General Organic Chemistry Research Articles

Development and Rasch Analysis of the Prior Knowledge of Chemistry Concepts Test for Pre-medical Students in the Philippines

Chemistry concepts are embedded in several contexts that are related to the future professional roles of pre-medical students. In the current academic landscape of pre-medical programs, an objective measurement of prior knowledge of chemistry concepts is necessary to promote students’ academic success. To address this issue, this study aimed to develop and validate the Prior Knowledge of Chemistry Concepts Test. This multiple-choice research instrument is designed to measure pre-medical students’ knowledge of essential chemistry concepts from pre-requisite chemistry courses in pre-medical programs in the Philippines. The final item pool, consisting of 26 general chemistry concepts and 21 general organic chemistry concepts was administered to 470 college students from four tertiary institutions in the Philippines. Item content validity indices (I-CVI) and kappa statistics guided initial revisions, while dichotomous Rasch analysis was utilized to determine the psychometric properties of the research instrument. The analysis provided evidence of adequate person and item reliability, item fit, local independence, and unidimensionality, although some items may be omitted in subsequent iterations. The application of the research instrument to assessment and evaluation was elaborated using the student ability and item difficulty logits along the person-item map. Suggestions for the improvement of the research instrument were also discussed.

Courses that Impact the Terminal Efficiency in the Dentistry Career at the University of Costa Rica (2007-2014)

The main objective of this study was to determine the failure rates of the courses in the curriculum of the Dentistry degree program at the University of Costa Rica for the cohorts from 2007 to 2014. Data from 736 records were used. The variables considered were the following: gender, age at admission, nationality, marital status, children, domicile, previous high school attended, admission exam scores, and approved courses. The data were obtained from the Student Application System, physical records, and the Supreme Electoral Tribunal of Costa Rica. Descriptive, bivariate, and multivariate analyses were performed. Among the students, 98% were Costa Rican, 68% were female, 79% were admitted based on their admission exam scores, 43% were admitted at the age of 18 or younger, 50% came from public schools, 77% resided in the Greater Metropolitan Area, and 95% were single and childless. The majority of study dropouts occurred in the first four cycles of the dentistry degree. The courses with the lowest overall success rate in the curriculum were service courses: General Chemistry, Organic Chemistry, and Elemental Mathematics. Among the core courses, the Pediatric Dentistry and Orthodontics Clinic and the Endodontics Clinic had the highest failure rates. Moreover, there was a statistically significant difference between the approval rates of the physics course and the school of origin. In the Dentistry degree program at University of Costa Rica, the failure rate is high in the first four cycles of the program, which is when service courses are mainly offered. As for the core courses, the Pediatric Dentistry and Orthodontics Clinic and the Endodontics Clinic had the lowest success rates.

Recent Developments on Photochemical Synthesis of 1,n-Dicarbonyls.

1,n-dicarbonyls are one of the most fascinating chemical feedstocks finding abundant usage in the field of pharmaceuticals. Besides, they are utilized in a plethora of synthesis in general synthetic organic chemistry. A number of 'conventional' methods are available for their synthesis, such as the Stetter reaction, Baker-Venkatraman rearrangement, oxidation of vicinal diols, and oxidation of deoxybenzoins, synonymous with unfriendly reagents and conditions. In the last 15 years or so, photocatalysis has taken the world of synthetic organic chemistry by a remarkable renaissance. It is fair to say now that everybody loves the light and photoredox chemistry has opened a new gateway to organic chemists towards milder, more simpler alternatives to the previously available methods, allowing access to many sensitive reactions and products. In this review, we present the readers with the photochemical synthesis of a variety of 1,n-dicarbonyls. Diverse photocatalytic pathways to these fascinating molecules have been discussed, placing special emphasis on the mechanisms, giving the reader an opportunity to find all these significant developments in one place.

