The Chemistry of Perfume: A Laboratory Course for Nonscience Majors

Article pubs.acs.org/jchemeduc

The Chemistry of Perfume: A Laboratory Course for Nonscience Majors Jennifer L. Logan* and Craig E. Rumbaugh Department of Chemistry, Washington & Jefferson College, Washington, Pennsylvania 15301, United States S Supporting Information *

ABSTRACT: “The Chemistry of Perfume” is a lab-only course for nonscience majors. Students learn fundamental concepts of chemistry through the context of fragrance, a pervasive aspect of daily life. The course consists of laboratories pertaining to five units: introduction, extraction, synthesis, characterization, and application. The introduction unit acquaints students with basic perfume terminology and the idea that chemical structure relates to scent. The extraction unit focuses on capturing and isolating fragrant essences from natural materials, whereas the synthetic unit considers mimicking such scents through chemical reactions. In the characterization unit, students analyze the components of perfume and fragrant materials. The course ends with the application unit in which students incorporate their fragrances into consumer products and toiletries. Curriculum structure, content, and student feedback are described. This perfume lab course results from an effort to increase interest in chemistry among nonscience students and encourage interdisciplinary learning. KEYWORDS: First-Year Undergraduate/General, Curriculum, Interdisciplinary/Multidisciplinary, Laboratory Instruction, Hands-On Learning/Manipulatives, Chromatography, Consumer Chemistry, IR Spectroscopy, Nonmajor Courses, Synthesis

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COURSE DESCRIPTION “The Chemistry of Perfume” course consists of units on (1) introduction, (2) extraction, (3) synthesis, (4) characterization, and (5) application. The lab experiments associated with each unit, related chemical concepts, and student learning outcomes are provided in Table 1. The introduction unit familiarizes students with basic perfume terminology and design as well as chemical structure and the relationship between certain functional groups and scent. The extraction unit examines different techniques for isolating and purifying the fragrant compounds from natural materials such as flowers, bark, and fruit. Chemical reactions are covered in the synthesis unit with the controlled, pure chemicals obtained through synthesis being compared to the complex (but variable) scents resulting from extraction. The characterization unit examines chromatography and how this family of analytical techniques can be used to determine the contents of a perfume and maintain quality control. Incorporating fragrances into consumer products is then addressed in the application unit. The design of this course covers topics fundamental to perfume chemistry. The Grasse Institute of Perfumery (GIP, located in Grasse, France), for example, offers a 5-day workshop for student perfumers that covers molecular structure, volatility, extraction techniques, synthetic methods, perfume creation, and functional application.10 Although the goal of this course is not to train future perfumers, the existence of such similarities between this course and the GIP emphasizes

he idea of teaching chemistry to nonscience majors through a practical application has been well established. Numerous articles in this Journal have documented courses that are interesting and informative as well as appealing and accessible for students, including food chemistry,1 science and art,2−4 environmental chemistry,5 and forensic science.6,7 One area that has not yet been presented as a course is fragrance chemistry. This is surprising given that fragrances are everywhere: in food, cleaning products, and toiletries. The process of isolating fragrant chemicals, either through extraction from natural materials or synthesis in the lab, illustrates basic concepts of organic chemistry. Characterizing the components of a fragrance requires analytical chemistry whereas incorporating such scents into the harsh matrix of consumer products (such as soap or laundry detergent) relies on an understanding of the physical chemistry of the scented molecule. Fragrance is, thus, a topic that encompasses a wide range of fundamental chemistry. The idea of connecting fragrance with chemistry is not new and has generated significant interest, as evidenced by numerous laboratory experiments and articles on this topic that have appeared in this Journal.8 To the best of our knowledge, however, no one has combined the wide variety of these activities into a course focused on the subject of perfume or fragrance chemistry. The closest such course was one described briefly (half a page) by S. R. Kaye on cosmetic science with a focus on product preparation.9 In this article, a lab-only course designed for nonscience majors on the chemistry of perfume is described. © 2012 American Chemical Society and Division of Chemical Education, Inc.

