Organic Chemistry Educators' Perspectives on Fundamental

Research: Science and Education edited by

Melanie M. Cooper

Organic Chemistry Educators' Perspectives on Fundamental Concepts and Misconceptions: An Exploratory Study

Department of Chemistry Clemson University Clemson, SC 29634

Jennifer M. Duis† Department of Chemistry, Carl Wieman Science Education Initiative, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada † Research was conducted while at the University of Northern Colorado, Department of Chemistry and Biochemistry, Greeley, CO 80639

In the 1970s, various subcommittees of the American Chemical Society's (ACS) Curriculum Committee developed a comprehensive report containing detailed topical outlines and performance objectives that covered the “standard” content for undergraduate courses in each area of chemistry including general, analytical, organic, inorganic, physical, and biochemistry (1, 2). While the ACS still has a committee that provides chemistry curriculum guidelines for ACS approved chemistry programs (now the Committee on Professional Training) (3), the extensive 1970s report has not been updated. Today short, general, topical guidelines for each area of chemistry continue to be provided for ACSapproved chemistry programs to follow (4, 5). The conceptual topics for organic chemistry currently include: • The understanding that our only way to molecular knowledge is through experimentation; correlating structure with reactivity and function through wet chemical methods, spectroscopy (notably nuclear magnetic resonance and infrared spectroscopy and X-ray crystallography), and use of computational methodology • Bonding and its consequences on molecular structure and reactivity • Interplay between electronic, steric, and orbital interactions in the behavior and properties of molecules • The dependence of structure and reactivity on context, the environment, whether gaseous, liquid, or solid; or in solution • Lewis and Brønsted acid-base chemistry • Stereochemistry and conformational analysis • Addition, elimination, substitution, and rearrangement mechanisms, and reactive intermediates • Functional groups, with particular emphasis on the centrality of the carbonyl group in organic reactions • Organic synthesis, including retrosynthetic analysis of target molecules • Synthesis and behavior of macromolecular species, including biomolecules such as proteins and polysaccharides and synthetic polymers (4)

The ACS topical guidelines are broadly accepted in the education community, as shown by the wide use of ACS discipline-specific exams. While general chemistry curriculum and topic coverage are frequently discussed in the chemical education literature and media (6-14), there is little general discussion of the curriculum or fundamental concepts of organic chemistry in the recent literature (15, 16). In fact, there appears to be a general assumption that the organic chemistry curriculum

346

Journal of Chemical Education

_

_

is either standard or open to a variety of approaches, all of which are valid. For example, the ACS Web site recently stated, “there are many excellent organic chemistry textbooks whose contents can provide a sound basis for organizing an introductory organic chemistry course” (5). While the majority of current undergraduate organic chemistry textbooks are quite uniform in content, this does not mean the same holds true for current curricula. Despite the homogeneity of modern undergraduate textbooks, “standards” used by the ACS exams, and topical guidelines, appeals for debate on the curriculum were raised soon after the 1970s curriculum report (15) and continue to be raised sporadically (16). Thus, this exploratory study was undertaken to assess what concepts tertiary-level organic chemistry educators believe are important, core, or fundamental in organic chemistry, and the misconceptions these educators observe in students. Furthermore, these results have been used to: (i) determine whether renewed discussion is required; and (ii) help to focus and orient such a discussion if it is determined to be timely for the community. Methodology Participants and Setting Subjects were solicited either in person or by electronic mail to participate in this exploratory study. Twenty-three tertiarylevel organic chemistry educators participated, 6 females and 17 males, with one to 48 years of experience teaching organic chemistry (average of 22 years, 74% with g10 years of experience) at three colleges, one two-year state college and 17 universities within the USA and one satellite campus on another continent. The majority (17 of 23, 74%), were employed by ACS-accredited institutions, all but one taught organic chemistry for majors, and 61% (14 of 23) also taught graduate organic chemistry at the time of the study. Data Collection and Analysis Initially, 5 organic chemistry educators who could provide a variety of perspectives on the teaching of organic chemistry, based on their differing teaching styles, participated in semistructured interviews to provide a purposeful sampling (17) of instructors. The interview protocol and preliminary results obtained informed the conversion of the interview to a survey protocol (administered via e-mail and contained in the supporting information) to continue data collection. Next, 18 additional organic chemistry educators, solicited directly by the author or

