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Abstract Volume 27 (2022) pp 15-20

Singlet Oxygen in Organic Chemistry

Crist N. Filer

PerkinElmer Health Sciences Inc., 940 Winter Street, Waltham, MA 02451, USA. PerkinElmer Health Sciences Inc., 549 Albany Street, Boston, MA 02118, USA. E-mail: crist.filer@perkinelmer.com.
Received January 4, 2021. Accepted January 5, 2021.

Published: 19 May 2022

Abstract. A multi-faceted polymer chemistry learning experience is highlighted in this laboratory experiment, where students work in pairs to synthesize, purify, characterize, and process a polyacrylate.  This synthesis is accomplished through a radical polymerization without the need for Schlenk flasks or other rigorous air-sensitive techniques.  The target polymer in this lab, poly(butyl methacrylate), allows for the analysis of diverse proton NMR spectra.  In addition, the long alkyl chain decreases the glass transition temperature of the resulting polymer, allowing for student exposure to polymer processing via an in-lab molding step.  This experiment is designed for second-year undergraduate students, and critical concepts learned in organic chemistry, such as radical initiation, propagation, and termination, are reinforced. In addition, spectroscopic analyses such as ¹H NMR splitting patterns, ¹H NMR chemical shifts, and bond identification via IR are included.  Furthermore, students are exposed to concepts that may not be covered in organic chemistry, such as polymer purification, characterization, and processing.

Key Words: KW Laboratories and Demonstrations; organic chemistry; second-year undergraduate; polymer chemistry; laboratory instruction; hands-on learning; alkenes; IR spectroscopy; NMR Spectroscopy

(*) Corresponding author. (E-mail: crist.filer@perkinelmer.com)

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