Didactic sequence to teach laboratory techniques in organic chemistry: analysis of terpenes in common medicines

Main Article Content

Brenda de Moraes Cordeiro
Carlos Magno Rocha Ribeiro

Abstract

This work presents a didactic sequence (DS) for teaching key laboratory techniques—continuous and discontinuous extraction, vacuum and atmospheric distillation, steam extraction, and thin-layer chromatography (TLC)—to first-year organic chemistry students. Grounded in inquiry-based learning and investigative methodology, the DS integrates various educational strategies: problem-based learning, theoretical and experimental investigation, and result discussions. The experiments used commercial dental and muscular pain medications and essential oils containing terpenes, analyzed by TLC. Implemented from 2017 to 2019 during seven weekly lab sessions of 3 to 4 hours each in an undergraduate organic chemistry course at Universidade Federal Fluminense, Brazil, the DS aimed to foster students’ deductive reasoning and understanding of the techniques’ interrelations, linking them to real-life medicinal products. The approach increased student engagement and participation, resulting in improved learning outcomes. This improvement was evident both in final exams and in more active and informed classroom discussions compared to previous years.

Article Details

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Author Biographies

Brenda de Moraes Cordeiro, Programa de Pós-Graduação em Ensino de Ciências da Natureza, Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Brasil

Bacharel em Química Industrial e graduanda no curso de Farmácia pela Universidade Federal Fluminense - UFF.

Carlos Magno Rocha Ribeiro, Programa de Pós-Graduação em Ensino de Ciências da Natureza, Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Brasil

Tem graduação em Engenharia Química pela Faculdade de Engenharia Química de Lorena (1985), atualmente USP interior, mestrado e doutorado em Química Orgânica pela Universidade de São Paulo, 1988 e 1992, respectivamente. Realizou um pós-doutarado na França, Universidade Renné Descartes nos anos 1992-1993, e na Universidade de Alicante (Espanha) nos anos de 2011-2012. É Professor Titular (Classe-E) da Universidade Federal Fluminense desde dezembro de 2015. Tem experiência na área de Química, com ênfase em Síntese Orgânica, atuando principalmente nos seguintes temas: aplicação de sais de tálio III em química orgânica, reação de Reformatsky assimétrica, aplicação de ultrasom e microondas em síntese orgânica e transformação química em produtos naturais. Estes estudos visam a síntese de produtos naturais terrestres e marinhos biologicamente ativos e fármacos. O Prof. tem ainda desenvolvido trabalhos na área de Ensino de Química, Divulgação Científica e Extensão, na publicação de livros e artigos científicos, bem como no desenvolvimento de produtos instrucionais para o ensino e divulgação científica como, por exemplo, áudios, vídeos, jogos e kits educacionais.

References

Ahmad, Z., Ammar, M., Sellami, A., & Al-Thani, N. J. (2023). Effective pedagogical approaches used in high school chemistry education: A systematic review and meta-analysis. Journal of Chemical Education, 100(5), 1796–1810. https://doi.org/10.1021/acs.jchemed.2c00739 DOI: https://doi.org/10.1021/acs.jchemed.2c00739

Bott, T. M., & Wan, H. (2013). Using essential oils to teach advanced-level organic chemistry separation techniques and spectroscopy. Journal of Chemical Education, 90(8), 1064–1066. https://doi.org/10.1021/ed300736j DOI: https://doi.org/10.1021/ed300736j

Caramay, C. S., & Ortega-Dela Cruz, R. A. (2023). Problem-based learning and its effects on achievement and attitude in science among grade 8 students. Investigações em Ensino de Ciências, 28(1), 97–110. https://doi.org/10.22600/1518-8795.ienci2023v28n1p97 DOI: https://doi.org/10.22600/1518-8795.ienci2023v28n1p97

Carrizo, M. A., Giménez, M. E., Barutti, M. E., & Cayo, I. J. (2022). El abordaje de pH en contexto áulico desde la interpretación de situaciones cotidianas. Educación Química, 33(2), 94–105. https://doi.org/10.22201/fq.18708404e.2022.2.79628 DOI: https://doi.org/10.22201/fq.18708404e.2022.2.79628