Published: February 21, 2012 613

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613−619

Journal of Chemical Education

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Table 1. Thematic Units Presented with Relevant Experiments, Assignments, Concepts, and Learning Objectives Lab Day 1: Perfume Design

Concepts

Student Learning Objectives

Introduction Volatility; basic perfume terminology (essential oils, notes, chords, blending)

Day 2: Molecular Modeling

Atoms; electrons, neutrons, protons; molecules; bonding; chemical formulas; Lewis dot structures; structural formulas; skeletal structures; functional groups; chirality

Day 3: Enfleurage

Polarity; solvent extraction; “like dissolves like”

Day 4: Distillation of Spices Day 5: Distillation of Citrusa

Distillation; solvent extraction; % yield

Maintain a lab notebook; use basic lab equipment; understand lab safety; describe scents; interpret chemical structures; recognize functional groups and their relation to fragrance

Extraction

Day 6: Synthesis of Fragrant Esters

Day 7: Thin-Layer Chromatography: What’s in my Fragrance? Day 8: Gas Chromatography: What’s in my Fragrance?

Become familiar with different extraction techniques; identify pros and cons of each method

Density; FT-IR; % yield

Synthesis Synthesis; chemical reactions; reactants vs products; % yield

Characterization Chromatography; stationary vs mobile phase; mixture separation; visualization methods; Rf values

Conduct a chemical reaction; consider “natural” extraction vs “artificial” synthesis

Encounter chromatography; recognize complexity of fragrant mixtures

Gas chromatography (injector, column, detector, temperature programming); designer vs imposter fragrances

Applications Day 9: Soap Synthesis

Surfactants; oil/water emulsion ; saponification

Incorporate fragrance into various consumer products; consider desirable qualities in terms of physical properties, safety, etc.

Day 10: Making Lotion Bath Bombsb

Viscosity; oil/water emulsion Acid−base chemistry

Day 11: Presentations

Group Project Various topics related to perfumes (e.g., marketing, safety, history, industry)

Day 12: Final Exam

Testing on concepts behind lab techniques

Research fragrance-related topic of choice; design and give a presentation

Exam a

This distillation lab can be replaced with an experiment in which liquid carbon dioxide is used to extract limonene from orange peel.11 bBath bombs were used in place of lotion making for the 2010 offering.

Fragrance chemistry is an interesting application-based topic that appeals to students of numerous backgrounds. Teaching such “consumer chemistry” provides students the opportunity to connect basic concepts with the real world, through examples that “both nourish and stretch our students’ understanding”.14 For chemistry students, application-based courses allow them to place their studies into the context of another field, avoiding the “tunnel vision” that may result from a specialized curriculum.15 Offering consumer chemistry courses, however, is not without controversy. An emphasis on chemical applications can “further confuse the distinction between science and technology”, ignoring the bigger questions and contributions in chemistry.16 Nevertheless, fragrance chemistry provides the basis for additional discussion on issues involving consumer safety, government regulations, and environmental concerns. For example, a recent study showed that the most abundant contaminants in a Spanish river were from fragrances found in personal care products.17 In addition, such a topic can spark additional interest in science in general, making students question what the science is behind different aspects of daily life.

the central role chemistry plays in perfumerya field that, at first glance, seems unrelated.

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RATIONALE At many four-year liberal arts colleges, to graduate, students must take a laboratory course to “promote an understanding of the nature or methods of scientific inquiry”.12 The rationale is to emphasize how science relates to larger societal issues. A report by the American Association for the Advancement of Science (AAAS) states that the natural sciences in the liberal arts curriculum should be multidisciplinary.13 Fragrance chemistry is such a topic, touching on the olfactory system (biology, neuroscience), the evocative memories that arise with a certain smell (psychology), cultural differences in perfume design and incense usage (sociology), and the business itself (e.g., the marketing and economics of a perfume). In addition, the development of techniques related to fragrance provides context to the history of chemistry. Distillation, for example, exists partially as a result of the desire to isolate fragrances from natural materials whereas the goal of providing more costeffective materials motivated the development of some classic syntheses. 614



