Organic Chemistry Laboratory Research Articles

Electrooxidative Cross-Coupling with Hydrogen Evolution to Construct C—N Bonds: Design and Exploration of Electrochemical Technology in Organic Chemistry Laboratory Teaching

Electrooxidative Cross-Coupling with Hydrogen Evolution to Construct C—N Bonds: Design and Exploration of Electrochemical Technology in Organic Chemistry Laboratory Teaching

Teaching of Organic Chemistry Laboratory for Improving Scientific Literacy: Research-Type Experiment and Innovation Ability

Teaching of Organic Chemistry Laboratory for Improving Scientific Literacy: Research-Type Experiment and Innovation Ability

Exploration and Practice on Teaching Reform of Organic Chemistry Laboratory

Exploration and Practice on Teaching Reform of Organic Chemistry Laboratory

Three-Part Approach to Remote/Residential Organic Chemistry Lab During the COVID-19 Pandemic

In the Spring 2021 Organic Chemistry Lab class at Penn State Schuylkill, COVID-19 restrictions and uncertainty required a flexible plan. The first 4 weeks of 15 were fully remote, and videos of standard organic techniques were used, followed by an exam. In the next 5 weeks, some students were in the lab and some were remote. A document camera was used to show one of the in-class students carrying out reaction experiments, mistakes and all, and this was broadcast to the remote students. In the final 6 weeks, the in-class students did a research project, report, and short presentation. The remote students were given a new literature project in which they were each assigned a process research chemistry paper from Organic Process Research and Development. They gave a longer presentation on the process used to prepare a drug. All three parts of the course are discussed in this paper.

Introduction of a Computational Chemistry Course-Based Undergraduate Research Experience (CURE) into an Advanced Organic Chemistry Lab: An Investigation of Propellane Formation

The introduction of basic computational chemistry concepts is becoming an integral part of any complete undergraduate curriculum in chemistry. The advanced organic chemistry course affords laboratory time in which some focused study of computational chemistry is possible. Although learning how to carry out basic computational manipulations is important, interest in computational chemistry can be instilled by carrying out a research-like experience. We incorporated a course-based undergraduate research experience (CURE) into our advanced organic chemistry lab course in which students, as a group, studied the spontaneous formation of strained propellane compounds from the corresponding anionic bridgehead bromide precursor compounds. Completing the calculations and data analysis as a class simulated a true research project, and led to the discovery of results from which interesting conclusions were drawn. Student feedback was generally very positive and suggested that this project gave them a strong sense for how computational chemistry research is conducted.

Nutritional Value Content in Mangrove Syrup From Sonneratia alba Fruit

Pedada fruit (Sonneratia alba) is a fruit of mangrove plants whose utilization can be improved through simple technology, namely the processing of Sonneratia alba fruit into syrup. Mangrove plants produce fruit that can be utilized as a processed beverage, one of which is Sonneratia alba fruit that has a sour taste and can be processed into fresh drinks in the form of mangrove syrup. The purpose of the study was to find out the nutritional value content of mangrove syrup from Sonneratia alba fruit. Research methods are experiments. We use proximal analysis, which includes tests on protein, fat, carbohydrate, and vitamin C. Proximal analysis is carried out at the organic chemistry laboratory, Faculty of MIPA Universitas Jenderal Soedirman. The results of our research show Processed mangrove syrup from Sonneratia alba fruit has nutritional content: protein 1.20%, fat 0.20%, carbohydrates 3.50%, and vitamin C 55.30%. Mangrove fruit from Sonneratia alba processed into syrup has a high nutritional and antioxidant value and is rich in fiber, which is good for health

Phytochemical Screening and in Vitro Evaluation of the Antibacterial Activity of Organic Extracts from the Root Bark of Cussonia arborea (Araliaceae)

