Combinatorial Solid-Phase Synthesis of Aromatic Oligoamides: A Research-Based Laboratory Module for Undergraduate Organic Chemistry

Document Type

Article

Publication Date

2-5-2016

Publisher

American Chemical Society

Abstract

A five-week, research-based experiment suitable for second-semester introductory organic laboratory students is described. Each student designs, prepares, and analyzes a combinatorial array of six aromatic oligoamides. Molecules are prepared on solid phase via a six-step synthetic sequence, and purities and identities are determined by analysis of LC–MS data. This experiment engages students in a research experience: none of the structurally diverse compounds prepared have been previously reported in the literature. After completion of this experiment, products are evaluated for their biological activity in the author’s research laboratory. Although execution of biological experiments falls outside the learning objectives in this course, these applications motivate students. Through these hands-on experiences, students learn about organic chemistry reactions and modern techniques, and their research skills are enhanced.

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