Understanding Of Organic Chemistry Research Articles

Probing the chemical ‘reactome’ with high-throughput experimentation data

High-throughput experimentation (HTE) has the potential to improve our understanding of organic chemistry by systematically interrogating reactivity across diverse chemical spaces. Notable bottlenecks include few publicly available large-scale datasets and the need for facile interpretation of these data’s hidden chemical insights. Here we report the development of a high-throughput experimentation analyser, a robust and statistically rigorous framework, which is applicable to any HTE dataset regardless of size, scope or target reaction outcome, which yields interpretable correlations between starting material(s), reagents and outcomes. We improve the HTE data landscape with the disclosure of 39,000+ previously proprietary HTE reactions that cover a breadth of chemistry, including cross-coupling reactions and chiral salt resolutions. The high-throughput experimentation analyser was validated on cross-coupling and hydrogenation datasets, showcasing the elucidation of statistically significant hidden relationships between reaction components and outcomes, as well as highlighting areas of dataset bias and the specific reaction spaces that necessitate further investigation.

Arrow-Rotation-Method “ARM”, a Simple and Fast Method for Interconverting Fischer Projections and Zigzag Structures

Different molecular representations are usually used to depict the three-dimensional (3D) structure of organic compounds. Mastering the skill of interconverting one form into another is essential for students to ensure success in organic chemistry. The traditional and recently developed methods for completing such interconversions that rely on 3D visualization of 2D paper (screen) structures, absolute configuration assignments, or multistep drawings that require 3D visualization are often time-consuming and difficult, especially for students with 3D visualization difficulties or a certain level of aphantasia, thus turning organic chemistry into a hurdle in their academic pathway. Given the importance of this topic and its impact on students’ understanding of organic chemistry, the Arrow-Rotation-Method (ARM) has been developed to interconvert zigzag structures and Fischer projections in a few simple steps that require only 2D visualization. A quantitative approach was used on a group of students enrolled in an introductory organic chemistry course to evaluate the time efficiency and usefulness of the new method. The results indicated that ARM significantly improved students’ performance in completing the various interconversions compared to the traditional methods and proved to be more student-friendly, time-efficient, and accurate, especially for compounds with multiple chiral centers. ARM was also successfully used to sketch the structure of complex compounds with multiple chiral centers upon conformational change.

The effect of productive failure in a digital inquiry environment on developing deep understanding and achievement of organic chemistry among secondary school students

This study measures the effect of productive failure instruction in a digital inquiry environment on developing deep understanding and achievement of organic chemistry among Saudi Arabian secondary school students. The study adopted the experimental design of control and experimental groups with pre- and post-measurements. The sample comprised 66 secondary school students from Wadi Al-Dawasir Governorate, Riyadh, Saudi Arabia, distributed into the experimental group (n = 32) and the control group (n = 34). The data collection utilised the deep understanding test and the achievement test of organic chemistry. The results revealed that there were statistically significant differences at α = 0.05 between the means of the scores of the experimental and control groups in the deep understanding level and the achievement test of organic chemistry in favour of the experimental group. Recommendations and suggestions are also presented in light of the study results.
 
 Keywords: Productive failure, digital inquiry environment, deep understanding of organic chemistry, the achievement of organic chemistry

Organic chemistry to stimulate meta-cognitive skill in natural material for development of module of medical plants

Medical plants are increasing attention worldwide due to their empirical efficacy and development. This study aims to develop a medical plants module on organic chemistry in natural materials to simulate the students' metacognitive skills. It investigates technique that refers to the research and development steps. Organic chemistry is in action; this program aims to improve learning and understanding of organic chemistry. Then, this investigation starts by examining the subject requirements in plant and natural material in organic chemistry that people frequently use as a medicine and a module as a learning resource. The results evaluate the students' metacognitive skills using the medical plant's modules significantly vary. Students' metacognitive skills are determined, and their ability in the scheduling feature is well developed. The potential of the local medicinal plant module can simulate students' metacognitive skills.