Active learning strategies on organic nomenclature using digital tools and collaborative work

The present document describes the most relevant results from an active-learning activity design as a complementary tool to improve learning process of organic nomenclature on students from general organic chemistry course at Universidad del Cauca. This process was developed using a defined method in three parts: planning, setting, and validating. The first stage, according to organic compounds, eight (8) different interactive class materials from Genial.ly website were design. Secondly, students from various academic programs participated, and through collaborative work, each student handled the interactive program during four sessions, spread accordingly to the topic: from hydrocarbons to acid derivates. Finally, through guided surveys and an evaluation test, the activity’s innovative dynamic efficiency was evaluated under three components: effectiveness, content, and perceptions of applied tools. Results threw a high grade of acceptance on most of participants (80-90 %). Same way, the final test among experimental and control groups showed better results belonging to students participating in the activity with a total of 71.4% of students that passed the evaluating test. Control group students presented a lower performance on the test with only 40% of evaluated students approved.

Development and Validation of Discovery-Based Modules in Teaching Chemistry

This study is focused on developing and validating the discovery-based modules in chemistry. This exploration was initiated in response to the criminology student's least-learned concepts in the general (organic) chemistry course. A descriptive–developmental approach was utilized and guided by the Analysis-Design-Development-Implementation-Evaluation (ADDIE) model in the development and validation of the discovery-based modules. In the study, two discovery-based modules were developed. Each module had the following parts: a pre-test, an overview, safety precautions, preparation, a review, the activity itself, a discussion after the activity, a post-activity test, an application, and a reference. Five (5) chemistry teacher experts and five (5) criminology student-users evaluated the aspects of the discovery-based modules using the validation and evaluation forms of the study. The researcher interviewed the criminology student-users using the validated interview guide questions to determine their feedback using the modules. Findings revealed that both chemistry teacher experts and criminology student-users rated the two developed discovery-based modules as excellent and strongly agreed on all pertaining aspects of the modules, in terms of objectives, content, format and language, presentation, and usefulness. The feedback of the student-users revealed interactive, well-designed, discovery-based, and outcome-based themes perceived as the characteristics of the developed chemistry modules. Therefore, it was concluded that the developed discovery-based modules in chemistry are valid, acceptable, and could be used as supplementary material for criminology students and further recommended for possible replication to cover the other least-learned chemistry concepts.

Happy 25th Anniversary, EurJOC!

Happy 25th Anniversary, EurJOC!

Lipid droplets understood through student designed 3D printed models of the seipin protein complex

Lipid droplets (LD’s) are organelles that play a key role in metabolism and human physiology, storing energy for cells to use when needed. Defects in LD metabolism can cause diseases such as obesity and lipodystrophy. LDs have a single phospholipid layer exterior and hold triglycerides and other lipids. Several different proteins are also found in the phospholipid exterior of an LD, for example GPAT (glycerol‐3‐phosphate O‐acyltransferase). LDs are assembled at the surface of the endoplasmic reticulum by the seipin protein complex, with the LD forming at the seipin site similar to “blowing a bubble”. We are undergraduate students at various levels in our training and have not encountered LDs in our coursework. However, we believe they are an important and intriguing model for teaching many introductory and more advanced biology and chemistry concepts. We designed a 3D printed model of the seipin complex (based on PDB file 6DS5, Yan 2018) that can be used in undergraduate teaching. This model, along with online videos and other tools, can be used to teach many topics through a hands‐on approach to learning. Topics we learned about while building our models and through the use of other materials included: protein structure, protein complexes, metabolism and its connection to different diseases, basic chemical structures, metabolic pathways, cellular structures, computational visualization of proteins, and the utilization of online tools such as the Protein Databank. LDs can be connected to content in many courses, including General Biology, General Chemistry, Biochemistry, Organic Chemistry, Genetics, Cell Biology and Physiology. Instructions for printing a copy of this model along with a list of other teaching resources can be made available to anyone who is interested.

Content, costs, and characteristics of United States prepharmacy curricula

IntroductionThe objective of this study was to examine pharmacy prerequisites and estimate the costs prospective students may incur to complete those requirements. MethodsPrepharmacy requirements for doctor of pharmacy (PharmD) degree programs in the United States (US) (n = 137) were sourced from school websites in 2018. Credit hour costs for community colleges, public four-year institutions, and private four-year institutions were collected. Chi-square and independent t-tests compared group differences. ResultsSchools required 66.12 ± 8.15 prerequisite credit hours (range 41 to 91 hours). All schools required one course in general chemistry and organic chemistry. A higher proportion of schools in 2018 required anatomy/physiology and statistics when compared to 2009. Estimated costs to complete prerequisites ranged from US $16,359 at a community college to US $187,800 for a bachelor's degree at a private institution. ConclusionsTrends in healthcare and education make it timely for schools to reconsider prerequisites. Renewed consideration should be given to identifying what is core to the profession and the minimum competencies students must demonstrate for entry into PharmD programs.

