The State of Organic Teaching Laboratories - Journal of Chemical

Research: Science and Education

The State of Organic Teaching Laboratories

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Gail Horowitz Department of Chemistry, Yeshiva University, New York, NY 10033; [email protected]

This article reviews and explores the changes that have taken place in the organic chemistry laboratory course over the last two to three decades. Reasons for this review are varied and multifaceted. The organic laboratory course is overdue for review. Most recent reviews (1, 2) have consisted of broad, multi-institution surveys and have not focused on issues of course content and pedagogy. Furthermore, it is important that organic educators be knowledgable about the history of organic laboratories and the changes they have undergone. It is only when educators are well informed about the organic laboratory’s history of curricular change that they can enact successful and effective reforms. This review will assess why certain organic laboratory reforms have succeeded while others have not. It will also demonstrate that the organic lab has indeed undergone significant pedagogical change in the last decades, particularly with regard to problems of student “cookbooking”. Additionally, this review will provide the reader with many examples of new and diverse experiments, as well as creative approaches to the course as a whole. Microscale One of the most dramatic changes that has taken place in the organic laboratory in the last two decades has been the growth and development of the microscale movement. This movement began about twenty years ago, when coauthors Mayo, Pike, and Butcher presented their first oral papers at 1984 BCCE (3) and ACS (4, 5) conferences and published their first edition of Microscale Organic Laboratory (6). Since then, the microscale movement has grown both exponentially and internationally (7, 8). One indication of this growth has been the number of microscale organic experiments published. To date, more than 150 microscale or, ganic experiments have been published in this Journal. Twenty-five percent of all Journal of Chemical Education organic experiments published in the last 20 years have been microscale experiments. Another indication of microscale’s growth is its pervasiveness in organic laboratory texts. At present, one cannot find a single organic laboratory manual that does not either feature or include a microscale or miniscale approach.

Readiness for Reform A detailed account of the spread of microscale has been described elsewhere (9, 10). A brief examination of the factors that led to its acceptance and proliferation is worthwhile, however, because the microscale movement is rare among educational reforms in that it both attracted a broad audience and has persisted over time. According to Pike (7), two coincident factors led to the acceptance and adoption of the microscale laboratory approach: an increased environmental awareness accompanied by a technological readiness. In the 1970s, events such as the publication of Silent Spring and the Chernobyl disaster made Americans increasingly aware 346

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of environmental issues. In this era of chemophobia, the EPA was founded. The environmental costs of running organic laboratories (chemicals, waste disposal, air handling, and liability insurance) began rising (10–12). Simultaneously, gravimetric, 1 spectroscopic, and chromatographic tools that allowed for the quick weighing and analysis of small quantities of material became increasingly available and affordable (7, 11, 13, 14). A rising environmental consciousness, the associated economic pressures, and the availability of technological tools created an atmosphere in which organic laboratory educators were ready and willing to adopt a microscale approach. Organic instructors were also receptive to microscale because it was an approach that was familiar to them from their graduate school and research experiences (14). As a result, the adoption of microscale did not require that chemists change their ideas about teaching, but rather that they simply change the equipment being used.

Educational Impact While, for the most part, a change to microscale did not signify a pedagogical change on the part of organic instructors, there is no question that the microscale revolution did affect the learning experiences of organic students. Certainly, students needed to learn to work more carefully when working with small quantities. As a result, microscale has improved the technical skills and manual dexterity of students (7). But microscale laboratories also have had a broader impact on students. The advent of microscale has exposed students to a greater variety of experiments (9, 12, 14, 15). Chemicals that are expensive, dangerous, or difficult to handle on the macroscale are often not problematic on the microscale. Microscale laboratories are more likely to use chemicals such as butyl lithium, sodium borohydride, or potassium tert-butoxide (6, 14–17). As a result, students conducting microscale experiments are much more likely to be exposed to reactions such as alkylation, phase-transfer catalysis, Wittig, or hydrogenation (6, 17–21). Unlike typical educational reforms that are transient or affect only select groups, the microscale approach has both persisted and spread. Perhaps lessons learned from the microscale experience can be applied to other chemical education reforms. Cookbooking and Pedagogical Reform In a 1979 article in this Journal entitled “Chemistry without a Cookbook”, Wade wrote the following critique of the typical organic chemistry laboratory course (22), Students can successfully complete the course ... without acquiring a fundamental understanding of the rationale behind any given manipulation or how it might be applied in another situation…. The students often have put little or no thought into the experiment, since they must simply follow instructions to achieve the proper result …

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Wade argued that giving students a cookbook of foolproof recipes leads to a lack of student thinking and learning. About a decade later, Pickering voiced similar concerns (23), Organic labs have degenerated into cooking…. There is some sort of cosmic futility in most organic labs. Make a white powder, prove that it is what you expect, donate it to chemical waste, again, and again, and again.

Both Wade and Pickering, as well as others (24), have argued vehemently against cookbook organic laboratories that encourage students to blindly follow recipes without thinking about what they are doing. A decade later, recent pages of this Journal (24–26) indicate that concerns about cookbooking and questions about how to best engage organic laboratory students persist. The organic chemistry education community, however, has been far from silent about the cookbooking issue. In fact, its response has been both diverse and prolific. Three principle approaches have been used by organic chemistry educators to get students to do more thinking in the laboratory. These approaches can be broadly categorized as discovery, inquiry, and project-based.

Discovery The most frequent and prevalent response to the cookbooking question has been the design of so-called discovery or puzzle experiments. Discovery experiments are experiments in which experimental outcomes are not told to students. Students must solve puzzles in order to determine what has transpired in their reactions (19–21, 23, 27–84). Discovery experiments typically feature synthetic puzzles in which students must discover the identity of a starting material or product or deduce the regioselectivity or stereoselectivity of a reaction.2 Often spectroscopic methods (IR and especially NMR) are required to solve such puzzles. Less typical discovery-based experiments (21, 43, 49, 60, 63) focus on purification techniques and try to encourage students to discover the basic principles that underlie these techniques. Because puzzle or discovery-based experiments force students to think about their experimental results, they discourage cookbooking.3 Since discovery experiments still provide students with explicit recipes to follow, however, they do not necessarily encourage students to think about the procedures they are following.

