The undergraduate organic chemistry course is a prerequisite course for many students who plan to pursue careers in chemistry and chemical engineering. It also serves those students who wish to pursue professional careers in medicine, dentistry, and veterinary sciences. Previous research on student learning in organic chemistry shows that students struggle to understand ideas such as acid-base reactions and structure-property relationships which are foundational concepts on which more complex concepts are built. Furthermore, the typical organic chemistry course emphasizes students use of the electron-pushing formalism to represent how bonds are formed and broken in chemical reactions. Expert organic chemists use this formalism to represent predicted reaction mechanisms that explain the formation of products. Numerous studies have characterized student difficulties using electron-pushing mechanisms in an expert-like way as well as associating underlying chemical principle with the representations. We suggest that deep understanding of chemical reactions and their underlying chemical principles can be developed by engaging students in causal mechanistic explanation as part of a transformed organic chemistry course that emphasizes students using their knowledge of electrostatics, structure-property relationships, and energy to engage in explanation of chemical phenomena. Our goal is to engage students in as specific type of explanation called in casual mechanistic explanation which includes reasoning about the underlying causal factors in conjunction with the underlying entities and their activities that bring the phenomenon about. The studies reported here use a qualitative approach to elicit student' written explanations and drawn reaction mechanisms for various chemical reactions. Students were sampled at multiple time points over the course of their two-semester organic course to investigate how student reasoning changes overtime. Students participants were enrolled in either the beforementioned transformed organic chemistry course or were enrolled in an untransformed course that we refer to as the traditional context. This traditional context served as a control group for which to compare possible changes in reasoning for students enrolled in the transformed course sequence. Findings suggest that student engagement in causal mechanistic reasoning varies depending on students' general chemistry and organic chemistry course experience as well as the nature of the prompt eliciting the reasoning. Findings also suggest that students are generally capable of drawing mechanistic arrows that would generally be considered correct, however triangulating student reasoning with a detailed analysis of students' drawings, we found that typical organic chemistry assessment items that lack a reasoning component may overestimate student understanding. Our investigations also revealed student difficulties invoking the correct nucleophilic substitution process for a given reaction. Students often invoked an SN1 mechanistic process incorrectly, despite their engagement in casual mechanistic reasoning. Implications of these findings for organic chemistry instruction and assessment are discussed along with implications for future research.

Reasoning about structure-reactivity and chemical processes is a key competence in chemistry. Especially in organic chemistry, students experience difficulty appropriately interpreting organic representations and reasoning about the underlying causality of organic mechanisms. As organic chemistry is often a bottleneck for students’ success in their career, compiling and distilling the insights from recent research in the field will help inform future instruction and the empowerment of chemistry students worldwide. This book brings together leading research groups to highlight recent advances in chemistry education research with a focus on the characterization of students’ reasoning and their representational competencies, as well as the impact of instructional and assessment practices in organic chemistry. Written by leaders in the field, Student Reasoning in Organic Chemistry is ideal for chemistry education researchers, instructors and practitioners, and graduate students in chemistry education.

Our goal as scientists is to help students make sense of the world by building on their prior knowledge and engaging with what they already understand. Undergraduate students bring with them a whole host of experiences from their prior educations and their prior experiences in the world. To be successful in their coursework and in future courses, students must make connections between their knowledge and the core ideas of a discipline. These connections are necessary for students to be successful in many of their courses as they move from a novice with disconnected understanding to a more integrated expert like understanding. Undergraduate organic chemistry is one such course and is often a prerequisite to many courses that are required for pre professional schools, such as medical and veterinary school. However, previous research shows that students often rely on surface level features and memorization to be successful in organic chemistry. In particular, prior research has found that students struggle with using mechanistic arrows, a tool used to predict the movement of electrons and predict reaction mechanisms. My work seeks to characterize and understand better ways to support students learning mechanistic arrows in organic chemistry.This dissertation focuses on how students use mechanistic arrows in both familiar and unfamiliar reactions. This work was situated within a transformed organic chemistry course that emphasizes students constructing explanations and developing and using models and explicitly making connections to structure property relationships and electrostatic and . However, students can take many combinations of courses throughout their time as undergraduates, and I explored how these different course types and backgrounds affected how students draw mechanistic arrows for both familiar and unfamiliar reactions.The studies in this dissertation used both quantitative and qualitative techniques to examine students use and understanding of reaction mechanisms. Student participants were sampled from both the two-semester transformed organic curriculum and a course that has not undergone a transformation, referred to in this dissertation as a traditional curriculum. By sampling students multiple times throughout both semesters and both course types, this allowed me to investigate the effect various course types and combinations had on students' responses.Findings suggest that students who took two semesters of the transformed course use their arrows to predict a plausible product more frequently that traditional students do for both a familiar and unfamiliar reaction. Furthermore, when exploring the different course combinations students take for organic chemistry, I found that students' ability to draw arrows varies depending on their organic chemistry course background. Students who most recently took the transformed curriculum were better able to make plausible predictions with their mechanistic arrows than the traditional students. While students who had the transformed curriculum for the first semester and switched to the traditional curriculum for the second semester did not draw plausible mechanisms as frequently as students who took the transformed curriculum for both semesters. This emphasizes the importance of consistent course environments that support students' engagement with the core ideas of a discipline. Additionally, I describe the process of developing a task designed to elicit students' explanations and understandings of an unfamiliar intramolecular reaction. Implications of this work on instructional coherence and future directions will be discussed.

As you can see, this "molecular formula is not very informative, it tells us little or nothing about their structure, and suggests that all proteins are similar, which is confusing since they carry out so many different roles.

Problem solving is central to the teaching and learning of chemistry at secondary, tertiary and post-tertiary levels of education, opening to students and professional chemists alike a whole new world for analysing data, looking for patterns and making deductions. As an important higher-order thinking skill, problem solving also constitutes a major research field in science education. Relevant education research is an ongoing process, with recent developments occurring not only in the area of quantitative/computational problems, but also in qualitative problem solving. The following situations are considered, some general, others with a focus on specific areas of chemistry: quantitative problems, qualitative reasoning, metacognition and resource activation, deconstructing the problem-solving process, an overview of the working memory hypothesis, reasoning with the electron-pushing formalism, scaffolding organic synthesis skills, spectroscopy for structural characterization in organic chemistry, enzyme kinetics, problem solving in the academic chemistry laboratory, chemistry problem-solving in context, team-based/active learning, technology for molecular representations, IR spectra simulation, and computational quantum chemistry tools. The book concludes with methodological and epistemological issues in problem solving research and other perspectives in problem solving in chemistry. With a foreword by George Bodner.