Predicting final grades in STEM courses: A path analysis of academic motivation and course-related behavior using self-determination theory

Within self-determination theory, a considerable amount of previous research has shown that autonomous motivation is associated with higher levels of academic achievement and wellness among students. However, it is notable that few studies have included large samples of undergraduates who are enrolled in science courses. Moreover, to our knowledge no previous research has investigated the associations among autonomous and controlled motivations, course attendance, time spent studying, perceived course difficulty, and final course grades simultaneously. The current study was designed to begin to fill this gap in the literature. In the fall (33 course sections) and spring (29 course sections) semesters, undergraduate students (N = 1284) who were enrolled in general chemistry, organic chemistry, and human anatomy and physiology courses responded to a 24-item survey at the beginning (Time 1) and at the end (Time 2) of the semester. The results revealed considerable stability in motivation over time as well as strong association between autonomous and controlled motivations at each time point. Autonomous motivation at Time 2 predicted higher levels of time spent studying and final course grades, and lower levels of perceived course difficulty. Controlled motivation at Time 2 predicted higher levels of course attendance, time spent studying, and perceived course difficulty, and lower levels of final course grades. These findings indicate that both autonomous and controlled motivations contribute to final course grades (albeit in opposite directions) and highlight the importance of creating need-supportive educational climates that facilitate the cultivation of autonomous motivation.

Measuring Changes in Undergraduate Chemistry Students’ Reasoning with Reaction Coordinate Diagrams: A Longitudinal, Multi-institution Study

The Reaction Coordinate Diagram Inventory (RCDI) was developed to measure chemistry students’ thinking and confidence when interpreting the kinetic and thermodynamic information encoded within reaction coordinate diagrams (RCDs). The RCDI was designed based upon analyses of qualitative data collected in semi-structured interviews with general chemistry students or organic chemistry students to ensure all items and distractors were grounded in students’ ideas and reasoning. A longitudinal, multi-institution research study was conducted using the RCDI to measure changes in undergraduate chemistry students’ reasoning with RCDs, and their confidence in doing so, at three points in time: (1) end of second-semester general chemistry, (2) beginning of first-semester organic chemistry, and (3) end of first-semester organic chemistry. The three institutions participating in this longitudinal study taught organic chemistry using either a traditional functional group curriculum or a mechanisms approach. Findings include evidence that individual students performed significantly better with significantly higher confidence as they progressed through courses, but that some RCD misconceptions, such as incorrectly assuming reaction progress indicates a time unit, are persistent throughout. Although two of the institutions taught organic chemistry using a mechanisms curriculum and one institution used the traditional functional group approach, no evidence exists of significant differences among students’ RCDI total score and average confidence across institutions.

Examining Some of the Challenges Students Face in Learning about Solubility and the Dissolution Process

Developing conceptual understanding of solubility and dissolution and the relationship to molecular structure, ionic salts’ charges, and enthalpy and entropy, play a significant role in the learning of chemistry. Dissolution and solubility are topics covered in general chemistry, quantitative analysis, biology, and organic chemistry. Alternative conceptions about some of the key chemistry principles can lead to students’ failure in understanding and accepting some of the future concepts. This study aims to examine some of the challenges and alternate conceptions that students face when learning about solubility and its relationship to Lewis structures and the driving force behind dissolution. A survey that consisted of ionic and molecular solubility related problems, short answers, and Likert-Type questions was given to 200 students in order to analyze their understanding of solubility, dissolution, alternate conceptions they possess, challenges they face in learning about the topics, and its relationship to Lewis dot structures and ionic charges. Our data indicates that students struggle with solving solubility and dissolution process related problems and rely on memorization to approach these problems. For ionic compounds, there seems to be a dependency on memorization and rote-learning of solubility rules instead of development of conceptual understanding of charges of ions and their relationship to entropy and enthalpy in the dissolution process. For molecular compounds, it should be noted that students lack mastery of determining molecular shape and its relationship to function but do emphasize the roles of Lewis structure and polarity in solubility. Finally, students do not attribute the combined effects of enthalpy and entropy as the driving forces behind dissolution and show very fragmented and naïve understanding of the concept.

