Academic Research Inspired Design of an Expository Organic Chemistry Lab Course

2017 Spring semester CH352 (Chemistry Major Lab II or Organic Chemistry Laboratory) was designed as a nineweek course. An Orientation session was held on the first week. Eight experiments were expected to be completed within a six-hour session per week. Six experiments were conducted based on contents published in the Journal of Chemical Education each with modifications from the original paper. One experiment was designed based on the research by Larrow and Jacobsen.⁸ Below is the list of experiments.

The course contents development was aided by two undergraduate researchers who performed senior projects in our laboratory. Experiments to be included in the organic chemistry laboratory course were then chosen after a discussion among the course instructors and the undergraduate researchers. They ran the experiments following the literature procedures and made proper modifications accordingly. As a part of their undergraduate thesis project, the lab manual was generated under the supervision of the instructor.

Six TAs were assigned to forty-six students enrolled in the course. TAs were selected among graduate students conducting research in organic chemistry laboratories. Previously at KAIST, each TA supervised two experiments. They were responsible for one experiment as a primary TA and one as a supportive TA. Hence, students rotated and were assisted by different TAs for each experiment.

As a means to maximize the TAs-students intellectual bonding, new TA-student mentorship has been implemented. A team of two TAs supervised 14–16 students for all eight experiments during the 2017 CH352 course. A two-day TA bootcamp was held prior to the 2017 spring semester. Every TA conducted all eight experiments using the undergraduate laboratory glassware and equipment. Modifications of experimental procedures and orders of additional necessary chemicals, glassware, and equipment were made accordingly based on the feedback of the TA bootcamp. Lab manuals were then updated accordingly.

The clear objective of the course was introduced to the students.

“This organic chemistry laboratory course is intended to provide students majoring in chemistry with fundamental and essential experimental skills and concepts in organic chemistry.”

The term “experimental skills” has been delineated as follows.

The term “concepts” has been delineated as follows.

After introducing the goals of the course, the discussion was transitioned to the safety in the laboratory.

Eighteen safety-related rules were introduced to students.¹⁴ Below are some of the outlined rules.

The instructor used personal lab experience stories as a means to draw students’ attention to the safety issues. For example, one faculty member instructed students from his own experience and observations that accidental chemical splashes have occurred frequently to a researcher working in a lab. He emphasized that, therefore, laboratory researcher should wear eye protection gear at all times while working in a lab. The engagement of instructor’s personal stories was not only effective in drawing students’ attention but providing them incentives to strictly abide with laboratory safety rules.

A Material Safety Data Sheet (MSDS) was introduced to students. An MSDS provides information about proper storage of a substance, first aid, spill response, safe disposal, toxicity, flammability, and additional useful materials. The MSDS searching method was explained to students. The instructor informed the students that thorough reading of the MSDS of chemicals prior to the experiment is mandatory and was enforced through the hand-written pre-lab note.

During the orientation session, the name, the affiliated research group, and the research interests (including a recently published paper) of each TA was provided by the instructor. Following a general introduction of the TAs, each TA was also asked to come to the stage to introduce themselves. This process helped the students familiarize themselves with the TAs. Furthermore, the introduction of each TA’s research interests and recent research achievements led the students to acknowledge them as organic chemistry experts and helped to generate a sense of reverence towards the TA team.

The grading policy of the course was delineated to the students. Below is the grading policy of 2017 CH352 course. Detailed explanation of each item will be discussed in the latter sections.

  Pre-lab notes                           25%
  Experiments and results PPT files       25%
  Mid-term paper                          25% 
  Final paper                             25%
		

Publishing research achievements in scientific journals is an indispensable process in scientific research. We designed the CH352 course to be the introductory course of scientific publication process. Various chemistry journals were introduced to students using the “web of knowledge” platform. Various numerical matrices associated with the journals were discussed. Representative journals specialized for organic chemistry were introduced. Methods on how to search chemistry articles were also taught. Students were reminded that a thorough referencing is expected for the midterm and final papers.

Scifinder is a representative search engine that provides access to sources of references, substances, and reactions in chemistry and related sciences. It became an indispensable tool for those practicing synthetic chemical research. During the CH352 orientation session, the role and functions of Scifinder as well as the way on how to install the program was introduced to the students. We encouraged students to use Scifinder for the preparations of pre-lab report, results PPT slides, and term papers.¹⁵

The development of various chemical structure editors has facilitated the organic chemistry writing process. Chemdraw, first developed in 1985 by David Evans, Sally Evans, and Stewart Rubenstein,¹⁶ is inarguably the most widely used molecular structure editor. Chemdraw software was introduced to students during the orientation and demos on how to draw chemical structures using this program were conducted. A protocol on how to install the software was also presented. Students were encouraged to use Chemdraw in generating chemical structures for the course reports.

The most common misconducts were introduced and the zero-tolerance policy against these misbehaviors was explained.

The importance of proper paraphrasing and referencing was stressed.¹⁷ We used turnitin (turnitin.com) as a platform to collect students’ reports and crosscheck plagiarism. This web-based service helped us to reduce the administrative workloads related to collecting and grading term papers and providing feedback to students. We noticed that the use of turnitin system had a preventive effect of keeping students away from plagiarism.

We explained to the students that experimental data fabrications as well as adoptions of peer’s data in writing their own reports are grave scientific misconducts. In the case of low yields or unexpected side products, we advised students to thoroughly analyze the experimental procedure and rationalize the results.

The role of TAs was pivotal for a successful laboratory course. Building a constructive relationship between TAs and students based on mutual trust was imperative. A thorough formal introduction of each TA helped to form a sense of respect among students. The instructor made clear that expression of inappropriate attitudes towards TAs such as the use of vehement language or violent behavior will not be allowed in any case.

Students were most satisfied with the newly implemented weekly results report style. 68% of students commented that they were satisfied with the new format of presenting their experimental results. They mentioned that time required to prepare the results report could be saved. While time-saving, the schemes and pictures-based PPT report style led students to pay attention to the actual experimental procedures and take pictures of noteworthy observations. Students have developed a habit of taking chronological notes during the lab session which is an essential part of organic chemistry research. Below are samples of responses from the students’ survey:

Notably, students showed great satisfaction with the TAs. 39% of respondents showed appreciation for the mentorship and guidance that TAs had shown. The head TA who previously had taught this course a few times informed us that this year’s TAs were more dedicated in teaching as compared to those in previous years’. We attribute these positive changes to the restructured TA allocation method. Allocating the same TAs for all experiments conducted during the semester to the same group of students enabled an interpersonal bond formation. Furthermore, the concise PPT-based experimental results report reduced the grading workload of the TA. Students expressed satisfaction with the new format of the midterm and final reports. They especially liked that they could expose themselves to actual research papers.

There was also positive feedback regarding the use of Chemdraw and the orientation session.

While students showed satisfaction with the JACS style term papers, they also answered that guidelines on how to write them were insufficient. We plan to hold a session on how to write a scientific report in the next laboratory course. 23% of students complained about the cleanness of shared glassware. 16% of students also replied that not enough explanations were given on how to use basic equipment such as rotovap. We will update the manual and hold an introductory session which will describe basic experimental operations such as washing glassware and using basic equipment in the laboratory. Prompt feedback on reports will have to be provided. A few students also informed us that a single experiment did not contain enough material to write up a JACS style term paper. One student pointed out the lack of intellectual excitement in the expository laboratory teaching style. We plan to apply problem-based instruction method to some experiments for the upcoming laboratory courses.