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The idea that momentous events may depend on some- me to modify my usual case study approach and try some-
thing as small as a molecule—a group of two or more thing new. I immediately knew that I wanted the class to
atoms held together in a definite arrangement—offers a write and title our own book, modeled after Napoleon’s But-
novel approach to understanding the growth of human tons, with each student contributing a chapter on a specific
civilization. A change as small as the position of a bond— molecule. This seemed to be a feasible goal with about 20
the link between atoms in a molecule—can lead to enor- students expected to enroll in the course. Since this is also a
mous differences in properties of a substance and in turn laboratory course, my colleague who taught the laboratory
can influence the course of history. component of the course also read the book and was equally
Napoleon’s Buttons: How 17 Molecules Changed History (1) excited about connecting laboratory work to such an ap-
proach. This article is our story of how one book shaped a
Many chemistry courses for nonscience majors either course for us at Dickinson College.
focus on the history of chemistry or employ a case study ap-
proach that connects chemistry to society, both of which are The Book
pedagogically sound and provide for excellent learning expe-
riences for undergraduates. Very few of these courses, how- Napoleon’s Buttons is an engaging account of 17 molecules
ever, actually challenge students to think on a deep level about (or in some cases groups of molecules) that have, like the tin
how an individual molecule can shape historical events and buttons worn by Napoleon and his army, greatly influenced
how these events can, in turn, have an impact on the field of the course of history. Although the book only briefly recounts
chemistry. The unique focus of such a course is on the role how the tin buttons crumbled in the bone-chilling cold, it
of chemistry in history rather than on the history of chemistry. becomes a metaphor for the way in which so many molecules
This article describes how such an approach was adopted at have altered a particular course of events. Some of the mol-
Dickinson College. ecules covered within the 17 chapters motivated voyages of
At Dickinson, all students must take two semesters of a exploration and discovery, some spurred advances in medi-
laboratory science. These two courses can be taken in any cine, law, and public policy, while others were pivotal in de-
department, and since this general education requirement was termining what we eat, drink, and wear and how we take
instated six years ago, none of our science departments offer care of ourselves. Most important—and the underlying theme
the traditional two semester lab sequence that was previously for each chapter in the book—is the notion that without these
offered here as well as at most liberal arts colleges. We are compounds the development of human civilization would
thus faced with the challenge of teaching students who will have been very different.
take only a single chemistry course during their college ca- Napoleon’s Buttons is full of examples of the importance
reers. As a result, there has been a shift in pedagogy among of the structure of each of the 17 molecules that affected his-
colleges and universities from the traditional survey courses tory. The structural formula for each of these molecules is
of the past toward courses that are more relevant to the non- given and the important or “functional” aspect of each mol-
science major. Many such courses are described in articles ecule is highlighted. Compounds composed of generally simi-
published in this Journal (2–4), including a recent one that lar structure, but with some slight differences, are also
discussed the goals and challenges of the introductory chem- presented. The authors frequently discuss how slight varia-
istry course for nonscience majors and in particular a unique tions in the structure of a molecule can make a large impact
chemical information assignment in which students re- on its properties.
searched urban legends, pollution in their hometowns, and For example, in Chapter 5 (Nitro Compounds), a simple
the relationship between chemistry and their majors (5). comparison of the structures of p-nitrotoluene to p-ami-
Also recently appearing in this Journal was an article that nobenzoic acid reveals that each compound has the same
presented the chemistry of MSG and described how it molecular formula (C7H7NO2) and contains a benzene ring
changed the food industry as well as our expectations for with two additional chemical groups located directly across
taste (6). Such articles demonstrate that molecules indeed from each other. However, the identity of the groups is dif-
have a “story” that goes beyond the chemical facts and it is ferent: a methyl and a nitro group are present in the
important to convey this if we are to produce scientifically nitrotoluene, while a carboxylic acid and an amine group are
literate students who understand the important role that sci- attached to the aminobenzoic acid. This difference in groups
ence and technology have played and will continue to play results in very different properties for each compound. p-
in their lives. Nitrotoluene can exhibit explosive properties while p-ami-
In October 2003, I read a review of a new book titled nobenzoic acid (PABA) is nonexplosive. In addition, PABA
Napoleon’s Buttons: How 17 Molecules Changed History by can absorb UV radiation, which resulted in the widespread
Penny Le Couteur and Jay Burreson (7). The book inspired use of this compound in sunscreen products.