Recent Developments in the Asymmetric Detrifluoroacetylative Reactions of in situ Generated Mono-Fluorinated Enolates

The development of an efficient and mild synthetic methodology for the construction of bioactive fluorine-containing molecules represents one of the hot research topics in general synthetic organic chemistry. In this review, some recent progresses achieved in the development of detrifluoroacetylatively generated mono-fluorinated enolates via CC bond cleavage and their asymmetric nucleophilic reactions for assembly of chiral quaternary C-F center containing compounds.

Assessment à la Mode: Implementing an Adaptable Large-Scale Multivariant Online Deferred-Grade Exam for Virtual Learning

The COVID pandemic forced many higher education institutions to pivot and switch to an online learning environment with minimal preparation. This transition was put in place during the middle of the spring semester, in March. During this transition, instructors had to quickly learn the tools of online teaching, navigate platforms like Webex and Zoom, and adapt their lectures to an online format. One of the biggest challenges during this transition was to administer common online exams to high enrollment undergraduate classes, such as general chemistry and organic chemistry, without compromising the integrity of the exam. The in-person chemistry common exam that is normally administered to students at New Jersey Institute of Technology (NJIT) had both multiple-choice and open-ended questions. In order to replicate this online, and to reduce the potential temptation to cheat, a robust multiple-choice and open-ended exam with multiple versions was required. Furthermore, this online exam had to be easily administered through our learning management system. What was developed included a blueprint for an online exam intended for large-scale distribution over multiple days with safeguards in place to protect the integrity of the examination. The exam employed deferred grading, a lockdown browser, multiple question variants, time controls, and controlled access to the completed exam to combat potential cheating. The exam resulted in average scores that were comparable to in-person exam scores from previous semesters, validating the proposed approach. In addition, polling results after administration of the exam showed strong student satisfaction with exam design and directions and student preference for webcam proctored exams.

Characterization of school of dentistry prerequisite courses and recommendations for admission.

There is minimal research characterizing admission prerequisites courses across schools of dentistry. The purpose of this study was to typify didactic and laboratory course requirements and compare requirements based on institution demographics. In July 2019, the researchers evaluated websites from 76 North American dental schools to collect information on required and recommended courses, credit hour requirements, and institution demographics. Sub-group analyses evaluated differences in course and credit hour differences based on institution funding, degree program, location, and Carnegie Classification. The most common required courses were general chemistry (97.4%), physics (93.4%), organic chemistry (92.1%), general biology (90.8%), communication (86.8%), and biochemistry (80.3%). The most common required laboratory courses were general chemistry (63.2%), organic chemistry (59.2%), general biology (55.3%), and physics (51.3%). Several institutions included unique course recommendations such as histology (40.7%), psychology (30.3%), art (18.4%), business (18.4%), sociology (15.8%), and embryology (14.5%). There were few differences based on institution classifications; however, differences were observed most often between institutions within and outside the United States. The study also identified 65.8% (n=50) of schools have letter of recommendation requirements and 46.1% (n=35) of schools require or recommend shadowing experiences with programs requesting a median of 60hours (range 20-300hours). The study offers a contemporary characterization of prerequisite requirements and recommendations. In addition, the study raises critical questions about whether these standards reflect expectations for entering learners, if these requirements truly relate to learner success, and if these requirements prepare learners to be future-ready graduates.

Development of the Reaction Coordinate Diagram Inventory: Measuring Student Thinking and Confidence

The Reaction Coordinate Diagram Inventory (RCDI) has been developed to measure student thinking and confidence with reaction coordinate diagrams (RCDs) and their correspondence to reaction mechanisms. The RCDI was designed using a sequential mixed-methods protocol, such that the questions and distractors in the instrument were generated based on an analysis of qualitative semi-structured interviews in which general chemistry and organic chemistry students were asked to describe the concepts embedded in the surface features of RCDs and to use the mechanistic information encoded in RCDs. The RCDI was administered to second-semester general chemistry students (n = 443), second-semester organic chemistry students (n = 227), and second-semester physical/biophysical chemistry students (n = 45). Descriptive statistics and item function are presented for each of the three samples. Qualitative and quantitative evidence for the validity and reliability of the data generated by the RCDI are also presented. Major categories of misconceptions assessed by the RCDI and data demonstrating the prevalence of these misconceptions for all three groups of students are presented.