Inquiry An open-ended inquiry approach, in which students must design part or all of the procedure, is another potential solution to the problem of students robotically following recipes. With inquiry-approach experiments, the instructor generally chooses an archetypal experiment (i.e., reaction of phenyl magnesium bromide with benzophenone) and then requires students to design the procedure for the experiment. Inquiry approaches are not uncommon in the general chemistry laboratory (85–90) but have rarely been implemented in the organic laboratory (91–95). This discrepancy (96) may stem from the fact that organic procedures are more complex and that their design requires much more student experience and knowledge.

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Projects A third method used to combat cookbooking has been the project-based approach. This method is not used as frequently as the discovery method but is much more prevalent than the inquiry method. Project-based approaches require students to work on multiweek research-like projects in which they must modify and adapt existing procedures to solve new synthetic problems. Two types of project-based approaches have been described at conferences (97–103), in journals (104–127), and in laboratory manuals (19–21). Some projects are open-ended: students are free to conduct any synthetic experiment that interests them (98, 102, 107, 108, 110, 113, 126). Students choose a precursor molecule or a synthetic target and then plan a multistep synthetic route involving their molecule of choice. Other projects are more narrow in scope. The instructor chooses the research question, which may be a synthetic route, target molecule, or functional group transformation (19, 20, 97, 99–101, 104–106, 109, 111, 112, 114–125, 127). Sometimes the topic chosen is based upon the instructor’s research area. What both project styles have in common is that they require students to conduct a primitive form of research in which they must conduct reactions that have never been tried before. Thus, unlike discovery-based experiments, in which the experimental outcome is not known to the student but is known to the instructor, with project-based experiments the outcome (will the experiment be successful?) is not known to the student or the instructor. Because project-based approaches more or less force students to think about both procedure and outcome, advocates of projects argue convincingly that projects successfully eliminate cookbooking (107, 126). Unfortunately, project-based experiments have a number of drawbacks. They can be costly and time consuming to implement (128), frustrating to students when they do not work (108, 120, 129), and dependent on expensive resources (primary literature, electronic databases, NMR instrumentation) that may not always be available.4 They also require extra attention to safety through screening of student procedures. As a result, even though instructors may be attracted to project-based experiments, financial, temporal, and logistical constraints discourage the adoption of projects. Discoverybased experiments, however, have become quite popular because they are easy to design and implement. Many traditional verification experiments can be readily converted to discovery experiments simply by removing information about experimental outcomes from student handouts (Table 1). Collaborative Learning Through the use of the discovery, inquiry, and projectbased approaches, organic laboratories have made significant inroads towards combating cookbooking. At the same time, the use of these new pedagogical approaches has also ushered in another pedagogical advance, collaborative learning. Collaborative learning refers to situations in which students work and learn together within small groups or teams (130). Discovery, inquiry, and project-based approaches all challenge students to think for themselves, rather than allowing them to blindly follow recipes. To facilitate and enable independent thinking, many instructors have turned to collaborative learning as a means of assisting students in negotiating


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Table 1. Traditional and Contemporary Approaches in the Organic Laboratory Attribute

Verification

Discovery

Projects

Inquiry

Narrow

Open-Ended

Topic chosen by

Instructor

Instructor

Instructor

Instructor

Student

Procedure

Given to students

Given to students

Adapted by students

Adapted by students

Adapted by students

Outcome known to students?

Yes

No

No

No

No

Outcome known to instructor?

Yes

Yes

Yes

No

No

Cost

Moderate

Moderate

Varies

Moderate

High

this new and unfamiliar learning process. Collaboration is often limited to the pooling of student results (individuals work on different substrates or employ different reaction conditions) (20, 27, 30, 32, 37, 45, 49, 54, 65, 131–140). Richer collaborations team up students to jointly design procedures (92, 93, 122), or to solve puzzles and problems (20, 28, 56– 58, 98, 141–143). Most collaborative labs are project-based approaches that group students into synthetic teams that are jointly responsible for everything from searching the literature, to conducting reactions, to analyzing experimental results (97–99, 101, 108, 109, 112, 116, 119, 126).

The Debate Continues Given the recent pedagogical advances in the organic laboratory, it is somewhat surprising to observe that arguments concerning cookbooking in organic labs persist (24, 25). In a recent article entitled “What’s Wrong with Cookbooks?”, Ault argues that “nothing” is wrong with cookbooks or with having organic students follow recipes (25). Monteyne and Cracolice vehemently disagree, declaring: “What’s wrong with cookbooks? … Everything!” (24) Both sides are correct. The key issue is not the use of cookbooks or recipes, but the blind use of them by students. As Pickering stated (23), The distinction between organic chemical research and cooking is not in the operations, but in that a cook is concerned only with the creation of a product while an organic chemist wants the answer to a question.

There is no question that synthetic organic chemists follow published procedures or recipes. The goal for organic teaching labs should not be the abolishment of recipes, but rather finding ways to get students to use recipes effectively so that they must think about what they are doing (144). Both the discovery and project-based approaches described above meet these conditions because they expect students to follow recipes, yet strongly encourage them to think about what they are doing. Technology and Modernization

Instrumentation It is clear that significant pedagogical shifts have taken place in the organic laboratory. At the same time, technological advances have also brought striking changes to the organic laboratory. Modern spectroscopic instrumentation has transformed the laboratory environment. Spectroscopy has found its way into the organic laboratory in both traditional and innovative ways. It has been used to identify and characterize reaction products (65, 66, 145–150), to determine 348


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product distributions (94, 151–156), and to create spectroscopic unknowns (94, 146, 157–169). In addition, it has been used to study less mainstream subjects such as: • the acidity of C⫺H bonds (170) • the relative stabilities of disubstituted cyclohexane conformers (171) • the molecular geometry of complex molecules (172) • the hindered rotation of sterically hindered Diels–Alder adducts (105, 106) • the hindered rotation about C⫺N amide bonds (173, 174) • magnetic nonequivalence (175) • enantiomeric purity (147, 176, 177) • keto–enol tautomerization (178)

Spectroscopic methods have also influenced the organic laboratory in other ways. They facilitated the spread of the microscale movement because they made feasible the analysis of small quantities of materials (7, 15). Spectroscopy has also been crucial in the implementation of discovery and project-based experiments. Without modern instrumentation, students could neither solve puzzles5 nor assess the experimental results of project-based work.

