Undergraduate Organic Chemistry Research Articles

Reaction Optimization Experiment for Undergraduate Capstone Organic Chemistry Laboratory Course

Reaction Optimization Experiment for Undergraduate Capstone Organic Chemistry Laboratory Course

Virtual Reality in an Eco-Niche Undergraduate Organic Chemistry Laboratory Course: New Practice in Chemistry Lab Teaching

Virtual Reality in an Eco-Niche Undergraduate Organic Chemistry Laboratory Course: New Practice in Chemistry Lab Teaching

Teaching abductive reasoning for use as a problem-solving tool in organic chemistry and beyond

The second-year undergraduate Organic Chemistry course sequence is often cited as one of the most, if not the most, challenging for students in the US. Thus, a persistent question remains: What is it about Organic Chemistry that makes the course so difficult for students? Herein, we put forward the hypothesis that a new mode of thinking and problem solving is expected of the students; these skills have not yet been developed in their prior scientific coursework and are often not deliberately taught in Organic Chemistry. This form of reasoning and problem solving, known as abductive reasoning, is highlighted for its connection to medical diagnosis and scientific thinking. We provide examples to showcase how instructors could explicitly foreground the reasoning process in their classroom. Ultimately, we argue that teaching how to reason using abduction may benefit students in both the short term (in the course) and the long term (in their careers as scientists and medical practitioners).

Metal-Free Ring-Opening Polymerization of Propylene Oxide: Synthesis and Characterization of Polyether in the Undergraduate Organic Chemistry Laboratory

Metal-Free Ring-Opening Polymerization of Propylene Oxide: Synthesis and Characterization of Polyether in the Undergraduate Organic Chemistry Laboratory

Integrating Bifunctional Catalysis into Senior Undergraduate Organic Chemistry: A Laboratory Experiment on the Asymmetric Michael Addition Reaction

Integrating Bifunctional Catalysis into Senior Undergraduate Organic Chemistry: A Laboratory Experiment on the Asymmetric Michael Addition Reaction

Microwave-Assisted Synthesis of Solvatochromic Dye and Analysis of Solvent Polarity in Undergraduate Organic Chemistry Laboratory

Microwave-Assisted Synthesis of Solvatochromic Dye and Analysis of Solvent Polarity in Undergraduate Organic Chemistry Laboratory

Merging Inline NMR Monitoring and Flow Chemistry in the Undergraduate Organic Chemistry Laboratory

Merging Inline NMR Monitoring and Flow Chemistry in the Undergraduate Organic Chemistry Laboratory

Ungrading in organic chemistry: students assessing themselves and reflecting on their learning

The focus on grades has diminished the focus on learning. One strategy that aims to return students’ attention to what they are actually learning (and not just earning) is ungrading. Ungrading is thought of as any strategy in which instructors do not assign a number or letter grade to students’ assignments and assessments. Instead, faculty may (1) provide thorough feedback and engage in dialogue with students about their work, and perhaps, (2) allow students to assign their own grade. Whichever style of ungrading they choose, the scholars that have been forging the path for ungrading come from a variety of fields and perspectives, including STEM instructors in more recent years. The focus on incorporating ungrading practices into the organic chemistry curriculum provided here is adapted from a variety of practitioners, and especially the foundational work of chemistry professor Clarissa Sorensen-Unruh. In addition to discussing the current ungrading practices in various fields, we will use this perspective article to share our own experience with and lessons learned from beginning to incorporate ungrading in the undergraduate organic chemistry curriculum, both as it relates to the implementation of the practice and our own perceptions of the student experience and learning outcomes. Ultimately, the goal is to allow students to see the significance of the process of learning and to engage in some metacognitive work that they can apply to different assignments, whether in our class or not. If we want students to focus on learning, perhaps they should do the grading themselves.

Incorporating Green Chemistry into Undergraduate Organic Chemistry Laboratory: Synthesis of Banana Oil

Incorporating Green Chemistry into Undergraduate Organic Chemistry Laboratory: Synthesis of Banana Oil

Improving Undergraduate Organic Chemistry Laboratories through Integration with Research: Prospects and a Model Study

Improving Undergraduate Organic Chemistry Laboratories through Integration with Research: Prospects and a Model Study

An Undergraduate Laboratory Module Integrating Organic Chemistry and Polymer Science.