Castro, M. C., Ramos, L. W. C., Alves, E. S., & Saqueti, B. H. F. (2021). Chemistry and food: A didactic sequence for teaching chemistry using the three pedagogical moments for teaching inorganic functions. Research, Society and Development, 10(14), e208101421914. https://doi.org/10.33448/rsd-v10i14.21914 DOI: https://doi.org/10.33448/rsd-v10i14.21914

DeFrancesco, J. V. (2021). Extraction and analysis of eugenol from cloves. Journal of Forensic Science Education, 3(1). https://jfse-ojs-tamu.tdl.org/jfse/article/view/41

Dhifi, W., Bellili, S., Jazi, S., Bahloul, N., & Mnif, W. (2016). Essential oils’ chemical characterization and investigation of some biological activities: A critical review. Medicines, 3(4), 25. https://doi.org/10.3390/medicines3040025 DOI: https://doi.org/10.3390/medicines3040025

Dougherty, C. M., Baumgarten, R. L., Sweeney, A., Jr., & Concepcion, E. (1977). Phthalimide, anthranilic acid, benzyne: An undergraduate organic laboratory sequence. Journal of Chemical Education, 54(10), 643–644. https://doi.org/10.1021/ed054p643 DOI: https://doi.org/10.1021/ed054p643

El Asbahani, A., Miladi, K., Badri, W., Sala, M., Addi, E. H. A., Casabianca, H., El Mousadik, A., Hartmann, D., Jilale, A., Renaud, F. N. R., & Elaissari, A. (2014). Essential oils: From extraction to encapsulation. International Journal of Pharmaceutics, 483(1–2), 220–243. https://doi.org/10.1016/j.ijpharm.2014.12.069 DOI: https://doi.org/10.1016/j.ijpharm.2014.12.069

Fagundes, T. da S. F., Dutra, K. D. B., Ribeiro, C. M. R., Epifanio, R. de A., & Valverde, A. L. (2016). Using a sequence of experiments with turmeric pigments from food to teach extraction, distillation, and thin-layer chromatography to introductory organic chemistry students. Journal of Chemical Education, 93(2), 326–329. https://doi.org/10.1021/acs.jchemed.5b00138 DOI: https://doi.org/10.1021/acs.jchemed.5b00138

García, M. de L. C., Gutiérrez, A. R., Mejía, A. R., & Mejía, T. A. G. (2024). Propuesta experimental docente para la síntesis de nanomateriales magnéticos: Nanopartículas magnéticas en montmorillonita. Educación Química, 35(1), 27–42. https://doi.org/10.22201/fq.18708404e.2024.1.85753 DOI: https://doi.org/10.22201/fq.18708404e.2024.1.85753

Genoveze, L. G. R., de Queirós, W. P., & Genovese, C. L. C. R. (2020). O ensino dos processos e usos do alumínio na perspectiva da Pedagogia Histórico-Crítica. Educación Química, 31(1), 62–83. https://doi.org/10.22201/fq.18708404e.2020.1.69234 DOI: https://doi.org/10.22201/fq.18708404e.2020.1.69234

Ghirardi, M., Marchetti, F., Pettinari, C., Regis, A., & Roletto, E. (2014). A teaching sequence for learning the concept of chemical equilibrium in secondary school education. Journal of Chemical Education, 91(1), 59–65. https://doi.org/10.1021/ed3002336 DOI: https://doi.org/10.1021/ed3002336

Ibrahim, N. H., Surif, J., Hui, K. P., & Yaakub, S. (2014). “Typical” teaching method applied in chemistry experiment. Procedia - Social and Behavioral Sciences, 116, 4946–4954. https://doi.org/10.1016/j.sbspro.2014.01.1054 DOI: https://doi.org/10.1016/j.sbspro.2014.01.1054

Jegstad, K. M. (2023). Inquiry-based chemistry education: A systematic review. Studies in Science Education, 59(1), 1–63. https://doi.org/10.1080/03057267.2023.2248436 DOI: https://doi.org/10.1080/03057267.2023.2248436