Molecular Modeling Another technological advance that has found its way into the organic laboratory is molecular modeling. Molecular modeling experiments are of two types: stand-alone, dry labs that center around modeling (17, 20, 21, 134, 141, 172, 173, 179–189) and modeling activities that are conducted in conjunction with, or in comparison to, wet, experimental work (35, 45, 50, 54, 74, 75, 106, 153, 190–202). In both cases, typical molecular modeling experiments explore topics such as regioselectivity (35, 45, 50, 182, 189, 191, 195, 197), stereoselectivity (54, 74, 192, 195, 196, 199, 202), and reaction mechanism (141, 190, 194). Another category of modeling experiments explores topics related to molecular geometry and conformation. Some of these experiments study simple molecules such as substituted ethanes or C3–C6 cycloalkanes (17, 20, 21, 186, 197, 203), while others examine more complex molecules, such as cyclohexane analogues, cyclooctane, or trisubstituted cyclobutanes (106, 134, 153, 172, 173, 179, 180, 183–185, 189, 198). Less typical modeling experiments attempt to correlate calculated properties (e.g., surface area, dipole moment, heat of formation) with experimental data (e.g., Rf, dipole moment, boiling point, melting point) (75, 179, 193, 195, 201).


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Modern Chemistry Modernization of the organic laboratory has not been limited to the technological and pedagogical changes described above. Modern techniques such as flash chromatography (6, 19, 63, 161, 204–218), combinatorial chemistry (136–140, 219–221), and green chemistry (21, 219, 222– 236), including microwave synthesis (35, 200, 219, 236– 243), have been incorporated into organic laboratories. Chiral chemistry, in the form of chiral resolution (18, 21, 244–249), enzymatic reactions (17, 20, 21, 176, 250–256), and chiral synthesis (33, 34, 62, 196, 211, 246, 255, 257–260) has also become part of the contemporary organic laboratory course. Electronic Information The computer age has also revolutionized the way that students access chemical literature and information. Information about physical and spectroscopic properties can be accessed through electronic versions of the CRC Handbook (261), the Merck Index (262), or from Web home pages such as Chemfinder (263), Sigmaaldrich (264), SDBS (265), or NIST Chemistry Webbook (266). Databases such as SciFinder Scholar (267) and Beilstein Crossfire (268) have revolutionized literature searching. Conclusion In a recent opinion piece entitled, “The Problem with Organic Chemistry Labs” (26), the sentiments of laboratory textbook author Jerry Mohrig sound familiar. Mohrig’s statement “bring thinking … back into our introductory organic chemistry labs” echoes Pickering’s “Bring thought back into the organic lab”(23) of almost two decades earlier. Nonetheless, the quantity and diversity of discovery-based experiments available to date illustrate that significant progress has been made towards accomplishing their goals. Dramatic changes, such as the almost universal adoption of microscale, the use of spectroscopy, and the incorporation of molecular modeling, illustrate that significant and lasting change is possible in the organic laboratory. While the pedagogical impact of some of these changes may be limited, important lessons about the robustness and persistence of curricular reform can be learned from all these transformations. Notes 1. The first fully digital class 1 precision balance was invented by Mettler Instrumente in 1973 (13). 2. Authors Creegan, Lehman, and Mohrig (19, 20, 37) use a discovery approach exclusively, but with a slightly different emphasis. Instead of having to solve chemical puzzles, students must solve situational problems or scenarios. 3. As an anonymous reviewer pointed out, “savvy” students can undo the benefits of discovery experiments by copying from a classmate, utilizing fraternity files, or finding the “answer” online. 4. For example, during the 2002–2003 academic year, a local university spent $26,000, $63,000, and $78,000, for access to Beilstein, Scifinder, and Science Citation Index, respectively. 5. Discovery-based or puzzle experiments can be thought of as the modern day equivalent of qualitative analysis. Discoverybased experiments provide much more powerful puzzles, however, principally because modern instrumentation allows for puzzles that are no longer just qualitative, but are quantitative as well (14). www.JCE.DivCHED.org

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Supplemental Material A bibliography is available in this issue of JCE Online.

Acknowledgments The author is most grateful to the following persons who consented to be interviewed, gave of their time, and offered valuable insights: George Kriz, Jerry Mohrig, Ronald Pike, and Mono Mohan Singh. The author wishes to thank three anonymous reviewers for their valuable feedback. Literature Cited 1. Johnson, A. W. J. Chem. Educ. 1990, 67, 299–303. 2. Moody, A. E.; Foster, K. A. J. Chem. Educ. 1997, 74, 587– 591. 3. Mayo, D. W.; Pike, R. M.; Butcher, S. S.; Hotham, J. R.; Butcher, D. L.; Meredith, M. L. In The Microscale Organic Laboratory, 8th Biennial Conference on Chemical Education, The Univeristy of Connecticut, Storrs, CT, August, 1984. 4. Mayo, D. W.; Butcher, S. S.; Pike, R. M.; Foote, C. M.; Hotham, J. R.; Page, D. S. In An Introductory Microscale Organic Laboratory Program, 187th National ACS Meeting, St. Louis, MO, April, 1984. 5. Butcher, S. S.; Mayo, D. W.; Foote, C. M.; Hotham, J. R.; Page, D. S.; Pike, R. M. In An Approach to Improving Air Quality in Instructional Laboratories, 187th National ACS Meeting, St. Louis, MO, April, 1984. 6. Mayo, D. W.; Pike, R. M.; Butcher, S. S. Microscale Organic Laboratory, 2nd ed.; John Wiley and Sons: New York, 1989. 7. Pike, R. M. Merrimack College, North Andover, MA. Personal Communication, April 28, 2005. 8. Singh, M. M. Merrimack College, North Andover, MA. Personal communication, April 6, 2005. 9. Zipp, A. J. Chem. Educ. 1989, 66, 956–957. 10. Szafran, Z.; Singh, M. M.; Pike, R. M. J. Chem. Educ. 1989, 66, A263–A267. 11. Pickering, M. J. Chem. Educ. 1984, 61, 861–863. 12. Editorial Staff. J. Chem. Educ. 1989, 66, 882. 13. Chemical Heritage Foundation. Pittcon Hall of Fame. http:// www.chemheritage.org/exhibits/pittcon/mettler.html (accessed Nov 2006). 14. Mohrig, J. R. Carleton College, Northfield, MN. Personal communication, June 17, 2005. 15. Kriz, G. West Washington University, Bellingham, WA. Personal communication, June 8, 2005. 16. Pavia, D. L.; Lampman, G. M.; Kriz, G.; Engel, R. G. Introduction to Organic Laboratory Techniques: A Microscale Approach, 1st ed.; Saunders College Publishing: New York, 1990. 17. Williamson, K. Macroscale and Microscale Organic Experiments, 4th ed.; Houghton Mifflin: New York, 2003. 18. Ault, A. Techniques and Experiments for Organic Chemistry, 6th ed.; University Science Books: Sausalito, CA, 1998. 19. Lehman, J. W. Operational Organic Chemistry: A Problem-Solving Approach to the Laboratory Course, 3rd ed.; Prentice Hall: Upper Saddle River, NJ, 1999. 20. Mohrig, J. R.; Hammond, C. N.; Schatz, P. E.; Morrill, T. C. Modern Project and Experiments in Organic Chemistry: Miniscale and Williamson Microscale, 2nd ed.; W. H. Freeman: New York, 2003.


