7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 1/7

The Chemistry of Perfume: A Laboratory Course for NonscienceMajors Jennifer L. Logan* and Craig E. RumbaughDepartment 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 contextof fragrance, a pervasive aspect of daily life. The course consists of laboratoriespertaining to five units: introduction, extraction, synthesis, characterization,and application. The introduction unit acquaints students with basic perfumeterminology and the idea that chemical structure relates to scent. Theextraction unit focuses on capturing and isolating fragrant essences from

natural materials, whereas the synthetic unit considers mimicking such scentsthrough chemical reactions. In the characterization unit, students analyze thecomponents of perfume and fragrant materials. The course ends with theapplication unit in which students incorporate their fragrances into consumerproducts and toiletries. Curriculum structure, content, and student feedback are described. This perfume lab course results fran 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

T he idea of teaching chemistry to nonscience majorsthrough a practical application has been well established.

Numerous articles in thisJournalhave documented courses thatare interesting and informative as well as appealing andaccessi ble for students, including food chemistry,1 science andart,2− 4 environmental chemistry,5 and forensic science.6,7 Onearea that has not yet been presented as a course is fragrancechemistry. This is surprising given that fragrances areeverywhere: in food, cleaning products, and toiletries. Theprocess of isolating fragrant chemicals, either through extractionfrom natural materials or synthesis in the lab, illustrates basicconcepts of organic chemistry. Characterizing the componentsof a fragrance requires analytical chemistry whereas incorporat-ing such scents into the harsh matrix of consumer products(such as soap or laundry detergent) relies on an understandingof the physical chemistry of the scented molecule. Fragrance is,thus, a topic that encompasses a wide range of fundamentalchemistry.

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 topicthat have appeared in thisJournal.8 To the best of ourknowledge, however, no one has combined the wide variety of these activities into a course focused on the subject of perfumeor fragrance chemistry. The closest such course was onedescribed briefly (half a page) by S. R. Kaye on cosmeticscience with a focus on product preparation.9 In this article, alab-only course designed for nonscience majors on thechemistry of perfume is described.

■ 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 eachunit, related chemical concepts, and student learning outcomesare provided in Table1. The introduction unit familiarizesstudents with basic perfume terminology and design as well aschemical structure and the relationship between certainfunctional groups and scent. The extraction unit examinesdifferent techniques for isolating and purifying the fragrantcompounds from natural materials such as flowers, bark, andfruit. Chemical reactions are covered in the synthesis unit withthe controlled, pure chemicals obtained through synthesis beingcompared to the complex (but variable) scents resulting fromextraction. The characterization unit examines chromatography and how this family of analytical techniques can be used todetermine the contents of a perfume and maintain quality

control. Incorporating fragrances into consumer products isthen 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 molecularstructure, volatility, extraction techniques, sy nthetic methods,perfume creation, and functional application.10 Although thegoal of this course is not to train future perfumers, the existenceof such similarities between this course and the GIP emphasizes

Published: February 21, 2012

Article

pubs.acs.org/jchemeduc

© 2012 American Chemical Society andDivision of Chemical Education, Inc. 613 dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 2/7

the central role chemistry plays in perfumery a field that, atfirst glance, seems unrelated.

■ RATIONALE At many four-year liberal arts colleges, to graduate, studentsmust take a laboratory course to“ promote an understanding of the nature or methods of scientific inquiry ” .12 The rationale isto emphasize how science relates to larger societal issues.

A report by the American Association for the Advancementof Science (AAAS) states that the natural sciences in the liberalarts curriculum should be multidisciplinary.13 Fragrancechemistry is such a topic, touching on the olfactory system(biology, neuroscience), the evocative memories that arise witha certain smell (psychology), cultural differences in perfumedesign 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 providescontext to the history of chemistry. Distillation, for example,exists partially as a result of the desire to isolate fragrances fromnatural materials whereas the goal of providing more cost-effective materials motivated the development of some classicsyntheses.

