Fall 2009 CONFCHEM


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Excellence in Education with CCLI: Notes from Recent Awardees

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"Implementation of FT-NMR Across the Chemistry Curriculum"

Debbie J. Beard,a William P. Henry,a R. Gregory Dunaway,b
aDepartment of Chemistry, Mississippi State University
bDepartment of Sociology, Mississippi State University

INTRODUCTION

Nuclear Magnetic Resonance (NMR) spectroscopic theories, experiments and hands-on instrumentation experience were implemented throughout the undergraduate laboratories (freshman through senior levels) at Mississippi State University (MSU).  The implementation of NMR spectroscopic theories and experiments into freshman level chemistry laboratories is a novel idea, especially at a large public university such as MSU.  Typically NMR spectroscopy is not usually introduced at the undergraduate level until the sophomore year of college in organic chemistry.  In the recent past, there was very little actual use of Fourier Transform (FT)-NMR by students in chemistry laboratory courses at MSU.  Hands-on experience by students on the NMR spectrometer had usually been limited to a single experiment in small upper-level courses such as the senior inorganic chemistry laboratory; courses with typically only chemistry majors. We expect this early introduction and spectrometer use for undergraduate students taking a freshman chemistry laboratory to improve not only their instrumentation skills but also their preparation for NMR spectroscopy in organic chemistry and other upper-level chemistry courses and encourage interest in STEM careers. Another unique contribution is the prospect that students will become more interested in science and engineering as a career and those who are STEM majors will be more proficient with instrumental techniques.

The current guidelines of the Committee on Professional Training1 (CPT) of the American Chemical Society (ACS) are very clear on its expectation for inclusion of instrumentation, and in particular NMR spectroscopy, in the chemistry curriculum.  An excerpt from this document states, “A department should have several major pieces of sophisticated equipment suitable for undergraduate instruction as well as for research. One of these must be an NMR spectrometer.”1  Later in this same document it is noted that the instrument should be an FT-NMR.  In addition, the most current proposed revision to this document states, “The laboratory experience should include synthesis of molecules, measurement of chemical properties and phenomena, “hands-on” experience with modern instrumentation, applications to real-world problems, and computational data analysis and modeling.”2 

The Department of Chemistry at MSU is fulfilling its teaching mission3 by providing undergraduate STEM students with excellent programs in modern-day chemistry to prepare the students for employment (industrial, governmental or clinical laboratories or secondary education), for graduate study, or for enrollment in professional schools.  In order to completely fulfill this mission, students must have hands-on access to modern-day instrumentation, and they must use this instrumentation to solve chemical problems.  In this context, it should be a high priority for the chemistry departments to obtain a Nuclear Magnetic Resonance spectrometer that will be used specifically for undergraduate education. 
NMR is a fundamental technique and has had an impact on all sub-disciplines of chemistry, and related fields.  As such, any high-quality undergraduate STEM education must include NMR spectroscopy, and a high-quality chemical education should involve extensive use of NMR throughout the curriculum.4-7  The integration of NMR spectroscopy across the chemistry curriculum has made a broad impact on the education of the diverse student population at MSU. Most of the students taking undergraduate chemistry laboratories are not majoring in chemistry; therefore, the instrumentation skills obtained by these students are valuable in their own disciplines.  The hands-on instrumentation experience gained by these non-chemistry majors enhances their education by exposing them to areas of science that can help them in the undergraduate research required for their own major.

Prior to obtaining the NSF CCLI grant, students in chemistry courses at MSU received very little hands-on experience with FT-NMR and, for the most part, the two NMR spectrometers in the Department of Chemistry at Mississippi State University were occupied by graduate students, postdocs, and faculty to support their research endeavors.  Therefore, the experience that undergraduates obtained on these instruments were typically limited to one or two experiments in small upper-level courses; courses that are primarily enrolled with only chemistry majors. 

Our main objectives are to improve the quality of the undergraduate laboratory experience, and to improve the students’ perceptions about chemistry and science in general.8-10  In addition, we aim to attract and retain students in chemistry, and in other scientific disciplines.  All too often, after one semester of freshman chemistry lab, students have the impression that chemists just do titrations, or that chemists just follow simple procedures much in the same way one might use a recipe for cooking.  These erroneous impressions must change!  Hands-on use of modern instrumentation will improve students’ motivation for studying science, increase their awareness about modern chemistry, and allow them to see the relevance of chemistry to their everyday lives’ and their future careers.  In addition to improving students’ attitudes and impression, our specific learning objectives for this project are as follows:

