Independent Synthesis Projects in the Organic Chemistry Teaching

Article pubs.acs.org/jchemeduc

Independent Synthesis Projects in the Organic Chemistry Teaching Laboratories: Bridging the Gap Between Student and Researcher Valerie A. Keller* and Beatrice Lin Kendall† Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States S Supporting Information *

ABSTRACT: Science educators strive to teach students how to be well-rounded scientists with the ability to problem solve, anticipate errors, and adapt to unexpected roadblocks. Traditional organic chemistry experiments seldom teach these skills, no matter how novel or contemporary the subject material. This paper reports on the success of a quarter-long organic chemistry laboratory experiment that takes the form of a research project designed to teach these real-life skills. Students took a three-step synthetic sequence from a literature source, and changed parameters to improve the yield. This involved library research and two levels of proposals, followed by a written report and a poster presentation. The goal was to simulate the different aspects of a research lab, from literature searches to problemsolving to presenting results. The students experienced unexpected difficulties and were graded on how they overcame these obstacles, rather than on how much they improved the yields. KEYWORDS: Second-Year Undergraduate, Organic Chemistry, Curriculum, Laboratory Instruction, Collaborative/Cooperative Learning, Communication/Writing, Inquiry-Based/Discovery Learning, Problem Solving/Decision Making, Spectroscopy, Synthesis

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BACKGROUND The purpose of an undergraduate education is to prepare students for their future careers with the background and skills needed to succeed. Traditional organic chemistry lab experiments may teach a particular experimental technique adequately, but many times may lack in developing the professional skills that students need to be innovative researchers. If a university education in chemistry is truly a bridge between academic knowledge and a professional environment, it must teach real-life skills such as searching literature, cooperative working, experiment planning, problemsolving, scientific writing, and presenting results along with laboratory techniques.1−3 The Honors Organic Chemistry III spring quarter lab project described here strove to expose students to these professional skills in a mock research environment within the teaching laboratory. In the process, students also gained additional chemical knowledge in the form of new reaction mechanisms that they may not have learned in the lecture portion of class. This quarter-long lab project gave students a holistic approach to chemistry that traditional lab experiments lack. The importance of this approach has been addressed by the American Chemical Society, which has described such a capstone experience as part of a curriculum needed for accredidation.4 Reviews have shown that the laboratory is an ideal medium for which to teach scientific literacy, which teaches knowledge along with soft skills such as critical thinking.5,6 A wide range of experiments have been designed over the years to introduce students to these professional skills. Library literacy is an © XXXX American Chemical Society and Division of Chemical Education, Inc.

extremely important component of a professional career, and many experiments have incorporated this into the curriculum, either with a single experiment or project.7−21 Open-ended and student-designed experiments have also been published. 7,9,10,13,14,17−19,22−27 Collaborative group experiments9,12−14,17−19,21,22,24−26 and experiments that involve presenting the results in either a mock research article, poster, or oral presentation7,9,12,13,18−21,23,24,26,27 form have similarly been developed. Laboratory experiments that both incorporate cooperative work and require students to problem solve in an open-ended structure have been shown to increase both metacognition and problem-solving skills.28,29 While many experiments have been designed to incorporate more than one aspect listed here, each department must choose different approaches based on their specific pedagogy and resources. This paper reports on the experience with a laboratory experiment that is an amalgam of these approaches. This experiment is unique in that it combines cooperative learning, library literacy, student translation of published reactions, experimental design based upon knowledge gained in the lab, and data presented in both written and poster presentation form. These specific criteria were tailored over the years to address the goals described below, as well as maximize the use of the teaching staff and other resources. Received: February 1, 2017 Revised: July 20, 2017

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DOI: 10.1021/acs.jchemed.7b00093 J. Chem. Educ. XXXX, XXX, XXX−XXX

Journal of Chemical Education

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Scheme 1. Three-Step Syntheses Performed in the 2016 Projects30−35