Objective: To assess the usefulness of Cussonia arborea in the treatment of bacterial infectious diseases.Study Design: Experimental analytical study.Place and Duration of Study: The study was done in the Laboratory of Hydrobiology and Environment of the Faculty of Sciences, University of Yaounde1; the Bacteriology Laboratory of the Yaoundé University Teaching Hospital; the Laboratory of Pharmacognosy and Pharmaceutical Chemistry of the Faculty of Medicine and Biomedical Sciences and the Laboratory of Organic Chemistry of the Faculty of Sciences of the University of Yaoundé I. The study was done in a period of six months.Methodology: The root bark of Cussonia arborea was collected in the village Yambéta (Central Region, Cameroon), dried and pulverized. Thereafter, two extractions were performed by embedding 200 g of powder in 2000 mL of 96° ethanol, and in a hydro-ethanolic mixture (30/70, v/v), respectively. Qualitative phytochemical screening was performed. Minimum inhibitory and bacterial toxicity were determined by macro-dilution in liquid medium on Staphylococcus aureus, Salmonella sp, Shigella sp and Proteus mirabilis provided by the Laboratory of Hydrobiology and Environment of the Faculty of Sciences, University of Yaounde1 and the Bacteriology Laboratory of the Yaoundé University Teaching Hospital.Results: Phytochemical screening revealed the presence of polyphenols (flavonoids, and tannins), alkaloids, quinones, saponins and, cardiac glycosides. However, coumarins were absent in the two extracts. The minimum inhibitory concentrations of the extracts ranged from 25 to 100 mg/mL, and the minimum bactericidal concentrations from 25 to 200 mg/mL. The ethanolic extract was bactericidal against Proteus mirabilis and Staphylococcus aureus, but bacteriostatic against Salmonella sp and Shigella sp. The hydro-ethanolic extract was bacteriostatic against Shigella sp and bactericidal against the other strains.Conclusion: The groups of polyphenols, alkaloids, quinones, saponins and, cardiac glycosides contained in the two extracts can justify the antibacterial activity observed against Staphylococcus aureus, Salmonella sp, Shigella sp and Proteus mirabilis.

Gas Chromatography–Mass Spectrometric Analysis of Derivatives of Dibenzalacetone Aldol Products

The aldol condensation reaction is one of the many synthesis reactions carried out in second semester organic chemistry laboratories. This reaction was integrated into a novel experiment requiring students to synthesize dibenzalacetone derivatives using the crossed-aldol condensation by reacting different types of benzaldehyde derivatives with acetone, followed by analyzing those products using spectrometric and spectroscopic methods, especially gas chromatography–mass spectrometry (GC–MS). The main objective of this 2 week lab experiment compared to other procedures in the literature was the analysis of the final aldol product using GC–MS methods rather than solely nuclear magnetic resonance (NMR) spectroscopic methods. During the first week’s 3 h laboratory period, students completed the reaction with a known benzaldehyde derivative and acetone to synthesize their aldol product. In the second week, students calculated the percent yield of their product, determined the product’s melting point range, and analyzed the product by thin-layer chromatography, NMR, and GC–MS methods. Students also strengthened their skills of spectral interpretation using NMR spectroscopy, especially distortionless enhancement by polarization transfer NMR, an NMR technique rarely covered in undergraduate organic laboratory sections. Students spent more classroom time during week two, analyzing GC–MS data. Students were shown how to use molecular model kits to understand the fragmentation of compounds in the mass spectrum. As a result, the students who performed this experiment increased their general knowledge of GC–MS spectrometric techniques, including identification of compounds based on their fragmentation pattern.

The Effects of Online Organic Chemistry Laboratory Videos on Students’ Perceptions and Intrinsic Motivation

The purpose of this exploratory study is to investigate students’ use and perceptions of online videos and intrinsic motivation toward the online videos in an organic chemistry laboratory course, which used online videos to assist students’ preparation and learning in the lab. Students’ responses to an anonymous survey showed that they watched the online videos one or more times based on their available time. Descriptive statistics showed that students had positive perceptions about the effect of online videos in terms of their preparation of labs, understanding the concepts, doing hands-on activities, and other aspects in the lab, which were consistent with their written comments. 44% of students showed positive intrinsic motivation toward the online videos according to items based on self-determination theory. Correlation results showed that the effect subscales were strongly related to each other, and students’ intrinsic motivation was significantly and positively related to students’ perceived effect of the online videos on their understanding and preparation with medium to large effect sizes. Inferential tests showed that students who had a positive perception of intrinsic motivation scored significantly higher on the understanding subscale with a medium to large effect size. The findings in this study suggest the online organic chemistry laboratory videos have significant potential to improve students learning and it is important to stimulate student intrinsic motivation toward the online videos which will help students benefits more from the effects of the online videos.