_

Vol. 88 No. 3 March 2011 pubs.acs.org/jchemeduc r 2011 American Chemical Society and Division of Chemical Education, Inc. 10.1021/ed1007266 Published on Web 02/08/2011

Research: Science and Education Table 1. General Chemistry Concepts Educators Reported Reviewing in Organic Chemistry Courses Concepts

Number of Responses

Acid-Base Chemistry

18

Orbital Hybridization

11

Bonding

9

Lewis Dot Structures

8

3-D Structures

8

Polarity

6

Intermolecular Forces

5

Resonance Structures

5

Thermodynamics and Kinetics

5

who responded to online invitations to participate (18, 19), completed the aforementioned surveys. Purposeful sampling was continued through direct e-mail solicitation followed by participant self-selection via invitations posted on the Web site (18) and listserv (19). Data were collected, after obtaining informed consent from each participant, in the form of transcriptions of semistructured interviews (20) and written responses to openended survey questions. Participants were asked to identify what general chemistry concepts they review or reteach in undergraduate organic chemistry, the concepts they believe are fundamental to organic chemistry, organic chemistry topics students find difficult, and the misconceptions they observe in students. In solicitation and informed consent documents, Nakhleh's definition of the term misconception, “any concept that differs from the commonly accepted scientific understanding” (21), was given as the interpretation intended for the study. Categorical or thematic analysis was applied to the interview transcripts and survey responses under the tradition of a basic or generic qualitative study, to identify recurrent patterns in the form of themes or categories (20). The identified themes related to the fundamental concepts of organic chemistry are additionally compared to the two most recent ACS topical guides for undergraduate organic chemistry. Results Most undergraduate organic chemistry courses have a general chemistry prerequisite. Thus, organic chemistry educators expect students to enter the course with an understanding of a number of general chemistry concepts. However, the participants find that they must review or reteach some of the general chemistry concepts they feel students will need in order to understand organic chemistry. On average, participants noted five general chemistry concepts they typically review in organic chemistry. Concepts noted by five or more participants (g22%) are summarized in Table 1. Additional general chemistry concepts noted by more than one participant include: electronegativity, equilibrium, mechanisms, and reaction coordinate diagrams. All participants named concepts they considered fundamental to organic chemistry (five concepts on average). These concepts overlapped between participants and with the ACS guidelines (4, 5); however, the responses varied considerably. Surprisingly, only one concept area, reaction mechanisms, was cited by more than half (16 of 23, 70%) of the participants. Additionally, only four concept areas were noted by more than

r 2011 American Chemical Society and Division of Chemical Education, Inc.