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COURSE DESIGN At this college, the academic year consists of fall, intersession, and spring terms. Intersession is a 3.5 week (17 day) January term. Intersession courses tend to be more “fun”, as faculty are encouraged to create a class reflecting their own interests, outside of the confines of typical departmental offerings. Faculty and students are each involved with one course, resulting in an intensive 3-week study of a topic. In the sciences, intersession is too brief for a traditional lecture and lab course. Instead, science faculty offer either a lecture-only or lab-only course. During the 2009 intersession term, a lab-only course on the chemistry of perfume was developed and offered as a course for nonscience majors. A total of 18 students (one chemistry major, the others all nonscience majors) enrolled in the course, ranging from second-year to fourth-year students. The course satisfied a laboratory requirement for graduation and, given its application-based topic, proved to be popular, resulting in a waitlist. The course was again offered in 2010 with a few modifications. Students met for four hours a day, four days a week, for three weeks. Of the twelve class meetings, ten consisted of lab, one was devoted to a final exam, and one comprised student presentations (Table 1). Each lab involved a prelab lecture in which concepts and procedures found in the lab manual were presented and conclusions from the previous lab were discussed. Students worked in pairs for the experiments, maintaining a lab notebook, and submitting their action logs and analysis the following day. In addition, students were assigned readings of a book by Luca Turin, The Secret of Scent.18

Figure 1. The perfume design lab introduces students to essential oils; top, middle, and base notes; chords; and volatility. In addition, students learn to keep a lab notebook, recording recipes, observations, and comments on what blends have pleasing or disagreeable scents. Here, common perfume supplies, including ethanol, smelling strips, palette-cleansing coffee beans, perfume bottles, and essential oils, are shown.

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COURSE CONTENT The course consisted of five units. Although detailed procedures and results are not provided, the sources of each lab are included. It should be noted that a wealth of fragrancerelated resources are available in this Journal. The Supporting Information contains an extensive list of these citations and how they could be incorporated into a perfume chemistry course.

Figure 2. In the molecular modeling lab, students learned how to draw Lewis dot structures, progressing to structural formulas, skeletal structures, and finally molecular models. Here, an example is provided using isopentyl acetate (banana scent). The goal was to teach them how to interpret chemical structures and ultimately recognize functional groups that commonly result in a characteristic fragrance.

students with a basic understanding of the language chemists use to draw their structures. This material was immediately relevant to the course in that future laboratories consisted of isolated chemicals and synthetic reactions. The concepts were also important, however, for better understanding the assigned Secret of Scent readings, as well as daily life issues, such as the structures found in pharmaceutical prescriptions.

Introduction Unit

The introduction unit introduced students to general terms in the perfume industry as well as basic chemical concepts. Unlike other application-based courses, no obvious textbook on fragrance chemistry exists for nonscience majors. Although the lack of a textbook is admittedly an obstacle, several alternatives are available. The Secret of Scent, a book that provides an enthusiastic description of perfumes and the art and science behind their creation, was used. Written at a level intended for the nonscientist, this nonfiction work includes basic fragrance-related chemistry.18 To introduce students to fragrance chemistry, the first lab was to design a perfume (Figure 1)19,20 using essential oils (i.e., the fragrant oils obtained from plant material through steamdistillation). Students began to develop proper lab safety, technique, and notebook-keeping skills. They also learned basic perfume terminology (essential oils, notes, and chords), as well as the concept of volatility. The second lab within the introduction unit was molecular modeling, where students learned how chemical structure relates to fragrance (Figure 2). The lab consisted of classroom activities involving Lewis dot and molecular modeling kits sprinkled throughout a lecture. The goal was to provide

Extraction Unit

The next unit in the course was the extraction of fragrant compounds from natural materials. Now that students had been introduced to essences and their importance in the perfume industry, a natural progression was to show them how such materials were traditionally obtained. The three primary extraction techniques in the modern fragrance industry are solvent extraction, distillation, and expression.21 In this course, the focus was on solvent extraction and distillation through three lab experiments: enfleurage, distillation of spices, and distillation of citrus. Enfleurage, a technique first used by the ancient Egyptians21 and later refined by the Grasse perfume industry, uses fat and solvent to extract fragrant oils from plant material (Figure 3). Both cold and hot enfleurage (also known as maceration, a technique involving heated oil, rather than fat) were used.22 615



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Figure 4. The synthesis unit introduced students to chemical reactions and the possibility of mimicking natural scents through synthesis in the lab. A carboxylic acid and alcohol were reacted in a Fischer esterification to produce esters with banana, rum, cinnamon, and wintergreen scents.