254 Effect of presentation method on understanding of organic chemistry in an undergraduate animal nutrition course

Abstract An educator’s goal is to always explain classroom material to his or her students in the most efficient way possible. Chemistry is a fundamental foundation to the study of animal nutrition, but the concepts of organic chemistry are very difficult to relay to students of animal science, possibly due to the different types of student learners. It could be that mode of presentation may aid in relaying this information to the students. The sample for this experiment included students enrolled in an animal nutrition course at Tarleton State University. Students were presented with five methods of presentation of carbohydrate molecular structure in a laboratory session, each with an increasingly tactile approach: written description, printed 2-dimensional model, printed 3-dimensional model, ball-and-stick model, and self-constructing molecular model kit. Students were then asked to complete a survey to address effectiveness of presentation method. Data were analyzed using SAS v. 9.4. When addressing effectiveness of presentation method, the written description and the printed 2-dimensional model were rated as slightly-to-moderately effective (48.4 and 67.8%, respectively), the printed 3-dimensional model was rated as moderately effective (58.1%), the ball-and-stick model was rated as very effective (48.4%), and the self-constructing model was rated as very-to-extremely effective (80.6%). Cluster analysis revealed that students chose any of the presentation methods over the written description with preference for the self-constructing model. Results are interpreted to mean that presentation of organic chemistry concepts in animal nutrition are more effective when kinesthetic presentation methods are employed.

ChemInform Abstract: From Fragmentation to Construction — From Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

AbstractReview: [228 refs.

From Fragmentation to Construction--from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three-Dimensional Polycyclic Aromatic Hydrocarbons.

Detailed insights gained from our research into the gas-phase chemistry of ionized and protonated diphenylalkanes and their congeners, obtained by extended synthesis of isotopically labeled model compounds and mass spectrometry, are presented and merged with those acquired during our development of a new family of polycyclic hydrocarbons, the centropolyindanes. Aside from a Personal Account that describes "two scientific lives in one", it is demonstrated, on the one hand, how our understanding of organic chemistry can help to shed light on the details of mass spectrometric fragmentation and to unravel, in a more fundamental way, the unimolecular reactivity of gaseous ions. On the other hand, it is shown how unexpected reactivity of related ions in solution, being subject to the very same fundamentals of organic chemistry, can lead to the construction of novel and, in part, unique three-dimensional polycyclic structures that may contribute to future research in material science. Two such apparently independent fields of organic chemistry may be seen as joint contributions of the art of science.

A Roadmap to Design Robust Redox Shuttles for Lithium-Ion Batteries

In designing robust, effective redox shuttles for overcharge protection in lithium-ion batteries, a variety of factors are necessary to consider and evaluate. The stability and reactivity of the radical cation form of a redox shuttle candidate are critical to extensive overcharge performance. Radical cations are subject to a variety of reactions because of their unpaired electron and positive charge, making them subject to nucleophilic attack and dimerization, among other reactions including disproportionation or premature reduction. Equally as important is the stability of the neutral form of the redox shuttle, which may decompose through reaction with electrolyte, SEI, and/or be reduced at the anode/electrolyte interface. Neither stability nor reactivity is easy to predict, although an understanding of organic chemistry can lead to some general guidelines for the design of less reactive species. Density functional theory (DFT) calculations can be used to predict energies of reaction and have been employed by Curtiss, Dahn, and our group. DFT calculations can also be used to compute oxidation and reduction potentials, helping to identify promising candidates before synthesizing materials. This presentation focuses on our work using DFT calculations to help us identify promising redox shuttles and to gain a better understanding of their reactivity and includes experimental data in support of some of the proposed mechanisms of decomposition.

Organic Chemistry in Action! What Is the Reaction?