Joseph, V. R. (2000). Experimental sequence: A decision strategy. Quality Engineering, 12, 387–393. https://doi.org/10.1080/08982110008962602 DOI: https://doi.org/10.1080/08982110008962602

Just, J., Bunton, G. L., Deans, B. J., Murray, N. L., Bissember, A. C., & Smith, J. A. (2016). Extraction of eugenol from cloves using an unmodified household espresso machine: An alternative to traditional steam-distillation. Journal of Chemical Education, 93(1), 213–216. https://doi.org/10.1021/acs.jchemed.5b00476 DOI: https://doi.org/10.1021/acs.jchemed.5b00476

Kazemi, A., Iraji, A., Esmaealzadeh, N., Salehi, M., & Hashempur, M. H. (2024). Peppermint and menthol: A review on their biochemistry, pharmacological activities, clinical applications, and safety considerations. Critical Reviews in Food Science and Nutrition, 1–26. https://doi.org/10.1080/10408398.2023.2296991 DOI: https://doi.org/10.1080/10408398.2023.2296991

Kowalczyk, A., Przychodna, M., Sopata, S., Bodalska, A., & Fecka, I. (2020). Thymol and thyme essential oil—New insights into selected therapeutic applications. Molecules, 25(18), 4125. https://doi.org/10.3390/molecules25184125 DOI: https://doi.org/10.3390/molecules25184125

Leite, D. O. D., Costa, L. R., Lopes, C. M. U., Rodrigues, A. Y. F., & da Costa, J. G. M. (2020). Physical properties of essential oils: An experimental tool in chemistry teaching. Research, Society and Development, 9(10), e5529108889. https://doi.org/10.33448/rsd-v9i10.8889 DOI: https://doi.org/10.33448/rsd-v9i10.8889

Marques, N. L. R., & da Rosa, C. T. W. (2023). Algumas implicações pedagógicas da Escola de Vygotsky para o ensino de ciências. Obutchénie. Revista de Didática e Psicologia Pedagógica, 7(3), 1–22. https://doi.org/10.14393/OBv7n3.a2023-72097 DOI: https://doi.org/10.14393/OBv7n3.a2023-72097

Moghaddam, M., & Mehdizadeh, L. (2017). Chemistry of essential oils and factors influencing their constituents. In A. M. Grumezescu & A. M. Holban (Eds.), Soft chemistry and food fermentation. A volume in Handbook of Food Bioengineering (pp. [páginas si se conocen]). Academic Press. https://doi.org/10.1016/B978-0-12-811412-4.00013-8 DOI: https://doi.org/10.1016/B978-0-12-811412-4.00013-8

Motokane, M. T. (2015). Sequências didáticas investigativas e argumentação no ensino de ecologia. Ensaio Pesquisa em Educação em Ciências, 17, 115–137. https://doi.org/10.1590/1983-2117201517s07 DOI: https://doi.org/10.1590/1983-2117201517s07

Novita, D., Kurnia, F. D., & Mustofa, A. (2020). Collaborative learning as the manifestation of sociocultural theory: Teachers’ perspectives. Exposure: Jurnal Pendidikan Bahasa Inggris, 9(1), 13–25. https://doi.org/10.26618/exposure.v9i1.2888 DOI: https://doi.org/10.26618/exposure.v9i1.2888

Nichols, L. (2019). Organic chemistry lab techniques. LibreTexts. https://libretexts.org

O’Shea, S. K., von Riesen, D. D., & Rossi, L. L. (2012). Isolation and analysis of essential oils from spices. Journal of Chemical Education, 89(5), 665–668. https://doi.org/10.1021/ed101141w DOI: https://doi.org/10.1021/ed101141w

Pelter, L. S. W., Amico, A., Gordon, N., Martin, C., Sandifer, D., & Pelter, M. W. (2008). Analysis of peppermint leaf and spearmint leaf extracts by thin-layer chromatography. Journal of Chemical Education, 85(1), 133–134. https://doi.org/10.1021/ed085p133 DOI: https://doi.org/10.1021/ed085p133

