analytical Chemistry, and the courses of Organic Chemistry I and II. During the same semester in which the course unfolds, students take, among others, Physical Methods in Organic Chemistry, a course aimed at explaining characterization techniques (UV spectroscopy, IR spectroscopy, NMR spectroscopy, MS) for organic compounds. Before attending the Synthesis and Extraction of Drugs course, the students attend only one other course that includes laboratory sessions (Quantitative Analysis of Drugs, a course carried out in a traditional expository instruction style1) (see SI S1, p S2). Students who start the course Synthesis and Extraction of Drugs lack theoretical and practical knowledge about chromatography or other basic techniques, such as
Table 1. Laboratory Notebook Contents (Units 1−13) and Learning Objectives Unit 1−3 4 5−6 4−8, 10 6−8, 10 9 11, 12 13 1−13 B
Learning Objectives Identify and execute an appropriate method for the separation/ purification of compounds (analytical/preparative) Follow a reaction by TLC and verify side reactions Gain experience from pitfalls and modify a protocol on the basis of literature search Carry out a chemical reaction Carry out a synthesis of a compound Access a databank and the primary literature Understand the meaning of “purity” Understand solid phase synthesis Write concise and appropriate reports DOI: 10.1021/acs.jchemed.8b01027 J. Chem. Educ. XXXX, XXX, XXX−XXX
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Scheme 2. Correspondence between Textbook and Laboratory Notebook Topicsa
a
Units 1−13 are the laboratory activities.
to be used in the Grignard reaction (Unit 10), and DMF for peptide synthesis (Unit 13)).16 The laboratory notebook is made up of (a) prelab sheets and (b) templates for a guided report of the activity that has been performed in the lab. Prelab sheets contain questions targeted at promoting the students’ thinking skills. Students must write down their answers before entering the laboratory. By working on these sheets, students reflect on how to conduct the experiments and what can be expected to happen during their execution. This teaching methodology is aimed at preventing the students’ common habit of collecting the teaching material and notes during lessons and setting them aside without revising and thinking about them before the lab sessions. Students need to study what has been done in the classroom day by day to activate the learning process during the lab activity as well: Actually, by filling in the prelab sheet, students are forced to apply in advance the theory rules they are to experiment later on. After the laboratory activity, students have to fill out a template relative to the completed unit (see SI S1, pp S3− S61). This activity helps students learn to focus on the key aspects of the experiments that have been performed and teaches them how to write a laboratory notebook correctly. Its format is in accordance with those that the chemical world requires. Prelab sheets and lab reports are corrected and returned to students as soon as possible before the following unit starts. Thanks to this, students reflect on their mistakes and are acquainted with how to correctly proceed.
group arrangement, which in a traditional course is often perceived as a shortcoming (the best scenario is believed to be the single-place laboratory in which students work by themselves), is regarded here as a positive element, as it favors the ability to communicate and work as a team (learning through social interactions). Several authors highlighted the positive effects of group work in Organic Chemistry laboratory courses.3−5,7,8,10 Accordingly, activities have been tailored to promote interactions between students. The available equipment consists of three melting point devices, two rotary evaporators, vacuum and inert gas lines (double manifolds), six magnetic stirring devices, six heating mantles, and glassware. The functioning expenditure (consumable material) is around EUR 2000 each year for chemicals and glassware (about EUR 30/year for each student); an additional EUR 1000 has been budgeted for Unit 13.