1)   All STEM students that matriculate through the freshman chemistry lab sequence obtain knowledge of and have hands-on experience with FT-NMR.  The students learn to relate how the chemical environment (i.e. electron density about an atom in a molecule and its neighboring nuclei) affects the observed chemical shift and splitting pattern.  The students gain an appreciation of the fact that NMR is the foundation for Magnetic Resonance Imaging (MRI).11

2)   All students enrolled in the organic labs are able to acquire, process and interpret 1D- and 2D-NMR spectra.  By the end of the two-semester organic lab sequence the students design/select appropriate NMR experiments to address scientific inquiry.

a)   For 1H NMR, students understand that chemically non-equivalent protons afford distinct NMR signals, the chemical shift of a proton is related to its chemical environment, the integral is directly proportional to the number of equivalent protons giving rise to the signal, the multiplicity of a signal is determined by neighboring spin-active nuclei, and that coupling constants can be used to determine connectivities. 

b)   For 13C NMR, students understand that chemically non-equivalent carbons afford distinct NMR signals, the chemical shift of a carbon is related to its chemical environment, and that the phase of the carbon signal in DEPT experiments is related to the number of protons directly bonded to the observed carbon. 

c)   For 2D-NMR experiments, the students understand that correlations can be used to determine connectivities; for 1H-1H-COSY, cross-peaks correspond to coupled protons, and for HETCOR, cross-peaks correspond to carbon-hydrogen bonds.

A fundamental understanding of each of these (a-c) is required for structure confirmation, and for structure elucidation.

3)   Upper-level students use this instrument in the physical, inorganic and analytical labs.  By using this instrument in a number of different courses and learning about this instrumental method from a variety of different viewpoints, students became better problem-solvers, and this enhances each student’s readiness to conduct undergraduate research.

4)   All faculty members and graduate teaching assistants that are responsible for an undergraduate teaching lab are trained on the FT-NMR spectrometer and effectively implement NMR experiments into their lab courses.

5)   By having hands-on experience with this instrument, students at the Mississippi University for Women (MUW) will have their education experience enhanced.

A chemistry student who enrolls as a freshman in the fall semester of 2008 and graduates after the spring semester of 2012, will be exposed to NMR spectroscopy in all of his or her chemistry labs.

DESCRIPTION OF PROJECT

A new console (Bruker AVANCE III) with user-friendly software was purchased for our existing 300 MHz NMR spectrometer and experiments that utilize this instrument were integrated and implemented throughout the chemistry laboratory curriculum from freshman through senior level laboratories. 

The goals of this project are as follows:

1)   All freshman chemistry laboratory students conduct one experiment each semester using the FT-NMR which impacts about 1,500 STEM students per year.

2)   All students in the undergraduate organic laboratories use FT-NMR extensively for structure determination which impacts about 200 STEM students per year.

3)   Students in the upper-level courses, which are primarily chemistry majors, get hands-on FT-NMR experience which impacts about 100 students per year.

a)   Students in the inorganic laboratory use the NMR for the characterization of inorganic and organometallic compounds, including multi-nuclear NMR experiments (i.e. 19F NMR, 31P NMR, etc.).

b)   Students in the physical chemistry laboratory, in the first semester laboratory, use the NMR to study kinetics and equilibrium.  In the second semester laboratory, the physical chemistry students investigate the basic physical principles of FT-NMR.

c)   Students in the analytical laboratories use the NMR for quantitative analysis in the Analytical I lab, and learned about the electronic components of the spectrometer in the Analytical II laboratory.

Curriculum Integration and Summary Description of Pedagogical Approaches. 

In this project, experiments were implemented throughout the chemistry laboratory curriculum at MSU, beginning with the freshman chemistry labs through the upper-level labs.4,7  Methods for incorporating this NMR spectroscopic technology were adapted from experiments published primarily in the Journal of Chemical Education.12-49 All STEM students completing the freshman chemistry laboratory sequence gained knowledge about and had hands-on experience with FT-NMR.  Students taking the organic chemistry laboratory sequence used NMR extensively for structure determination and to address scientific inquiry. Students taking the upper-level laboratories (analytical, physical and inorganic), conducted experiments relevant to each area, and expanded the students’ knowledge of NMR.  The upper-level students required very little training on the operation of the research-dedicated high-field instruments (600 MHz NMR), and students were able to design and execute experiments as part of their own research projects. Efforts at all levels prepare the students for undergraduate research.

Although traditionally NMR is not discussed until the end of the Organic Chemistry I course, this pedagogy of introducing NMR spectroscopy in the freshman laboratory allowed students to discover NMR principles empirically prior to a formal introduction in the lecture course.  Reinforcement of NMR principles during the lecture course followed the discovery experience in the laboratory course. This is fundamentally a constructivist view pedagogically.