_

one-third of the organic chemistry educator participants: correlation between structure and properties (10 of 23, 43%), acid-base chemistry (9 of 23, 39%), structure and bonding (9 of 23, 39%), and functional group chemistry and properties (9 of 23, 39%). Finally, two of the topic areas delineated by the ACS guidelines for undergraduate organic chemistry at the time of this study (Detailed Consideration of Polyfunctional Substances and Concepts in Molecular Recognition) were not mentioned by any of the participants (5). The concepts noted by five or more participants (g22%) as fundamental to organic chemistry are summarized in Table 2. Additionally, fundamental concepts noted by more than one participant include: equilibrium and its effects, electronegativity, reaction coordinate and energy diagrams, nucleophilicity and electrophilicity, synthesis, molecular orbital theory and its consequences, and kinetics versus thermodynamics. More than one-third (35%, 8 of 23) of the participants noted supplementary factors other than ACS-recommended fundamental organic chemistry concepts, such as independent thought and formal operational thinking, the language of chemistry, the real-world relevance of organic chemistry, and focusing on understanding, not memorization. Every participant also named organic chemistry topics that consistently cause students difficulty. Difficult organic chemistry concepts noted by five or more participants (g22%) are summarized in Table 3. While one of the main goals of this project had been to learn more about student misconceptions in organic chemistry, 9 of the 23 participants (39%) were unable to provide any specific misconceptions that they had seen in their students, and several placed comments in the misconception area of the survey that might be more accurately categorized as a “difficult organic chemistry concept”. Several participants did not seem to believe that their students held true misconceptions and instead noted “common student errors” or “just a particular point that a particular student didn't master”. However, more than 30 different student misconceptions were noted by 14 of the 23 (61%) organic chemistry educators who participated. Misconceptions noted by more than one participant include: carbon atoms have more-than or less-than four bonds, electrons flow toward negative or uncharged sites, resonance is a fast exchange of electrons, resonance is an equilibrium, resonance states are compounds that exist in real time, and hydroxide or alkoxide ions can be present in reaction mechanisms carried out in acidic solution (also noted in ref 22). Additionally, several misconceptions noted by these 14 instructors have previously been reported in the literature, including: bond breaking is exothermic (23-25), hydrogen bonding is any bond involving hydrogen (22, 26, 27), and methanol dissociates into CH3þ and OH- (22). Finally, the participants were asked to list which organic chemistry concepts they felt were particularly important for later chemistry learning. In this case, consensus among instructors was minimal, with only four concepts noted by five or more participants (g22%), as summarized in Table 4. Additional organic chemistry concepts important for later chemistry learning noted by more than one participant include: functional groups, structure correlations with properties, major functional group reactions, nucleophilicity and electrophilicity, polarity, electronegativity, 3-D structure and molecular shapes, stereochemistry; and “how organic chemistry works”.

pubs.acs.org/jchemeduc

_

Vol. 88 No. 3 March 2011

_


347

Research: Science and Education Table 2. Fundamental Organic Chemistry Concepts Cited by Organic Chemistry Educators Fundamental Concepts

Number of Responses

Reaction Mechanismsa,b

16

Correlation between Structure and Properties/Reactivitya

10

Acid-Base Chemistrya,b a

9

a

Structure and Bonding ; 3-D Nature of Molecules

b

9

Functional Groupsb (Functional Group Chemistry/Properties)a

9

Electron Delocalizationa/Resonance

5

a

Directly correlates with points in the ACS's Organic Chemistry Topical Supplement (5). b Directly correlates with topics in the current ACS Organic Chemistry Supplement (4).

Table 3. Difficult Organic Chemistry Concepts Reported by Organic Chemistry Educators Concepts

Number of Responses

Reaction Mechanisms

15

Acid-Base Chemistry

12

Synthesis

9

Stereochemistry

9

Resonance (Electron Delocalization)

9

Molecular Orbital Theory

6

Spectroscopy

6

Polarity

6

SN1, SN2, E1, E2 Reactions

5

Curved-Arrow Formalism

5

Table 4. Organic Chemistry Concepts Cited as Important for Later Chemistry Learning Concepts

Number of Responses

Acid-Base Chemistry

8

Reaction Mechanisms

7

Structure-Reactivity

6

Kinetics

5

Discussion and Conclusions This exploratory study of 23 tertiary-level organic chemistry educators revealed instructor opinion in: • General chemistry concepts important for learning organic chemistry • Which concepts the participants find fundamental or important to undergraduate organic chemistry • Other factors that are important for success in organic chemistry • Which organic chemistry concepts students find difficult • What chemistry misconceptions undergraduate organic chemistry students have • Which organic chemistry concepts are important for later chemistry learning

Interestingly, more consistency appeared across participants' responses to which general chemistry concepts need to be “retaught” than for any other question asked of the sampled organic chemistry educators. In particular, 78% (18 of 23), the largest number of participants who identified the same concept 348


