Organic Chemistry
Organic Chemistry
Increasing Student Success in CHEM 316-17-18 by Matching Course Progression to Intellectual Development
Nanine Van Draanen and Alan Kiste
Department fo Chemistry and Biochemistry
California Polytechnic State University
San Luis Obispo, CA 93407
Project Abstract
Organic chemistry is typically taught via the "functional group approach" that mirrors neither the way organic chemists think about their subject nor accounts for the developing intellectual requirements of the field. We have deconstructred the topics in organic chemistry into three broad categories: structure, mechanism, and synthesis. With an emphasis on making parallel the rigors of the material with the intellectual development of the students, we anticipate both an increase in student success and retention and mastery of the material.
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Review the description of the CSU systemwide initiative supporting faculty redesigning their courses to improve student success.
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Why did you redesign your course?
The yearlong organic chemistry sequence is a resource-intensive course with a poor success rate. The D/F/W rate for the first two quarters (CHEM 316 and 317) hovers near 20% regardless of instructor or quarter taught. With over 450 students enrolling in CHEM 316 each year, that leaves about 90 students needing to repeat a 5-unit course. In addition, a poor performance in CHEM 316 hinders student success in the subsequent two quarters. We thought we could improve student learning and success by redesigning the course.
What did you change through the redesign?
We examined the way organic chemistry is traditionally taught and the way practicing organic chemists actually approach their subject, and realized the two were quite different. Organic chemistry is a vast body of work, but it builds upon some fundamental blocks of knowledge. We decided to focus on those blocks and making their importance the focus of the course.
Why will the "redesign" lead to better learning?
Organic chemistry is a vast and rather overwhelming field, and in the effort to add modern material to the historical base, textbooks have become longer and longer, and in the push to cover material, learning is often lost: it's an issue of quantity overwhelming the quality. By acceeding the simple fact that no student can learn every reaction over a year, we have elminated that pressure. Instead, understanding the construct of organic chemistry by thoroughly exploring its three main themes--structure, mechanism, and synthesis--we believe students will understand the material (not just memorize the reactions) and learn to apply fundamental principles to new situations. Thus students will be able to figure out just about any problem in organic chemistry. This focus on the principles allows more time in class to work problems, rather than presenting yet another reaction to memorize. The order of our class also follows the intellectual development available to students: we focus first on molecules from every angle. From there, we bring molecules together, showing how they will interact and introducing reaction mechanisms. Finally, the highest level of intellectual rigor, synthesis, is saved for the final quarter. Sythesis requires an in depth understanding of structure and mechanism and thus builds upon the prior two quarters in an intellectually appropriate way.
Course and Student Background
What course are you redesigning? CHEM 316, 317, 318, Organic Chemistry I, II, III. This is an upper division, major/support course that serves approximately 450 students/year at Cal Poly San Luis Obispo.
Who are your students? The yearlong organic chemistry course serves a variety of majors. It is a required class for all Chemistry and Biochemistry students, and is a foundational course for all pre-health majors, including pre-medical and pre-veterinary students. Because of its central role in allied health prerequisites, we have a wide variety of majors who opt to take this course, including Biology, Nutrition, Kinesiology, Animal Science, and the occasional Business, Physics, History, and Social Studies major who is also pre-med. The prerequisiste, strictly enforced, is to have completed a year of general chemistry. There are no other required competencies, other than a willingness to learn and to work hard!
Learning Outcomes and Redesign Activities
Learning Objective 1: Students will demonstrate the ability to analyze organic structures based on bonding, resonance, functional groups, shape, conformation, stereochemistry and conjugation.
Learning Objective 2: Students will identify the structures of organic compounds utilizing IR, 1H and 13C NMR, UV-Vis, and Mass spectroscopies.
Learning Objective 3: Students will be able to name organic compounds.
Learning Objective 4: Students will be able to identify and rank the acidities and basicities or organic compounds.
Learning Objective 5: Students will use structural characteristics of organic compounds to predict the products of chemical reactions based on the fundamental mechanisms of substitution, elimination, addition, protonation/deprotonaion, and simple combinations of those mechanisms (such as acylation mechanisms.)
Learning Objective 6: Students will use the reactivity of molecules to predict rational synthetic strategies of more complex molecules.
In this course redesign, all structural concepts are learned first as a method to predict the reactivity of molecules later. Then, this reactivity information is used to propse synthetic strategies toward more complex compounds. As students learn a particular structural characteristic of molecules (eg. functional groups) they learn the spectroscopic technique(s) that provides evidence for that characteristic (eg. IR spectroscopy.) They will then use these spectroscopic techniques as evidence to solvet the mechanistic and synthetic problems that will be presented later.
Students will be assessed using written exams that present modern chemistry from the recent chemical liturature and require students to apply their learning to novel situations. Because the material comes from the current literature, the lesson that memorization is useless for succeeding on the exams is reinforced.
In order to provide additional time in the course for more detailed examination of structure/reactivity relationships, topics of secondary importance (in particular, nomenclature) are presented outside of class in screencasts and electronic homework assignments. Students are evaluated by the electronic homework system based on their ability to correctly name compounds from the structures or their ability to draw structures from the name.
