Engaging Students in Organic Chemistry Volume 2

Mastering organic chemistry requires a substantial amount of practice and feedback, but traditionally graded organic chemistry courses do not reflect this reality. An alternative grading model called specifications grading, which focuses on high standards, feedback, and continuous improvement, is ideal for promoting mastery in organic chemistry courses. Partially incorporating specifications grading into my courses has transformed all aspects of my teaching, from designing assessments and providing feedback to writing letters of recommendation. My courses use a hybrid grading system, with specifications-graded aspects mixed with a traditional points-based system. In this chapter, I discuss the design and implementation of this grading system along with advantages and disadvantages. Reminiscent of the historical apprenticeship model of organic chemistry education, specifications grading approaches are well suited to the nature of the subject and are likely to grow in importance and prevalence in the coming years.

Returning to the in-person classroom after a period of online learning during the height of the COVID-19 pandemic brought to light unique challenges regarding student preparation and attitudes about course expectations. A greater number of students are lacking the basic study and learning skills required for higher education. In many organic chemistry courses, these new obstacles are exacerbated by the continued challenges that have historically surrounded the course and must be addressed to provide for students a welcoming and supportive learning environment. With this goal in mind, a large enrollment organic chemistry sequence was redesigned by structuring the class to increase student engagement and accountability. During class, students are taught active study strategies, including a study cycle around each class to avoid cramming before exams, and how to read a textbook. Students are incentivized to prepare to actively participate during class by completing a low-stakes formative assessment due before each class. Additionally, scaffolded practice is introduced throughout the lecture, using polling software to encourage participation. After the week’s material is introduced, activities designed to reinforce the material at an introductory level are assigned midweek. The final class of the week is entirely devoted to practicing more challenging application-based questions, where students have the opportunity to practice with their classmates and ask TAs and the instructor questions. Preliminary results suggest that this highly structured and scaffolded course design lowers the DWF rates, and promotes greater overall participation during class.

There are many strategies for incorporating active learning into the organic chemistry classroom. For an instructor looking to add some of these practices to their course, the issue is not a lack of options. The problem is one of adoption. That is, how do we make it easier for instructors to transition their teaching from passive lecturing to more active learning practices? Organic Chemistry is a dense course packed with material to cover, such that adding active learning components can feel like they come at the cost of cutting required course content. Prelecture videos and assignments are ways to free up time in lecture for more engaging activities without sacrificing important material. Transitioning away from standard passive lectures will certainly require effort, but the payoff is more than just increased student test scores and chemical comprehension. Active learning can help create a sense of community in the classroom and illuminate the significance of organic chemistry in a larger context. These are outcomes that any instructor hopes to instill in their course.

Active learning has been shown to have myriad benefits for students. Many techniques, such as Peer-Led Team Learning, Just-in-Time-Teaching, Classroom Responses Systems, POGIL, Flipped or Semi-Flipped classrooms, and Game-based Learning have become widespread in STEM courses over the last decade. However, approaches that combine the arts and/or pop culture into project-based learning have been largely limited to the humanities through the use of expressivism and multimodal pedagogy or the use of Makerspace pedagogy. In this chapter, two different project-based learning activities that enhance student engagement and application of organic chemistry are highlighted along with their positive impact on student engagement, retention from Organic I to Organic II, critical thinking, and scientific communication in organic chemistry courses. A decrease in DFW rates was also observed with implementation of the projects in the organic sequence.

The chapter describes the development and redesign of a laboratory-based NMR spectroscopy assignment for Organic Chemistry I Laboratory students at the University of Tampa. Initial iterations were adapted from a published guided inquiry-based activity that was designed to improve a student’s ability to interpret ¹H and ¹³C NMR spectra using NMR prediction software. However, implementation of this assignment revealed specific challenges related to technological barriers, student engagement, understanding, and implementation of concepts. Drawing on pedagogical literature and expertise in structure elucidations, a revised assignment was designed to emphasize the structure-spectra relationship using a highly scaffolded, guided-inquiry assignment utilizing web-based prediction tools. Long term gains are still being assessed, but thus far, the redesigned activity has been better received by both faculty and students.

To make the organic chemistry lab apply to the real world, we created a forensics lab in organic chemistry. This lab used qualitative tests to identify the substances. This lab was separated into three sections - testing urine, blood, and drugs. For the urine experiment, the three samples were urine, urine + sugar, and urine + ketone. These liquids were tested with Benedict’s solution and 2,4-dinitro­phenylhydrazine. The students tested for real and fake blood using hydrogen peroxide. The last series of experiments were to test powders and identify these powders as cocaine, ecstasy, gamma-hydroxy butyrate, and ketamine. The powders were tested with acetyl chloride, sodium bicarbonate, and 2,4-dinitro­phenylhydrazine to determine the identity of each compound. The students really enjoyed this lab, as it applied the tests used in a previous qualitative organic chemistry lab to real life.

A Fischer esterification—an acid-catalyzed reaction between a carboxylic acid and an alcohol—is a popular laboratory exercise in the undergraduate organic chemistry lab. Traditional examples often produce liquid esters, such as banana oil, which can be identified by aroma. In this guided inquiry experiment, students synthesized and characterized solid esters, selected for ease of purification and handling. Students were provided with a list of possible carboxylic acids and alcohols but not the specific reactants assigned to each group. After synthesis, they compared the observed melting point range of their product to a reference table. Furthermore, students recorded the IR, ¹H NMR, and ¹³C NMR spectra of their product to confirm their conclusions from the melting point range. This activity required application of critical thinking skills and was widely reported by students as both challenging and enjoyable.

