Microwave-aided reactions of aniline derivatives with formic acid : inquiry-based learning experiments

• Autorzy: Mycak Michael , Doležal Rafael , Bílek Martin , Kolář Karel

Identyfikatory

DOI

10.2478/cdem-2022-0008

• Języki publikacji: EN

Abstrakty

EN

The synthesis of amides belongs to traditional experimental tasks not only in organic chemistry exercises at universities but also at chemically focused secondary schools or in special practices at general high schools. An example of such a synthesis may be the preparation of acetanilide via reaction of aniline with acetic acid or acetic anhydride. However, both of these reactions are associated with a rather long reaction time and certain hazards that limit their straightforward use in pedagogical practice. Conveniently, the reaction of aniline with acetic acid may be significantly optimised if it is performed under solvent-free conditions in the presence of microwaves, which reduces considerably the reaction time and provides very good yield, compared to traditional heating by a heating nest. In this study, the main pedagogical aim of the experimental design is elucidation of the influence of the structure of the amines on the course of the reaction with formic acid through inquiry-based learning. Specifically, the proposed experiments consist in investigation of the chemical yield achieved in microwave assisted reactions of aniline and its derivatives with formic acid in such a way that is adequate for constructive learning of undergraduate chemistry students. The selected series of amines involves aniline, 4-methoxyaniline, 4-chloroaniline, and 4-nitroaniline. In accordance with the chemical reactivity principles, students gradually realise that the influence of the substituent is reflected in the reaction yield, which grows in the following order: N-(4-nitrophenyl)formamide ˂ N-(4-chlorophenyl)formamide ˂ N-phenylformamide ˂ N-(4-methoxyphenyl)formamide. Therefore, the results of the experiments enable students to discover that stronger basicity of the amine increases the yield of the amide. In order to deepen the students’ chemical knowledge and skills, the concept of the experiments was transformed to support inquiry-based student learning. The proposed experiments are intended for experimental learning in universities educating future chemistry teachers, but they may be also utilised in the form of workshops for students at secondary schools of a general educational nature.

Słowa kluczowe

EN

inquiry-based learning; amide synthesis; microwave synthesis; amine structure; amide yield

PL

nauka oparta na zapytaniu; synteza amidów; synteza mikrofalowa; struktura amin

• Wydawca: Towarzystwo Chemii i Inżynierii Ekologicznej
• Czasopismo: Chemistry-Didactics-Ecology-Metrology
• Rocznik: 2022
• Tom: R. 27, NR 1-2
• Strony: 135--151
• Opis fizyczny: Bibliogr. 65 poz., rys., tab., wykr.

Twórcy

autor

Mycak Michael

• Grammar School of Dr. Emil Holub, Na Mušce 1110, 53401 Holice, Czech Republic

autor

Doležal Rafael

• Department of Chemistry and Chemistry Education, Faculty of Education, Charles University, M.D. Rettigové 4, 116 39 Prague, Czech Republic

• https://orcid.org/0000-0001-9495-3934

autor

Bílek Martin

• Department of Chemistry and Chemistry Education, Faculty of Education, Charles University, M.D. Rettigové 4, 116 39 Prague, Czech Republic

• https://orcid.org/0000-0002-1076-4595

autor

Kolář Karel

• Department of Chemistry and Chemistry Education, Faculty of Education, Charles University, M.D. Rettigové 4, 116 39 Prague, Czech Republic

• https://orcid.org/0000-0001-6155-7361

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Uwagi

Opracowanie rekordu ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023).