At the University of Chicago, roughly 250 students take either three quarters of Organic Chemistry or three quarters of Honors Organic Chemistry during the academic year, which are combined lab and lecture courses. Of those, only about 30 elect to take the honors track contingent on a B+ or higher average in general chemistry. Within the honors class there are typically three lab sections, giving a relatively small student to Teaching Assistant (TA) ratio. This, on average, is 10 students per TA in the honors sequence compared to 15 students per TA in the regular sequence. The honors sequence covers the same material at the same pace as the regular sequence, but delves much deeper into examples, applicability, and molecular orbital theory. The first two quarters of the honors organic chemistry sequence have identical experiments as the main organic chemistry track, and so this project sets the class apart and gives the lab portion a more in-depth inquiry that is expected from an honors class. The shared experiments are a mix of traditional and inquiry-based laboratories and provide training on all the

major techniques required in a modern organic chemistry lab. However, they do not introduce how to search, read, and analyze the scientific literature. Another area of need in these preliminary laboratories is student experience with experiment design. Several experiments require students to calculate the amount of reagents needed prior to coming to lab, but a majority of procedural details are given in the lab manual, such as size of glassware, amount of solvent, and molar equivalents. Finally, in order to give students a manageable amount of work, lab reports are short and do not require scientific writing skills. These experiments do give students a good background with techniques and the hands-on experience of performing reactions; however, they do not take students to a level of critical thinking that an honors class requires. In addition to the pedagogical reasons for implementing this project in an honors class, there were logistical reasons that highlighted this decision. As noted above, the student to TA ratio in the honors class is relatively low. This experiment necessitates more individualized guidance compared to more standard experiments, and this B



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Many experiments developed to teach scientific literacy, and more specifically problem-solving, involve either a single reaction/target molecule or a completely open-ended project. The decision to expand beyond a narrow procedural goal is explained above. However, it was decided to implement a more rigid framework compared to an entirely student defined project in order to build in a more graduated hierarchy of problem-solving levels. The students started with a published synthesis in order to gain confidence with experiment design. Then, students repeated three of the transformations in order to not only learn from their mistakes, but also improve upon them. Since the types of optimizations were not dictated, the students had the opportunity to identify the largest problem in the synthesis and attempt to solve it. When students perform a reaction only once, for example in a traditional experiment, they do not have the opportunity to go beyond identifying a problem with their execution of a procedure. Therefore, it was felt that organizing the project into execution and optimization portions created an appropriate balance between structure and creativity. Most of the capstone projects referenced above involve presenting data as either a written report, a poster, or an oral report. A conscious decision was made to require all three methods since professional scientists need all these skills in order to be successful. The exercise of preparing a written report in the form of a research article and a poster was designed to show that, in order to be effective, a poster cannot be merely a manuscript that is placed on the wall. A wellstructured poster also requires a good oral presentation to enhance the depth and detail of the research. This project was conceived as a cooperative group assignment due to the large amount of work that was assigned, exceeding the amount of time that should be reasonably expected from one student. In addition, there is evidence that cooperative group learning increases student attitudes, understanding of concepts, performance on assignments, and more importantly the increased ability to solve open-ended or illdefined problems through metacognition.28,29 Many undergraduate chemistry curricula for lecture and laboratory have been developed that show the positive impact of cooperative and collaborative learning.36−40 In this project, performing a synthesis as part of a group relieves the pressure that comes from a failed reaction since the results are aggregated. It also presents the opportunity to find multiple paths toward a common goal. And finally, group work mimics both a research and professional environment, helping to bridge the gap between undergraduate learning experience and the lab bench.

smaller ratio helps foster the amount of oversight and help that is needed for such an open-ended project. For these reasons, this quarter-long project was taught in the spring quarter of the honors organic chemistry sequence from its inception over 10 years ago.