Understanding stereochemistry, particularly the R and S configuration of chiral centers, poses persistent challenges for organic chemistry students due to the abstract, particulate-level reasoning required. To address this, we developed a web-based extended reality (webXR) activity designed to improve students’ spatial reasoning and conceptual understanding of stereochemistry through immersive, interactive learning. Designed for second-year undergraduate students, the activity integrates the real-world context of glutathione to guide students through identifying chiral centers, assigning substituent priorities, rotating molecules, and determining R or S configurations. The activity includes scaffolded instruction, gamification elements, and interactive three-dimensional visualizations. A pilot implementation with 315 students in an Organic Chemistry I course included over 90% of students reporting improved visualization of 3D molecules and over 85% expressing increased confidence in assigning stereochemistry. Open-ended survey responses (N = 310 and N = 308) further highlighted the activity’s engaging nature, while also identifying areas for improvement. This chapter highlights the use of webXR to enhance organic chemistry students’ perceived understanding of complex molecular concepts and visualization skills.

Organic chemistry provides an ideal opportunity within the curriculum for students to apply concepts to new situations. Software-based technological tools can be utilized to engage students with the course material, as they lend themselves to helping students develop critical thinking skills. Rather than memorizing concepts, trends, and mechanisms, software-based provide students with the tools to grasp organic chemistry principles and mechanisms more effectively. Computational activities and augmented reality provide students with diverse learning opportunities, moving beyond traditional textbook limitations to foster a deeper understanding. This chapter explores various technological tools to enhance chemistry education, including computational activities for concept derivation, augmented reality for mastering stereochemistry, visualization tools for conceptual understanding, and generative AI for writing laboratory reports.

In the Indian context, guided-inquiry approaches are not yet an integral part of teaching-learning processes in chemistry classrooms at the undergraduate level, especially in state colleges affiliated with the university system that cater to a large fraction of students. A small group of chemistry teachers, teaching organic chemistry at colleges in Mumbai, were introduced to the Process-Oriented Guided Inquiry learning approach through programs organized at the Homi Bhabha Centre for Science Education (a National Centre of the Tata Institute of Fundamental Research) for orienting teachers towards research-informed practices related to chemistry education. Inspired by this experience, a study was conducted in Mumbai colleges to gather first-hand information on the challenges involved in implementing such instructional materials in Indian classrooms. Encouraging feedback from students prompted teachers to recognize their need to evolve as facilitators and implement group work in the classrooms. As next steps, they engaged in conducting workshops for students (and teachers) that helped them make this transition and also understand the needs of students in such settings. Building on their field experience, teachers began to design their own guided-inquiry activities, primarily for first-year Indian undergraduate students. These activities were piloted in classrooms to gain insights into their strengths and weaknesses and pinpoint areas where adjustments were needed for better learning outcomes, particularly related to language, clarity, question flow, examples used, and concepts addressed. This chapter highlights our experiences using guided-inquiry material, both in offline and online modes with students from different colleges across India.

The term Open Educational Resources (OER) describes teaching-learning materials and resources located in the public domain; its usage, re-mix, and redistribution with no or limited constraints. The richness and diversity of content available in OER can be harnessed to create opportunities for fruitful students’ engagement. Teachers need to be exposed to OER and and shown how to develop such resources. The authors of the current paper were exposed to OER during a workshop held in a local college in Mumbai in 2018. All participants of this workshop were invited to send proposals to the global mentoring programme of the Open Education for a Better World (OE4BW) conducted by the University of Nova Gorica (UNG) and the UNESCO Chair on Open Technologies for OER and Open Learning at the Jožef Stefan Institute (JSI), Slovenia. As part of this, the authors developed the following courses for the OE4BW programme held in 2019, 2020 and 2023: (1) Organic Chemistry of food, (2) Nucleophilic substitution, (3) Organic synthesis - The retrosynthesis way, (4) Pericyclic reactions, and (5) Basics of stereochemistry. This paper will primarily focus on the insights gained in the creation of OER. In addition, the authors’ experiences in using OER in regular undergraduate classroom teaching and the students’ feedback will also be presented.

The importance of polymeric materials in modern society is immense. The development of such materials in the 1930s and the rapid commercialization after World War II has had a dramatic impact on the well-being of most citizens in the world. The high standard of living found in many countries would not have been possible without this development. Yet, polymer science does not yet occupy a prominent place in the B.S. Chemistry curriculum at most U.S. academic institutions. The Committee on Professional Training of the American Chemical Society has recognized the importance of polymer science and has made some feeble attempts to encourage its incorporation into the undergraduate chemistry curriculum. However, as yet, its guidelines for ACS-approval do not require a formal course in polymer science. Nonetheless, polymer science may be effectively included in the undergraduate chemistry curriculum. Most particularly, this can be done in the beginning organic chemistry course. This can begin as early as the third week of the first semester with the treatment of alkene chemistry and continue through a discussion of carboxylic acid derivatives in the second semester. This approach has been successfully utilized to generate student enthusiasm (many students are woefully unaware of the impact of polymer science on their daily lives) and enhance performance in the course. Aside from the chemistry involved, a description of milestones in the development of polymer science and the lives of prominent scientists involved serve to stimulate student interest.