Integrating Advanced High School Chemistry Research with Organic

Mar 1, 2008 - This paper describes and discusses the unique chemistry course opportunities beyond the advanced placement-level available at a science ...
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In the Classroom edited by

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  David L. Byrum Ruamrudee International School Bangkok, Thailand  10510

Integrating Advanced High School Chemistry Research with Organic Chemistry and Instrumental Methods of Analysis Brian J. Kennedy Thomas Jefferson High School for Science and Technology, Alexandria, VA 22312; [email protected]

Thomas Jefferson High School for Science and Technology (TJHSST) is a Virginia Governor’s School for mathematics, science, and technology that was established in 1985.1 This institution offers a dynamic, specialized learning environment for selected students with high ability, aptitude, and interest in STEM who seek a comprehensive, challenging curriculum with emphasis in these disciplines. The nearly 1800 students enrolled come from six northern Virginia school districts: Arlington, Fairfax, Fauquier, Loudoun, and Prince William Counties, as well as the cities of Fairfax and Falls Church. Each year, a new freshman class of approximately 400–500 students is enrolled through a competitive admissions process, with projected enrollment expected to reach 2000 students over the next few years. Students complete a four-year science sequence from 9th–12th grade that (at a minimum) includes biology, chemistry, physics, and geosystems. One course, 9th grade biology, is taught through the Integrated Biology, English, and Technology program, which is unique to our school. In chemistry, students must complete Honors Chemistry I before the optional Advanced Placement (AP) Chemistry. Honors Chemistry I is based on the Virginia Standards of Learning, but at an advanced level (1). Although it is required in the 10th grade, 40–80 students elect to take it as an accelerated option during summer school prior to 10th grade, which provides them more options during the regular school year. After Chemistry I, the next elective chemistry course in sequence is AP Chemistry, which enrolls ~180 students each year. The focus of this article is to discuss two chemistry electives beyond the AP level—Introduction to Organic Chemistry with Instrumental Methods of Analysis (2), and Chemical Analysis Research or Mentorship. Both of these courses have been offered at this school since its inception, although methods and practices have transitioned over time to reflect changing pedagogy and student interests and motivations. All seniors are required to complete a senior research project to earn their TJHSST Diploma. Research conducted either oncampus (in one of 12 science and technology research laboratoList 1. Organic Chemistry Course Instrumentation and Equipment Mel-Temp melting point apparatus (Laboratory Devices, Inc.) Microscale organic chemistry glassware (Ace Glassware); standard labware–glassware FT–IR spectrometer, model 380 (Thermo-Electron Corp.) Visible spectrometers (Spectronic 20D+), (Thermo-Electron Corp.) UV–vis spectrophotometer, model UV-2401PC (Shimadzu) Spectrofluorophotometer, model RF-1501 (Shimadzu) Gas chromatograph with FID, model Autosystem XL (Perkin Elmer) Refractometer, model Abbe 3L (Bausch and Lomb) Polarimeter, model SR6, (Polyscience Corporation)

ries) or off-site (at government, corporate, and academic research and development laboratories) enables students to investigate the real world’s most challenging—and often fundamental— problems in science and technology. Many partner organizations and laboratories are listed on the school’s Web site.1 The senior research courses were established with the development of the school as the capstone courses for students. Chemical Analysis Research is one of these 12 offerings. Although a variety of lab investigations within each course are standard labs, curricula have been adapted to integrate advanced investigations that are more contemporary with recent progress in science. These offerings currently provide opportunities to learn advanced, chemistry-related topics for students who are highly motivated and academically prepared. The main purpose of this article is to provide some information about these advanced offerings—and labs selected from this Journal and other pertinent sources—with the goal of assisting others in gaining insight for developing similar programs. The intention is to illustrate how valuable this Journal can be for educators who desire to develop their own unique course offerings. Developments such as those described herein can be modified for a variety of learning styles and abilities. Organic Chemistry and Instrumental Methods of Analysis Course Overview This advanced elective course covers an array of topics designed to further prepare students for their senior research projects, either in chemistry or other disciplines. Currently 60 students are enrolled in three different sections of the course. The course textbook is Organic Chemistry, sixth edition(3); the laboratory textbook is Microscale Organic Laboratory, fourth edition (4). The course only meets about 225 minutes per week so is limited in comparison to a college course. Topics include introductory reactions and mechanisms, stereochemistry, and a comprehensive coverage of nomenclature and spectroscopy for most organic molecules using IR, MS, and NMR. The general outline of lab experiments follows a selection from the laboratory textbook (4), including “Determination of Physical Properties, Microscale Separations, Distillation, Esterification Reactions of Isopentyl Acetate with GC Analysis” and other labs of student interest, such as the “Synthesis of Nylon”. Some students also work independently to complete the “Qualitative Organic Analysis” scheme for identifying an unknown organic compound. The laboratory is well equipped for most types of experiments with fume hoods, vacuum lines, distilled water still, high-precision balances, and so forth; the lab also has a variety of advanced chemical instrumentation for student use, outlined in List 1. When necessary, MS and NMR data (5) are provided for students.

