Multi-step Synthesis of Hexaarylbenzene for Organic Chemistry Lab

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 24 (2019) pp 170-173

Multi-step Synthesis of Hexaarylbenzene for Organic Chemistry Lab

Ashley N. Lamm,*^,† Dillon Puhl^†, Abbigail Cox^†, and Joshua J. Pak^‡

^†Department of Chemistry, Biochemistry and Physics, Eastern Washington University, Science 226, Cheney, Washington 99004, alamm@ewu.edu;^‡Department of Chemistry, Idaho State University, Pocatello, Idaho 83209
Received September 11, 2019. Accepted November 11, 2019.

Published: 20 December 2019

Abstract. Over the last two decades, green chemistry has become a routine and important topic in undergraduate organic chemistry curriculum. Despite increasing attention to green chemistry in lectures, there is little corresponding increase in the number of diverse green organic laboratory experiments. This laboratory sequence offers students an introduction to sustainable chemistry concepts and provides research-applicable reactions to synthesize polycyclic aromatic hydrocarbons from simple readily available starting materials. During this multi-step experiment, students gained practical experience performing central organic reactions such as oxidation, condensation and Diels-Alder. Students were encouraged to apply various synthetic techniques to obtain their products, and were assessed on their understanding of the reactions and characterization of their products.

Key Words: Laboratories and Demonstrations; organic chemistry; hands-on learning/manipulatives; aldehydes/ketones; green chemistry; oxidation/reduction; synthesis; aromatic compounds; reactions

(*) Corresponding author. (E-mail: alamm@ewu.edu )

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Supporting Materials:

The Supporting Information available includes: Laboratory Procedures for Students and Supporting Information and Notes for Instructors. (1880 KB)