Our Research Questions Our research questions are: 1) how different modes of teaching and learning, such as deductive and inductive, affect students' learning of the organic chemistry synthesis; 2) how various deficiencies in learning the basic categories of chemical knowledge affect students' ability to solve problems in organic synthesis.

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Background Inductive teaching is based on the belief that learning occurs best when it is based on the learners experiences and interactions with phenomena. The inductive teaching is also known as discovery or inquiry-based teaching, and is also related to the so-called learning cycles. In the latter, phenomena are explored before concepts are named. The deductive teaching is based on the belief that learning occurs best from a highly structured presentation of content. The deductive teaching is also called direct instruction. The instructors typically start with the definition of the concept, and provide various examples of how this concept works. Students are then asked to achieve concept mastery, via an examination of given examples and solving problems that are related to the concept. Science teaching at the lecture level is almost exclusively deductive. If it is inductive, it is an exception. In the laboratory courses, the teaching approaches are pure deductive, such as in the case of lab demonstration, mostly inductive, such as a guided inquiry, and mixed deductive-inductive, such as in a structured inquiry. Our goal We are very interested in learning more about the inductive and deductive teaching and learning and exploring further its relevance to teaching organic chemistry synthesis. Chemistry is a science that can be approached from both practical and theoretical ends. If the former is out of balance over the latter, students become the cooks, that is they perform the laboratory experiments without truly understanding the chemical concepts behind them. If the theoretical side is emphasized without a proper reality check in the laboratory, the students become proficient in the so-called paper chemistry, when they believe that everything they put on the paper must be true. A proper balance between the theoretical and practical knowledge must be achieved, especially in the design of the new synthetic pathways. Such design requires lots of abstract thinking, in addition to the knowledge of the basic reactions and the reaction conditions that were experienced in the lab. Particularly difficult is the design of the multi-step chemical syntheses, in which the students are given the structure of the molecule they need to synthesize, the so-called target molecule, a list of the available starting materials and reagents, and are then asked to devise the synthetic pathways which will yield the target molecule. There are presently two strategies taught. The first strategy is to give the students various examples of the multi-step syntheses, in the direction from the starting materials to the target molecules, and then ask them to design new synthetic pathways, with new targets, based on these known cases. This strategy does not work well, since the new target inevitably requires new approach, at least in some steps, and the sequence of the steps often has to be changed. Typically, a student starts and then abandons the synthetic design, since he/she cannot come up with the required steps. Sometimes they do, if the things click, but in some other examples things do not click for them, and they become frustrated. They do not have a reliable problem-solving method that would guide them from the starting materials to the target molecule. The second strategy does provide such a reliable method. It is called the retro-synthesis. It teaches students how to think backwards, and how to mentally break up the target molecule into the smaller sub-targets, and so on, until they reach the starting materials. This strategy is ideal for teaching students the abstract thinking and problem-solving skills, and it helps them develop their own creative solutions to the synthetic problems. The retro-synthesis not only allows for different solutions of the synthetic problems, but actually encourages the creative process in which the individual solutions are devised. Unfortunately, the retro-synthesis was never developed at the level that is amenable to the undergraduate students. All currently available undergraduate textbooks have a very limited number of retro-synthetic examples, typically less than five. The examples given in different textbooks are either the same or very similar. The available textbooks for the organic synthesis are too advanced, and require knowledge of a multitude of reactions, and are typically at the graduate or post-graduate level. We plan to develop a series of problems in the organic synthesis and to teach them both inductively and deductively. The retrosynthetic way is more amenable to the inductive way of teaching and the classical synthesis is better dealt with in an inductive way of teaching. We also plan to develop a set of synthetic problems that are related to the chemistry of meteorites, which we will link with another ongoing project, on application of the retrosynthesis to astrobiology. We have separate funding for this project, from the Wisconsin Space Grant Consortium.

List of Helpful Resources & References 1) R. Grumbine, L. Hecker, and A. Littlefield, National Science Foundation Research in Disabilities: Biology Success!, grant report (2005), and the references cited therein. This is a great source, which combines the theoretical review, the experimental design, and the assessment for teaching inductively and deductively. 2) W. F. Lawhead, The Voyage of Discovery, A Historical Introduction to Philosophy, Second Edition, Wadsworth/Thomson Learning, Belmont, CA, p. 215, and the original work of Francis Bacon, The New Organon (various editions exist). Lawhead is a great textbook, which is used at UW-Parkside in the philosophy course on great thinkers. The original work of Francis Bacon is surpisingly readable, and it shows nicely the application of the inductive method to the scientific thinking. 3) The Universal Design for Learning, multiple references, many on the web, particularly well organized is: http://www.cast.org/research/udl/index.html 4) Felder, R. M. & Brent, R. (2005). Understanding Student Differences. Journal of Engineering Education, 94(1), 57-72. This article continues along the main themes of the previous work by Felder, but it is much expanded and extremely well referenced (123 references). Particularly useful is the newest material on assessment and on the questions for further study. 5) Prince, M. & Felder, M. (2007). The many Faces of Inductive Teaching and Learning. Journal of College Science Teaching, 36(5), 14-20. This paper focuses on the inductive teaching/learning methods, such as the inquiry-based, problem-based, project-based and other types. It is particularly useful as it shows how various terminologies of some popular teaching/learning methods really boil down to the basic inductive approach. 6) Wirth, K.R. & Perkins, D. (2007) Learning to Learn. http://www.macalester.edu/geology/wirth/CourseMaterials.html This is an exceptionally well written article, with numerous citations and useful tables on the subject of the art of learning. 7) Grumbine, R., Hecker, L., and Littlefield, A., National Science Foundation Research in Disabilities: Biology Success!, grant report (2005), and the references cited therein. This is a great source, which combines the theoretical review, the experimental design, and the assessment for teaching inductively and deductively. Vera Kolb web site