Polymer science is receiving wider acceptance in the organic chemistry community; thus, it is imperative to include it in the undergraduate organic chemistry curriculum. Despite the ever-increasing popularity of the topic of polymer chemistry in undergraduate curricula, a comprehensive laboratory experiment module describing a polypeptide synthesis by ring-opening polymerization of N-carboxyanhydride (NCA ROP) and a homopolymer synthesis by activators-regenerated by electron-transfer for atom transfer radical polymerization (ARGET ATRP) has yet to be proposed. Herein, we report a semester-long, ten week undergraduate laboratory module focusing on the synthesis and analytical characterization of polyalanine and polystyrene for an advanced organic chemistry class. Students received hands-on-experiences in synthesizing polymers followed by their characterization via proton nuclear magnetic resonance (1H NMR) spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), gel permeation chromatography (GPC), thermogravimetry (TGA), differential scanning calorimetry (DSC), and transmission electron microscopy (TEM), which are not well-presented in the typical organic chemistry curricula. These engaging hands-on lessons in the newly designed laboratory module not only increase students' interests in an interdisciplinary environment of organic chemistry and polymer science but also cultivate their research interests and communication skills and promote critical thinking.

Application of α-bromination reaction on acetophenone derivatives in experimental teaching: a chemical innovation experiment engaging junior undergraduates

The α-bromination reaction of carbonyl compounds is a significant topic in the field of organic chemistry. However, due to the lack of suitable brominating reagents, the application of this reaction in undergraduate organic chemistry experiments is limited. In this study, three junior undergraduates successfully conducted an innovative experiment under the guidance of teachers. The bromination of various acetophenone derivatives was investigated by employing pyridine hydrobromide perbromide as the brominating agent, with a focus on exploring the effects of reaction time, reaction temperature, and dosage of the brominating agent. The results demonstrated that 4-chloro-α-bromo-acetophenone could be synthesized at 90 ℃ using 4-chloroacetophenone as a substrate and acetic acid as a solvent with a molar ratio of substrate to brominator being 1.0:1.1. Through the experimental teaching of 18 junior undergraduates, it was observed that all the students successfully completed the experiment within a time frame of 4–5 h, with a notable achievement yield exceeding 80% observed in 14 students. This innovative experiment exhibits significant advantages in terms of safety, high yield, cost-effectiveness, and repeatability. Furthermore, while reinforcing fundamental skills in chemistry experimentation among students, it enhances their scientific literacy levels and fosters innovation consciousness as well as practical aptitude. Consequently, this approach is highly suitable for widespread implementation and integration into undergraduate experimental pedagogy.

Using Flipped Classroom Modules to Facilitate Higher Order Learning in Undergraduate Organic Chemistry.

In an ongoing effort to incorporate active learning and promote higher order learning outcomes in undergraduate organic chemistry, a hybrid ("flipped") classroom structure has been used to facilitate a series of collaborative activities in the first two courses of the lower division organic chemistry sequence. An observational study of seven classes over a five-year period reveals there is a strong correlation between performance on the in-class activities and performance on the final exam across all classes; however, a significant number of students in these courses continue to struggle on both the in-class activities and final exam. The Activity Engagement Survey (AcES) was administered in the most recent course offering included in this study, and these preliminary data suggest that students who achieved lower scores on the in-class activities had lower levels of emotional and behavioral/cognitive engagement and were less likely to work in collaborative groups. In total, these findings suggest that if students can be guided to engage more successfully with the in-class activities, they are likely to be more successful in carrying out the higher order learning required on the final exam. In addition to the analyses of student performance and engagement in the in-class activities, the implementation of the flipped classroom structure and suggestions for how student engagement in higher order learning might be improved in future iterations of the class are described herein.

Atmospheric solids analysis probe mass spectrometry: An easy bolt-on for the synthetic undergraduate teaching laboratory.