Fragrance chemistry is an interesting application-based topicthat appeals to students of numerous backgrounds. Teachingsuch “ consumer chemistry ” provides students the opportunity to connect basic concepts with the real world, throughexamples that “ both nourish and stretch our students’

understanding” .14 For chemistry students, application-basedcourses allow them to place their studies into the context of another field, avoiding the “ tunnel vision” that may result froma specialized curriculum.15

Offering consumer chemistry courses, however, is not without controversy. An emphasis on chemical applicationscan “ further confuse the distinction between science andtechnolog y ” , ignoring the bigger questions and contributions inchemistry.16 Nevertheless, fragrance chemistry provides the basis for additional discussion on issues involving consumersafety, government regulations, and environmental concerns.For example, a recent study showed that the most abundantcontaminants in a Spanish river were from fragrances found inpersonal care products.17 In addition, such a topic can spark additional interest in science in general, making studentsquestion what the science is behind different aspects of daily life.

Table 1. Thematic Units Presented with Relevant Experiments, Assignments, Concepts, and Learning Objectives

Lab Concepts Student Learning Objectives

IntroductionDay 1: Perfume Design Volatility; basic perfume terminology (essential oils, notes, chords,

blending)Maintain a lab notebook; use basic lab equipment; understand lab safety;

describe scents; interpret chemical structures; recognize functionalgroups and their relation to fragrance

Day 2: MolecularModeling

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

ExtractionDay 3: Enfleurage Polarity; solvent extraction;“ like dissolves like” Become familiar with different extraction techniques; identify pros and

cons of each methodDay 4: Distillation of

SpicesDistillation; solvent extraction; % yield

Day 5:Distillation of Citrusa

Density; FT-IR; % yield

SynthesisDay 6: Synthesis of

Fragrant EstersSynthesis; chemical reactions; reactants vs products; % yield Conduct a chemical reaction; consider“ natural” extraction vs“ artificial”

synthesis

CharacterizationDay 7: Thin-Layer

Chromatography: What’ s in my Fragrance?

Chromatography; stationary vs mobile phase; mixture separation; visualization methods;R f values

Encounter chromatography; recognize complexity of fragrant mixtures

Day 8: GasChromatography: What’ s in my Fragrance?

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

ApplicationsDay 9: Soap Synthesis Surfactants; oil/water emulsion ; saponification Incorporate fragrance into various consumer products; consider desir

qualities in terms of physical properties, safety, etc.Day 10: Making Lotion Viscosity; oil/water emulsionBath Bombsb Acid− base chemistry

Group ProjectDay 11: Presentations Various topics related to perfumes (e.g., marketing, safety, history,

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

ExamDay 12: Final Exam Testing on concepts behind lab techniques

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

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619614

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 3/7

■ 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 areencouraged 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 thechemistry of perfume was developed and offered as a course fornonscience 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 coursesatisfied a laboratory requirement for graduation and, given itsapplication-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 studentpresentations (Table1). Each lab involved a prelab lecture in which concepts and procedures found in the lab manual werepresented and conclusions from the previous lab werediscussed. Students worked in pairs for the experiments,maintaining a lab notebook, and submitting their action logsand analysis the following day. In addition, students wereassigned readings of a book by Luca Turin,The Secret of Scent .18

■ COURSE CONTENTThe course consisted of five units. Although detailedprocedures and results are not provided, the sources of eachlab are included. It should be noted that a wealth of fragrance-

related resources are available in thisJournal. The SupportingInformationcontains an extensive list of these citations andhow they could be incorporated into a perfume chemistry course.Introduction Unit

The introduction unit introduced students to general terms inthe perfume industry as well as basic chemical concepts. Unlikeother application-based courses, no obvious textbook onfragrance chemistry exists for nonscience majors. Althoughthe lack of a textbook is admittedly an obstacle, severalalternatives are available.The Secret of Scent , a book thatprovides an enthusiastic description of perfumes and the artand science behind their creation, was used. Written at a levelintended 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 (Figure1)19 ,20 using essential oils (i.e.,the fragrant oils obtained from plant material through steam-distillation). Students began to develop proper lab safety,technique, and notebook-keeping skills. They also learned basicperfume terminology (essential oils, notes, and chords), as wellas the concept of volatility.

