Placing Science into Its Human Context: Using ... - ACS Publications

Dec 12, 2001 - Jeffrey I. Seeman**. Chemical Heritage Foundation, Philadelphia, PA 19106-2702, and SaddlePoint Frontiers, 12001 Bollingbrok Place,...
0 downloads 0 Views 118KB Size
Chemistry for Everyone

W

Placing Science into Its Human Context: Using Scientific Autobiography to Teach Chemistry† Felix A. Carroll* Department of Chemistry, Davidson College, Davidson, NC 28036; [email protected] Jeffrey I. Seeman** Chemical Heritage Foundation, Philadelphia, PA 19106-2702, and SaddlePoint Frontiers, 12001 Bollingbrok Place, Richmond, VA 23236-3218; [email protected]

Chemistry is usually taught from both a practical and a conceptual point of view, with an emphasis on both experimental observations and theoretical explanations. Sometimes names of chemists are associated with various aspects of chemistry, as is illustrated in Table 1, and the use of personal names in this way can help us classify and remember information. Usually, however, the chemist’s name alone provides little substantive understanding of the chemistry itself, nor does it describe much about the “named” person. Electrons, nuclei, orbitals, bonds, and reaction mechanisms cannot be directly observed with the human eye, so many students initially perceive chemistry to be an abstract subject having no obvious connection to their own experiences. Some textbooks, especially those written for nonscience majors, focus on topics such as environmental science that have a direct connection to the students’ lives and interests. In addition, the value of historical anecdotes in the teaching of chemistry has long been recognized (1). As Benfey pointed out, “both [Christopher K.] Ingold and [James Bryant] Conant took it for granted that the only way to understand science was to see its episodes in historical, developmental context” (2). Not only does studying the historical perspective help make abstract concepts more real for students, but it also improves their comprehension of chemical information by helping them frame important chemical concepts within the time element of progress in science. There is particular value in viewing the historical aspect of chemistry through a study of the lives of important chemists because the development of chemical concepts can then be seen in the context of the experiences of fellow human beings. Bowden commented that “Boyle’s law, for example, becomes somewhat less cold and abstract if we can connect it with a face, even if the face is topped with a wig” (3). Studying scientific biography and autobiography is especially valuable for upper-level students because this approach to learning chemistry teaches them not only the facts but also the process of science. In essence, the students learn that the development of science is a function of the people who develop it and the environment in which they live.1 There are many possible methods for incorporating scientific biography and autobiography into chemistry classes. The most appropriate method for a particular course is a function of the level of the course and the goals of the students and professor. In introductory courses, short biographical statements are often included in textbooks or are interjected into lectures by professors. This type of “incidental information”

can help make a human connection with the abstract concepts and does not require much class time. At the senior undergraduate or beginning graduate school level, however, students have the necessary background to begin to view historical developments in relationship to other ideas. In addition, faculty in these courses are more likely to present selected topics in greater depth instead of emphasizing equally all of the chapters in a prescribed textbook. Thus, scientific biography and autobiography may be used most appropriately and most effectively in senior undergraduate and graduate school courses. We report here one approach for incorporating scientific autobiography into a senior undergraduate course on advanced organic chemistry. The specific objectives of this teaching method are 1. to teach major concepts in organic chemistry; 2. to show science as a human experience; 3. to demonstrate how research programs are peopledependent (i.e., how the personalities of the investigators influence their research); 4. to illustrate how findings that are significant in one time period can remain significant in subsequent decades and also can form the basis for subsequent hypotheses and research; Table 1. The Use of Names of Chemists in Science Category

Illustrative Example

Fundamental unit

Avogadro’s number

Mathematical relationship Beer’s law Thermodynamic function

Gibbs free energy

Name of an element

Seaborgium (Sg)

Compound

Danishefsky’s dienea

Class of compounds

Lewis acids and bases

Reagent

Adams catalyst

Qualitative test

Gilman test

Reaction

Diels–Alder reaction

Principle

Markovnikov’s rule

Apparatus

Erlenmeyer flask

Academic institution

Pasteur Institute

Company

E. I. Dupont de Nemours and Company

Foundation

The Camille and Henry Dreyfus Foundation

Award or prize

Nobel Prize

Journal title

Justus Liebigs Annalen der Chemie

a(E)-1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene:

† Presented in part at the 213th National Meeting of the American Chemical Society, San Francisco, CA, April 13–17, 1997.