_


_

area for any question in the exploratory study, noted acid-base chemistry as a typically reviewed topic from general chemistry. As for concepts fundamental to organic chemistry, while some overlap occurred with the participants' views and the guidelines set forth by the ACS (4, 5), it is interesting that each participant had quite different perspectives. No topic area was noted by all participants as fundamental to undergraduate organic chemistry and ultimately the participants' responses showed more variations than similarities. In addition, of the topic areas from the ACS topical supplement to organic chemistry, only two participants noted the correlation of physical properties with molecular structure and chemical kinetics, while the detailed consideration of polyfunctional substances and concepts in molecular recognition were not mentioned by any of the participants. Furthermore, experimental techniques were absent from all but two participants' responses, even though organic chemistry courses are habitually accompanied by a mandatory organic laboratory course. However, it is possible that the participants may not have found the laboratory relevant to the questions being asked. The results of this study suggest that the ACS Organic Subcommittee of the Curriculum Committee's assessment that “on the whole teachers of organic chemistry clearly agree on what is important in the discipline” may not hold true today (2). There may be considerably more differences between individual instructors' presentation of undergraduate organic chemistry than previously thought. All participants noted multiple organic chemistry topics that students consistently find difficult, but only 61% (14 of 23) noted specific examples of chemistry misconceptions. While more than 30 chemistry misconceptions were noted, some of which have also been observed by researchers studying students in other areas of chemistry, it was apparent that not all of the study participants were necessarily aware of or actively seeking out misconceptions in their students. It is possible that chemistry educators fail to look for their students' misconceptions, as students' misunderstandings may appear to be highly individualized on the surface. However, the results of ongoing research with organic chemistry students (28), and phenomenographical studies in a variety of content areas (for example, work referenced in 29, 30), suggest that there may be a limited number of qualitatively different ways to understand a particular concept or phenomenon. Thus, it is reasonable to suggest that the limited number of different conceptions students have about organic chemistry concepts not only can be discovered but they can also be used to improve chemistry education. Knowledge of students' conceptions and misconceptions is especially important from the constructivist viewpoint, as students' conceptions and misconceptions


_


Research: Science and Education

must be engaged during instruction in order for deep and correct understanding to be achieved (31-43). Additionally, these results suggest that new assessments need to be designed to elicit students' explanations or descriptions of their conceptions. Typical assessment approaches may not reveal students' underlying conceptions. Finally, in contrast to general chemistry concepts important for organic chemistry, the concepts the organic chemistry educator participants considered important for later chemistry learning had very little overlap. This result may be related to a lack of consensus in the desired learning outcomes of introductory organic chemistry courses. The results presented here provide a foundation for a more targeted discussion of the topic. Overall, only one topic area, acid-base chemistry, consistently appeared in the top three topics noted by participants. This topic is indeed important, as acid-base chemistry is a fundamental concept for understanding organic chemistry at all levels (4, 5, 44-46). Because this topic is clearly identified as a critical learning outcome of undergraduate organic chemistry, ongoing research has built upon this finding and the results from a current study of undergraduate organic chemistry students' conceptions of acid-base chemistry will be reported in due course (28). Acknowledgment Qualitative research guidance from Maria Lahman, valuable guidance and manuscript comments from Loretta Jones and Laurel Schafer, and participants' contributions are gratefully acknowledged. Literature Cited 1. Bunce, S. C.; Adams, K. A. H.; Butler, L. C.; Cronyn, M. W.; Cucci, M. W.; Cutshall, T. W.; Denny, D. B.; Gist, L. A.; Gleason, R. W.; Griffin, W. W.; Kotnik, L. J.; Marcelli, J.; Massie, S. P.; Norcross, B. E.; Poel, R. J.; Rodgers, J. E.; Santiago, P. J.; Silveira, A.; Smith, G. W.; Squibb, S. D.; Vikin, J.; Walsh, E. J.; Weatherbee, C.; Weller, L. E.; Wilder, P., Jr. J. Chem. Educ. 1972, 49, 761–762. 2. Butler, L. C.; Bunce, S. C.; Adams, K. A. H.; Artz, R. J.; Cronyn, M. W.; Cutshall, T. W.; Denny, D. B.; Gleason, R. W.; Hoops, S. C.; Kumler, P. L.; Marcelli, J.; Mungall, W. S.; Norcross, B. E.; Silveira, A.; Slezak, F. B.; Smith, G. W.; Squibb, S. D.; Vikin, J.; Walsh, E. J.; Weatherbee, C.; Weller, L. E. J. Chem. Educ. 1976, 53, 25–26. 3. American Chemical Society, Committee on Professional Training. Degree Program Guidelines and Supplements, 2009. http://portal. acs.org/portal/acs/corg/content?_nfpb=true&_page Label=PP_ SUPERARTICLE&node_id=1584&use_sec=false&sec_url_var= region1&__uuid=ec2551d0-87e4-4194-a696-77cf772a8135 (accessed Dec 2010). 4. American Chemical Society, Committee on Professional Training. Organic Chemistry Supplement, 2009. http://portal.acs.org:80/ portal/PublicWebSite/about/governance/committees/training/ acsapproved/degreeprogram/CTP_005614 (accessed Dec 2010). 5. American Chemical Society. Organic Chemistry Topical Supplement to the Undergraduate Professional Education in Chemistry Guidelines, 2007. 6. Tomorrow. The Report of the Task Force for the Study of Chemistry Education in the United States; American Chemical Society: Washington, DC, 1984; p 81.