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TEACHING MATERIALS AND TOPIC OF THE LECTURES Students are provided with a tailored textbook written by the lecturer,11 the content of which is described in Scheme 2 (see SI S1, p S62, Table of Contents) and a laboratory notebook (Scheme 2, SI S1, pp S3−S61). The classes are carried out according to the topic sequence of the textbook. During the lessons related to Chapter 3 of the textbook,11 students must independently register to the journal Web site, download the four articles chosen by the lecturer,12−15 and examine the discussion-worthy sections (the ones regarding chemical synthesis, schemes of synthesis, and experimental sections). Every synthesis described in these articles is explained in the textbook as well as during the lectures, both with regard to the retrosynthetic scheme, the reaction mechanisms, the characteristics of the reagents, the required glassware, and how a described procedure can be translated into practice. In this way, students acquire the ability to find and download a given article from the Web site of journals and to understand how to put into practice the synthesis described in the primary literature. In this way, they also become familiar with the current English technical terminology for the organic chemistry laboratory. Students are also involved in the choice of reagents and solvents, among those available on the market by accessing the Internet, that are needed for the synthesis they are asked to perform (for example, silica, nitric acid (Unit 4), diethyl ether
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LABORATORY PRACTICE The laboratory practice includes one afternoon laboratory activity per week (see SI S1, p S4). With few exceptions, the laboratory assignments are carried out in a time span of 1 day: The laboratory schedule we have adopted requires that a few previously performed, practical activities are carried out by the lecturer (e.g., weighing the products obtained in Unit 5, collecting the crystallized products, and placing them in a desiccator, if needed (see SI S1, p S4)). Without this collaboration, there would be a significant overlapping and fragmentation of activities throughout the afternoon laboratories, causing confusion and disorientation among students. C
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laboratory techniques, the ability to interpret what is happening within the reaction vessel to act according to the problem that may present itself throughout the reaction. In other words, students must acquire observational skills to understand the key aspects of a reaction and must interpret the phenomena they are seeing if these have not been reported and explained along the protocol. The reduction of 4-nitrophenol (Unit 5) provides a good example to inductively understand, on the basis of a laboratory experience, that a protocol, as detailed as it may be, cannot explain all that is needed to carry out successfully (with a satisfactory yield of the product) a given reaction. During the lectures, students are generally told (textbook)11 what the most common reducing agents in organic chemistry are, and, in particular, they are alerted to the fact that NaBH4 is stable in an alkaline environment and that it rapidly deteriorates only in an acid environment, releasing hydrogen; on the contrary, in Unit 5, reduction is carried out with NaBH4 in an alkaline environment, but gas develops. Students are invited to proceed with the reduction of 4-nitrophenol following the procedure described in a protocol that can be downloaded from the Web18 that does not include any comment on or any explanation of the specific mechanism of the reaction. Conducting the reaction as described in the protocol in an uncritical way would lead to low yields of the product (see SI S1, p S32). The topic of the in-class discussion and prelab sheet of the following day is built on the understanding that although a protocol is available, critical thinking is necessary to perform a synthesis. Suggestions to improve the yields are then sought and experimented in the following lab session (Unit 6, see SI S1, p S28). In this way, the concept of “explorative reaction” is also introduced. Unit 7 deals with the synthesis of paracetamol (acetaminophen). Following the in-class discussion about three available protocols,18,20,21 some groups decided to test a different one with respect to that proposed by the lecturer20 (see SI S1, p S36). Then, their results (yields) were discussed during the lesson, after the lab activity; two videos about paracetamol synthesis22,23 were shown to students as well. This method led students to effectively acquire an awareness of the existence of different glassware and ways of performing a reaction. Furthermore, the search (prelab sheet) of the shortcomings within an article24 that describes the synthesis of an impurity that can be formed during the synthesis of paracetamol offers the opportunity to explain how to read an article from the point of view of the person who would repeat the reaction (see SI S1, p S36). The correspondence between the way to proceed in the laboratory and the way in which the procedure is reported in the chemistry section