Figure 3. The extraction unit involves cold enfleurage where plant material was pressed into a layer of fat, allowing the fragrant compounds to adsorb into the fat, from which they could be isolated through solvent extraction. Here, roses were used for illustrative purposes, though jasmine is the traditional flower associated with enfleurage.22 The petals are frequently replaced until the fat is saturated, a process that can take several months.

depend on seasonal conditions) in a controlled and optimized reaction. The idea of using chemistry to (cheaply) mimic nature is a focus of numerous industries and is an example of how a concept learned in the lab can apply to daily life. In addition, the development of new perfumes as a result of new discoveries provides historical perspective and can initiate a discussion on how the desire to produce a less expensive perfume led to progress in organic chemistry.26,27 Fougère Royale (1884), for example, was the first perfume to incorporate a synthetic chemical (coumarin, found naturally in tonka beans).26

Hot enfleurage was more successful because a measurable quantity of oils was obtained within a single lab period, whereas the 3-week intersession was not enough time for cold enfleurage. The latter, however, is not to be entirely dismissed considering its importance to the French perfume industry. (Jasmine, for example, requires cold enfleurage because the molecules responsible for its fragrance break down with heat.) This technique is presented as a demo by preparing a series of experiments to depict how the fat layer looks after 1, 2, and 3 months of exposure to plant material. If this course were done during a normal 13-week term, the cold enfleurage experiment could be successfully carried out as a semester-long effort. Following the enfleurage lab, students moved on to distillation. Not only does this technique originate from ancient civilization, but it also plays a role in the modern world (e.g., the liquor and petroleum industries). In two separate laboratories, students steam-distilled spices (cloves, cinnamon sticks, and nutmeg)23 and citrus (oranges, lemons, and limes)24 to obtain mixtures of essential oils and water. The essential oils were then isolated through solvent extraction. For citrus distillation, students used an FT-IR to compare their product to a published spectrum of limonene, the oil found in orange peel. The extraction unit thus taught students to consider such parameters as time, labor, and expense in assessing the costbenefits of fragrant oil extraction. Although many advocate the use of “natural products” in the food and fragrance industry, economics often dictates otherwise.

Characterization Unit

Now familiar with where fragrances come from, students next encountered how to determine what they had. The idea of identifying a single component had already been introduced to the students by running an FT-IR of the distilled citrus oil in an effort to identify limonene. Perfumes and many fragrant essences, however, represent complex mixtures. As a result, chromatography in which mixtures are separated into components plays a primary role in the perfume industry.28,29 Imposter fragrances, for example, derive from gas chromatography−mass spectrometry (GC−MS) results of designer perfumes. To introduce students to chromatography, the first lab consisted of thin-layer chromatography (TLC) adapted from an experiment developed by Pelter et al.30 For example, students compared distilled spice oil to eugenol, the primary component in clove oil (Figure 5). The exercise provided a visual demonstration of chromatography and the meaning of stationary and mobile phases. Following the TLC experiment, students were introduced to gas chromatography (GC). Emphasis was placed on the idea that now an instrument would be used to accomplish what they had manually done with the TLC lab (Figure 5). An experiment comparing imposter and designer fragrances was developed based on Mowery et al.31 Additional experiments could involve analysis of a perfume’s headspace32 or even comparison of components in the liquid perfume to the headspace, emphasizing the possible difference between what is applied to the skin and what reaches the nose.31 Introducing solid-phase microextraction (SPME) would allow one to capture the scent of a live flower, spices,33 herbs, and consumer products (e.g., shampoo).34