Acceleration and Deceleration Factors on the Hydrolysis Reaction of 4,6-O-Benzylidene Acetal Group.

The benzylidene acetal group is one of the most important protecting groups not only in carbohydrate chemistry but also in general organic chemistry. In the case of 4,6-O-benzylidene glycosides, we previously found that the stereochemistry at 4-position altered the reaction rate constant for hydrolysis of benzylidene acetal group. However, a detail of the acceleration or deceleration factor was still unclear. In this work, the hydrolysis reaction of benzylidene acetal group was analyzed using the Arrhenius and Eyring plot to obtain individual parameters for glucosides (Glc), mannosides (Man), and galactosides (Gal). The Arrhenius and Eyring plot indicated that the pre-exponential factor (A) and ΔS⧧ were critical for the smallest reaction rate constant of Gal among nonacetylated substrates. On the other hand, both Ea/ΔH⧧ and A/ΔS⧧ were influential for the smallest reaction rate constant of Gal among diacetylated substrates. All parameters obtained suggested that the rate constant for hydrolysis reaction was regulated by protonation and hydration steps along with solvation. The obtained parameters support wide use of benzylidene acetal group as orthogonal protection of cis- and trans-fused bicyclic systems through the fast hydrolysis of the trans-fused benzylidene acetal group.

Teaching Collaborations and Scientific Practices through a Vertically Scaffolded Biodiesel Laboratory Experience

Guiding students to become practicing scientists entails teaching them the specialized ways of collaborating, writing, and thinking that these professionals utilize every day. Laboratory experiences provide unique opportunities for student-centered curricular activities that mimic these skills. The biodiesel laboratory experience described here connects previously published biodiesel exercises in an intentionally scaffolded experience that models for students the types of collaboration and communication skills they will need if they choose to enter a STEM profession. The collaboration is vertically scaffolded to span multiple courses (general chemistry, organic chemistry, and physical chemistry) with opportunities for future connections with additional upper-division courses. The experience is writing intensive with a focus on both scientific writing through formal laboratory reports and writing for communication with nonscientists. By encountering this experience repeatedly throughout their chemistry coursework, students have the opportunity to develop the habits of working scientists.

Comparison of first-year grade point average and national board scores between alternative admission track students in a chiropractic program who took or did not take preadmission science courses.

We compared first-year cumulative grade point average and a composite score on part I of the National Board of Chiropractic Examiners (NBCE) exam for first-year alternative admission track program (AATP) students who did and did not take three specific undergraduate courses: general chemistry, organic chemistry, and anatomy and physiology. All AATP students in 2015 (n = 50) were evaluated for the course history of general chemistry and anatomy and physiology compared to their first-year cumulative grade point average and NBCE part 1 scores using independent t-tests. Students in the AATP who took general chemistry tended to score higher overall on the NBCE exams (p = .038, r = .229). Organic chemistry and anatomy and physiology had no statistical effect on improving board scores. First-year cumulative grade point average seemed to be unaffected by any of the undergraduate courses evaluated. There was a statistically significant difference in composite NBCE part 1 score between AATP students who had and had not taken general chemistry 1 before admission. There were no differences in first-year GPA between AATP students who had and had not taken undergraduate chemistry and A&P courses.

Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores

A scalable, cost-efficient and simple synthetic pathway towards potential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmacophores linked by the four methylene group chain were synthesized in 33, 35 and 39 % overall yield after a four-step synthetic route starting from three commercially available N-aryl piperazines. The anilino piperidine precursor was easily prepared in three steps, as previously published, starting from 4- piperidone. The synthesis presented in this paper could be of interest for heterocyclic and general organic chemistry. The newly designed compounds possessing two pharmacophores, opioid and D2/D3, are potentially useful pharmacological probes. Of particular interest would be the simultaneous binding to both opioid and D2/D3 receptors, and the resulting pharmacological responses may be useful for the further understanding of tolerance and dependence phenomena in opioid clinical use and/or abuse.

Book Review of Advanced General Organic Chemistry

Book Review of Advanced General Organic Chemistry