of an article will be fully exploited during the following lessons and discussion about the four references downloaded by the students12−15 and the activity performed during the following days. Unit 8 leads to the synthesis of phenacetin,20 with its purity evaluated by TLC, mp in comparison with a standard, and qHNMR (Unit 12). Technical difficulties (anhydrous, inert atmosphere) introduce students to the more challenging Grignard reaction (Unit 10). Unit 9 deals with the search for triphenylethene compounds on the SciFinder database25 and therefore of the primary literature to which it refers. The first synthetic route of these compounds is described in one12 of the four articles12−15 that students previously downloaded and that has been analyzed in the textbook.11 During this unit, students have to find a second
The topics of the units do not include the spectroscopic characterization of the compounds under study. In other words, IR and NMR spectra of the synthesized or separated products have not been routinely acquired. Their acquisition would be a time-consuming activity because it would require students to visit the University Instruments Centre, which lies in another building. Furthermore, because the “Instrumental Characterisation of Organic Compounds” course that deals with these topics runs simultaneously, students are not prepared to understand the acquired spectra. However, at the end of the laboratory notebook units that requires spectra, students are reminded that the necessary characterization of compounds must include the application of instrumental methodologies. However, to explain to the students the concept of the purity of a given compound, quantitative 1H NMR spectra (qHNMR) have been acquired by the lecturer and are discussed at the end of the course. Units 1−3 (part A of the laboratory notebook) deal with the general chemistry laboratory procedures used for the isolation and purification of a given compound. A common thread has been followed in the selection of the starting materials of these units (benzoic acid and methyl benzoate) to have the least dispersive vision possible. Benzoic acid has been chosen for the experience of liquid−liquid extraction (Unit 1) and analytical (TLC, Unit 1) and preparative (column) chromatography (Unit 2) and for the technique of the purification of a solid (crystallization, Unit 3). One sample of a student’s crystallized product has been assessed in its purity by qHNMR in comparison with the crude compound. Students can then easily compare the various techniques (highlighting their difficulties and pros and cons), and the study of a single compound helps them not to break up their attention. If the time for another unit was available, then the course would be implemented by an esterification reaction of benzoic acid through a reaction with methanol in an acid environment and purification of the product through a distillation at reduced pressure; as a consequence, it would be possible to compare purification through distillation and purification through column chromatography (Unit 2). The ester thus obtained could be subsequently employed in the Grignard reaction (synthesis of triphenylmethanol, Unit 10). In this course, other experiences have been prioritized, omitting this esterification reaction but maintaining the determination of the boiling point of methyl benzoate depending on pressure through the use of the nomograph (Unit 10). Units 4−10 (part B of the Laboratory Notebook) deal with the synthesis of a given compound. Units 4−8 deal with the multistep synthesis of phenacetin. The phenacetin synthesis, starting from phenol, has been selected because it is a multistep synthesis and allows the students to test a wide range of chemical reactionssome of which require an anhydrous environment. All intermediates have been purchased, allowing small-scale syntheses. Furthermore, the intermediates and solvents are not expensive and not significantly dangerous. In Unit 4,17 students learn how to monitor a reaction and verify that side products can be also formed according to the reaction mechanism and structure of the starting material. Unit 518,19 is the first unit aimed at the complete preparation of a chemical compound. Students have so far attended only one laboratory course that, in addition, is carried out in the traditional way (Quantitative Analysis of Drugs). They are used to strictly following a protocol, whereas the synthesis of a product also requires, aside from a knowledge of the basic D
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Figure 1. Grades obtained by students during academic years 2017/18 (n = 48) and 2018/19 (n = 50).
Figure 2. Results of the University Teaching Evaluation Questionnaire concerning the course “Synthesis and Extraction of Drugs”. Questions to students: (1) Is the learning material adequate to the study of the subject? (2) Does the lecturer stimulate/motivate interest toward the subject? (3) Are the laboratory activities useful to learn the subject? (4) Are the rooms and the equipment used in the laboratory activities adequate? (5) Overall, are you satisfied with the teaching of the course? Completed questionnaires n = 42 in 2017/18 and n = 55 in 2018/19.