Synthesis Unit

In the synthesis unit, students were taught an alternative approach to obtaining scented compounds: chemical reactions. The lab in this unit consisted of a condensation reaction between an alcohol and carboxylic acid to produce a fragrant ester (Figure 4).25 Students were assigned one of four different reactions resulting in either ethyl cinnamate (cinnamon), isobutyl propionate (rum), isopentyl acetate (banana), or methyl salicylate (wintergreen). An important point in this unit was that whereas extraction can produce a more complex bouquet of aromas, synthesis could yield a less expensive product (whose quality does not 616



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Figure 5. Students first learned to do TLC followed by GC in the characterization unit. Here, a schematic of a TLC plate shows that clove oil obtained through distillation contains primarily eugenol, as well as a second (minor) component. These results were confirmed by GC as the eugenol standard has the same retention time as the main clove oil peak. TLC thus provided a simple introduction to chromatography, helping to explain the mechanics of the seemingly complex GC instrument.

Application Unit

The final unit of the course examined applications of fragrances to consumer products (Figure 6). 35 In two separate

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HAZARDS

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STUDENT ASSESSMENT

The laboratories described in this course consist of a variety of chemicals. MSDS forms should be made available and consulted prior to each experiment. In particular, dichloromethane (used in the distillation laboratories) is a possible carcinogen. Diethyl ether (synthesis lab), ethyl acetate, and hexanes (TLC lab) are volatile and highly flammable. Sodium hydroxide (soap lab) is corrosive. It should also be noted that some students may exhibit heightened sensitivity to the concentrated fragrances used in the perfume, soap, lotion, and bath bomb laboratories, possibly developing a rash upon exposure to the skin. Gloves and goggles should be worn at all times, and the lab should be well-ventilated.

Students were assessed with a safety quiz (50 pts), lab technique (50 pts), 10 lab reports (50 pts each), a multiplechoice final exam (100 pts), and a presentation (100 pts) (800 pts total). The safety quiz tested course policies and ensured students understood the safety regulations. All students began the term with the full 50 points assigned to lab technique. Using poor laboratory technique or judgment and violations of safety regulations resulted in point deductions. Lab reports were graded based on completion of a prelab assignment, a conclusion in which students summarized the lab and their key findings, and postlab questions that tested their understanding of the concepts. To ensure that students were reading The Secret of Scent, each postlab included one question based on the assigned material. The final exam tested students on concepts encountered in each of the laboratories. For the presentation, students chose a topic related to perfume and then gave a 10−12 min presentation using PowerPoint. Topics varied from fragrance marketing to hazardous materials and perfume history. One pair of students even produced a commercial, celebrating the official “debut” of Eau de Cougar, a fragrance created during the perfume design lab. The second time that the course was offered, a participation grade was included based on class discussions following each unit.

Figure 6. The application unit incorporated fragrances into consumer products. Here, tangible results from laboratories involving the preparation of lotion, soap, and bath bombs are shown.

laboratories, students made soap and lotion based on experiments developed by S. T. Mabrouk.36,37 The soap lab was actually split into two parts. Students made soap earlier in the semester, letting it harden for two weeks. They then characterized the soap, measuring pH and conducting lathering tests. Concepts included surfactants and oil/water emulsions. The lotion lab followed up the discussion of surfactants and also introduced viscosity. An advantage of these two laboratories was that students created tangible products that they could take home and use. An alternative lab was the making of bath bombs.38 Composed of sodium bicarbonate and citric acid, bath bombs fizzle when dropped into water, thus prompting a discussion on acid−base chemistry. 617



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analyze them will hopefully demystify the practice of science, instilling a greater appreciation for what scientists do. Our hope is that engaging students in such hands-on chemistry will pique their interest in the science of everyday life.

Discussion focused on concepts and issues related to each unit, as outlined in Table 1.

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EVALUATION OF COURSE Students took a pre- and postcourse survey regarding their background in science and outlook on chemistry (Table 2).