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Chemical Analysis Research Course Overview The Chemical Analysis Research course integrates many aspects of chemistry with the physical and natural sciences. Numerous students are involved in the TJHSST mentorship program who are also engaged in research at local government, Table 1. Research Course Student Activities by Time Period Month

Research Project Activities

August

Post research topics on forum; submit summer initiative materials

September

Complete introductory labs: FT–IR, visible spectroscopy, fluorescence, synthesis (inorganic; organic) Continue proposal development and preliminary presentations

October

Continue introductory labs; develop research project Progress reports become due twice per month

November

Submit final research proposal Compile material safety data sheets; order materials Begin research

December

Conduct research and lab work Enter science fair competitions

January– February

Conduct research and lab work Participate in science fair competitions (using preliminary data and results if project is not yet complete)

March– April

Complete research and share that information with other students

May–June

Write project final report; make final presentations; defend research project Lab cleanup

List 2. Example Research Projects for 2006, Including Mentorships [M] Development of an improved method for avian malaria diagnosis in African penguins [M] Dissection of thrombospondin-1 signaling through CD47/SIRP interaction [M] Refractive index determination of bacillus spores using immersion refractometry [M] The effect of ZJ43 administration on PCP-treated mice [M] Self-decontaminating fabrics for applications against chemical agents [M] Preparation, synthesis, analysis of luminescent emitters OLEDs (13, 14) Development of forensic chemistry learning module integrating spectroscopy Analysis of spectrophotometry, FT–IR, and dipsticks for urine glucose concentration (15, 16) Synthesis and characterization of biodiesel from several sources (17, 18) Quantitative analysis of water quality by chemical and spectroscopic methods (19, 20) Plastic surface modification using polyelectrolytes (21) Optimizing power output of Shewanella putrefaciens microbial fuel cells (22, 23, 24, 25, 26) Synthesis and characterization of Schiff base compounds and bioinorganic models (27, 28) Solubility property determination of extension to Bayer’s reaction for PUI synthesis (29, 30) Synthesis of polymer matrices to mimic “lotus effect” and test for anticorrosion properties (31)