Purcell, S. C., Pande, P., Lin, Y., Rivera, E. J., Paw U, L., Smallwood, L. M., Kerstiens, G. A., Armstrong, L. B., Robak, M. T., Baranger, A. M., & Douskey, M. C. (2016). Extraction and antibacterial properties of thyme leaf extracts: Authentic practice of green chemistry. Journal of Chemical Education, 93(8), 1422–1427. https://doi.org/10.1021/acs.jchemed.5b00891 DOI: https://doi.org/10.1021/acs.jchemed.5b00891

Ribeiro, C. M. R., Valverde, A. L., Ribeiro, M. M. J., Souza, T. S. G., Fagundes, T. S. F., Bittencourt, L. B., Dutra, K. D. B., & Epifanio, R. de A. (2015). A videoaula “Cromatografia em camada delgada” e a motivação da aprendizagem nas disciplinas experimentais de química orgânica dos cursos de química, engenharia química e farmácia da UFF. Revista Virtual de Química, 7(3), 1030–1055. https://doi.org/10.5935/1984-6835.20150056 DOI: https://doi.org/10.5935/1984-6835.20150056

Rodríguez-Arteche, I., & Martínez-Aznar, M. (2016). Introducing inquiry-based methodologies during initial secondary education teacher training using an open-ended problem about chemical change. Journal of Chemical Education, 93(9), 1528–1535. https://doi.org/10.1021/acs.jchemed.5b01037 DOI: https://doi.org/10.1021/acs.jchemed.5b01037

Sereda, G. A. (2006). A sequence of linked experiments, suitable for practical courses of inorganic, organic, computational chemistry, and NMR spectroscopy. Journal of Chemical Education, 83(6), 931–933. https://doi.org/10.1021/ed083p931 DOI: https://doi.org/10.1021/ed083p931

Silva, R. S., Ribeiro, C. M. R., Borges, M. N., & Blois, G. S. O. (2009). Óleo essencial do limão no ensino de cromatografia em camada delgada. Química Nova, 32(8), 2234–2237. https://doi.org/10.1590/S0100-40422009000800042 DOI: https://doi.org/10.1590/S0100-40422009000800042

Sjöström, J., & Talanquer, V. (2014). Humanizing chemistry education: From simple contextualization to multifaceted problematization. Journal of Chemical Education, 91(8), 1125–1131. https://doi.org/10.1021/ed5000718 DOI: https://doi.org/10.1021/ed5000718

Tako, K. V., & Kameo, S. Y. (2023). Metodologia da pesquisa científica dos conceitos teóricos à construção do projeto de pesquisa (70 p.). Editora Amplla. https://ampllaeditora.com.br/books/2023/03/MetodologiaPesquisa.pdf DOI: https://doi.org/10.51859/amplla.mpc119.1123-0

Taleuzzaman, M., Pooja, J., Rishabh, V., Zeenat, I., & Mirza Aamir, M. (2021). Eugenol as a potential drug candidate: A review. Current Topics in Medicinal Chemistry, 21(20), 1804–1815. https://doi.org/10.2174/1568026621666210701141433 DOI: https://doi.org/10.2174/1568026621666210701141433

Xavier, V., Spréa, R., Finimundy, T. C., Heleno, S. A., Amaral, J. S., Barros, L., & Ferreira, I. C. F. R. (2023). Terpenes. In M. Carocho, S. A. Heleno, & L. Barros (Eds.), Natural secondary metabolites (pp. [páginas si se conocen]). Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_5 DOI: https://doi.org/10.1007/978-3-031-18587-8_5

Yang, H., Huang, X., Yang, M., Zhang, X., Tang, F., Gao, B., Gong, M., Liang, Y., Liu, Y., Qian, X., & Li, H. (2024). Advanced analytical techniques for authenticity identification and quality evaluation in essential oils: A review. Food Chemistry, 451, 139340. https://doi.org/10.1016/j.foodchem.2024.139340 DOI: https://doi.org/10.1016/j.foodchem.2024.139340