The second lab within the introduction unit was molecularmodeling, where students learned how chemical structurerelates to fragrance (Figure2). The lab consisted of classroomactivities involving Lewis dot and molecular modeling kitssprinkled throughout a lecture. The goal was to provide

students with a basic understanding of the language chemistsuse 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 werealso important, however, for better understanding the assignedSecret of Scent readings, as well as daily life issues, such as thestructures found in pharmaceutical prescriptions.Extraction Unit

The next unit in the course was the extraction of fragrantcompounds from natural materials. Now that students had beenintroduced to essences and their importance in the perfumeindustry, a natural progression was to show them how suchmaterials were traditionally obtained. The three primary extraction techniques in the modern fragrance industry aresolvent extraction, distillation, and expression.21 In this course,the focus was on solvent extraction and distillation throughthree lab experiments: enfleurage, distillation of spices, anddistillation of citrus.

Enfleurage, a technique first used by the ancient Egyptians21

and later refined by the Grasse perfume industry, uses fat andsolvent to extract fragrant oils from plant material (Figure3).Both cold and hot enfleurage (also known as maceration,atechnique involving heated oil, rather than fat) were used.22

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, areshown.

Figure 2. In the molecular modeling lab, students learned how to draw Lewis dot structures, progressing to structural formulas, skeletalstructures, and finally molecular models. Here, an example is provided

using isopentyl acetate (banana scent). The goal was to teach themhow to interpret chemical structures and ultimately recognizefunctional groups that commonly result in a characteristic fragrance.

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619615

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 4/7

Hot enfleurage was more successful because a measurablequantity of oils was obtained within a single lab period, whereasthe 3-week intersession was not enough time for coldenfleurage. The latter, however, is not to be entirely dismissedconsidering its importance to the French perfume industry.(Jasmine, for example, requires cold enfleurage because themolecules 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 3months of exposure to plant material. If this course were doneduring a normal 13-week term, the cold enfleurage experimentcould be successfully carried out as a semester-long effort.

Following the enfleurage lab, students moved on todistillation. Not only does this technique originate from ancientcivilization, but it also plays a role in the modern world (e.g.,the liquor and petroleum industries). In two separatelaboratories, students steam-distilled spices (cloves, cinnamonsticks, 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 citrusdistillation, students used an FT-IR to compare their product toa published spectrum of limonene, the oil found in orange peel.

The extraction unit thus taught students to consider suchparameters as time, labor, and expense in assessing the cost- benefits of fragrant oil extraction. Although many advocate theuse of “ natural products” in the food and fragrance industry,economics often dictates otherwise.Synthesis Unit

In the synthesis unit, students were taught an alternativeapproach 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 fragrantester (Figure4).25 Students were assigned one of four differentreactions resulting in either ethyl cinnamate (cinnamon),isobutyl propionate (rum), isopentyl acetate (banana), ormethyl salicylate (wintergreen).

An important point in this unit was that whereas extractioncan produce a more complex bouquet of aromas, synthesiscould yield a less expensive product (whose quality does not

depend on seasonal conditions) in a controlled and optimizedreaction. The idea of using chemistry to (cheaply) mimic natureis a focus of numerous industries and is an example of how aconcept learned in the lab can apply to daily life. In addition,the development of new perfumes as a result of new discoveriesprovides historical perspective and can initiate a discussion onhow the desire to produce aless expensive perfume led toprogress in organic chemistry.26 ,27 Fouge  ̀re Royale (1884), forexample, was the first perfume to incorporate asy ntheticchemical (coumarin, found naturally in tonka beans).26

Characterization Unit

Now familiar with where fragrances come from, students nextencountered how to determine what they had. The idea of identifying a single component had already been introduced tothe students by running an FT-IR of the distilled citrus oil in aneffort to identify limonene. Perfumes and many fragrantessences, however, represent complex mixtures. As a result,chromatography in which mixtures are separatedintocomponents plays a primary role in the perfume industry.28 ,29

Imposter fragrances, for example, derive from gas chromatog-raphy −mass spectrometry (GC−MS) results of designerperfumes.