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EXPERIMENT DESIGN

Goals and Objectives

The quarter-long experiment detailed here strove to expose students to many of the trials and excitement of research work as well as the skills needed to succeed in a lab. Specifically, the goals of this experiment were to train students to • search for and obtain literature articles • evaluate the literature for relevance • prepare an experiment based on published results • problem solve • organize and implement an open-ended problem • work within a group to accomplish a common goal • present results in a professional manner The experiment was designed for a group to perform a threestep synthesis30−35 as published and then propose and execute three optimization reactions. The five syntheses used in the 2016 class are summarized in Scheme 1. A copy of the lab manual from that year is available in the Supporting Information. The choice of a three-step synthesis for the projects was made to help students develop proficiency in several aspects of lab work. First, a multistep synthesis provides several literature search targets, whether reactions or compounds. This gives students the opportunity to experience a larger volume of material when evaluating literature hits as well as the potential for having a larger range of difficulties. Second, purification and characterization were not merely exercises, but necessary components to make sure that an intermediate was appropriate, whether in identity or purity, to carry on to the next step. Each student was required to collect, prepare, and either obtain or submit their samples for characterization (mp, MS, IR, NMR). They themselves determined if the reaction was successful or not by fully analyzing their spectra. Third, completion of a later synthetic step is not as easy as first thought due to the propagation of errors or impurities along the sequence. The project was designed to highlight this point by purposefully having students repeat steps through optimization. Students learned that advanced intermediates were precious commodities and would therefore treat them as such by being more careful and deliberate in lab. They also learned to scale down reactions or run test reactions in order to save frontier material. These problem-solving lessons were learned in the execution portion of the experiment. Finally, a synthetic sequence gives the project the cohesiveness that several separate reactions would lack. This way students have a more invested emotional attachment to their project since they are all working toward reaching one shared end point. Part of their background research for this project was to give context to their synthetic sequence, and this was often a pharmaceutical target. The arc of this project introduced students to the skills of research, but also put them in a framework of the broader research community. Since many of them were not chemistry majors, this was a chance to put their chemical knowledge into a broader context that included their intended career path.

Preparation

Prior to coming to lab, the students had 2 weeks to prepare their projects and came up with detailed plans for how to accomplish the execution and optimization of the synthetic sequence. The schedule for the project is shown in Table 1. Each teaching assistant assigned groups of three or four students and determined which project would be performed. Most often the TAs had taught the honors class for the entire year and knew the students well. It was found that if students chose their own groups, some groups would be disproportionally strong or weak, and the TAs could better manage pairing stronger with weaker students as well as matching compatible personalities and separating dependent friends. In addition, this alleviated any awkward situation where one student was not chosen by any group. These issues are well-documented, with C



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ended, with the goal of performing three separate optimization reactions. Students could choose to optimize one reaction three different ways, or three different reactions. They could keep the substrates identical to those of the published route, or slightly change functional groups to increase reactivity. Each student performed his or her own optimizations, but the three reactions needed to make a cohesive project when written up with the rest of the group. The proposals for optimization needed to be detailed, like the execution procedure, and approved by both the lab director and TA before students could perform the optimization portion of the lab. Each group met with the lab director close to the time that the optimization procedure was due in order to make sure that everyone was making progress with the project and that the optimizations were appropriate for an undergraduate lab. This was a practical matter to ensure that all students were proposing and performing safe reactions in addition to dealing with the logistics of time management, equipment and chemical procurement, and fair distribution of labor. Even though there were limits specified in the lab manual, such as no experiments involving extremely high heat, long reaction times, high toxicity, or sensitivity to water or oxygen, students still needed guidance on choosing appropriate reaction conditions. This was often the moment when students understood the difference between abstract knowledge and the logistics of running such reactions.

Table 1. Honors Organic Chemistry Spring Quarter Lab Project Schedule Week

Description

Assignment

1 2 3 4 5 6 7 8 9 10

Library presentation Preparation Synthesis execution Synthesis execution Synthesis execution Optimization Optimization Optimization Poster presentation Write up

None Procedure for synthesis execution Meeting with lab director Procedure for optimization None Draft of lab report None None Poster Lab report

heterogeneous groups preferred to maximize student learning.41 The students were required to attend a training session given by the science librarian that detailed how to search and obtain literature. This started with a basic understanding of the components of a citation, then went into how to search SciFinder and Reaxys using both structures and key terms. Since journals are not the only source of chemical information, handbooks, encyclopedias, and other reaction compilations were discussed. Finally, students were given a tutorial on how to download and use ChemDraw. The students obtained the primary article30−35 that their project was based on as well as any background articles they deemed necessary. This was done in a similar way to a research search, where cited articles were obtained and read followed by a search based on structure, reaction, and keywords. This was an organic process, where students honed in on literature hits and then discussed the articles with their TA to further assess viability. Many times the students would need to complete a refined search, since they were learning how to evaluate literature on its reliability and feasibility. This learning was ongoing throughout the project, but mainly occurred before the optimization proposal was due as well as when students ran into unexpected problems in their optimizations. Since the TAs and the lab director needed to approve all reactions performed, students were supported while learning about literature search techniques and article evaluation. Once the preliminary literature search had been performed, students took the primary article and translated the experimental procedure into step-by-step instructions that scaled the reaction to no more than 5 g of starting material. This included what reactions would be performed, what size flasks or other glassware was needed, the amounts of reagents and solvents to be used, detailed descriptions of the purification procedures, and how the products would be characterized, as well as an outline of the time it would take to perform the tasks on each day. This was to ensure that students were not being overly optimiztic about what could be accomplished in a 4 h lab period. A formal written procedure for executing the synthetic sequence was then submitted to the teaching assistant to be graded. Students could not start working in lab until their TA approved the procedure. This made sure that everyone was prepared, since time in lab was limited, and much of it could be wasted by rereading articles and other preparatory tasks. Before and during the weeks of executing the synthesis, students also searched the literature for related reactions in order to find alternate reaction conditions for optimizing their reactions. The optimization portion of the project was open-