1618

(CH3)3SiO

Journal of Chemical Education • Vol. 78 No. 12 December 2001 • JChemEd.chem.wisc.edu

OCH3

Chemistry for Everyone 5. to provide insight into the process of science by showing how individuals’ research programs develop and grow over a multi-decade time period; 6. to involve an entire class in an activity that encourages both self-directed learning and cooperative learning; 7. to give students an opportunity to engage the chemical literature; and 8. to provide teaching and class presentation opportunities to the students.

As these objectives indicate, incorporation of scientific autobiography is primarily intended to enhance the learning of chemical concepts and to increase students’ understanding of the role of individual scientists in the advancement of the field.2 However, the teaching method we have developed also accomplishes other important goals by helping students to become more independent learners. In particular, students who are not already familiar with using the primary chemical literature may find that reading journal references in the context of a scientific autobiography can help them understand research publications as part of a developing field of science and not as abstract repositories of dry experimental data on a library shelf. In addition, this teaching method gives students experience with working in teams, preparing and using visual aids, and making group presentations to fellow students and faculty. These activities may be incorporated much more naturally into classes based on scientific autobiography than in traditional, lecture-based chemistry courses.3 Results Scientific autobiography has been used as a vehicle for teaching chemistry in a senior undergraduate course in advanced organic chemistry at Davidson College during four different years. We describe here in some detail the first use of this teaching method because we have both short-term and long-term evaluations from students in this class, but results for other classes are similar. In all cases the scientific autobiography was From Cologne to Chapel Hill by Ernest L. Eliel (4), which was chosen because the class discussion was scheduled for a time at which students would have just finished studying stereochemistry and conformational analysis.4,5 The following specific papers from different time periods of Eliel’s career were selected for student study and class discussion: 1. 1940s: chirality due to isotopic substitution (5); 2. early 1950s: conformational analysis and reactivity of conformationally mobile systems (6); 3. late 1950s: kinetic and equilibrium methods for conformational analysis (7); 4. 1960s: conformational analysis of saturated heterocycles (8); 5. 1980s: enantioselective synthesis (9).

The students were already familiar with the use of the chemistry library and had some experience with the use of the primary chemical literature. The five students in the class were given several weeks to read the Eliel autobiography. Then, working individually or in teams of two, they prepared reports on the specific research papers assigned to them.6,7 For convenience, students were given reprints of the selected

publications. Faculty support was available, but the students generally needed very little assistance in understanding the chemistry in their assigned papers, in no small measure because they were encouraged to discuss the publications extensively within their teams. When the time in the semester for class discussion of the book arrived, the students used one 50-minute class period to present a summary of each research paper to fellow class members. The presentations indicated that the students were quite able to understand and then present in their own words the important chemical concepts in each research article.8 The summaries were prepared on flip chart pages, which were posted after completion of the presentations. As a result, the entire room became “enveloped” with posters summarizing Eliel’s most notable publications arranged in chronological order.9 Because the papers were written over a period of nearly 40 years, the posters gave a vivid illustration of the progress of science during the latter half of the 20th century. During the next class meeting, the students briefly reviewed the chemistry in each paper and then discussed the research and its place in Eliel’s career. The class discussion brought into focus how the human condition can influence a person’s decision to become a scientist, where to study chemistry, what professional positions to undertake, and what research projects to pursue. Students noted the impact of advances in instrumentation on the nature of scientific research, and they commented on the importance of meetings, seminars, informal discussions, and collaborative relationships in helping researchers develop and explore new ideas. They also saw how Eliel’s different research efforts fit together into a coherent pattern of increasing complexity of topics on a central theme. It is our opinion that this approach to teaching chemistry does achieve the goals stated above. Some of the topics presented by students, such as the use of heterocyclic compounds in enantioselective synthesis, would not otherwise have been covered in this course on physical organic chemistry. This exercise also helped students learn more about the culture of contemporary chemistry than is available just from reading textbooks and attending lectures. In addition, this approach accomplished the goal of helping students enhance the skills needed for learning new material through individual study of the primary literature and through group participation. Although this teaching method does not generate quantitative data for evaluation, student course evaluations and subsequent comments reinforce the conclusion that it was successful. In end-of-semester evaluations, the students reported that they enjoyed taking greater responsibility for their own learning and for working cooperatively with each other. They also indicated that they appreciated the opportunity to learn about the human face of scientific research. The following comments from these course evaluations summarize students’ immediate reactions to this teaching method. Learning about Eliel’s life caused me to be more interested in understanding the chemistry in the journal articles. We were able to see how the logical progression of his scientific research coincided with his life. I enjoyed learning about the life of a famous chemist. We spend most of our time worrying about the chemistry, but the lives of the people who do the work are also important. I definitely found the experience of reading the