To introduce students to chromatography, the first labconsisted of thin-layer chromatograph y (TLC) adapted from anexperiment developed by Pelter et al.30 For example, studentscompared distilled spice oil to eugenol, the primary componentin clove oil (Figure5). The exercise provided a visualdemonstration of chromatography and the meaning of stationary and mobile phases.

Following the TLC experiment, students were introduced togas chromatography (GC). Emphasis was placed on the ideathat now an instrument would be used to accomplish what they had manually done with the TLC lab (Figure5). Anexperiment comparing imposter and designer fragrances wasdeveloped based on Mowery et al.31

Additional experiments could involve analysis of a perfume’ sheadspace32 or even comparison of components in the liquidperfume to the headspace, emphasizing the possible difference betw een what is applied to the skin and what reaches thenose.31 Introducing solid-phase microextraction (SPME) wouldallow one to capture the scent of a liveflo wer, spices,33 herbs,and consumer products (e.g., shampoo).34

Figure 3. The extraction unit involves cold enfleurage where plantmaterial was pressed into a layer of fat, allowing the fragrantcompounds to adsorb into the fat, from which they could be isolatedthrough solvent extraction. Here, roses were used for illustrativepurposes, though jasmine is the traditional flower associated withenfleurage.22 The petals are frequently replaced until the fat is

saturated, a process that can take several months.

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

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619616

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 5/7

Application Unit

The final unit of the course examined applications of fragrancesto consumer products (Figure6).35 In two separate

laboratories, students made soap and lotion based onexperiments developed by S. T. Mabrouk.36 ,37 The soap lab was actually split into two parts. Students made soap earlier inthe semester, letting it harden for two weeks. They thencharacterized the soap, measuring pH and conducting latheringtests. Concepts included surfactants and oil/water emulsions.The lotion lab followed up the discussion of surfactants andalso introduced viscosity. An advantage of these twolaboratories was that students created tangible products thatthey could take home and use.

An alternative lab was the making of bath bombs.38

Composed of sodium bicarbonate and citric acid, bath bombsfizzle when dropped into water, thus prompting a discussion onacid− base chemistry.

■ HAZARDS

The laboratories described in this course consist of a variety of chemicals. MSDS forms should be made available andconsulted prior to each experiment. In particular, dichloro-methane (used in the distillation laboratories) is a possiblecarcinogen. Diethyl ether (synthesis lab), ethyl acetate, andhexanes (TLC lab) are volatile and highly flammable. Sodiumhydroxide (soap lab) is corrosive. It should also be noted thatsome students may exhibit heightened sensitivity to theconcentrated fragrances used in the perfume, soap, lotion,and bath bomb laboratories, possibly developing a rash uponexposure to the skin. Gloves and goggles should be worn at all

times, and the lab should be well-ventilated.■ STUDENT ASSESSMENT

Students were assessed with a safety quiz (50 pts), labtechnique (50 pts), 10 lab reports (50 pts each), a multiple-choice final exam (100 pts), and a presentation (100 pts) (800pts total). The safety quiz tested course policies and ensuredstudents understood the safety regulations. All students beganthe 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 prelabassignment, a conclusion in which students summarized the lab

and their key findings, and postlab questions that tested theirunderstanding of the concepts. To ensure that students werereadingThe Secret of Scent , each postlab included one question based on the assigned material. The final exam tested studentson concepts encountered in each of the laboratories. For thepresentation, students chose a topic related to perfume andthen gave a 10−12 min presentation using PowerPoint. Topics varied from fragrance marketing to hazardous materials andperfume history. One pair of students even produced acommercial, celebrating the official“ debut” of Eau de Cougar ,a fragrance created during the perfume design lab. The secondtime that the course was offered, a participation grade wasincluded based on class discussions following each unit.