Logistics of Large Numbers of Students.  In order to handle the large numbers of students taking freshman chemistry laboratories, the lab schedule for the NMR experience was staggered. Sections of freshman laboratories running at the same class period were staggered such that one week a section running concurrently with another section would perform the NMR experiment while the other section performed a different lab experiment then the following week the experiments were switched with each other. By doing this, 1,500 freshman laboratory students performed the NMR experiment over a two week period.

Another time saver was the fact that the students ran the experiment at the NMR spectrometer but then processed their data offline. The students proceeded to the computer lab located in the same building as the NMR spectrometer to transfer their data (ftp) from the NMR to a computer in the computer lab and then processed their NMR data using the SpinWorks software.50  They made a hard copy of their spectrum on a printer in the same computer lab.  This project was facilitated by the addition of a computer lab in the chemistry building for offline processing of NMR data. The Department of Chemistry purchased 8 computers, 2 printers, 5 computer tables, 3 desks, 20 chairs, word processing software, ChemDraw software, and EndNote software at a cost of $12,000 for a new computer laboratory for cyber infrastructure for the undergraduate laboratory students. The computer lab provides infrastructure for the students for the teaching laboratories as well as for their undergraduate research projects in STEM areas.  ChemDraw and EndNote assists students with preparation of laboratory reports, term papers, undergraduate research reports, journal publications, poster presentations and all other aspects of their professional STEM development.

ACTIVITIES

The PIs developed documents for the undergraduate laboratory students describing the theory of NMR at a level appropriate to the course and specific to the NMR experiments being covered in the course.  The PIs also generated a “NMR Challenge” for each of the different chemistry laboratory courses. The “NMR Challenge” was an exercise covering NMR theory questions related to the specific type of NMR experiment that they were going to run. The PIs developed documents describing “how to operate the AVANCE 300 MHz NMR spectrometer”, “how to use FileZilla to ftp their data to the computer lab”, and “how to process their data using SpinWorks”. These documents were placed on myCourses by the graduate teaching assistant. MyCourses is the Blackboard-based website managed by Mississippi State University for students to access materials for each course that they take at MSU. The PIs also developed pre-lab lectures so that each graduate teaching assistant (TA) covered the same NMR content during their pre-lab lecture as another TA teaching the same chemistry laboratory course.

The order of activities for the NMR experience was as follows: One week prior to the NMR lab, the TAs loaded the following documents on myCourses: NMR theory, NMR Challenge, specific NMR experiment, how to operate the NMR, how to ftp their data, and how to process their data. Students first performed a survey developed by the sociologist working on this project. Details of the survey and evaluation process are described below.  The week before the NMR lab, the TA informed the freshman chemistry lab students to come to the computer lab instead of the normal freshman chemistry lab location. Once the students arrived in computer lab, they were given a brief lecture by the TA on NMR theory. The TA then described the NMR experiment to the class and explained how to put the NMR data in their lab report which was due the following week. The students were assigned partners and each pair drew a number from a “hat” to determine the order of which group went first and so on. Two groups of students were taking to the NMR Facility while the remaining students worked on their NMR Challenge and waited for their turn. Each of the two freshman chemistry laboratory students in the group ran the NMR experiment while the other two students in the other group worked on their NMR Challenge. When the first group finished running their NMR experiment they then proceeded to the computer lab to tell the third group to go to the NMR Facility and work on their NMR Challenge while the second group finished running their NMR experiment. And the first group transferred their NMR data to a computer lab computer then process and printed their NMR data then they worked on their NMR Challenge until the laboratory period ended. This procedure allowed for a continuous flow of students from the NMR Facility to the computer lab and kept all students busy. For every 3 hour laboratory period, 24 students can obtain hands-on experience on the modern-day NMR spectrometer by using these logistics and hundreds of students each semester can obtain this rewarding experience. One week following the NMR lab, the students were giving a post-lab survey.

Evaluation.  In order to determine the impact of utilizing the NMR spectrometer, we conducted a detailed evaluation.  There are three main groups of students that we evaluated, the freshman lab students, organic lab students, and upper-level students (analytical, physical and inorganic labs).  In our evaluations, we assessed two main categories: “attitudes” and “knowledge”.  Dr. Dunaway, a sociologist, led the assessment of student attitudes and perceptions, while the instructor responsible for each lab course evaluated the students’ knowledge.  In anticipation of receiving the NSF CCLI award, data was gathered to evaluate students in appropriate chemistry courses to provide a comparison group to those classes that used the NMR spectrometer after the grant was awarded.