technique is widely used in the medicinal chemistry field, and it requires specific practical knowledge. The synthesis of FmocPhe(4-NO2)NH2 on Sieber amide resin was chosen for the significantly low price of starting materials and because a high amount of dangerous trifluoroacetic acid is not necessary for the cleavage. During the lab activity, the lecturer plays the role of facilitator. He interacts with the students, helps them perform the activities better, and reflects on what they are doing.
synthetic route of a derivative of this chemical class. (Only two synthetic routes are reported on SciFinder for the compound that the lecturer selected.) The comparison with the route discussed in the textbook allows a motivated choice of the path that the student intends to follow for the synthesis on the basis of safety, yields, costs, scale required, and time. In this way, students realize that many methods may be followed to synthesize a given compound and learn how to select the most appropriate method for their needs. The synthesis of triphenylmethanol (Unit 10)26 is included to challenge students with a technically difficult synthesis; due to the large number of videos available on the Web,27−30 the student can independently search how to realize the synthesis. Units 11 and 12 (part C of the laboratory notebook) deal with the concept of purity, and, in particular, Unit 12 deals with the determination of the % purity by qHNMR of phenacetin synthesized by the students during Unit 8, of which they have already performed a qualitative assessment. In this way, students can experience the meaning of “purity”. Unit 13 (part D of the laboratory notebook) deals with solid-phase peptide synthesis, a bridge between “classical” and combinatorial chemistry, described in the textbook.11 This
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ASSESSMENT OF THE LEARNING RESULTS The final assessment has been partially transformed into an activity that is part of the training process. Grade assessment refers to (a) the prelab sheets and laboratory notebook templates compilation (see SI S2 for an example of a filled lab notebook), (b) the analysis of the synthesis of a given compound as reported in an article published in an English pharmaceutical journal (J. Med. Chem., Bioorg. Med. Chem.), and (c) an oral test (see SI S1, Assessment Table, page S65). In fact, to stimulate students’ reasoning, critical thinking, teamwork skills, and interest, as a part of the final exam, the students’ teams that took part in the E
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laboratory activities are asked to describe in written form from a theoretical and practical point of viewall of the preliminary work that is needed to successfully translate into practice, in the laboratory, the synthesis of a given compound reported in the primary literature that has not been performed before. The lecturer selects from an article an appropriate target compound (the synthesis of which is proportionate to students’ theoretical knowledge of organic chemistry) and purposely introduces one or more mistakes into the experimental part; students have to identify and correct mistakes, describe the procedure and the mechanism of reaction, link the reaction scheme to what happens within the reaction mixture, explain how to monitor the reaction, justify the number of equivalents shown, and state the correct glassware necessary for the synthesis (one article for each group of students; see SI S2 for an example of written exam). In their work, students are encouraged to access the Internet, SciFinder, books,31 and any other resources that they wish to use, with the help of the lecturer for finding it. This activity can also be carried out at home to link it to their professional future. The oral test is based on a discussion about the laboratory notebook content and on the four assigned bibliographies12−15 as well as on the chemical part of the article selected by the lecturer (see SI S1, p S63, for the list of articles) or of a previously unknown article.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Luca Costantino: 0000-0001-5334-8084 Notes
The authors declare no competing financial interest.