Experiment Execution and Optimization: Examples of Performance

Students had 3 weeks with which to perform the three synthetic steps outlined in their project. However, the timing of each 4 h lab period was entirely up to the students. Students that were not careful with purification and characterization could end up spending time on a doomed reaction before they realized that something had gone wrong, and learned the lesson of proper and full characterization the hard way. Sometimes students did not fully characterize a compound and started the following step with a byproduct instead of the intended target. They also did not realize that its purity must be high in order to ensure the best possible outcome of the following step. While many took the entire time to perform an experiment, some realized that they could run more than one reaction simultaneously and therefore save time for other reactions or for dealing with setbacks. Some students performed the execution steps more than once, especially if their optimization was for the second or third step and they needed to build up an adequate amount of starting material. In this segment of the project, students learned these time management skills from both their TA and fellow students. They could see the rewards of multitasking first hand as well as see how proper time management could mean the difference between success and failure. Following the execution and contingent on approval, students had 3 weeks to complete their optimization reactions. The success students experienced and the problems they faced in these weeks varied widely for multiple reasons. For example, students wishing to run three optimization reactions on the third step in the sequence realized that they must repeat the first two steps in order to have enough material to optimize in addition to perform three optimization reactions. If students wanted to use chemicals that were not in the primary literature procedure, they needed to request these at least 1 week in advance. This chemical request form is available in the Supporting Information. Students sometimes did not realize that obtaining chemicals takes time, and did not have alternate D



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Scheme 2. Samples of Student Optimization Reactions from 2016

reactions, 33% either matched or exceeded the literature yield. In the optimization portion, 37% of reactions exceeded the group’s highest yield of their original reaction, with all groups experiencing at least one successful optimization. Since each student needed to perform three reactions each in the execution and optimization portions, on average each student reached their goal of improving on a published yield with one reaction in both the execution and optimization parts. While actual yields were not a basis for grading the project, these accomplishments point to successful problem-solving as well as the project goal of preparing experiments based on published results.

plans if their chemicals were not in stock. However, some students distributed labor extremely well and coordinated their efforts within the group to streamline the optimization process. In short, a little preparation and cooperation went a long way. The teaching assistants would give advice for how to best accomplish goals, but they did not dictate how students should divide their time both in and out of lab. Examples of some optimization reactions are shown in Scheme 2. This scheme compares the outcome of the executed reaction with one optimized yield as well as the published yield. These samples show the variety of results that students experienced. While most students did not achieve yields as high as those published, some did in fact exceed the published yield. With respect to the 2016 student results, 84% of students completed all three steps of the synthesis successfully in the execution portion, and 100% succeeded in two steps. Of these

Data Presentation

Once the experiments had been completed, each group was required to write a final lab report that was similar to a E



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published journal article and create a poster to present their findings to the class. Many students tended to procrastinate writing the report until shortly before it was due, and this caused problems in the past. More prepared students would sometimes take a larger share of writing the report in order to produce a better assignment for the group. The timeline has now been changed so that a rough draft is due once the synthesis execution has been completed. The draft helped students manage their time as well as practice scientific writing and ensure a more equal distribution of labor. For many students, this class was the first time they had created a scientific poster in any setting. The posters from previous years were on display in the laboratory hallways, and this helped students recognize effective presentation styles. Online guides to poster construction and presentation were also provided by the instructor and science librarian. Students in each lab section held a presentation session at the end of the quarter. This helped simulate a professional environment, such as a conference, while also giving students the satisfaction of publicly highlighting project successes. Samples of a student lab report and poster are available in the Supporting Information.