For the freshman lab students, we were most interested in determining how the lab experience affected their attitudes toward science and chemistry.8-10  Our evaluation included a series of web-based surveys given to all STEM students matriculating through the freshman lab sequence.  Our survey instrument included standard questions soliciting students’ general knowledge of chemistry, laboratory protocol and use, attitudes about chemistry and science, and past experience with chemistry.  The students were asked to input their current major, so that data from students within and among different disciplines can be compared and assessed. The survey was administered three separate times for each lab course.  The initial survey was given during the first week of class.  The data gathered from this survey was used as a baseline to determine overall disposition.  A subsequent survey was given within a week of completing the NMR experiment.  This survey included the same questions as the first survey, but also included questions regarding the students’ experience with NMR spectrometer.  A final survey was administered during the last week of the course.  Again, the same questions were asked, but the final survey included overall impressions of the course content, laboratory experiments and individual sense of achievement.  All surveys were self-administered by the student accessing a secure web page.  Students were informed of how to access the web-based surveys on their course syllabus.  Students received email messages to remind them to participate for the second and third surveys.  The email messages included directions for accessing the web page survey.  All students were informed in writing that their participation in the surveys is voluntary.  Students were also informed that their individual responses would be aggregated and their identity would remain anonymous.  Each survey took approximately 5-10 minutes to complete.

The organic lab students were similarly evaluated in terms of their attitudes toward chemistry and the use of instrumentation using web-based surveys.  All other lab students (i.e. analytical, physical and inorganic labs) were similarly evaluated, through questions that determine whether the students’ understanding and comfort level with NMR spectroscopy have increased by virtue of having been exposed to NMR in different contexts while matriculating from freshman through senior level chemistry laboratory courses.  Though, it should be borne in mind that for the first implementation cycle, the students in these course did not have the benefit of hands-on use of the NMR spectrometer in their earlier courses (In fact, this may be largely true in the second implementation cycle, as well).  The students’ basic understanding of NMR, and their ability to use NMR data to solve chemical problems was evaluated by administering carefully crafted laboratory exams that posed questions to the students at various cognitive levels.50 

Evaluation of student performance on lab exams was used to gauge how well we are meeting our specific learning objectives. Since many of the students in the undergraduate chemistry laboratory courses are not chemistry majors, questions were posed to these students that determine whether they believe the laboratory experience will be beneficial to them in their future careers. 

Data gathered from the surveys was compiled into an aggregated data file.  Data was statistically examined to see if students reflect improvements or enhancements to their experiences and perceptions about chemistry over the course of the semester. After one full year of implementation, the evaluation data was compiled and a thorough formative assessment was conducted.  After the analysis of the data, a round table discussion of this data was conducted by the PIs that focused on any deficiencies discovered through formative assessment, and explored possible modifications of our implementation plan. At the end of this project in March 2010, Dr. Dunaway and the PIs will meet to determine the overall effectiveness of this project, and to what extent the modifications made as a result of the formative assessment were successful. Assessment of the long-term impact of this project will continue even after the project funding period, by way of exit interviews with graduating chemistry majors.
Data obtained from the evaluation process and survey data from students were compiled and these data indicated the following: Students had a more enjoyable lab experience because of their hands-on NMR experience, had a good understanding of NMR theory and instrumentation, appreciated the role of computers in science, understood the importance of NMR to chemists for structure determination, understood how to conduct research using the NMR spectrometer, were challenged intellectually, NMR experience gave them a positive experience with technology, understood chemical principles being studied better because of their NMR experience, could explain how NMR worked, said science became more interesting because of the NMR lab experience, said the NMR skills obtained would be valuable for their future, and some students indicated that they would consider changing their major to a STEM area because of the hands-on experience they obtained on the NMR spectrometer. The average score on the NMR problem set for all laboratory sections was 85% which we consider to be a good indication that the students understood the NMR theory. The average score on the NMR lab report for all sections was 92% which is good indication that students understood the NMR experiment performed.