High costs and student numbers can often hinder implementation of mass spectrometry (MS) in the undergraduate teaching laboratory, often with technicians running samples on students' behalf, and the implementation of MS only in discrete or isolated experiments. This study explores the use of atmospheric solids analysis probe MS (ASAP-MS) as a relatively low-cost, benchtop instrument, and its potential for application as a 'bolt-on' to existing undergraduate organic chemistry experiments. Thirteen products synthesised in undergraduate laboratory experiments were analysed by ASAP-MS, along with their starting materials. Analysis was carried out with a Waters RADIAN ASAP mass spectrometer, at four different cone voltages simultaneously to provide fragmentation information. Out of the 13 undergraduate experiments, ASAP-MS was shown to be complementary in 11 of these, either through simple analysis of the precursor ion or by a more complex analysis of the fragments. ASAP-MS provided spectra that both complement and enhance intended learning outcomes in existing organic chemistry experiments, showing its versatility as a bolt-on technique. Moving forward, ASAP-MS will be integrated into the University of Surrey's undergraduate teaching laboratory.

Examining the role of assignment design and peer review on student responses and revisions to an organic chemistry writing-to-learn assignment

Research on student learning in organic chemistry indicates that students tend to focus on surface level features of molecules with less consideration of implicit properties when engaging in mechanistic reasoning. Writing-to-learn (WTL) is one approach for supporting students’ mechanistic reasoning. A variation of WTL incorporates peer review and revision to provide opportunities for students to interact with and learn from their peers, as well as revisit and reflect on their own knowledge and reasoning. However, research indicates that the rhetorical features included in WTL assignments may influence the language students use in their responses. This study utilizes machine learning to characterize the mechanistic features present in second-semester undergraduate organic chemistry students’ responses to two versions of a WTL assignment with different rhetorical features. Furthermore, we examine the role of peer review on the mechanistic reasoning captured in students’ revised drafts. Our analysis indicates that students include both surface level and implicit features of mechanistic reasoning in their drafts and in the feedback to their peers, with slight differences depending on the rhetorical features present in the assignment. However, students’ revisions appeared to be primarily connected to the peer review process via the presence of surface features in the drafts students read (as opposed to the feedback received). These findings indicate that further scaffolding focused on how to utilize information gained from the peer review process (i.e., both feedback received and drafts read) and emphasizing implicit properties could help support the utility of WTL for developing students’ mechanistic reasoning in organic chemistry.

A Comprehensive Inquiry-Based Comparative Experiment for an Undergraduate Organic Chemistry Laboratory Course: Elucidating the Formation Process of N-Phenylbenzamide

A Comprehensive Inquiry-Based Comparative Experiment for an Undergraduate Organic Chemistry Laboratory Course: Elucidating the Formation Process of <i>N</i>-Phenylbenzamide

Correction to “Crossed Aldol Reactions in Water Using Inexpensive and Easily Available Materials as a Tool for Reaction Optimization Teaching in an Undergraduate Organic Chemistry Laboratory”

Correction to “Crossed Aldol Reactions in Water Using Inexpensive and Easily Available Materials as a Tool for Reaction Optimization Teaching in an Undergraduate Organic Chemistry Laboratory”

How to Identify–with as Little as One Question–Students Who Are Likely to Struggle in Undergraduate Organic Chemistry

How to Identify–with as Little as One Question–Students Who Are Likely to Struggle in Undergraduate Organic Chemistry

A safe-at-home benzoin condensation from imitation almond extract

Abstract COVID-19 remote learning forced instructors to scramble for meaningful organic laboratory experiences safe enough to perform at home. While resources are available for laboratory experiments at home, organic synthesis suffers from issues involving safety, availabilities of reagents, difficulties measuring reagents, and difficulties analyzing products. We report a new take on the classic benzoin condensation using safe and commonly available reagents, capable of being setup with commonly available kitchen materials, and displaying visible and distinctive product. This experiment is aimed at reinforcing concepts of carbonyl chemistry in the undergraduate organic chemistry laboratory.

Microwave-Assisted Extraction of Trimyristin from Nutmeg using Ethanol: A Greener Approach for the Undergraduate Organic Chemistry Laboratory

Microwave-Assisted Extraction of Trimyristin from Nutmeg using Ethanol: A Greener Approach for the Undergraduate Organic Chemistry Laboratory