Revisiting a Green Polymerization of Aspartic Acid for a Second-Semester Introductory Organic Chemistry Laboratory: Improvements, Learning Objectives, and Post-Laboratory Assignment

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 23 (2018) pp 221-226

Revisiting a Green Polymerization of Aspartic Acid for a Second-Semester Introductory Organic Chemistry Laboratory: Improvements, Learning Objectives, and Post-Laboratory Assignment

Sydney Andrzejak, Stefani Moyer, Brandon Quillian, and Nathaniel Shank*

Department of Chemistry and Biochemistry, Georgia Southern University, Savannah, GA 31419, nshank@georgiasouthern.edu
Received August 7, 2018. Accepted September 19, 2018.

Published: 25 October 2018

Abstract. As polymeric materials continue to play a pivotal role in modern society, it is imperative that chemists entering the workforce are properly trained in the fundamentals of the science. Chemistry curricula across the country are rapidly changing to provide better polymer instruction to satisfy this demand for both industry and academia. To help facilitate this, new course work and labs need to be vetted and interwoven into the curriculum. Here is described the implementation of a two-step, green synthesis of sodium poly(aspartate) (PAA) into a second-year organic chemistry laboratory course that interweaves polymer chemistry concepts with traditional organic chemistry–carboxylic acid derivative reactivity, understanding acyl substitution reactions and mechanisms, interpreting IR and ¹H NMR data, and calculating percent yield. These objectives also delve into the fundamental principles of Le Chatelier’s principle, stoichiometry and solubility. This experiment provides modifications to existing literature protocols to improve safety, learning outcomes, and product purity. The protocol has been performed successfully over several semesters in multiple sections of a second-semester organic chemistry laboratory.

Key Words: Laboratories and Demonstrations; organic chemistry; polymer chemistry; carboxylic acids; equilibrium hands-on learning / manipulatives; polymerization; second-year undergraduate spectroscopy

(*) Corresponding author. (E-mail: nshank@georgiasouthern.edu )

Article in PDF format (203 KB) HTML format

Supporting Materials:

The Supporting Information including a detail experimental procedure with student friendly set-up pictures, hazards, spectroscopic data, and a student handout that includes postlab questions and notes for the instructor. (648 KB)