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S Supporting Information *

Table 2. Course Evaluation Responses Question What is your attitude toward chemistry? If you could take another science course, would you be interested? If you could take another lab course, would you be interested? Overall evaluation of the course

ASSOCIATED CONTENT

More information on each of the laboratories is provided as well as a list of additional experiments, resources, and books that could be incorporated into a course on perfume chemistry. The citations are categorized according to the thematic units (introduction, extraction, synthesis, characterization, and application) described in this article.This material is available via the Internet at http://pubs.acs.org.

Precoursea Postcoursea 2.7 (±1.0) NA

3.8 (±0.8) 2.9 (±1.1)

NA

2.9 (±0.8)

NA

4.5 (±0.6)

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a

Ratings are based on a scale of 1 (dislike; no interest; poor) to 5 (like; high interest; excellent). Averages (± standard deviations) are provided for 18 students (surveyed in the 2009 offering).

AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected].

Students were asked about their attitude toward chemistry on a scale of 1 (dislike) to 5 (like). Before the course, the average response was 2.7, whereas, after the course, the average increased to 3.8, indicating a higher level of interest in chemistry. When asked if they would want to take another science course or another lab course, the general response was 2.9 for both types (on a scale of 1 (no interest) to 5 (high interest)). Given that 87% of the students had enrolled in the course simply to satisfy a graduation requirement, these responses were promising. In general, student feedback was positive. The overall evaluation of the course was 4.5 (with 1 being poor and 5 being excellent). The favorite laboratories were the applicationbased ones (soap, lotion, and bath bombs) whereas the least favorite lab was the molecular modeling one. This intense activity would admittedly be better handled in a traditional lecture and lab course. One student, however, commented that he enjoyed it because “it was like solving logic games.”

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ACKNOWLEDGMENTS The authors would like to thank the students who have taken the Chemistry of Perf ume course for their enthusiasm and participation. Special thanks are also given to Michael Leonard for his input and encouragement.

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REFERENCES

(1) Miles, D. T.; Bachman, J. K. J. Chem. Educ. 2009, 86, 311−315. (2) Smieja, J. A.; D’Ambruoso, G. D.; Richman, R. M. J. Chem. Educ. 2010, 87, 1085−1088. (3) Uffelman, E. S. J. Chem. Educ. 2007, 84, 1617−1624. (4) Nivens, D. A.; Padgett, C. W.; Chase, J. M.; Verges, K. J.; Jamieson, D. S. J. Chem. Educ. 2010, 87, 1089−1093. (5) Schwartz, A. T.; Bunce, D. M.; Silberman, R. G.; Stanitski, C. L.; Stratton, W. J.; Zipp, A. P. J. Chem. Educ. 1994, 71, 1041−1044. (6) Nienhouse, E. J. J. Chem. Educ. 1985, 62, 1047−1049. (7) Esslinger, W. G. J. Chem. Educ. 1985, 62, 777. (8) A list of these JCE references is provided in the Supporting Information. (9) Kaye, S. R. J. Chem. Educ. 1980, 57, 641. (10) Grasse Institute of Perfumery, http://www.prodarom.com/ anglais/gip/index_gip.php (accessed Jan 2012). (11) McKenzie, L. C.; Thompson, J. E.; Sullivan, R.; Hutchison, J. E. Green Chem. 2004, 6, 355−358. (12) Washington & Jefferson College Catalog, http://wiki.washjeff. edu/pages/viewpage.action?pageId=41945432 (accessed Jan 2012). (13) The Liberal Art of Science: Agenda for Action; Report of the Project on Liberal Education and the Sciences; AAAS: Washington, DC, 1990. (14) Mason, D. S. J. Chem. Educ. 2004, 81, 9. (15) Porter, L. A. J. Chem. Educ. 2007, 84, 259−264. (16) Tro, N. J. J. Chem. Educ. 2004, 81, 54−57. (17) Gómez, M. J.; Herrera, S.; Solé, D.; García-Calvo, E.; Fernández-Alba, A. R. Anal. Chem. 2011, 83, 2638−2647. (18) Turin, L. The Secret of Scent; Harper Collins: Publishers: New York, 2006. (19) Lab inspired by: Aftel, M. Essence and Alchemy: A Natural History of Perfume; Gibbs Smith: New York, 2001. (20) Additional introductory material can be found in: Ellena, C. Chem. Biodiversity 2008, 5, 1147−1153. (21) Fortineau, A. D. J. Chem. Educ. 2004, 81, 45−50. (22) Guenther, E. The Essential Oils Vol. 1: History, Origin in Plants, Production, Analysis; D. Van Nostrand Company, Inc.: New York, 1948; pp 188−200.

