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