Outreach Activities:  It is now possible for the Department of Chemistry at Mississippi State University to enhance the educational experience of students outside of the university. In particular, the opportunity to learn about the capabilities and use an NMR spectrometer will help to excite pre-college/community college students about science and may serve to interest them in pursuing careers in a STEM field. Of course, it is particularly attractive to interest students in underrepresented groups in science and engineering in order to increase their numbers majoring in these disciplines.  Outreach was accomplished through a workshop for high school chemistry teachers and community college chemistry faculty.  This workshop was conducted on the campus of MSU over a two day period during the summer following the second year of implementation. The workshop attendees were trained in the implementation and integration of NMR spectroscopy into their high school and community college chemistry curriculum. During this workshop we also included other instrumental techniques and computational chemistry to help the teachers integrate modern techniques into their chemistry curriculum. The workshop attendees were given separate formal lectures on FT-NMR, FTIR, UV-Vis, Mass Spectrometry, X-Ray Crystallography, and Computational Chemistry. Each teacher conducted an experiment and obtained hands-on experience on the NMR spectrometer, the FTIR, the UV-Vis, and completed a conformational study a common pain killer using computational chemistry software. The teachers were given the PowerPoint lectures given by the workshop faculty members who included Drs. Debbie J. Beard, William P. Henry, and Svein Saebo (Computational Chemistry) which they could use in their chemistry laboratory setting in their high school or community college.  The Department of Chemistry at Mississippi State University will continue to offer this spectroscopy and computational chemistry workshop each summer for high school chemistry teachers and community college chemistry professors.  In addition, the department will also offer a week long “boot camp” for high school students during the summer where students will conduct fun-filled experiments that will excite them about chemistry and help prepare them for college level chemistry courses.  The high school students will get hands-on experience on modern instrumentation and conduct experiments related to forensics, polymer science, nanotechnology, and environmental chemistry.  In conclusion, student use of the NMR spectrometer and other modern instruments at the high school, community college and university levels will serve to interest all students in STEM disciplines which will aid in the recruitment of students interested in chemistry careers.

CONCLUSIONS

This project is a collective re-enforcement of the NMR theory and hands-on experience gained during the students’ freshman year. The experience a student gains in their freshman year gets reinforced when they take organic chemistry and again in analytical chemistry, inorganic chemistry and finally again in physical chemistry. By the time a chemistry major graduates from the Department of Chemistry at Mississippi State University, they will be well-prepared for graduate school and have the skill sets to handle advanced NMR spectroscopy. The non-chemistry majors will have skills to help them master the operation of instrumentation that they may encounter in their major and career. Most science and engineering (non-chemistry) majors at MSU take 2 semesters of freshman chemistry and 2 semesters of organic chemistry, therefore, they receive a tremendous amount of hands-on NMR experience to help them in their STEM major and career. This training of students, on modern and comprehensive analytical techniques, at MSU and students at other schools which do not have access to NMR instrumentation for teaching and research purposes, is essential to the educational learning environment goals of MSU and our nation.

The benefit to undergraduate students taking the laboratories is that it gives them training on the latest advancements in NMR technology. This hands-on experience with a 300 MHz NMR will be more in line with the latest instrumentation available today in academe and industry which these laboratory students will encounter once they graduate from MSU and start their careers in STEM areas. The NSF CCLI grant enhanced MSU’s ability to provide a more detailed research experience for the undergraduate students. 

We were able to logistically handle a large number of students obtaining hands-on experience on the NMR spectrometer or what we call “Maximum Exposure in Minimum Time Period” by staggering labs that run concurrently to maximize use. Timing and continuous flow of activities was accomplished to maximize NMR theory exposure and hands-on use/training in an individualized setting. Students work in pairs to run the NMR spectrometer and process their data remotely in the new computer lab established by the Department of Chemistry to assist with this project.
The survey data indicate that the project has been effective at making the freshman laboratory experience more rewarding for the students. In addition, the students learned and retained a significant amount of NMR theory through the laboratory exercise. While it is hard to evaluate whether this project retained or recruited STEM majors, the responses from the students suggest that it had a positive reinforcement on the importance and intellectual challenge associated with these majors.

In conclusion, it can be done! This project has had a broad impact at Mississippi State University on approximately 1,500 MSU students per year from STEM disciplines. Retention of underrepresented students in STEM disciplines is enhanced through outreach activities to area high school, community colleges and HBCU students not having access to NMR instrumentation.

ACKNOWLEDGEMENTS

The PIs would like to acknowledge the National Science Foundation for support of this project (DUE-0633119). Mississippi State University and the MSU Department of Chemistry are also acknowledged for contributing significantly to this project. The author’s would also like to thank Drs. Laura Anna (Millersville University), Eddie Brown (Lee University), Greg Grant (University of Tennessee-Chattanooga), Darrell Iler (Greenville College) and Jerry Manion (University of Central Arkansas) for sharing their laboratory experiments and supplemental material with us. Lastly, we would like to thank all the MSU graduate and undergraduate students that gave comments and suggestions to help make this project a success.

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