JChemEd.chem.wisc.edu • Vol. 78 No. 12 December 2001 • Journal of Chemical Education

1619

Chemistry for Everyone book and doing the project worthwhile. The book was a good read and contained enough historical facts about chemistry to make it interesting. …The project was a good opportunity to first learn the chemistry presented in the article and then go back and read about what was going on in his life and the circumstances surrounding the publication.

These short-term evaluations were recently reinforced by comments from two students in the first class to experience this teaching method. When asked to review the experience after a period of nearly five years, one of them wrote that the experience with scientific autobiography was one of the things he remembered in most detail about the advanced organic chemistry course. The second student responded that We began a transition that has continued in graduate school by spending more time learning about points or ideas that were of greater interest to us within a subject. The ability to discuss this transition with a partner helped to define what we were doing more clearly. The process of taking more responsibility for what and how we learned was great preparation for graduate school.

Other Options Although we have used only Eliel’s From Cologne to Chapel Hill (4) in class, we believe that many other biographies and autobiographies would also serve well for this learning experience.2,10 In addition to presenting chemistry information in the context of an interesting human story, many of these works offer unique perspectives on particular controversies in organic chemistry, and some also provide students valuable insights into the ethical concerns of researchers. The choice of one book over the others can be based on the particular topics covered in the course, the level of the course, the scientific interests of the students and the professors, and considerations such as the geographical and cultural backgrounds of the students. We particularly recommend books in which the scientist has been involved in multiple professional careers or research in significantly different areas of science. Furthermore, studying more than one scientist’s life and career is likely to provide an even richer, more panoramic learning experience. Conclusions Scientific biography and autobiography can help students at the advanced undergraduate and graduate school levels gain a deeper understanding of fundamental chemical concepts and can increase their enthusiasm for learning chemistry. Biographical and autobiographical material can also give students a better understanding of the human component in the development of important ideas in science. The technique of collaborative learning, which is more commonly used in other disciplines, may be introduced more effectively into chemistry courses through the use of scientific biography and autobiography than through group consideration of abstract chemical concepts alone. Students can see the critical role that personal contacts play in the development of new ideas and in establishing collaborative relationships. They can recognize the impact of new instruments and new techniques 1620

on the expanding frontiers of chemistry. They can also see how successful chemists have overcome adversity and have made important discoveries even without access to instrumentation that we may now take for granted. Acknowledgments We thank Ernest L. Eliel for identifying what he considered some of his seminal publications, for providing reprints of the papers used for class discussion, and for autographing a photograph distributed to all class members in the first class. Koji Nakanishi, John D. Roberts, Andrew Streitwieser, and Cheves Walling and the late Donald Cram and Raymond Lemiux provided helpful recommendations concerning their publications that might be useful for this teaching approach. We express appreciation to W. S. Aldridge, T. E. Curey, N. C. Kallan, J. M. Keller, and M. M. Payne for their enthusiastic participation in the first trial of this new learning experience. We thank Barry R. Sickles for helpful assistance with this project. We are grateful to the three reviewers for many helpful comments and suggestions. A portion of the work by one of us [JIS] was performed at Philip Morris, Richmond, VA, and we thank Philip Morris for its support. We also acknowledge the Chemical Heritage Foundation for partial support of this work and thank Arnold Thackray for his encouragement and support during JIS’s tenure as a Senior Fellow of Chemical Education at the CHF. W