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Research: Science and Education 21. Pavia, D. L.; Lampman, G. M.; Kriz, G.; Engel, R. G. Introduction to Organic Laboratory Techniques: A Small Scale Approach, 2nd ed.; Brooks Cole: New York, 2005. 22. Wade, L. G. J. Chem. Educ. 1979, 56, 825–826. 23. Pickering, M. J. Chem. Educ. 1988, 65, 143–144. 24. Monteyne, K.; Cracolice, M. S. J. Chem. Educ. 2004, 81, 1559–1560. 25. Ault, A. J. Chem. Educ. 2002, 79, 1177. 26. Mohrig, J. R. J. Chem. Educ. 2004, 81, 1083–1085. 27. Adrian, J. C. J.; Hull, L. A. J. Chem. Educ. 2001, 78, 529– 530. 28. Bendorf, H. D.; McDonald, C. E. J. Chem. Educ. 2003, 80, 1185–1186. 29. Breton, G. W. Chemical Educator 1999, 4, 134–136. 30. Cabay, M. E.; Ettlie, B. J.; Tuite, A. J.; Welday, K. A.; Mohan, R. S. J. Chem. Educ. 2001, 78, 79–80. 31. Cawley, J. J.; Linder, P. E. J. Chem. Educ. 1997, 74, 102–104. 32. Centko, R. S.; Mohan, R. S. J. Chem. Educ. 2001, 78, 77– 79. 33. Ciaccio, J. A. J. Chem. Educ. 1995, 72, 1037–1039. 34. Ciaccio, J. A.; Bravo, R. P.; Drahus, A. L.; Biggins, J. B.; Concepcion, R. V.; Cabrera, D. J. Chem. Educ. 2001, 78, 531– 533. 35. Cook, A. G.; Kreeger, P. K. J. Chem. Educ. 2000, 77, 90–91. 36. Cooley, J. H.; Williams, R. V. J. Chem. Educ. 1997, 74, 582. 37. Creegan, F. Process-Oriented Guided-Inquiry Learning in the Organic Chemistry Laboratory. http://creegan.washcoll.edu/ gilabs/ (accessed Nov 2006). 38. Crouch, R. D. J. Chem. Educ. 1994, 71, A200–A202. 39. Crouch, R. D.; David, N.; Todd, D. J. Chem. Educ. 1995, 72, A6–A7. 40. Crouch, R. D.; Holden, M. S. J. Chem. Educ. 2002, 79, 477– 478. 41. Crouch, R. D.; Holden, M. S.; Romany, C. A. J. Chem. Educ. 2004, 81, 711–712. 42. Crouch, R. D.; Holden, M. S.; Weaver, T. M. Chemical Educator 1998, 3 (3), 1–8. 43. Dickson, H.; Kittredge, K. W.; Sarquis, A. M. J. Chem. Educ. 2004, 81, 1023–1025. 44. Gingrich, H. L.; Pickering, M. J. Chem. Educ. 1991, 68, 614– 615. 45. Graham, K. J.; Skoglund, K.; Schaller, C. P.; Muldoon, W. P.; Klassen, J. B. J. Chem. Educ. 2000, 77, 396–397. 46. Hathaway, B. A. J. Chem. Educ. 1987, 64, 367–368. 47. Hill, R. K.; Barbaro, J. Experiments in Organic Chemistry, 2nd ed.; Contemporary Publishing Company: Raleigh, NC, 2000. 48. Holden, M. S.; Crouch, R. D. J. Chem. Educ. 2001, 78, 1104– 1105. 49. Horowitz, G. J. Chem. Educ. 2003, 80, 1039–1041. 50. Hull, L. A. J. Chem. Educ. 2001, 78, 420–421. 51. Jarret, R. M.; McMaster, P. D. J. Chem. Educ. 1994, 71, 1029– 1031. 52. Jarret, R. M.; New, J.; Hurley, R.; Gillooly, L. J. Chem. Educ. 2001, 78, 1262–1263. 53. Jarret, R. M.; New, J.; Patraitis, C. J. Chem. Educ. 1995, 72, 457–459. 54. Klassen, J. B.; Graham, K. J.; Muldoon, W. P. J. Chem. Educ. 1999, 76, 985–986. 55. Krishnamurty, H. G.; Jain, N.; Samby, K. J. Chem. Educ. 2000, 77, 511–513. 56. Latimer, D. J. Chem. Educ. 2003, 80, 1183–1184.