Discovery-Based Bromination of Alcohols: An Organic Chemistry Experiment Supporting Spectroscopic Analysis and Mechanistic Reasoning

The bromination of six isomeric alcohols is adapted to a discovery-based organic chemistry laboratory experiment, whereby students are provided an alcohol starting material and are charged with determining the product or product mixture produced using relevant spectroscopic data. The experiment solidifies NMR analysis skills while reinforcing the mechanistic reasoning that supports the study of organic reactions. The laboratory is highly customizable and can be adapted to align with available instrumentation to best meet the needs of students, and it has been successfully implemented at three separate universities.

New Look at the Competitive Nucleophilic Substitution Reaction in the Pentanol Series

Substitution reactions of alcohols are some of the simplest experiments performed in undergraduate organic chemistry laboratory settings. However, the use of gas chromatography (GC) as an analytical tool for these reactions can be at times laborious and time-consuming. In this work, 1-pentanol, 2-pentanol, 3-pentanol, and 2-methyl-2-butanol were reacted with a 50/50 mixture of ammonium chloride–ammonium bromide in water to yield the corresponding alkyl bromide and alkyl chloride mixtures. Aliquots of the reaction mixture were analyzed using proton nuclear magnetic resonance (1H NMR) spectroscopy and verified by GC. Secondary to secondary carbocation rearrangements were observed in the nucleophilic substitution reactions of 2- and 3-pentanol yielding a mixture of 2- and 3-substituted alkyl halides, while the primary and tertiary alcohols yielded the expected products. Students were assessed on their observations and explanations with the majority of them able to identify the correct reasoning for the alkyl halides mixture formation. 1H NMR spectroscopy provided an inexpensive and quicker method to analyze the mixture and expose the students to the secondary to secondary carbocation rearrangement in the nucleophilic substitution reaction in the pentanol series.

Measuring and Fostering Preservice Chemistry Teachers’ Scientific Reasoning Competency

Developing scientific reasoning (SR) is a central goal of science-teacher education worldwide. On a fine-grained level, SR competency can be subdivided into at least six skills: formulating research questions, generating hypotheses, planning experiments, observing and measuring, preparing data for analysis, and drawing conclusions. In a study focusing on preservice chemistry teachers, an organic chemistry lab course was redesigned using problem-solving experiments and SR video lessons to foster SR skills. To evaluate the intervention, a self-assessment questionnaire was developed, and a performance-based instrument involving an experimental problem-solving task was adapted to the target group of undergraduates. The treatment was evaluated in a pre-post design with control group (cook-book experiments, no SR video lessons) and alternative treatment group (problem-solving experiments, unrelated video lessons). Interrater reliability was excellent (ρ from 0.915 to 1.000; ICC (A1)). Data analysis shows that the adapted instrument is suitable for university students. First insights from the pilot study indicate that the cook-book lab (control group) only fosters students’ skill in observing and measuring, while both treatment groups show an increase in generating hypotheses and planning experiments. No pretest-posttest differences were found in self-assessed SR skills in the treatment groups. Instruments and data are presented and discussed.

Proof of Concept for a Thin-Layer Chromatography Digital Badge Assignment Within a Laboratory Practical Exam for a Nonchemistry Majors’ Organic Chemistry Lab

Digital badges are credentials earned via a digital presentation to demonstrate the mastery of a technique. They have been utilized in General Chemistry laboratory courses as an assessment tool and to document students’ development of a skill. A digital badge assignment was developed for thin layer chromatography (TLC) and integrated into a laboratory practical exam in a large-enrollment Organic Chemistry laboratory course for science majors. The students filmed themselves carrying out the TLC technique while explaining why specific steps were taken. After completing the filming, they applied the TLC technique off-camera to identify an unknown. Detailed directions, filming prompts, and rubrics are provided for this digital badge. The assignment was updated on the basis of the results from quantitative and qualitative data collected from around 800 students and a dozen GTAs. This data was also analyzed to explore the affordances and challenges of implementing a badge within a laboratory practical. Data included students’ pre- and post-perceptions of their knowledge, experience, and confidence, scores on the laboratory practical and written final exam, and student and GTA responses to short-answer survey questions. The most helpful resources for the badge were the directions, filming prompts, and rubrics, while the challenges included filming oneself, time limits, and uploading videos to the learning management system (LMS). Overall, we believe the challenges students faced with the digital badge assignment were outweighed by the positive cognitive, psychomotor, and affective learning outcomes resulting from coupling a digital badge assignment with the identification of an unknown as complementary components of a required laboratory practical.