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

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

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619617

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 6/7

Discussion focused on concepts and issues related to each unit,as outlined in Table1.

■ EVALUATION OF COURSEStudents took a pre- and postcourse survey regarding their background in science and outlook on chemistry (Table2).

Students were asked about their attitude toward chemistry on ascale of 1 (dislike) to 5 (like). Before the course, the average

response was 2.7, whereas, after the course, the averageincreased to 3.8, indicating a higher level of interest inchemistry. When asked if they would want to take anotherscience course or another lab course, the general response was2.9 for both types (on a scale of 1 (no interest) to 5 (highinterest)). Given that 87% of the students had enrolled in thecourse simply to satisfy a graduation requirement, theseresponses were promising.

In general, student feedback was positive. The overallevaluation of the course was 4.5 (with 1 being poor and 5 being excellent). The favorite laboratories were the application- based ones (soap, lotion, and bath bombs) whereas the leastfavorite lab was the molecular modeling one. This intenseactivity would admittedly be better handled in a traditionallecture and lab course. One student, however, commented thathe enjoyed it because

“

it was like solving logic games.”

■ EXTENSION OF COURSE Although this course was offered over an intense 3-week period,the laboratories could be offered separately on a weekly basisduring the course of a normal semester. In addition, such acourse could be developed further to include a lecturecomponent. Several concepts, fundamental to chemistry, werecovered in the laboratories and could be taught in greater detailduring a lecture. Possible textbooks are listed in theSupportingInformation. The topic could also be incorporated into atraditional 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.

■ CONCLUSION A laboratory course for nonscience majors on the chemistry of perfume was developed. The primary goal was to instill anappreciation and interest in chemistry in students who arepursuing studies in other fields. The topic of perfume isinterdisciplinary, encouraging students to relate chemistry withother subjects. Such connections are the hallmark of a liberalarts education and can help students develop or increase theirscientific awareness. Encouraging the students to consider where the components in a product come from or how to

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

■ ASSOCIATED CONTENT*S Supporting Information

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

■ AUTHOR INFORMATION

Corresponding Author

* E-mail:jlogan@washjeff.edu.

■ ACKNOWLEDGMENTSThe authors would like to thank the students who have takenthe Chemistry of Perfumecourse for their enthusiasm andparticipation. Special thanks are also given to Michael Leonardfor his input and encouragement.

■ 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 theseJCE references is provided in theSupporting

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) Go  ́mez, M. J.; Herrera, S.; Sole  ́ , D.; García-Calvo, E.;

Ferna  ́ndez-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. Biodiversity2008 , 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.

Table 2. Course Evaluation ResponsesQuestion Precoursea Postcoursea

What is your attitude toward chemistry? 2.7 (± 1.0) 3.8 (± 0.8)If you could take anothersciencecourse, would you be interested?

NA 2.9 (± 1.1)

If you could take anotherlab course, would you beinterested?

NA 2.9 (± 0.8)

Overall evaluation of the course NA 4.5 (± 0.6)a Ratings are based on a scale of 1 (dislike; no interest; poor) to 5(like; high interest; excellent). Averages (± standard deviations) areprovided for 18 students (surveyed in the 2009 offering).

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619618

7/30/2019 ed2004033[1]

http://slidepdf.com/reader/full/ed20040331 7/7

(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 , 2nded.; D.C. Heath and Company: Lexington, MA, 1994; pp 385−399.(26) de Nicolaï, P.Chem. Biodiversity2008 , 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.; RoyalSociety 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).

Journal of Chemical Education Article

dx.doi.org/10.1021/ed2004033 | J. Chem. Educ. 2012, 89, 613 −619619