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57. McDonald, C. E. J. Chem. Educ. 2000, 77, 750–751. 58. McElveen, S. R.; Gavardinas, K.; Stamberger, J. A.; Mohan, R. S. J. Chem. Educ. 1999, 76, 535–536. 59. McGowens, S. I.; Silversmith, E. F. J. Chem. Educ. 1998, 75, 1293–1294. 60. Montes, I.; Lai, C.; Sanabria, D. J. Chem. Educ. 2003, 80, 447–449. 61. Moroz, J. S.; Pellino, J. L.; Field, K. W. J. Chem. Educ. 2003, 80, 1319–1321. 62. Mosher, M. D.; Kelly, C. O.; Mosher, M. W. J. Chem. Educ. 1996, 73, 567–568. 63. Nash, J. J.; Meyer, J. A.; Everson, B. J. Chem. Educ. 2001, 78, 364–365. 64. Nielsen, J. T.; Duarte, R.; Dragojlovic, V. Chemical Educator 2003, 8, 241–243. 65. Novak, M.; Heinrich, J.; Martin, K. A.; Green, J.; Lytle, S. J. Chem. Educ. 1993, 70, A103–A110. 66. Novak, M.; Heinrich, J. J. Chem. Educ. 1993, 70, A150–A154. 67. Padias, A. B.; Baron, J. A. Chemical Educator 1998, 3 (3), 1–11. 68. Palleros, D. R. Experimental Organic Chemistry, 1st ed.; John Wiley & Sons, Inc.: New York, 2000. 69. Pearsall, M.; Rosan, A. M.; Conrad, J. S.; Hendrickson, C. A.; Pacchia, A. L.; Schantz, D. J. J. Chem. Educ. 1995, 72, A29–A30. 70. Pellegrinet, S. C.; Colombo, M. I.; Testero, S. A.; Sierra, M. G.; Rúveda, E. A. Chemical Educator 2002, 7, 155–158. 71. Pelter, M. W.; Macudzinski, R. M.; Passarelli, M. E. J. Chem. Educ. 2000, 77, 1481. 72. Pickering, M. J. Chem. Educ. 1990, 67, 524–525. 73. Pickering, M. J. Chem. Educ. 1990, 67, 436–437. 74. Pienta, N. J.; Crawford, S. D.; Kropp, P. J. J. Chem. Educ. 1993, 70, 682. 75. Poon, T.; Bodolosky, S. A.; Norris, C. M. J. Chem. Educ. 1999, 76, 983–985. 76. Schaller, C. P.; Klassen, J. B.; Asmus, L.; Graham, K. J.; Johnson, B. Chemical Educator 2001, 6, 10–14. 77. Sgariglia, E. A.; Schopp, R.; Gavardinas, K.; Mohan, R. J. Chem. Educ. 2000, 77, 79. 78. Shadwick, S. R.; Mohan, R. S. J. Chem. Educ. 1999, 76, 1121– 1122. 79. Silversmith, E. F. J. Chem. Educ. 1991, 68, 688. 80. Silversmith, E. F. J. Chem. Educ. 1998, 75, 221. 81. Todd, D. J. Chem. Educ. 1992, 69, 584. 82. Todd, D.; Pickering, M. J. Chem. Educ. 1988, 65, 1100–1101. 83. Wachter-Jurcsak, N.; Reddin, K. J. Chem. Educ. 2001, 78, 1264–1265. 84. Cooley, J. H. J. Chem. Educ. 1991, 68, 503–504. 85. Abraham, M. R.; Pavelich, M. J. Inquiries into Chemistry, 2nd ed.; Waveland: Prospect Heights, IL, 1994. 86. Bauer, R. C.; Birk, J. P.; Sawyer, D. J. Laboratory Inquiry in Chemistry, 2nd ed.; Brooks/Cole: Pacific Grove, CA, 2005. 87. Cooper, M. Cooperative Chemistry Laboratory Manual, 2nd ed.; McGraw-Hill: New York, 2002. 88. Ege, S. N.; Coppola, B. P.; Kleinman, R. W.; Lawton, R. G.; Marsh, E. N. G.; Nolta, K. V. Investigations in Chemistry, 8th ed.; Hayden-McNeil: Plymouth, MI, 2000. 89. March, J.; Shaw, D. Discovery and Analysis in the Laboratory, 1st ed.; Harcourt Brace: Orlando, FL, 1997. 90. Wink, D. J.; Gislason, S. F.; Kuehn, J. E. Working with Chemistry: A Laboratory Inquiry Program, 2nd ed.; W. H. Freeman and Company: New York, 2004.


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Research: Science and Education 91. Amsterdamsky, C. J. Chem. Educ. 1998, 75, 219. 92. Browne, L. M.; Blackburn, E. V. J. Chem. Educ. 1999, 76, 1104–1107. 93. Neeland, E. G. J. Chem. Educ. 1999, 76, 230–231. 94. Reeve, A. M. J. Chem. Educ. 2004, 81, 1497–1499. 95. Stoub, D. G. Chemical Educator 2004, 9, 281–284. 96. Ault, A. J. Chem. Educ. 2004, 81, 1569. 97. Adsmond, D.; Balanda, P.; Frank, D. In Implementation of a Collaborative Research-Based Organic Chemistry 2 Laboratory Course at Ferris State University, 18th Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 21, 2004. 98. Gottfried, A.; Reynolds, B. P.; Coppola, B. P. In Honors Cup: Incorporating a Synthetic Project Competition in an Undergraduate Organic Chemistry Lab, 18th Biennial Conference on Chemical Education, University of Iowa, Ames, Iowa, July 21, 2004. 99. Hoyt, T.; Hanson, J. In Emulating Research in the Second-Year Organic Laboratory: Synthesis Projects, 18th Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 21, 2004. 100. Morsch, L.; Kim, P. In Student Perceptions of Class-Based Research in Sophomore Organic Chemistry Laboratory, 18th Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 21, 2004. 101. Reeve, A. In Fisher Esterification as an Integrated Project for First Semester Organic Lab, 18th Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 20, 2004. 102. Rutherford, D. In 18th Implementing Student-Designed Research Projects in the Organic Chemistry Course: The Pet Molecule Project, Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 21, 2004. 103. Sarkar, S. In Enhancing Student Engagement through Experimental Design in Organic Chemistry Laboratory, 18th Biennial Conference on Chemical Education, Iowa State University, Ames, Iowa, July 20, 2004. 104. Bobbitt, J. M.; Huang, S. J. J. Chem. Educ. 1974, 51, 58–60. 105. Callahan, R.; Bynum, K.; Prip, R.; Rothchild, R. Chemical Educator 1998, 3 (2), 1–21. 106. Callahan, R.; Marshall, K.; Rothchild, R.; Rosmarion, K. Chemical Educator 2001, 6, 227–234. 107. Chisholm, M. G. J. Chem. Educ. 1975, 52, 739–741. 108. Davis, D. S.; Hargrove, R. J.; Hugdahl, J. D. J. Chem. Educ. 1999, 76, 1127–1130. 109. DeLannoy, P.; Mann, D.; Maycock, J.; Davidson, C. Chemical Educator 1999, 4, 65–67. 110. Dobrev, A. J. Chem. Educ. 1996, 73, 856. 111. Doyle, M. P. J. Chem. Educ. 1973, 50, 358. 112. Gallet, C. J. Chem. Educ. 1998, 75, 72–77. 113. Graham, K. J.; Schaller, C. P.; Johnson, B. J.; Klassen, J. B. Chemical Educator 2002, 7, 376–378. 114. Hanna, S.; Wrobleski, J. T.; Bohanon, J. T.; Peace, B. W. J. Chem. Educ. 1971, 48, 556–557. 115. Hiegel, G.; Belloli, R. J. Chem. Educ. 1971, 48, 825–826. 116. Hull, L. A. J. Chem. Educ. 2001, 78, 226–227. 117. Kharas, G. B. J. Chem. Educ. 1997, 74, 829–831. 118. Kovacic, P. J. Chem. Educ. 1972, 49, 846. 119. Kroll, L. J. Chem. Educ. 1985, 62, 516–518. 120. Letcher, R. M. J. Chem. Educ. 1980, 57, 220–221. 121. Neckers, D. C. J. Chem. Educ. 1970, 47, 700–702.