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academic, and private research institutes. Students in Chemical Analysis Research are expected to complete an independent or group research project and compete in contests such as the TJHSST Science Fair or the Intel Science Talent Search. The combination of Chemical Analysis Research with Organic Chemistry is valuable for students, especially those desiring to pursue collegiate studies in the natural and physical sciences or areas such as medicine. Students must complete AP Chemistry prior to being admitted to the Chemical Analysis Research course. Work on projects usually begins during the third year in the form of topic research and proposal writing, and continues with a required submission of a preliminary proposal and collaboration via an Internet discussion board before the fall semester begins (see the online supplement). This timeline allows adequate opportunity for students to acquire materials and thoroughly develop ideas. Since chemistry overlaps with many science and technology areas, students are encouraged to collaborate with some of the other twelve technology labs in the development of their ideas and in the completion of projects. The school year activities are outlined in Table 1. As they progress toward completion of their detailed project proposals, students select from and complete a variety of introductory labs to learn more about available instrumentation. Many of these labs were implemented or modified from articles within this Journal. As a means of introducing students to the lab, we start the school year by completing an inorganic synthesis experiment, “Preparation and Spectrophotometric Analysis of Hexaaminenickel(II) Chloride” (6). This experiment provides students the opportunity to revisit topics such as visible spectrometry, handling volumetric glassware, using equipment, and functioning safely and efficiently in the laboratory. As proposal development continues, students who may do projects involving fluorescence would complete the lab, “Determination of Riboflavin in Vitamin Tablets” (7, 8, 9). Students who may do visible spectrometry would complete the lab, “Colorimetric Determination of Iron in Vitamin Tablets” (10), or others may do a UV experiment such as “Spectrophotometric Analysis and Modeling of Sunscreens” (11). Others who plan to integrate gas chromatography into their projects may complete the experiment, “A Quantitative Gas Chromatographic Ethanol Determination” (12) to determine the percentage of ethanol in mouthwash. As students complete their introductory experiments and their proposals, they are soon able to begin projects of their own design. List 2 shows several representative project areas for the 2006 school year. Many of these projects are extensions of articles in this Journal that students read, as shown. Students ultimately complete preliminary stages of their projects in time to compete in school and regional science fair competitions. Project completion culminates with a final presentation and defense of students’ work and an evening poster session with other research laboratories. This is also an opportunity for parents to come just before graduation to see the finished projects. In order to improve student research and course opportunities, several recent grant-based projects were made possible through the Dominion Foundation (32), for water quality investigations, and the Lemelson–MIT InvenTeam program (33), for the development of a microbial fuel cell, elaborated upon below (22–26). In addition, several corporate sponsorships were also generated in conjunction with the Thomas Jefferson Partnership Fund, Inc. (34). The mission of the Thomas Jefferson Partnership

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Fund is to build and maintain a self-sustaining fund to support new student learning opportunities and innovative research experiences that otherwise would not be possible. As such, some of their efforts have enabled corporate partnerships that provided funding for the purchase of a UV–vis spectrometer and FT–IR spectrometer. Other equipment purchases and lab upgrades were made possible through parent contributions. One of the most successful interdisciplinary projects was created through the Massachusetts Institute of Technology (MIT) Lemelson–InvenTeam grant program (33). Students collaborated during their junior year to complete background research and apply for a grant to complete research on microbial fuel cells. The project goals of the TJHSST InvenTeam were to evaluate and optimize microbial fuel cells (MFCs) to be effective devices that could simultaneously remediate wastewater and generate power. The student researchers utilized original prototypes to test specific mechanisms such as the oxidation of fuel by various bacteria cultures, the performance of different membrane–electrode configurations, the effects of varying mediators, and circuit configurations—all of which are vital factors that contribute to the performance of a microbial fuel cell. The TJHSST InvenTeam was composed of students derived from three different school technology laboratories: prototyping, chemical analysis, and biotechnology. The InvenTeam was further divided into seven groups with the collective goal being to improve MFCs in order to someday permit widespread commercial use. The first research group, from the prototyping lab, was responsible for constructing the MFCs used by other researchers. Three student groups from the chemistry lab focused largely on experimenting with the electrochemical components of the fuel cell. Three groups of biotechnology researchers cultured and tested three different types of bacteria. With the conclusion of the project, the TJHSST InvenTeam was able to combine findings to propose a design for an efficient MFC, which may someday be incorporated into local wastewater treatment facilities. Conclusion This article provides an overview of several advanced high school chemistry course offerings. The ultimate goals of the described courses are to provide high school students with advanced scientific, experimental learning opportunities. Students who complete the three years of chemistry through the introductory organic chemistry course can complete high school having learned many chemical concepts and methods that would normally be learned in a variety of upper-level college courses. The combination of this curriculum with the chemical analysis research course enables students to explore a variety of advanced topics of their own interests through an entirely exploratory, research-based approach. Note

1. TJHSST Web Site. http://www.tjhsst.edu (accessed Nov 2007).

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Supporting JCE Online Material

http://www.jce.divched.org/Journal/Issues/2008/Mar/abs393.html Abstract and keywords Full text (PDF) with links to cited URLs and JCE articles Supplement Document summary of the senior chemical analysis research laboratory student handbook

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