Characterization of First-Semester Organic Chemistry Peer-Led Team Learning and Cyber Peer-Led Team Learning Students’ Use and Explanation of Electron-Pushing Formalism Sarah Beth Wilson † and Pratibha Varma-Nelson* ,‡ † Department of Chemistry, University of Evansville, Evansville, Indiana 47722, United States ‡ Department of Chemistry & Chemical Biology, Indiana University-Purdue University Indianapolis (IUPUI), Indianapolis, Indiana 46202, United States ABSTRACT: The purpose of this parallel convergent mixed methods study was to characterize organic chemistry students’ expression of electron-pushing formalism skills who had participated in peer-led team learning (PLTL) and cyber peer-led team learning (cPLTL), a synchronous online version of peer-led team learning (PLTL) workshops. A new electron-pushing formalism analytic framework was developed from a review of the literature in addition to analysis of students’ interview artifacts, using a constant-comparison process. Utilization of this new electron-pushing formalism analytic framework for coding student interview artifacts revealed that cPLTL students were significantly less likely to successfully draw the product suggested by the curved arrows than their PLTL classmates. Implications for instructors are suggested, including encouraging students to verbally explain their rationale while drawing mechanisms as well as optimizing graphical collaborative learning activities for online learners. KEYWORDS: First-Year Undergraduate/General, Second-Year Undergraduate, Chemical Education Research, Organic Chemistry, Collaborative/Cooperative Learning, Internet/Web-Based Learning, Problem Solving/Decision Making, Distance Learning/Self Instruction, Constructivism, Mechanisms of Reactions FEATURE: Chemical Education Research ■ INTRODUCTION The roots of electron-pushing formalism (EPF) 1 extend from a paper by Kermack and Robinson, 2 who described the movement of electron density from areas of high electron density to areas of low electron density in the conjugated π system of butadiene. The curved arrows of EPF are “a symbolic device for keeping track of electron pairs in chemical reactions... as covalent bonds are formed and broken.” 1,3-5 Practicing organic chemists consider EPF to be fundamental for communication and problem-solving to predict the products of reactions, 6,7 including the regio- or stereochemistry of products. 3 Due to the centrality of EPF to organic chemistry, a wealth of EPF instructional strategy literature exists. 4, 5,8-19 A reaction mechanism is the complete description of a reaction pathway, including any reactive intermediates 20 and the curved arrows which represent the flow of electrons at each step of the reaction pathway. Since the publication of Morrison and Boyd’s first organic chemistry textbook in 1959, “reaction mechanisms have become a mainstay of organic chemistry courses.” 3,21-23 As written by Sykes on page one of his Guidebook to Mechanism in Organic Chemistry: 24 The chief advantage of a mechanistic approach, to the vast array of disparate information that makes up organic chemistry, is the way in which a relatively small number of guiding principles can be used, not only to explain and interrelate existing facts, but to forecast the outcome of changing the conditions under which already-known reactions are carried out, and to foretell the products that may be expected from new ones. Thus, EPF could be an alternative to copious rote memorization for organic chemistry students because mecha- nisms give students “a logical means to predict pro- ducts”. 25 Klein’s Organic Chemistry textbook, used by this institution, provided explanations of the rules and assumptions of this formalism to the students. 26 Regrettably, a number of studies of novices’ understanding of EPF have revealed that the symbolism often has limited meaning for students. 3,6,7,27-32 This finding aligns with the proposition that the hardest part of students’ learning science is the requirement that students practice multilevel thought, connect- Received: May 23, 2018 Revised: October 22, 2018 Article pubs.acs.org/jchemeduc Cite This: J. Chem. Educ. XXXX, XXX, XXX-XXX © XXXX American Chemical Society and Division of Chemical Education, Inc. A DOI: 10.1021/acs.jchemed.8b00387 J. Chem. Educ. XXXX, XXX, XXX-XXX Downloaded via UNIV OF SOUTH DAKOTA on November 6, 2018 at 21:10:41 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.