evenly to the project, points could be deducted from the lab report or the discretion points or both. To gauge how well the group members worked together, a confidential group evaluation form was required for every student. This helped to hold students accountable for their actions and to encourage a fair distribution of labor. This form is also available in the Supporting Information

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APPLICABILITY AND DRAWBACKS This experiment was designed to be a capstone project for the honors organic chemistry sequence; however, its applicability reaches beyond such a specialized course. For example, the framework of the project can be applied to an inorganic chemistry synthesis or to physical chemistry experiments. The actual execution portion of the project does not have a bearing on the skills gained by performing the different aspects (planning, proposing, optimizing, problem-solving, writing, and presenting), and therefore can be utilized by other fields of chemistry. While there were many benefits to this project, there could be several drawbacks to running such a complicated endeavor. The first was that although this was an honors course, a few students did not perform well with such an open-ended project and needed more guidance than was given in the lab manual. These students generally did not ask for help, and it was not until late in the project that this became apparent. This was one reason that all students were required to meet with the lab director in addition to their teaching assistant to discuss their proposals. While students were expected to perform independently in order to bolster problem-solving skills, some students needed more direction and their grade was assigned accordingly. Another drawback to such an extensive project was the amount of preparation time involved for the teaching staff. With five different projects, the number of chemicals and equipment needed was quintupled from a normal experiment. In addition, for the optimization portion, students were allowed to request chemicals that were not part of the original published protocol. This involved submitting a chemical request form, the lab director approving or denying the request, and the lab manager ordering and stocking the chemical. While this seems trivial, on average each student ordered two to three chemicals in a class of 30 students. Students were also allowed to request additional equipment, such as chromatography columns, microscale glassware, and extra flasks. This needed to be supplied by and then returned to the lab technician. While the University of Chicago is lucky enough to have these types of laboratory positions, other institutions may not have the staff needed to support such an experiment. This experiment also required a larger budget than typical lab experiments, due to the wide variety of chemicals and equipment needed. This obstacle could be overcome by one of the following ways. First, the number of projects available to the students could be limited to one or two. This would cut down on the variety of chemicals and equipment needed. Second, options for the optimization phase could be limited, such as varying only time, temperature, or solvent. While these restrictions would cut down on the creative aspect of this experiment, they could emphasize the variety of outcomes a reaction could have. Students were often struck by what a wide range of yields result from identical reactions in the execution phase. Increasing the number of similar or identical reactions will emphasize this phenomenon.

Grading

Students were graded on the preparation, execution, and presentation portions of the experiment. In order to ensure equity over the whole class, a grading rubric was provided, and the average lab scores from all sections were compared and normalized if needed. For the preparation portion, students needed to write a proposal for both the execution of synthesis and optimization portions of the lab. The group received an identical grade for the execution proposal, but individual grades for the optimization proposals. Students were evaluated on their experimental design and problem-solving abilities based on identification of targets to optimize, proper analysis of literature sources, anticipation of problems, and realistic time management. The execution portion of the students’ grade was based on their laboratory notebook pages. Students prepared their procedures in a carbonless copy notebook prior to coming to lab, and then wrote down their data and observations while performing the experiments. These notebook pages were graded for containing the proper reactions, physical data on reagents and solvents, waste disposal instructions, safety considerations, procedures, observations during the experiments, and all data measured for each isolated product. In addition, each student was given discretionary points by his or her teaching assistant based on adherence to safety rules, promptness to class, consideration for others, collaboration with group members, cleanliness in lab, and overall attitude and preparedness. This evaluation form is available in the Supporting Information. Finally, the students were graded on presentation based on their lab report and poster. The lab report was written as a group, and students were told to delegate tasks evenly. The report was graded on putting the project in a broader context, accurately discussing data, evaluating results including yield and spectral analysis, identifying problems and how they were solved, presenting experimental details, and proposing future experiments. Since this was a group report, each member of the group received the same score for this portion. The group also created a poster to present to the class, and the content, visuals, and an oral presentation of the poster were graded. However, if it had come to light that one student had not contributed F



