Less Cookbook and More Research! Synthetic Efforts Toward JBIR-94 and JBIR-125: a Student-Designed Research Project in a Sophomore Organic Chemistry Lab

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 19 (2014) pp 028-033

Less Cookbook and More Research! Synthetic Efforts Toward JBIR-94 and JBIR-125: a Student-Designed Research Project in a Sophomore Organic Chemistry Lab

Michael A. Christiansen,* Cathy L. Crawford, Chad D. Mangum

Utah State University, Uintah Basin Regional Campus: 320 North Aggie Blvd, Vernal, UT, 84078, m.christiansen@usu.edu
Received August 9, 2013. Accepted January 23, 2014.

Published: 15 February 2014

Abstract. In light of the meaningful learning gains that can be obtained through a genuine research experience, chemistry educators have had a longstanding interest in making teaching labs less “cookbook-like” and more research-driven [1]. With this mindset, we recently restructured our two-semester sophomore organic chemistry lab course to include a synthesis project that was chosen, designed, and carried out by students. This led to progress toward the syntheses of JBIR-94 and JBIR-125, two antioxidative/anticancer natural products that have yet to be assembled through organic chemistry. The major drawback of our course redesign is that it requires close supervision by an instructor or TA experienced in synthetic chemistry and is limited to small class sizes. Its up-front cost is also prohibitive; however, this can be minimized by employing synthetic steps that involve reagents already available on-site. The advantage of this restructuring is encapsulated by highly-positive student feedback and enthusiasm, which led all participating students to continue working on the project after the semester had ended. Exam performance is also discussed. For reference, complete and reproducible experimental details and full copies of student evaluation results are included as Supporting Materials.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: m.christiansen@usu.edu)

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Supporting Materials:

The Supporting Materials include full experimental details (including spectroscopic data, full-color photographs, and illustrations), written with sufficient clarity to be employable in synthetic lab courses, for the following transformations: 3 ® 4 and 4 ® 5 from Scheme 1, and 8 ® 9 and 9 ® 10 from Scheme 2. It also includes full copies of student evaluations, which were administered using the IDEA Center Student Ratings system [27], course syllabi, and a detailed cost breakdown. (6.5 MB)