precipitation: 4.2–4.3). Understanding the chemical processes tom laboratory manual sites provided by publishers of scien-
leading to acid rain is a major step in developing methods to tific textbooks and manuals: Chemical Education Resources
work towards the prevention of this problem. It is impor- (10) and Catalyst (11) allow choices from a large selection of
tant to stress how an understanding of chemistry is benefi- experiments developed for various courses (general, health sci-
cial to society as a whole, not only as seen in the examples ence, organic chemistry) and are focused on basic and ap-
contained in Napoleon’s Buttons, but also for the future life- plied chemical principles.
time of the students. Therefore, a customized laboratory manual can be readily
An interesting and comprehensive laboratory component assembled to coincide with the chapters of Napoleon’s But-
relevant to chapters in Napoleon’s Buttons can easily be com- tons presented in this article, or with additional chapters. For
posed using experiments from widely available resources. For example, all of the common resources mentioned above in-
example, experiments complementary to the chapters refer- clude experiments involving the testing of foods or juices for
enced in Tables 2 and 3 are readily found in general or non- ascorbic acid (Chapter 2 of Napoleon’s Buttons) using a com-
science major chemistry laboratory manuals such as Chemistry mon titration technique as well as the analysis of various dyes
in Context (8) and Chemical Investigations for Changing Times (Chapter 9 of Napoleon’s Buttons) using thin-layer chroma-
(9). Similar experiments are also accessible online through cus- tography.
as a small unit. The project also lends itself to group work. 3. Gooch, E. E. J. Chem. Educ. 2002, 79, 820.
In fact, two students in the class who were both psychology 4. Giunta, C. J. J. Chem. Educ. 2001, 78, 623.
majors chose Ritalin as their topic. Neither wanted to aban- 5. Pence, L. E. J. Chem. Educ. 2004, 81, 764–768.
don the topic, so they did the project as a pair and it worked 6. Ault, A. J. Chem. Educ. 2004, 81, 347–355.
very well. In short, the possibilities for classroom and labo- 7. Dalton, L. Chem. Eng. News 2003, 81 (40), 42.
ratory topics and format are endless. 8. Stratton, W.; Steehler, G.; Pienta, N.; Middlecamp, C. Chemistry
in Context: Applying Chemistry in Society (laboratory manual), 4th
W
Supplemental Material ed.; McGraw-Hill Higher Education: New York, 2003.
The student handout describing the project is available 9. Hassell, C.; Marshall, P.; Hill, J. Chemical Investigations for
in this issue of JCE Online. Changing Times, 10th ed.; Pearson Education, Inc.: New Jer-
sey, 2004.
Literature Cited 10. Brooks/Cole. Chemical Education Resources. http://
1. Le Couteur, P.; Burreson, J. Napoleon’s Buttons: How 17 Mol- n-cerlabs.brookscole.com (accessed July 2005).
ecules Changed History; Tarcher/Putnam: New York, 2003. 11. Pearson Custom Publishing. Catalyst. http://www.
(Note: the paperback version has a slightly different title: pearsoncustom.com/database/science.html (accessed July 2005).
Napoleon’s Buttons: 17 Molecules That Changed History). 12. General Chemistry Web Page. http://www.library.dickinson.edu/
2. Lerman, Z. M. J. Chem. Educ. 2003, 80, 1234. courses/chemistry/genchem04.htm (accessed July 2005).