Discovery-based labs, in which students learn a chemical concept through collecting data in an experiment, instead of through lecture, have been heavily adopted in the general chemistry curriculum. These labs have been shown to enhance student’s understanding of the material, improve engagement in the learning process, and increase student responsibility for learning the material. Unfortunately, data collection in organic chemistry is slow and students rarely collect significant amounts of data. As such, few examples exist of these types of discovery-based experiments in the undergraduate curriculum. We aim to design a discovery-based laboratory demonstrating the relative reactivity of electrophiles and nucleophiles in carboxylic acid derivatives for inclusion into the Carthage College organic chemistry curriculum. Our initial goal was to evaluate the relative effectiveness of synthesizing aspirin from salicylic acid using a variety of carboxylic acid derivatives via microwave irradiation. Unfortunately, we ran into problems with polymerization, toxicity of materials, and cost. Due to these issues, we altered the experiment to evaluate the effectiveness of treating acetic anhydride or ethyl acetate with either phenol or aniline. Each student will attempt their own nucleophilic acyl substitution and the class will combine their data at the end of the class to evaluate the trends. Our preliminary results indicate this new discovery-based lab will provide appropriate results for students to determine the relative reactivity of ethyl acetate and acetic anhydride as well as the relative nucleophilicity of phenol and aniline.       <br/>

Teaching the relative reactivity of carboxylic acid derivatives through a discovery-format laboratory

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.