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ERIC Number: EJ1269330
Record Type: Journal
Publication Date: 2020-Aug
Pages: 4
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
Getting the Classroom Closer to Research Work: Undergraduate Students Prepare "N"- Hexylcinnamamide
Varela, Carla L.; Cabral, Ana M. T. D. P. V.; Barbosa, Isabel R.; Costa, Saul C.; Silva, Elisiário J. T.; Roleira, Fernanda M. F.
Journal of Chemical Education, v97 n8 p2366-2369 Aug 2020
Amides are usually prepared using amines and acyl halides, which often implies a two-step procedure. Alternatively, coupling reagents can be used in a single-step reaction with good yields, which seems to be suitable for organic chemistry laboratory classes. This work was designed to synthesize "N"-hexylcinnamamide through a one-step reaction from cinnamic acid using the coupling reagent benzotriazol-1-yloxytri(pyrrolidino)phosphonium hexafluorophosphate (PyBOP). The purification of "N"-hexylcinnamamide, using various laboratory techniques, as well as its structural elucidation by spectroscopic methodologies, is also addressed. In addition, the theoretical partition coefficient (log "P") values of "N"-hexylcinnamamide and of cinnamic acid are predicted. The proposed experiment is developed in three laboratory classes and is planned for second-year undergraduate students. In summary, it is expected that students broaden their knowledge about amide synthesis, laboratory techniques, and spectroscopic characterization, especially IR and NMR. Besides the pedagogical enhancements, this activity also allows students to be in contact with research work based on the chemical modification of natural products according to a medicinal chemistry approach.
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A