Nitrophenol Violet as a New Tool for Studying of Kinetics of Reactions in Solutions

This experimental lab set is for students taking college chemistry courses. It includes four laboratory works and completely illustrates the important parts of chemical kinetics, namely the determination of the rate constant and the determination of the factors influencing its value. They can be used in a laboratory set for a physical chemistry laboratory course, or separately, using only one or two of the four laboratory exercises for general, colloid, and organic chemistry laboratory courses, as well as biological and industrial catalysis. The experiment forms an understanding of the possibilities of controlling the reaction rate and an understanding of intermolecular interactions in solutions. The classical effects of the rate constant are considered, such as the effects of salt and solvent, as well as micellar catalysis. The main focus is on the following factors: increasing polarity of the medium or ionic strength decelerates the reactions between Dyez+ and HO– and accelerates that of Dyez– with HO–; solubilization of reagents by micelles of cationic, nonionic, and zwitterionic surfactants accelerates the reactions between Dyez+ and HO– and decelerates the reaction of Dyez– with HO–; anionic micelles decelerate both of them. Interest in micellar effects is due to both theoretical application in the study of reaction mechanisms, structure and dynamics of nanosized aggregates in solution, and practical application, for example, in organic synthesis, in industry. Quantitative data processing was carried out according to the Bronsted–Bjerrum and Scatchard equations, as well as linear dependences of solvation energies. The experiment also provides students with practical experience in using the spectrophotometer, as well as graphical and numerical analysis of the data obtained. A new anionic triphenylmethine dye 3,3′-dinitrophenolsulfonephthalein (nitrophenol violet, NPV) was proposed for the study of chemical kinetics. NPV reacts with alkali faster than anionic dyes such as bromophenol blue and phenolphthalein. This property of NPV reduces laboratory practice time.

Incorporating Interlab Collaborations into the Organic Chemistry Teaching Laboratories

Collaborative experiences have been widely integrated into the classroom and laboratory, with goals to build time management, communication, and team-working skills. Most reported laboratory collaborations occur between students within the same lab section, which could limit the potential benefits of these experiences. Presented herein is an organic chemistry laboratory model in which students collaborate across lab sections (i.e., interlab collaborations) to complete discovery-based, medicinal-chemistry-focused experiments. These experiences provide opportunities for students to reflect on and improve upon their team-working skills. Over the past three years, interlab collaborations have been offered at Muhlenberg College to 105 students in two types of organic chemistry courses. Assessment data, including notebook evaluation scores, peer- and self-evaluations, lab report scores, and student reflections, suggest that these experiences could help build time management, communication, organizational, and data-recording skills. These laboratories could give students a realistic view of collaborative work and allow for the intentional development and assessment of team-working skills in any introductory or upper-level chemistry laboratory. Furthermore, this model provides a framework for reducing lab section sizes by half, a change which has been needed during COVID-19, while still completing the planned lab curriculum.

Student-Generated Infographics for Learning Green Chemistry and Developing Professional Skills

This paper addresses the incorporation of a scaffolded infographic project into a majors’ organic chemistry laboratory. Students were given the freedom to choose their topic with the stipulation that it must be relevant to both organic and green chemistry. This scaffolded project consisted of the following eight phases: (i) summarizing and evaluating an existing infographic, (ii) delving into green chemistry literature, (iii) proposing infographic topic, (iv) gathering components for the infographic, (v) analyzing infographic maker websites, (vi) creating infographic and providing peer feedback on first drafts, (vii) revising infographic and providing final feedback, and (viii) posting infographic on Twitter. Since this was a semester-long project implemented in a remote environment, a variety of instructional technologies including Flipgrid, Perusall, FeedbackFruits Peer Review, Google Jamboard, and chemical drawing software were utilized. The analysis of the project’s impact on cognitive gains through Student Assessment of Learning Gains and through pre- and post-test responses indicated the achievement of positive learning gains on green chemistry knowledge and skills. This activity was viewed favorably by students, with most indicating a desire for similar assignments implemented in future courses.