www.JCE.DivCHED.org

•

122. Pienta, M. J.; Regitz, C.; Richards, J.; Sorrell, T. N. J. Chem. Educ. 1993, 70, 841–843. 123. Poon, T.; McIntyre, J. P.; Eller, C. F.; Eller, L. R.; Jones, K. M.; Massello, W.; Norris, C. M.; Oelrich, J. A.; Pluim, T. A.; Dorigo, A.; Davis, D. J.; Davis, M. A.; Izumi, H. K.; Kelley, K. H.; Melamed, M. L.; Poplawski, S. E.; St. Clair, J. M.; Stokes, M. P.; Wheeler, W. C.; Wilkes, E. E. J. Chem. Educ. 1999, 76, 1523–1524. 124. Potter, N. H.; McGrath, T. F. J. Chem. Educ. 1989, 66, 666– 667. 125. Russell, R. A.; Switzer, R. W.; Longmore, R. W.; Dutton, B. H.; Harland, L. J. Chem. Educ. 1990, 67, 168–169. 126. Ruttledge, T. R. J. Chem. Educ. 1998, 75, 1575–1577. 127. Vyvyan, J. R.; Pavia, D. L.; Lampman, G. M.; Kriz, G. J. Chem. Educ. 2002, 79, 1119–1121. 128. Fife, W. K. J. Chem. Educ. 1968, 45, 416–418. 129. Silberman, R.; McConnell, J. J. Chem. Educ. 1968, 45, 267– 268. 130. Cooper, M. M. An Introduction to Small-Group Learning, In Chemists’ Guide to Effective Teaching, Pearson Prentice Hall: Upper Saddle River, NJ, 2005; pp 117–128. 131. Breston, G. W. J. Chem. Educ. 2000, 77, 81–83. 132. Colombo, M. I.; Bohn, M. L.; Ruveda, E. A. J. Chem. Educ. 2002, 79, 484–485. 133. Hahn, R. C. J. Chem. Educ. 1997, 74, 836–838. 134. Horowitz, G. J. Chem. Educ. 2004, 81, 1006–1009. 135. Jarret, R. M.; New, J.; Karaliolios, K. J. Chem. Educ. 1997, 74, 109–110. 136. Miles, W. H.; Gelato, K. A.; Pompizzi, K. M.; Scarbinsky, A. M.; Albrecht, B. K. J. Chem. Educ. 2001, 78, 540–542. 137. Birney, D.; Starnes, S. D. J. Chem. Educ. 1999, 76, 1560– 1561. 138. Duarte, R.; Nielsen, J. T.; Dragojlovic, V. J. Chem. Educ. 2004, 81, 1010–1015. 139. Gung, B.; Taylor, R. T. J. Chem. Educ. 2004, 81, 1630–1632. 140. Kittredge, K. W.; Marine, S. S.; Taylor, R. T. J. Chem. Educ. 2004, 81, 1494–1496. 141. Horowitz, G.; Schwartz, G. J. Chem. Educ. 2004, 81, 1136– 1139. 142. Jarret, R. M. J. Chem. Educ. 2001, 78, 525–526. 143. Zahedkargaran, H.; Smith, L. F. J. Chem. Educ. 2001, 78, 1379–1380. 144. Coppola, B. P.; Lawton, R. G. J. Chem. Educ. 1995, 72, 1120– 1121. 145. Andersh, B. Chemical Educator 2000, 5, 20–23. 146. Clark, T. J. J. Chem. Educ. 1995, 72, 375–377. 147. Hanson, R. W. J. Chem. Educ. 1976, 53, 400. 148. Reyes, J.; Morton, M. J. Chem. Educ. 2001, 78, 781. 149. Strom, L. A.; Anderson, J. R.; Gandler, J. R. J. Chem. Educ. 1992, 69, 558. 150. Zhi, Z.; Yang, X.; Lu, L.; Wang, X. Chemical Educator 2000, 5, 187–189. 151. Brown, T. M.; Dronsfield, A. T.; Ellis, R. J. Chem. Educ. 1990, 67, 518. 152. Clavier, J. W. Chemical Educator 2000, 5, 64–66. 153. Cook, A. G. J. Chem. Educ. 1993, 70, 865–866. 154. Grant, A.; Latimer, D. J. Chem. Educ. 2003, 80, 670. 155. Mosher, M. D.; Meisenbach, S. Chemical Educator 2002, 7, 356–358. 156. Smith, R. E., IV; McKee, J. R.; Zanger, M. J. Chem. Educ. 2002, 79, 227.