In addition, other topics that are no longer considered modern organic chemistry and/or are not synthetically useful will be curtailed or eliminated (eg. radical halogenation reactions.)
Teaching Tips
A significant challenge in redesigning any course is deciding which content to teach. This is particularly true in the quarter system. The most obvious place to offload in-class work in the first quarter of Organic Chemistry is with nomenclature topics. Less than 1 hour total of class time was spent on discussions of nomenclature. Students were given the handout posted below, two "pencasts" were posted on the class website in which I went over examples, they worked on nomenclature problems from the book, and were assigned online nomenclature homework questions from the SmartWork website associated with the textbook.
All of this out-of-class work provided time to introduce all of the spectroscopies (IR, 1H and C13 NMR, UV-Vis, and Mass Spec) in the first quarter. Typically only IR and C13 NMR are introduced in the first quarter in our current sequence. However, introducing all of the spectroscopies in the first quarter means that each can be used to provide solid evidence for the claims we are making about the structure of organic molecules.
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Accessibility, Affordability, and Diversity
Access to the online homework assignments were provided free by the publisher, and were compatible with all free modern web browser software. Online pencasts were distributed via CalPoly's course management software and were also compatible with all free modern web browser software. All course handouts were delivered via the course management softare via PDF. All materials are accessable through campus computing resources.
Pencasts were not captioned, but could be captioned if a student submitted a request through the on-campus Disability Resource Center.
Impact on Teaching and Learning
The historical (2004-2010) average DFW rate for 316 is 16.7%, and the average student GPA in the course over the same period of time is 2.29. However, the DFW for the redesigned CHEM 316, Winter quarter, was 7.8% and the average student GPA in the course was 2.9.
The historical average student evaluation response to the question "How do you rate this course?" on a 1-4 Likert scale where 4 is "strongly agree" is 2.90/4.00 for the last 3 years for CHEM 316. This historical average for all departmental courses during the same time is 3.00/4.00 The average student evaluation response to the same question for the redesigned CHEM 316, Winter quarter was 3.11/4.00.
The historical (2004-2010) average DFW rate for 317 is 20%, and the average student GPA in the course over the same period of time is 2.27. However, the DFW for the redesigned CHEM 317, Spring quarter, was 17% and the average student GPA in the course was 2.39.
The historical average student evaluation response to the question "How do you rate this course?" on a 1-4 Likert scale where 4 is "strongly agree" is 3.30/4.00 for the last 3 years for CHEM 317. This historical average for all departmental courses during the same time is 3.00/4.00. However, The average student evaluation response to the same question for the redesigned CHEM 317, Spring quarter was 3.37/4.00.
The historical (2004-2010) average DFW rate for 318 is 17%, and the average GPA for the course over the same period of time is 2.40. The DFW rate for the redesigned CHEM 318, Fall 2014 was 19% and the GPA was 2.94. A comparison of the average raw score on the ACS Organic Chemistry standardized exam between the redesigned course (47) and a non-redesigned course (49) shows no statistically significant difference using a two-tailed t-test, assuming unequal variances.
The historical average student evaluation response to the question "How do you rate this course?" on a 1-4 Likert scale where 4 is "strongly agree" is 3.20/4.00 for the last 3 years for CHEM 318. This historical average for all departmental courses during the same time is 3.00/4.00. However, The average student evaluation response to the same question for the redesigned CHEM 318, Fall quarter was 3.36/4.00.
Overall, the historical (2004-2010) average DFW rate for the entire sequence is 46.7% , while the overall DFW for the redesigned sequence was 36.5%. Our primary goal was to reduce the DFW rate without reducing rigor. Our objectives were met in that the DFW rate decreased and the comparison of students' raw scores on the ACS standardized exam indicate that the course was at least as rigorous as the traditional course, and students rated the course more highly than students taking the traditional course.
The two midterms and the final exam for the winter quarter are posted below.
Midterm 1: mean = 70% (SD=18), high score = 92%, minimum = 25%.
Midterm 2: mean = 67% (SD=17), high score = 92%, minimum = 23%
Final Exam: mean = 63% (SD=12), high score = 93% minimum = 37%.
CHEM 316 Midterm 1
First quarter Exam 1
CHEM 317 Midterm 2
First quarter Exam 2
CHEM 316 Final Exam
First quarter final exam.
About Us
Nanine Van Draanen is a professor and chair of the Department of Chemistry and Biochemistry at Cal Poly, San Luis Obispo. She joined the faculty in 1996 after 8 years of R&D experience in the pharmaceutical industry. She has taught organic and medicinal chemistry throughout her years at Cal Poly. She took a two year leave of absence to explore approaches to enhacing student success in organic chemistry by teaching at California Lutheran University. The experience she gained at CLU forms the basis of this redesign project.
Alan Kiste is an assistant professor of Chemistry and Biochemistry at Cal Poly, San Luis Obispo who specializes in discipline-based educational research. During his post-doctoral work at the University of Michigan, Ann Arbor, he has taught organic chemistry utilizing the same structure-reactivity approach used in this redesign project.
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