Student Satisfaction with Synchronous Online Organic Chemistry Laboratories: Prerecorded Video vs Livestream

The widespread transition to online teaching as a result of the global pandemic moved chemistry laboratory experiences online. At UBC’s Okanagan campus, organic chemistry laboratory instruction was delivered synchronously to maximize student interactions with their teaching assistants. Two methods of online delivery were employed: (1) students gathered with a teaching assistant via Zoom to watch a prerecorded video of the laboratory procedure and (2) students gathered on Zoom to watch a livestream of the teaching assistant performing the experiment in the laboratory. A single TA implemented both methods, one in each of two laboratory sections. Student satisfaction with the two delivery methods was compared using a survey and semistructured interviews. Overall, the livestream section received significantly more positive feedback in all aspects, including student investment, perceived conceptual gains, understanding of glassware and techniques, ability to make proper experimental observations, engagement in critical thinking and problem-solving, and general satisfaction with their online lab experience. However, students expressed the belief that the primary role of a teaching laboratory is hands-on experience with chemistry equipment and techniques and that their experience was lacking in this aspect regardless of the lab delivery method. Students described two principal advantages of the livestream delivery. One was the inclusion of opportunities to witness mistakes or unexpected outcomes and then having to take part in the development of a resolution to address those errors; such opportunities were absent for students watching a prerecorded and edited video with a predetermined conclusion. A second aspect was that waiting periods inherent in the live performance of an experimental procedure allowed for unstructured interactions among students and the TA, both to discuss the experiment and to simply socialize. Overall, students believed that neither pedagogy compared favorably to a traditional in-person teaching laboratory experience, but the livestream method proved to be a highly superior approach for a synchronous online laboratory.

Promoting the Diversity, Equity, and Inclusion in Organic Chemistry Education through Undergraduate Research Experiences at WSSU

Undergraduate research is well recognized as an effective high-impact educational practice associated with student success in higher education. Actively engaging students in research experiences is considered as one of the several high-impact practices by many agencies including the American Chemical Society. Developing and maintaining an active undergraduate research program benefits both the faculty and students especially those from under-represented minority groups (URM). The infusion of research experiences into undergraduate curriculum enables students from all backgrounds to develop independent critical thinking skills, written and oral communications skills that are very important for successful careers in “STEM” area. Several strategies and activities such as a Peer Mentoring Program (PMP), funded research activities, the infusion of research into organic chemistry labs, undergraduate professional development, research group meetings, presentations at regional/national conferences, and publishing as co-authors on peer-review papers are vital in creating a welcoming research group that promotes the diversity, equity, and inclusion in organic chemistry education. The experiences working on funded research projects, presenting their research data at conferences and publishing papers as co-authors will greatly increase the under-represented minority (URM) students’ chance in landing a job or getting admitted into graduate/professional programs in STEM area.

Uji Beberapa Dosis Minyak Daun Kemangi Ocimum basilicum Linnaeus sebagai Atraktan terhadap Bactrocera spp. pada Tanaman Cabai

Fruit flies, Bactrocera spp., are the primary pests on chili plants (Capsicum annuum Linnaeus). A safe and effective control uses traps combined with an attractant from basil leaf oil (Ocimum basilicum Linnaeus). This study aimed to determine the attractiveness of basil leaf oil against fruit flies at several different doses. This research was carried out in Organic Chemistry Laboratory STIFARM Padang, in Tabek Patah Tanah Datar area West Sumatra, and in the Pest Disease Observation and Development of Biological Agents Laboratory, Bukittinggi, West Sumatra, from June to August 2020. The treatment was in the form of different doses of basil leaf oil, which was 0,5 ml per trap, 1.0 ml per trap, 1.5 ml per trap, 2.0 ml per trap, and 2.5 ml per trap. The experiment used a completely randomized design with five treatments and three replications. This study found two species of fruit flies around chili plants, namely Bactrocera papayae and Bactrocera carambolae, which were dominated by male B. papayae. The traps containing 1.5 ml of basil leaf oil attracted the most fruit flies. Temperature and humidity significantly affect the abundance of individual fruit flies.

Electrochemical Generation and Use in Organic Synthesis of C-, O-, and N-Centered Radicals.

During the last decade several research groups have been developing electrochemical procedures to access highly functionalized organic molecules. Among the most exciting advances, the possibility of using free radical chemistry has attracted the attention of the most important synthetic groups. Nowadays, electrochemical strategies based on these species with a synthetic purpose are published continuously in scientific journals, increasing the alternatives for the synthetic organic chemistry laboratories. Free radicals can be obtained in organic electrochemical reactions; thus, this review reassembles the last decade's (2010-2020) efforts of the electrosynthetic community to generate and take advantage of the C-, O-, and N-centered radicals' reactivity. The electrochemical reactions that occur, as well as the proposed mechanism, are discussed, trying to give clear information about the used conditions and reactivity of these reactive intermediate species.