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FEEDBACK AND ASSESSMENT Over the years there has been continued positive feedback from the students on the course evaluations about the impact this project has had on their learning. A general version of this capstone project has been used for over 10 years, and this specific design for the last five. Students often cite this lab project as the reason they chose the honors sequence for their organic chemistry requirement. Some of the responses in the course evaluations are as follows: Performing the optimizations was, however, a great opportunity, and I would recommend taking this class spring quarter solely for this lab. The lab was actually pretty interesting this quarter. I feel like it was closer to what actual organic chemistry research looks like instead of the labs from the past two quarters. This was the first quarter in which I felt like I was actually learning how a lab works. The synthesis project was quite useful in teaching how frustrating lab research can be. The lab project was a good way of tying everything together and seeing how actual synthesis works. In these course evaluations, students were asked to comment on the following questions: “Did the experiments help you understand the course material? Did the experiments teach you useful lab techniques?” Students responded with 85% positive comments to these questions over the past five years. This indicates that students were thinking about how the project fits into the class as a whole, and reflects a positive attitude in the class. In addition, 44% of these comments mentioned either an increase in metacognition or an accomplishment of the project goals rather than a simple yes answer. This bolsters literature evidence that introducing students to research skills in the framework of a class increases problem-solving as well as helps transition the student into a research frame of mind.28,38 When asked “What aspects of the course should be retained?”, 62% mentioned the synthesis project. In 2016 students were asked “Did your library and literature search skills improve with this project and if so, how?”, and 90% of responses were affirmative. These answers show that students valued the project and thought it was a worthwhile exercise in addition showing that the goals of the project have been met. With respect to student lab scores, the students have performed consistently from the fall and winter quarters into the spring quarter. Over the past five years, the average lab score was 87% for the fall, 88% for the winter, and 87% for the spring. This shows that the students continued to perform well when given greater independence with experimental design, problem-solving, and structuring group work. In addition, the change in presenting data from a structured question and answer style to a more professional type of scientific writing and poster presentation also did not result in a drop in scores.

their own detailed experiment protocol from both a published experiment as well as adapt experiments from related sources; problem-solving, every group experienced at least one unexpected setback and had to come up with a solution in order to complete the project goals; scientific writing, the students were required to write a comprehensive lab report that covered the background, results, conclusion, and experimental details; presentation skills, the students produced and presented a poster that summarized their findings over the course of the project. These skills were not emphasized in standard organic chemistry experiments, where the equipment, procedure, and analysis were written out for the students. While the extent to which students had improved over the course of the quarter varied, the project was designed to promote these skills and reward students for successfully implementing them. It is extremely gratifying to hear the positive feedback and to realize that the goals for the lab have been communicated well. While it is difficult to gauge the level to which students have learned these varied research skills, it is adequate to state that exposure to research skills in a teaching environment is important to the overall mission of education and makes this experiment unique and innovative. This experiment takes a step toward producing students with the professional skills they will need in a career, regardless of the discipline.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available on the ACS Publications website at DOI: 10.1021/acs.jchemed.7b00093. Laboratory manual, teaching assistant notes, evaluation forms, chemical request form, chemical list, and representative student work (PDF)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Valerie A. Keller: 0000-0003-2131-4925 Present Address †

Beatrice Lin Kendall is currently at the Department of Chemistry, Skidmore College, 815 N. Broadway, Saratoga Springs, NY 12866. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The Mass Spectrometry Facility used to obtain student spectra was made possible by the NSF instrumentation grant CHE1048528. Vera Dragisich and Britni Ratliff are acknowledged for their help in preparing this manuscript. Daniel Ahn, Abigail Chang, Timothy Csernica, and Danylo Lavrentovich are acknowledged for their contribution to this article. The authors thank the faculty, staff, and graduate students who have made this project possible throughout the years. Specifically, Andrea Twiss-Brooks and the other science librarians at the University of Chicago are acknowledged for their long and continued support. This project could not be accomplished without their help. And finally, the undergraduate students who have performed this honors project are acknowledged for their dedication, hard work, and feedback.

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CONCLUSION Over the course of this quarter-long project, students were exposed to the professional skills outlined above that are key to producing well-rounded professional scientists:1−4 library search skills, the students were required to obtain specific journal articles, search the literature for similar reactions, as well as evaluate the search hits for their relevancy; cooperative work, the students worked in a group to develop complementary research objectives, share data, and reach a common goal; experiment planning, the students were required to prepare G



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Independent Synthesis Projects in the Organic Chemistry Teaching

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