_

7. Abelson, P. H. Science 1990, 249 (4966), 225. 8. The Liberal Art of Science: Agenda for Action: The Report of the Project on Liberal Education and the Sciences; American Association for the Advancement of Science: Washington, DC, 1990. 9. Spencer, J. N. J. Chem. Educ. 1992, 69 (3), 182. 10. Lloyd, B. W.; Spencer, J. N. J. Chem. Educ. 1994, 71 (3), 206–209. 11. McMinn, D. G.; Nakamaye, K. L.; Smieja, J. A. J. Chem. Educ. 1994, 71 (9), 755–758. 12. Ege, S. N.; Coppola, B. P.; Lawton, R. G. J. Chem. Educ. 1997, 74 (1), 74–83. 13. Carroll, M. K. Chem. Eng. News 2010, 88 (22), 7. 14. Cooper, M. J. Chem. Educ. 2010, 87 (3), 231–232. 15. Wheeler, D. M. S.; Wheeler, M. M. J. Chem. Educ. 1979, 56 (7), 462–464. 16. Goldish, D. M. J. Chem. Educ. 1988, 65 (7), 603–604. 17. Creswell, J. W. Qualitative Inquiry and Research Design: Choosing among Five Traditions; Sage Publications, Inc.: Thousand Oaks, CA, 1998; p 125. 18. American Chemical Society. American Chemical Society Division of Organic Chemistry, 2008. http://www.organicdivision.org/ (accessed Dec 2010). 19. Chemistry Education Discussion List. Discussion of Organic chemistry educators: Graduate student research inquiry in archived messages of November 2004, [email protected]. 20. Merriam, S. B. Qualitative Research and Case Study Applications in Education: Revised and Expanded From Case Study Research in Education, revised ed.; Jossey-Bass Publishers: San Francisco, CA, 1998; p 74. 21. Nakhleh, M. B. J. Chem. Educ. 1992, 69, 191–196. 22. Barrows, N. J. Students' Problem-Solving Strategies, Mental Models, and Representational Preferences in Organic Chemistry: Nucleophilic Alkyl Substitution and Elimination Reactions. Ph.D. Dissertation, University of Northern Colorado, Greeley, CO, 2005. 23. Galley, W. C. J. Chem. Educ. 2004, 81, 523–525. 24. Barker, V.; Millar, R. Int. J. Sci. Educ. 2000, 22, 1171–1200. 25. Kind, V. Resource Descriptions;Beyond Appearances: Students' Misconceptions about Basic Chemical Ideas, 2004. http:// assessment-ws.wikispaces.com/file/view/Beyond-appearances.pdf (accessed Dec 2010). 26. Henderleiter, J.; Smart, R.; Anderson, J.; Elian, O. J. Chem. Educ. 2001, 78, 1126–1130. 27. Schmidt, H.-J., Students' Understanding of Molecular Structure and Properties of Organic Compounds. Annual Meeting of the National Association for Research in Science Teaching, St. Louis, MO, 1996. 28. Duis, J. M. Acid/Base Chemistry and Related Organic Chemistry Conceptions of Undergraduate Organic Chemistry Students. Ph.D. Dissertation, University of Northern Colorado, Greeley, CO, 2008. 29. Marton, F. Phenomenography. In The International Encyclopedia of Education, 2nd ed., Husen, T., Postlethwaite, T. N., Eds.; Pergamon: Oxford, U.K., 1994; Vol. 8, pp 4424-4429 and references therein. 30. Orgill, M. Phenomenography. In Theoretical Frameworks for Research in Chemistry/Science Education; Bodner, G. M.; Orgill, M. K., Eds.; Pearson Prentice Hall: Upper Saddle River, NJ, 2006; pp 132-151 and references therein. 31. Acar, B.; Tarhan, L. Res. Sci. Educ. 2007, 5, 349–373. 32. Ben-Zvi, R.; Eylon, B. S.; Silberstein, J. J. Chem. Educ. 1986, 63, 64–66. 33. Chandrasegaran, A. L.; Treagust, D. F.; Mocerino, M. Chem. Educ.: Res. Pract. 2007, 8 (3), 293–307.