•


351

Research: Science and Education 157. Almy, J. J. Chem. Educ. 2004, 81, 708. 158. Alonso, D. E.; Warren, S. E. J. Chem. Educ. 2005, 82, 1385– 1386. 159. Branz, S. J. Chem. Educ. 1985, 62, 899–900. 160. Castro, C.; Karney, W. J. Chem. Educ. 1998, 75, 472. 161. Feist, P. L. J. Chem. Educ. 2004, 81, 109–110. 162. Fleischer, J. M. J. Chem. Educ. 2002, 79, 1247. 163. Glagovich, N. M.; Shine, T. D. J. Chem. Educ. 2005, 82, 1382–1384. 164. Kandel, M.; Tonge, P. J. J. Chem. Educ. 2001, 78, 1208. 165. Marchand, A. P.; Jackson, D. J. Chem. Educ. 1976, 53, 390– 391. 166. McGoran, E. C.; Melton, C.; Taitch, D. J. Chem. Educ. 1996, 73, 88. 167. Rowland, A. T. J. Chem. Educ. 1995, 72, A160–A162. 168. Thompson, E. M.; Almy, J. J. Chem. Educ. 1982, 59, 109. 169. Wood, W.; Price, D. Chemical Educator 2002, 7, 226–232. 170. Rowland, A. T. J. Chem. Educ. 2003, 80, 311. 171. Kutateladze, A. G.; Hornback, J. M. J. Chem. Educ. 2001, 78, 81. 172. Anderson, E. L.; Li, D.; Owen, N. L. J. Chem. Educ. 1992, 69, 846–849. 173. Jensen, B. L.; Fort, R. C., Jr. J. Chem. Educ. 2001, 78, 538– 540. 174. LeFevre, J. W. J. Chem. Educ. 1990, 67, A278–A280. 175. Colborn, R. E. J. Chem. Educ. 1990, 67, 438. 176. Lee, M. J. Chem. Educ. 1993, 70, A155–A158. 177. McGoran, E. C.; Cutter, B.; Morse, K. J. Chem. Educ. 1979, 56, 122–124. 178. Drexler, E. J.; Field, K. W. J. Chem. Educ. 1976, 53, 392– 393. 179. Bailey, R. A. J. Chem. Educ. 1989, 66, 836–837. 180. Fitzgerald, J. P. J. Chem. Educ. 1993, 70, 988–990. 181. Gavin, T. J. Chem. Educ. 2005, 82, 953–957. 182. Hessley, R. K. J. Chem. Educ. 2000, 77, 794–797. 183. Hanks, T. W. J. Chem. Educ. 1994, 71, 62–66. 184. Jarret, R. M.; Sin, N. J. Chem. Educ. 1990, 76, 153–155. 185. Lipkowitz, K. J. Chem. Educ. 1984, 61, 1051–1052. 186. Montes, I.; Prieto, J. A.; Garcia, M. Chemical Educator 2002, 7, 293–296. 187. Simpson, J. M. J. Chem. Educ. 1989, 66, 406–407. 188. Simpson, J. M. J. Chem. Educ. 1994, 71, 607–608. 189. Wong, C.; Currie, J. Teaching with CAChe: Exercises on Molecular Modeling in Chemistry. http://www.cachesoftware.com/ pdfs/TeachingWithCAChe.pdf (accessed Nov 2065). 190. Bellomo, K. A.; Bush, R. C.; Sands, R. D. J. Chem. Educ. 1993, 70, A122–A126. 191. Crouch, R. D.; Holden, M. S.; Samet, C. J. Chem. Educ. 1996, 73, 916–917. 192. Eisenberg, R. L. Chemical Educator 1998, 3 (4), 1–17. 193. Hessley, R. K. J. Chem. Educ. 2000, 77, 203–205. 194. Hessley, R. K. J. Chem. Educ. 2000, 77, 202–203. 195. Jones, M. E. J. Chem. Educ. 2001, 78, 867–868. 196. Lee, M.; Garbiras, B.; Preti, C. J. Chem. Educ. 1995, 72, 378– 390. 197. Martin, N. H. J. Chem. Educ. 1998, 75, 241–243. 198. Midland, M. M.; Beck, J. J.; Peters, J. L.; Rennels, R. A.; Asirwatham, G. J. Chem. Educ. 1994, 71, 897–898. 199. Palmer, D. R. J. J. Chem. Educ. 2004, 81, 1633–1635. 200. Shaw, R.; Severin, A.; Balfour, M.; Nettles, C. J. Chem. Educ. 2005, 82, 625–629.