Supplemental Material

Annotated lists of resource material for six other scientific autobiographies are available in this issue of JCE Online. Notes 1. As has been discussed by Fuller (10), understanding the function of individual scientists is also central to the study of the philosophy of science. An early and influential philosophy of science, first proposed by Sir Francis Bacon and known as the Baconian ideal (11), holds that science is a body of steadily accumulating facts that are independent of their investigators. As Medawar noted, however, “The idea of naive or innocent observation is philosophers’ make-believe” (12). Indeed, scientists act in ways that parallel human behaviors in other professional and nonprofessional endeavors, such as engaging in competition for resources, rewards and prestige (10, 11, 13–15) as well as providing negative sanctions on each other (10). Popper’s falsification philosophy of science clearly points to the role of the scientist as more than an observer but instead as an active participant (16). The classical–nonclassical ion debate in physical organic chemistry provides a vivid example of the human component in the practice of science in recent years. A compilation of papers (17), a debate in book format (18), a close personal perspective (19a), and an impartial review (20) are available, as are many other works referenced in these publications. For an earlier example of how personal interactions can drive research, see the Robinson–Ingold controversy regarding credit for the origin of understanding, classifying, and naming electronic factors in organic chemistry (19g,h, 21, 22h–j). The human role in the scientific process is recognized in the professional codes of conduct of the American Chemical Society (23) and other organizations (24), which describe the ideal behaviors for scientists as researchers, student advisors,

Journal of Chemical Education • Vol. 78 No. 12 December 2001 • JChemEd.chem.wisc.edu

Chemistry for Everyone journal editors, manuscript authors, and reviewers (25). 2. Several works provide information about important chemists of the past (3, 22) and 20 autobiographies of eminent chemists have appeared in the Profiles, Pathways and Dreams series (19). 3. Two publications describe teaching methods that incorporate cooperative learning into the classroom portion of organic chemistry (26) and others discuss the use of cooperative learning in the laboratory and in distance learning situations (27). 4. This activity was scheduled so that students gave presentations after they had completed chapters on stereochemistry and conformational analysis in the textbook (28). 5. Additional factors influencing the selection of this book were the geographic location of Davidson (about 100 miles west of the University of North Carolina at Chapel Hill) and the clarity and brevity of the book (most students report that no more than three hours was required to read the volume). 6. We find that the number of copies of the book needed for this exercise is a function of the number of students in the class and the number of weeks in advance students are told about the project. One copy is probably adequate for three students if the students are told about the project three weeks in advance. 7. In subsequent years, class sizes have varied from two to eight students, so small class size is not an impediment to this way of teaching chemistry. 8. The five students in the first class were very capable students, as were those in subsequent classes. The great majority of the students taking this advanced organic chemistry course have gone on to graduate school or medical school. 9. More recently, students have used PowerPoint presentations. While the computer presentations have definite advantages, this approach eliminates the possibility of encircling the lecture room with posters, as was done in the first class. 10. A short list of seminal publications distributed over the chosen scientist’s career provides an optimum resource for this teaching/learning experience. Such lists were kindly provided by the late Donald Cram and Raymond Lemiux and by Koji Nakanishi, John D. Roberts, Andrew Streitwieser, and Cheves Walling and are found in the supplemental material.W

Literature Cited 1. Herron, J. D. J. Chem. Educ. 1975, 52, 179–180. Bargallo, M. Rev. Soc. Quim. Mex. 1975, 19, 90–92. Kirschenbaum, L. J. J. Chem. Educ. 1975, 52, 193. Moseley, C. G. J. Chem. Educ. 1976, 53, 578. 2. Benfey, T. Bull. Hist. Chem. 1996, 19, 19–24. 3. Bowden, M. E. Chemical Achievers. The Human Face of the Chemical Sciences; Chemical Heritage Foundation: Philadelphia, PA, 1997. 4. Eliel, E. L. From Cologne to Chapel Hill; Seeman, J. I., Ed.; American Chemical Society: Washington, DC, 1990. 5. Eliel, E. L. J. Am. Chem. Soc. 1949, 71, 3970–3972. 6. Eliel, E. L. Experientia 1953, 9, 91–93. 7. Eliel, E. L.; Ro, R. S. J. Am. Chem. Soc. 1957, 79, 5992–5994. Eliel, E. L.; Ro, R. S. Chem. Ind. (London) 1956, 251–252. 8. Eliel, E. L.; Knoeber, M. C. J. Am. Chem. Soc. 1968, 90, 3444– 3458. Eliel, E. L.; Knoeber, M. C. J. Am. Chem. Soc. 1966, 88, 5347–5349. 9. Lynch, J. E.; Eliel, E. L. J. Am. Chem. Soc. 1984, 106, 2943–2948. Eliel, E. L.; Lynch, J. E. Tetrahedron Lett. 1987, 4813–4816.

