Getting the Classroom Closer to Research Work: Undergraduate Students Prepare N‑Hexylcinnamamide

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-he...

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Bibliographic Details
Published inJournal of chemical education Vol. 97; no. 8; pp. 2366 - 2369
Main Authors Varela, Carla L, Cabral, Ana M. T. D. P. V, Barbosa, Isabel R, Costa, Saul C, Silva, Elisiário J. T, Roleira, Fernanda M. F
Format Journal Article
LanguageEnglish
Published Easton American Chemical Society and Division of Chemical Education, Inc 11.08.2020
Division of Chemical Education, Inc
American Chemical Society
Subjects
Amides
Amines
Chemical synthesis
Chemistry
Cinnamic acid
College Science
College students
Coupling
Halides
Laboratories
Laboratory Experiments
Laboratory Procedures
Natural products
NMR
Nuclear magnetic resonance
Organic Chemistry
Reagents
Science Experiments
Spectroscopy
Students
Teaching methods
Undergraduate Students
Undergraduate study
Hands-On Learning/Manipulatives
amides
Laboratory Instruction
Acids/Bases
Second-Year Undergraduate
Inquiry-Based/Discovery Learning
Organic Chemistry
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Summary: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.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.8b00604