Presentations of Our Project at Various Professional Conferences Since we are applying chemical synthesis to astrobiology and also have various teaching projects on infusion of astrobiology into the chemistry curriculum, we have combined our efforts in these projects and the present Wisconsin Teaching Scholar project, and have produced the following presentations. Presentation 1) The abstract for the presentation at the Bioastronomy 2007, in San Juan, Puerto Rico, July 16-21, 2007: Application of the Retro-synthetic Principles to Astrobiology Vera M. Kolb Department of Chemistry University of Wisconsin-Parkside, Kenosha, WI 53141 [email protected] The design of the prebiotic synthesis of the complicated target molecules such as RNA requires multiple steps. The synthesis needs to utilize the starting materials and reagents that we believe were available in the prebiotic times. There are presently two synthetic strategies utilized. The first strategy is in the direction from the starting materials to the target molecules, which is based on the known chemically feasible cases. This strategy is based on the chemical intuition. The second strategy, which is considered to be more systematic and more fail-proof, is called the retro-synthesis. It requires the scientists to think backwards, and to mentally break up the target molecule into the smaller sub-targets, and so on, until the starting materials are reached. In contrast with the traditional retro-synthesis, the prebiotic version may include various paths which have low yields. The selectivity factor is what we are looking for. We illustrate the utility of the retro-synthetic method on several examples that are relevant to astrobiology. Thanks are expressed to the University of Wisconsin System for the 2007-2008 Wisconsin Teaching Scholar appointment of VMK to carry out a part of this project. Presentation 2) Teaching Organic Synthesis via Inductive and Deductive Methods: Examples from Prebiotic Chemistry, at the University of Wisconsin System Chemistry Faculty Meeting, Green Bay, WI, October 19-20, 2007, Poster #2: Teaching Organic Synthesis via Inductive and Deductive Methods: Examples from Prebiotic Chemistry Vera M. Kolb Department of Chemistry University of Wisconsin-Parkside, Kenosha, WI 54141 [email protected] The prebiotic syntheses of the target molecules such as sugars, nucleic acids, or heterocyclic compounds likely require multiple steps. These syntheses need to utilize the starting materials that we believe were available in the prebiotic times, or which have been found on the meteorites, such as Murchison. There are presently two synthetic designs utilized. The first is in the direction from the starting materials to the target molecules. This strategy utilizes mostly a deductive method. The second strategy, which is considered to be more systematic, is the retrosynthesis. It requires thinking backwards, to mentally break up the target molecule into the smaller sub-targets, and so on, until the starting materials are reached. This method utilizes mostly inductive method. In contrast with the traditional synthesis, the prebiotic version may include various paths which have low yields. The students are encouraged to find multiple synthetic pathways, regardless of the yields. Each proposed synthesis has a potential value of elucidating chemistry on meteorites, or on the early Earth. Thanks are expressed to the UW-System for the Wisconsin Teaching Scholar award and to the Wisconsin Space Grant Consortium/NASA, for sponsoring this work.

Project Summary: We have investigated inductive and deductive ways of teaching retrosynthesis. In the Fall of 2007 we have developed an entirely new course for the Advanced Organic Chemistry 401, and have introduced two new textbooks. The results of students' work indicate that students did master the concept of retrosynthesis at a functioning level. In addition, we have found that the common problem for students' failure to execute organic synthesis in a correct way (either by the regular or retro- synthesis) is the mix-up in the learning categories. For example, when the students mixed up the regiochemistry rules, their syntheses were doomed from that point on.