10. Fuller, S. Philosophy of Science and its Discontents; Westview: Boulder, CO, 1989; see in particular pp 1–5, 11, 27, 63, 113, 124–131, 145–151, and references cited therein. 11. Woodward, J.; Goodstein, D. Am. Sci. 1996, 84, 479–490. 12. Medawar, P. The Art of the Soluble; Metheun: London, 1967; pp 132–133. 13. Chemical Research—2000 and Beyond: Challenges and Visions; Barkan, P., Ed.; American Chemical Society: Washington, DC, 1998. 14. Gaston, J. Originality and Competition in Science; University of Chicago Press: Chicago, 1973. 15. Bard, A. J. Chem. Eng. News 1999, 77 (Sep 16), 5. 16. Popper, K. Postscript to the Logic of Scientific Discovery; Open Court: Chicago, 1983. Popper, K. The Logic of Scientific Discovery; Basic Books: New York, 1959. 17. Nonclassical Ions: Reprints and Commentary; Bartlett, P. D., Ed.; Benjamin: New York, 1965. 18. Brown, H. C. The Nonclassical Ion Problem, with comments by P. v. R. Schleyer; Plenum: New York, 1977. 19. The following are in the Profiles, Pathways and Dreams series; Seeman, J. I., Ed.; published by the ACS and Oxford University Press. (a) Roberts, J. D. The Right Place at the Right Time; 1990. (b) Eliel, E. L. From Cologne to Chapel Hill; 1990. (c) Cram, D. J. From Design to Discovery; 1990. (d) Djerassi, C. Steroids Made It Possible; 1990. (e) Lemieux, R. U. Explorations with Sugars: How Sweet It Was; 1990. (f ) Havinga, E. Enjoying Organic Chemistry, 1927–1987; 1991. (g) Prelog, V. My 132 Semesters of Studies of Chemistry; 1991. (h) Barton, D. H. R. Some Recollections of Gap Jumping; 1991. (i) Nozoe, T. Seventy Years in Organic Chemistry; 1991. (j) Nakanishi, K. A Wandering Natural Products Chemist; 1991. (k) Dewar, M. J. S. A Semiempirical Life; 1992. (l) Calvin, M. Following the Trail of Light: A Scientific Odyssey; 1992. (m) Mark, H. From Small Organic Molecules to Large: A Century of Progress; 1993. (n) Stone, F. G. A. Leaving No Stone Unturned: Pathways in Organometallic Chemistry; 1993. (o) Merrifield, R. B. Life During a Golden Age of Peptide Chemistry: The Concept and Development of Solid-Phase Peptide Synthesis; 1993. (p) Huisgen, R. The Adventure Playground of Mechanisms and Novel Reactions; 1994. (q) Walling, C. Fifty Years of Free Radicals; 1995. (r) Birch, A. J. To See the Obvious; 1995. (s) Streitwieser, A. A Lifetime of Synergy with Theory and Experiment; 1997. (t) Johnson, W. S. A Fifty-Year Love Affair with Organic Chemistry; 1998. 20. Walling, C. Acc. Chem. Res. 1983, 16, 448–454. 21. Saltzman, M. D. J. Chem. Educ. 1980, 57, 484–488. 22. (a) Tseulos, G. D.; Wickey, C. A Guide to Archives and Manuscript Collections in the History of Chemistry and Chemical Technology; Chemical Heritage Foundation: Philadelphia, PA, 1987. (b) Chemical Heritage Foundation Staff. Introducing the Chemical Sciences, Revision of the CHF Reading List; Chemical Heritage Foundation: Philadelphia, PA, 1998. (c) Howsam, L. Scientists since 1660: A Bibliography of Biographies; Ashgate: Brookfield, VT, 1997. (d) Biographical Memoirs of Fellows of the Royal Society, The Royal Society: London, 1955–. (e) For a series of brief biographies of deceased members of the U.S. National Academy of Sciences, written by members familiar with the deceased’s life and work, see approximately 35 volumes published under the title Biographical Memoirs; National Academy Press: Washington, DC. In the 1930s, these books were published by Columbia University; since then, the publishers have changed several times. (f ) For a continuing list-

JChemEd.chem.wisc.edu • Vol. 78 No. 12 December 2001 • Journal of Chemical Education