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REFERENCES
(1) Domin, D. S. A review of laboratory instruction styles. J. Chem. Educ. 1999, 76 (4), 543−547. (2) Bertram, A.; Davies, S. E.; Denton, R.; Fray, M. J.; Galloway, K. W.; George, M. W.; Reid, K. L.; Thomas, N. R.; Wright, R. R. From cook to chef: facilitating the transition from recipe-driven to openended research-based undergraduate chemistry lab activities. New Directions 2014, 10 (1), 26−31. (3) Kelly, O.; Finlayson, O. A hurdle too high? Students’ experience of a PBL laboratory module. Chem. Educ. Res. Pract. 2009, 10 (1), 42−52. (4) Kelly, O.; Finlayson, O. Providing solutions through problembased learning for the undergraduate 1st year chemistry laboratory. Chem. Educ. Res. Pract. 2007, 8 (3), 347−361. (5) Smith, C. J. Improving the school-to-university transition: using a problem-based approach to teach practical skills whilst simultaneously developing students’ independent study skills. Chem. Educ. Res. Pract. 2012, 13 (4), 490−499. (6) Flynn, A. B.; Biggs, R. The development and implementation of problem-based learning format in a fourth-year undergraduate synthetic organic and medicinal chemistry laboratory course. J. Chem. Educ. 2012, 89 (1), 52−57. (7) Browne, L. M.; Blackburn, E. V. Teaching introductory organic chemistry: a problem-solving and collaborative-learning approach. J. Chem. Educ. 1999, 76 (8), 1104−1107. (8) Weaver, M. G.; Samoshin, A. V.; Lewis, R. B.; Gainer, M. J. Developing student’s critical thinking, problem solving, and analysis skills in an inquiry-based synthetic organic laboratory course. J. Chem. Educ. 2016, 93 (5), 847−851. (9) Quattrucci, J. G. Problem-based approach to teaching advanced chemistry laboratories and developing student’s critical thinking skills. J. Chem. Educ. 2018, 95 (2), 259−266. (10) McDonnell, C.; O’Connor, C.; Seery, M. K. Developing practical chemistry skills by means of student-driven problem based learning mini-projects. Chem. Educ. Res. Pract. 2007, 8 (2), 130−139. (11) Costantino, L.; Barlocco, D. Laboratorio di Preparazione Estrattiva e Sintetica dei Farmaci; Aracne Editrice, Canterano (RM), Italy, 2017. (12) Lubczyk, V.; Bachmann, H.; Gust, R. Antiestrogenically active 1,1,2-tris(4-hydroxyphenyl)alkenes without basic side chain: synthesis and biological activity. J. Med. Chem. 2003, 46 (8), 1484−1491. (13) Lovely, C. J.; Bhat, A.; Coughenour, H. D.; Gilbert, N. E.; Brueggemeier, R. W. Synthesis and biological evaluation of 4(hydroxyalkyl)estradiols and related compounds. J. Med. Chem. 1997, 40 (23), 3756−3764. (14) Choi, C.; Li, J. H.; Vaal, M.; Thomas, C.; Limburg, D.; Wu, Y. Q.; Chen, Y.; Soni, R.; Scott, C.; Ross, D. T.; Guo, H.; Howorth, P.; Valentine, H.; Liang, S.; Spicer, D.; Fuller, M.; Steiner, J.; Hamilton,
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STUDENT PERFORMANCE EVALUATION Figure 1 reports the available grades obtained by the students. Data concerning academic year 2017/18 are related to the 48 students, out of 54, that passed the exam. Data concerning academic year 2018/19 are related to the 50 students, out of 58, that passed the exam up to now; among these students, two received grades lower than 6, and they must take the oral exam again.
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STUDENT COURSE ASSESSMENT The results of the student appraisal of the course, carried out following the approach adopted in the 2017/18 and 2018/19 academic years and described in the present article, were good. Figure 2 shows the results of the University Teaching Evaluation Questionnaire concerning this course.
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CONCLUSIONS Considering the number of students attending the course, the here-reported strategy seems to be a good compromise between inquiry and expository learning. The course feedback forms filled out by the students reported very positive judgements (very educational course, stimulating, intriguing, really interesting); over time, attendance at the lectures has not declined at all, and the students’ behavior during both lectures and laboratory activities has been particularly active. At the end of our course, students have developed critical thinking regarding practical organic chemistry, the competencies to retrieve data for the synthesis of a given compound, and the ability to use these data to plan its synthesis in a chemistry laboratory.