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EXTENSION OF COURSE Although this course was offered over an intense 3-week period, the laboratories could be offered separately on a weekly basis during the course of a normal semester. In addition, such a course could be developed further to include a lecture component. Several concepts, fundamental to chemistry, were covered in the laboratories and could be taught in greater detail during a lecture. Possible textbooks are listed in the Supporting Information. The topic could also be incorporated into a traditional chemistry curriculum. For example, chromatography experiments would fit nicely into an analytical course whereas fragrance extraction or synthesis would be a natural part of organic chemistry.

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CONCLUSION A laboratory course for nonscience majors on the chemistry of perfume was developed. The primary goal was to instill an appreciation and interest in chemistry in students who are pursuing studies in other fields. The topic of perfume is interdisciplinary, encouraging students to relate chemistry with other subjects. Such connections are the hallmark of a liberal arts education and can help students develop or increase their scientific awareness. Encouraging the students to consider where the components in a product come from or how to 618



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(23) Williamson, K. L. Macroscale and Microscale Organic Experiments, 2nd ed.; D.C. Heath and Company: Lexington, MA, 1994; pp 106− 109. (24) Wilcox, C. F. Experimental Organic Chemistry: A Small-Scale Approach; Macmillan Publishing Company: New York, 1988; pp 221− 226. (25) Lab is based on one developed at Washington & Jefferson College for the organic chemistry class. A similar lab is described in: Williamson, K. L. Macroscale and Microscale Organic Experiments, 2nd ed.; D.C. Heath and Company: Lexington, MA, 1994; pp 385−399. (26) de Nicolaï, P. Chem. Biodiversity 2008, 5, 1137−1146. (27) Bogert, M. T. J. Chem. Educ. 1925, 8, 1311−1334. (28) Bicchi, C.; Rubiolo, P.; Cordero, C. Anal. Bioanal. Chem. 2006, 384, 53−56. (29) van Asten, A. TrAC, Trends Anal. Chem. 2002, 21, 698−708. (30) Pelter, L. S.; Amico, A.; Gordon, N.; Martin, C.; Sandifer, D.; Pelter, M. W. J. Chem. Educ. 2008, 85, 133−134. (31) Mowery, K. A.; Blanchard, D. E.; Smith, S.; Betts, T. A. J. Chem. Educ. 2004, 81, 87−89. (32) Knupp, G.; Kusch, P.; Neugebauer, M. J. Chem. Educ. 2002, 79, 98−100. (33) Wang, Y.; Ocariz, J.; Hammersand, J.; MacDonald, E.; Bartczak, A.; Kero, F.; Young, V. Y.; Williams, K. R. J. Chem. Educ. 2008, 85, 957−958. (34) Galipo, R. C.; Canhoto, A. J.; Walla, M. D.; Morgan, S. L. J. Chem. Educ. 1999, 76, 245−248. (35) Background information can be found in: The Chemistry of Fragrances: From Perfumer to Consumer, 2nd ed.; Sell, C. S., Ed.; Royal Society of Chemistry: Cambridge, U.K., 2006. (36) Mabrouk, S. T. J. Chem. Educ. 2005, 82, 1534−1537. (37) Mabrouk, S. T. J. Chem. Educ. 2004, 81, 83−86. (38) Excellent Living Guide, http://www.excellentlivingguide.com/ 2009/11/bath-bombers-unite/ (accessed Jan 2012).

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The Chemistry of Perfume: A Laboratory Course for Nonscience Majors

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