352


•

201. Simpson, J. M.; Rivera, O. J. Chem. Educ. 2001, 78, 942– 943. 202. Stedman, B.; Lee, M.; Hanks, T. W. Chemical Educator 1996, 1 (5), 1–14. 203. Bays, J. P. J. Chem. Educ. 1992, 69, 209–215. 204. Bell, W. L.; Edmondson, R. D. J. Chem. Educ. 1986, 63, 361. 205. Deal, T. S. J. Chem. Educ. 1992, 69, 939. 206. Feigenbaum, A. J. Chem. Educ. 1984, 61, 649. 207. Fessenden, R. J.; Fessenden, J. S.; Feist, P. L. Organic Laboratory Techniques, 3rd ed.; Brooks/Cole: Pacific Grove, CA, 2001. 208. Horowitz, G. J. Chem. Educ. 2000, 77, 263–264. 209. Jacobson, B. M. J. Chem. Educ. 1988, 65, 459. 210. Krause, J. G. J. Chem. Educ. 1991, 69, 790. 211. Langrebe, J. A. Organic Laboratory: Microscale and Standard Scale Experiments, 4th ed.; Wadsworth, Inc.: Belmont, CA, 1993. 212. Levine, S.; Barboriak, K. D.; Cho, H. S. J. Chem. Educ. 1988, 65, 79. 213. Mohrig, J. R.; Hammond, C. N.; Schatz, P. E.; Morrill, T. C. Techniques in Organic Chemistry: Miniscale, Standard Taper Microscale, and Williamson Microscale, 1st ed.; W. H. Freeman: New York, 2003. 214. Pontén, F.; Ellervik, U. J. Chem. Educ. 2001, 78, 363. 215. Shusterman, A. J.; McDougal, P. G.; Glasfeld, A. J. Chem. Educ. 1997, 74, 1222–1223. 216. Silveria, A. J.; Evans, J. M. J. Chem. Educ. 1995, 72, 374– 375. 217. Thompson, W. J.; Hanson, B. A. J. Chem. Educ. 1984, 61, 645. 218. Wade, L. G., Jr. J. Chem. Educ. 1978, 55, 208. 219. Doxsee, K. M.; Hutchinson, J. E. Green Organic Chemistry: Strategies, Tool, and Laboratory Experiments, 1st ed.; Brooks/ Cole: Pacific Grove, CA, 2004. 220. Wolkenberg, S. E.; Su, A. I. J. Chem. Educ. 2001, 78, 784– 785. 221. Drouin, J.; Costante, J.; Guibe-Jampel, E. J. Chem. Educ. 1997, 74, 992–995. 222. Bennett, G. D. J. Chem. Educ. 2005, 82, 1380–1381. 223. Blunt, S. B.; Hoffman, V. F. Chemical Educator 2004, 9, 370– 373. 224. Cave, G. W.; Raston, C. L. J. Chem. Educ. 2005, 82, 468– 469. 225. Esteb, J. J.; Gligorich, K. M.; O’Reilly, S. A.; Richter, J. M. J. Chem. Educ. 2004, 81, 1794–1795. 226. French, L. G.; Stradling, S. S.; Dudley, M.; DeBottis, D.; Parisian, K. Chemical Educator 2001, 6, 25–27. 227. Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Chem. Educ. 2004, 81, 874–876. 228. Goodwin, T. E. J. Chem. Educ. 2004, 81, 1187–1190. 229. Hailstone, E.; Huther, N.; Parsons, A. F. J. Chem. Educ. 2003, 80, 1444–1445. 230. Hulce, M.; Marks, D. W. J. Chem. Educ. 2001, 78, 66. 231. Jones-Wilson, T. M.; Burtch, E. A. J. Chem. Educ. 2005, 82, 616–617. 232. Leung, S. H.; Angel, S. A. J. Chem. Educ. 2004, 81, 1492– 1493. 233. McKenzie, L. C.; Huffman, L. M.; Hutchinson, J. E. J. Chem. Educ. 2005, 82, 306–310. 234. Palleros, D. R. J. Chem. Educ. 2004, 81, 1345–1347. 235. Reed, S. M.; Hutchinson, J. E. J. Chem. Educ. 2000, 77, 1627–1629.


•

www.JCE.DivCHED.org

Research: Science and Education 236. Santos, E. S.; Gavilan Garcia, I. C.; Lejarazo Gomez, E. F. J. Chem. Educ. 2004, 81, 232–238. 237. Baldwin, B. W.; Wilhite, D. M. J. Chem. Educ. 2002, 79, 1344. 238. Bari, S. S.; Bose, A. K.; Chaudhary, A. G.; Manhas, M. S.; Raju, V. S.; Robb, E. W. J. Chem. Educ. 1992, 69, 938–939. 239. Elder, J. W. J. Chem. Educ. 1994, 71, A142–A144. 240. Elder, J. W.; Holtz, K. M. J. Chem. Educ. 1996, 73, A104– A105. 241. Mirafzal, G.; Summer, J. M. J. Chem. Educ. 2000, 77, 356– 357. 242. Parquet, E.; Lin, Q. J. Chem. Educ. 1997, 74, 1225. 243. White, L.; Kittredge, K. W. J. Chem. Educ. 2005, 82, 1055– 1056. 244. Baar, M.; Cerrone-Szakal, A. L. J. Chem. Educ. 2005, 82, 1040–1042. 245. Cesare, V.; Stephani, R. J. Chem. Educ. 1997, 74, 1226. 246. Mak, K. K. W. J. Chem. Educ. 2004, 81, 1636–1640. 247. Sheardy, R.; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646–647. 248. Sen, S. E.; Anliker, K. S. J. Chem. Educ. 1996, 73, 569–575. 249. Krumpolc, M. J. Chem. Educ. 1991, 68, A176–A178. 250. Bozak, R. E.; Prater, M. E.; Hicks, R. J. J. Chem. Educ. 1991, 68, 427. 251. Bugg, T. D. H.; Lewin, A. M.; Catlin, E. R. J. Chem. Educ. 1997, 74, 105–107. 252. Lee, M.; Huntington, M. J. Chem. Educ. 1994, 71, A62–A66. 253. McClure, C. K.; Chenault, H. K. J. Chem. Educ. 1996, 73, 467–470.

www.JCE.DivCHED.org

•

254. Patterson, J.; Sigurdsson, S. T. J. Chem. Educ. 2005, 82, 1049– 1050. 255. Pohl, N.; Clague, A.; Schwarz, K. J. Chem. Educ. 2002, 79, 727–728. 256. Besse, P.; Bolte, J.; Veschambre, H. J. Chem. Educ. 1995, 72, 277–278. 257. Bradley, L. M.; Springer, J. W.; Delate, G. M.; Goodman, A. J. Chem. Educ. 1997, 74, 1336–1338. 258. Burke, A.; Dillon, P.; Martin, K.; Hanks, T. W. J. Chem. Educ. 2000, 77, 271–272. 259. Hanson, J. J. Chem. Educ. 2001, 78, 1266–1268. 260. Lipkowitz, K.; Naylor, T.; Anliker, K. S. J. Chem. Educ. 2000, 77, 305–307. 261. CRC: Handbook of Chemistry and Physics. http:// www.hbcpnetbase.com/ (accessed Nov 2006). 262. The Merck Index Online. http://library.dialog.com/bluesheets/ html/bl0304.html (accessed Nov 2006). 263. Chemfinder.com: Database and Internet Searching. http:// chemfinder.cambridgesoft.com/ (accessed Nov 2006). 264. Sigma-Aldrich. http://www.sigmaaldrich.com/ (accessed Nov 2006). 265. Spectral Database for Organic Compounds SDBS. http:// www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi?lang=eng (accessed Nov 2006). 266. NIST Chemistry WebBook. webbook.nist.gov/chemistry (accessed Nov 2006). 267. SciFinder Scholar. http://www.cas.org/SCIFINDER/SCHOLAR/ index.html (accessed Nov 2006). 268. CrossFire Beilstein. http://www.mdl.com/products/knowledge/ crossfire_beilstein/ (accessed Nov 2006).


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