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S1: Description of the course in the Chemistry and Pharmaceutical Technologies program; laboratory notebook; textbook (table of contents and notes); list of the written exams (academic year 2018/19); assessment table; and introducing chromatography (PDF) S2: Filled laboratory notebooks and written exams performed by representative students and reproduced with permission (PDF)
ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.8b01027. F
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G. S. Use of parallel-synthesis combinatorial libraries for rapid identification of potent FKBP12 inhibitors. Bioorg. Med. Chem. Lett. 2002, 12 (10), 1421−1428. (15) Wei, L.; Wu, Y. Q.; Wilkinson, D. E.; Chen, Y.; Soni, R.; Scott, C.; Ross, D. T.; Guo, H.; Howorth, P.; Valentine, H.; Liang, S.; Spicer, D.; Fuller, M.; Steiner, J.; Hamilton, G. S. Solid-phase synthesis of FKBP12 inhibitors: N-Sulfonyl and N-carbamoylprolyl/ pipecolyl amides. Bioorg. Med. Chem. Lett. 2002, 12 (10), 1429−1433. (16) Sigma-Aldrich. www.aldrich.com (accessed March 1, 2019). (17) PrepChem. Synthesis of 4-Nitrophenol. http://www.prepchem. com/synthesis-of-4-nitrophenol/ (accessed March 1, 2019). (18) Ellis, F. Paracetamol − A Curriculum Resource; Royal Society of Chemistry: London, 2002. http://www.rsc.org/learn-chemistry/ content/filerepository/CMP/00/000/047/Paracetamol_web.pdf (accessed March 1, 2019). (19) Furniss, B.; Hannaford, A.; Smith, P. W. G.; Tatchell, A. R. Vogel’s Textbook of Practical Organic Chemistry, 5th ed.; Pearson Prentice Hall: Essex, U.K., 1989; pp 894−895. (20) Furniss, B.; Hannaford, A.; Smith, P. W. G.; Tatchell, A. R. Vogel’s Textbook of Practical Organic Chemistry, 5th ed.; Pearson Prentice Hall: Essex, U.K., 1989; pp 985−986. (21) Naik, S.; Bhattacharjya, G.; Talukdar, B.; Patel, B. K. Chemoselective Acylation of Amines in Aqueous Media. Eur. J. Org. Chem. 2004, 2004 (6), 1254−1260. (22) Synthesis of Paracetamol (Acetaminophen). https://www. youtube.com/watch?v=xY33L8SqMo4 (accessed March 1, 2019). (23) Synthèse du Paracetamol. https://www.youtube.com/watch?v= LhGWfotbWL8 (accessed March 1, 2019). (24) Rao, A. S.; Lalitha, S.; Srinivasan, K. K.; Moorkoth, S.; Zaraha, H.; Jadon, S.; Matsa, R.; Sagiraju, R. Synthesis and in Vitro Antimicrobial Evaluation of 5′-Acetamido-2′-hydroxy Chalcone Derivatives. Res. J. Chem. Sci. 2014, 4 (2), 56−59. (25) SciFinder. https://scifinder.cas.org/ (accessed March 1, 2019). (26) Zhang, T. The Grignard Synthesis of Triphenylmethanol. Org. Chem.: Indian J. 2015, 11 (8), 288−292. (27) The Grignard Reaction: Triphenylmethanol. https://www. youtube.com/watch?v=Raeh26H8S7Y (accessed March 1, 2019). (28) Synthesis of Triphenylmethanol. https://www.youtube.com/ watch?v=k5VwidV5ehc (accessed March 1, 2019). (29) Preparation of Triphenylmethanol via Grignard, Expt. 8. https://www.youtube.com/watch?v=Pgv0y8iSBWk (accessed March 1, 2019). (30) UTSC - Chemistry Lab Grignard Reaction Experiment. https://www.youtube.com/watch?v=s3sShnm1ArM (accessed March 1, 2019). (31) Furniss, B.; Hannaford, A.; Smith, P. W. G.; Tatchell, A. R. Vogel’s Textbook of Practical Organic Chemistry, 5th ed.; Pearson Prentice Hall: Essex, U.K., 1989.
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