_


_


349

Research: Science and Education 34. Chou, C.-Y. Proc. Natl. Sci Counc., Repub. China, Part D 2002, 12 (2), 73–78. 35. Costu, B.; Ayas, A.; Niaz, M. Chem. Educ.: Res. Pract. 2010, 11 (1), 5–16. 36. Demirciog lu, G.; Ayas, A.; Demirciog lu, H. Chem. Educ.: Res. Pract. 2005, 6 (1), 35–51. 37. Dhinsda, H. S. Aust. J. Educ. Chem. 2002, 60, 19–23. € 38. Ozmen, H.; Ayas, A. Chem. Educ.: Res. Pract. 2003, 4 (3), 279–290. 39. Taber, K. S. Chemical Misconceptions;Prevention, Diagnosis and Cure, Vol. I: Theoretical Background; Royal Society of Chemistry: London, 2002. 40. Tan, K.-C. D.; Taber, K. S.; Goh, N.-K.; Chia, L.-S. Chem. Educ.: Res. Pract. 2005, 6 (4), 180–197. 41. Treagust, D. F. Int. J. Sci. Educ. 1988, 10 (2), 159–169. 42. Tsai, C.-C.; Chou, C. J. Comp. Assist. Learn. 2002, 18, 157–165.

350


_


_

43. Unal, S.; C-alik, M.; Ayas, A.; Coll, R. K. Res. Sci. Tech. Educ. 2006, 24 (2), 141–172. 44. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; HarperCollins Publishers: New York, NY, 1987. 45. Stewart, R. The Proton: Applications to Organic Chemistry; Academic Press, Inc.: Orlando, FL, 1985. 46. Eubanks, I. D.; Eubanks, L. P. Preparing for Your ACS Examination in Organic Chemistry: The Official Guide; ACS DivCHED Examinations Institute: Clemson, SC, 2002; p 170.

Supporting Information Available Survey questions developed from the initial interview protocol. This material is available via the Internet at http://pubs.acs.org.


_


Organic Chemistry Educators' Perspectives on Fundamental

Recommend Documents