1621

Chemistry for Everyone ing of recent works in the history of chemistry, including biographies and autobiographies, see Chemical Heritage; Chemical Heritage Foundation: Philadelphia, PA. The following (g– j) are important biographies and autobiographies in the field of organic chemistry. (g) Todd, A. R. A Time to Remember: The Autobiography of a Chemist; Cambridge University Press: Cambridge, 1983. (h) Robinson, R. Memoirs of a Minor Prophet; Elsevier: Amsterdam, 1976. (i) Williams, T. I. Robert Robinson, Chemist Extraordinary, Clarendon: Oxford, 1990. (j) Leffek, K. T. Sir Christopher Ingold, A Major Prophet of Organic Chemistry; Nova Lion: Victoria, BC, 1996. (k) Tarbell, D. S.; Tarbell, A. T. Essays on the History of Organic Chemistry in the United States 1875–1955, Folio: Nashville, 1986. (l) Great Chemists; Farber, E., Ed.; Interscience: New York, 1961. (m) American Chemists and Chemical Engineers; Miles, W. D., Ed.; American Chemical Society: Washington, DC, 1976. (n) Miles, W. D.; Gould, R. F., Eds.; American Chemists and Chemical Engineers, Vol. 2; Gould: Guilford, CT, 1994. (o) Smith, H. M. Torchbearers of Chemistry: Portraits and Brief Biographies of Scientists Who Have Contributed to the Making of Modern Chemistry; Academic: New York, 1949. (p) James, L. Laureates in Chemistry; American Chemical Society: Washington, DC, 1993. (q) Jaffe, B. Crucibles: The Story of Chemistry, 4th rev. ed.; Dover: New York, 1976. (r) Ipatieff, V. N. The Life of a Chemist; Eudin, X. J.; Fisher, H. D.; Fisher, H. H., Eds.; Stanford University Press: Stanford, CA, 1946. (s) Hargittai, I. Candid Science: Conversations with Famous Chemists; Imperial College Press: London, 2000. (t) Ogilvie, M. B.; Harvey, J. D. Biographical Dictionary of Women in Science; Routledge: New York, 2000. 23. The Chemist’s Code of Conduct; adopted by the American Chemical Society Board of Directors, June 3, 1994. Ethical Guidelines to Publication of Chemical Research; American Chemical Society Publications Division, Jan 1994; endorsed by the Society Committee on Publications. 24. See, for example, Code of Ethics; The American College of Toxi-

1622

25.

26.

27.

28.

cology. Integrity in Scientific Research; American Association for the Advancement of Science: Washington, DC. American College of Physicians Ethics Manual; American College of Physicians: Philadelphia, PA. AGU Policy on Misconduct in Science; American Geophysical Union: Washington, DC. Panel on Scientific Responsibility and the Conduct of Research. Responsible Science, Volume I: Ensuring the Integrity of the Research Process; National Academy Press: Washington, DC, 1992; and Responsible Science, Volume II: Background Papers and Resource Documents; National Academy Press: Washington, DC, 1993. Alberts, B.; Shine, K. Science 1994, 266, 1660–1661. Committee on the Conduct of Science, National Academy of Sciences. On Being a Scientist; National Academy Press: Washington, DC, 1989. Alberts, B.; White, R. W.; Shine, K. Proc. Natl. Acad. Sci. USA 1994, 91, 3479–3480. Council of Biology Editors, American Institute of Biological Sciences. Peer Review in Scientific Publishing, Papers from the First International Congress on Peer Review in Biomedical Publication; Council of Biology Editors: Chicago, 1991. Korenman, S. G.; Berk, R.; Wenger, N. S.; Lew, V. J. Am. Med. Assoc. 1998, 279, 41–47. Committee on the Responsible Conduct of Research, Institute of Medicine. The Responsible Conduct of Research in the Health Sciences; National Academy Press: Washington, DC, 1989. Dinan, F. J.; Frydrychowski, V. A. J. Chem. Educ. 1995, 72, 429–431. Kampmeier, J. A.; Varma-Nelson, P.; Wedegaertner, D. Peer-Led Team Learning: Organic Chemistry; Prentice-Hall: Upper Saddle River, NJ, 2001. Coppola, B. P.; Lawton, R. G. J. Chem. Educ. 1995, 72, 1120– 1122. Lagowski, J. J. Pure Appl. Chem. 1999, 71, 845–850. Glaser, R. E.; Poole, M. J. J. Chem. Educ. 1999, 76, 699–703. Browne, L. M.; Blackburn, E. V. J. Chem. Educ. 1999, 76, 1104–1107. Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole: Pacific Grove, CA, 1998; Chapters 2 and 3.

Journal of Chemical Education • Vol. 78 No. 12 December 2001 • JChemEd.chem.wisc.edu