New directions in the project I became involved in broadening my project to include investigation of the problems that students have with categorizing their knowledge. This new initiative is described below. This initiative was addressed at the SENCER SoTL Workshop in Portland, Maine, August 1-3, 2007. The students often have problems with categorizing their knowledge. If the knowledge ends up in a wrong category, the students may produce a nonsense answer. The categorization of knowledge is important both in the deductive and inductive learning modes and problem solving. In the deductive mode the premises, axioms, and equations are the starting points of learning and problem solving, but they may be mixed and matched improperly by the students, who may not see their proper connections. Inductive learning and problem solving is thinking in a backwards fashion, from the observed phenomenon to its possible causes. A complex phenomenon, often of an interdisciplinary nature, is explained via a proper connection between the categories of knowledge that students already have and an analysis of similarities and dissimilarities between those previously learned truths and the elements of the complex phenomenon and its presumed etiology. Many possible explanations may exist, and the students may have trouble evaluating them. Although this way of thinking and problem solving promotes creativity on the part of the student, it also may be much longer and more frustrating than the more straightforward deductive reasoning. My specific goal is to research the common confusions that student have between the categories of knowledge. I have already researched the advantages and pitfalls of the deductive and inductive teaching and learning, including the most recent pedagogical findings. First, I have studied the deductive method, originally proposed by Aristotle, and the inductive method, proposed by Francis Bacon. Bacon pointed out to the troubles of the Aristotle's method, namely that it becomes a house of cards if the original premises are incorrect. Bacon's induction method is better, he felt, since the progress towards the solution of the problem is constantly checked and guided by the similarities, differences, and quantitative relationships of the known phenomena. However, Bacon's system becomes a house of cards also if the unrelated phenomena are considered related, namely if the categories of phenomena are wrong. If we claim that things are similar but they actually belong in the dissimilar categories, Bacon's inductive method will fail. This is where I got the idea to do research on the categorization process of the learners. Students are likely to have troubles with proper categorization (as I see it daily in teaching chemistry). My proposed study will start with learning more on the causes of improper categorization of the science phenomena, including the improper language use, with Wittgenstein as the main source. SENCER project

Career Relevance & Impact: This project was very helpful to me in injecting new teaching ideas and approaches to the courses I teach. Particularly important was my recent finding from the analysis of students' work that the mixing up of the knowledge categories was a common reason for students' underperformance. Based on this, I am now teaching more about various categories of knowledge and how they can be distinguished. Much more analyses of students' work are needed. I am now finding that I understand more about the teaching process, and teaching is becoming much more rewarding to me. Through the Wisconsin Teaching Scholar training I am now equipped with new tools which make me a much better teacher. Also, by applying these new tools, I am looking at the teaching as a process in which some experimentation can be done, and the results can be evaluated, similar to the research process in my field (chemistry).

Methodologies & Types of Evidence of Student Learning Which Are Gathered Fall 2007: At the beginning of the semester I was working on my IRB form. I have submitted it and it was approved. I have discussed the project with the students in my class (Advanced Organic Chemistry 402) and all of them (10 students) have signed the consent form on September 25, 2007. I feel that this was an important beginning. I have now collected pieces of students' work for the analysis. Below is the copy of the consent form and of the IRB proposal. Informed Consent Form The undersigned student, who is registered in the Advanced Organic Chemistry 402, agrees to let the instructor, Professor Vera Kolb, use the analysis of the students' work, such as exams, term paper, and in-class written exercises, in her research on the use of deductive vs. inductive problem-solving techniques in organic synthesis. Both ways of problem-solving will be explained in the classroom. The student will use either method in solving problems, according to his/her preference. The instructor will analyze students work in light of the method chosen. The instructor hopes to present her results to the groups of professional educators for an input and evaluation, both in the oral and written forms, and possibly in the form of a publication. No student will be identified by name, gender, age, home or e-mail address, or by the student registration number. The student's name and date of the signature: ________________________________ Research Proposal for IRB Vera Kolb Chemistry Department Title of the proposal: Teaching Organic Synthesis via Classical (Deductive) and Retrosynthetic (Inductive) Modes This proposal has been funded by the Wisconsin Teaching Scholar Program. I am interested in helping students solve organic synthetic problems. For the first time, I intend to instruct them how to solve these problems in two ways, deductive and inductive. According to the educational theory and practice, students learn better if they can choose from the learning styles which suit them better. Traditionally, the synthesis is taught almost exclusively via deductive method. Only a limited number of examples that are solved via the inductive method exist in the undergraduate textbooks. At this stage of the project, I am preparing various examples of the synthetic problems, which I shall solve in the class by both methods. I shall explain to the students how each method works. The students will choose whichever method they prefer in their synthetic assignments. I would like to be able to evaluate students performance as a result of this instructional innovation. My normal teaching activity will include the analysis of the students' work, such as exams, term paper, and in-class written exercises, to see which method students prefer, and which type of problems they are experiencing in each method. I would like to be able to present the analysis of the students' work to the group of peers, within the Wisconsin Teaching Scholars and other groups, and at various meetings. Thus I need the IRB approval. In the future, after I analyze these initial data, reflect upon them, and adjust my teaching in response to them, I would like to submit a more extensive IRB application to include some questionnaires, interview, or surveys. At this point of time, I feel, this is premature. Thus, I only ask for the permission to make public the analysis of the students work. I would appreciate having the approval ASAP. I teach class this semester, and I am now doing the part on organic reaction mechanisms. I will start teaching synthesis in October. The Informed Consent Form is enclosed, as well as the Certificate that I have completed the UW-P Human Subjects tutorial.

Preliminary Findings, Results, Conclusions, & Implications: Please see the Project Summary.