The Organic Chemistry in Action! (OCIA!) program is a set of teaching resources designed to facilitate the teaching and learning of introductory level organic chemistry. The OCIA! program was developed in collaboration with practicing and experienced chemistry teachers, using findings from Chemistry Education Research (CER). The program was developed as an alternative mode of teaching the prescribed high school organic chemistry curriculum in Ireland. The program aims to improve learners’ attitudes towards, interest in and understanding of organic chemistry. The OCIA! program has been trialed with 87 students in six high schools. The effectiveness of the program was evaluated using three methods: feedback from the chemistry teachers in the experimental group (n = 6), feedback from the students in the experimental group (n = 87) and quasi-experimental comparison with students in a control group (n = 117). The evaluation has shown that this project was effective in improving the students’ attitudes towards,...

Nomenclature101.com: A Free, Student-Driven Organic Chemistry Nomenclature Learning Tool

Fundamental to a student’s understanding of organic chemistry is the ability to interpret and use its language, including molecules’ names and other key terms. A learning gap exists in that students often struggle with organic nomenclature. Although many resources describe the rules for naming molecules, there is a paucity of resources available to actively and independently practice naming and drawing molecules and receiving feedback; plus, many of these resources are of low quality. Furthermore, students often do not see the real-life applications of the molecules they are naming. Our team created www.nomenclature101.com to respond to the learning gap and the lack of quality resources and to provide a link to real-life applications. This Web site hosts a free, interactive, online, bilingual (English/French) learning tool that draws from a bank of almost 1000 questions. This online learning tool is student-driven; it allows students to tailor their learning to their needs by creating customized nomenclature quizzes and providing immediate feedback. Nomenclature101.com has three key learning objectives; after working through the quizzes and other learning supports, students can (i) identify functional groups in a given molecule, (ii) name a molecule, given its structure, and (iii) draw a molecule, given its name. The learning tool is designed for high school chemistry and introductory organic chemistry courses. Students can use the tool independently or based on specific recommendations from their instructor; additionally, instructors could generate and print quizzes to use as part of their course assessment.

Organic Chemistry in Action! Developing an Intervention Program for Introductory Organic Chemistry To Improve Learners’ Understanding, Interest, and Attitudes

The main areas of difficulty experienced by those teaching and learning organic chemistry at high school and introductory university level in Ireland have been identified, and the findings support previous studies in Ireland and globally. Using these findings and insights from chemistry education research (CER), the Organic Chemistry in Action! (OCIA!) program was developed. OCIA! is an evidence-based program designed to facilitate the teaching and learning of high school and introductory undergraduate organic chemistry. The purpose of this program is to improve learners’ attitudes towards, interest in, and understanding of organic chemistry. The development and implementation of the OCIA! program has proven that the findings from CER can be effectively implemented into high school classrooms, working within the constraints of a prescribed curriculum. It is hoped that the ideas and approaches taken in the OCIA! program can be adapted for use at high school and introductory undergraduate organic chemistry ...

Using Chemical Knowledge to Uncover New Biological Function: Discovery of the Cylindrocyclophane Biosynthetic Pathway.

An understanding of organic chemistry can play a central role in uncovering enzymes with new biochemical functions. We have recently identified the enzymes involved in the biosynthesis of the cylindrocyclophanes, a structurally unique family of natural products, and found that this pathway employs a remarkable macrocyclization event that requires functionalization of an unactivated carbon atom. This work illustrates the potential of using chemically guided approaches for enzyme discovery.

Coordination chemistry at carbon

Electron-rich allenes and heterocumulenes are commonly described by the regular notations of organic chemistry. Following on from published results and recent computational studies, we present here a host of crystallographic and reactivity data, as well as theoretical results, that indicate a highly non-canonical bonding situation in many members of this series. These must actually be interpreted as coordination compounds, in which carbon serves as a 'central atom' that interacts with its 'ligand sphere' via donor-acceptor bonds, even if these internal ligands themselves are carbon based. This captodative description is not limited to compounds that supposedly comprise a carbon(0) centre, a peculiar oxidation state that can be probed experimentally by geminal diauration. As the available data suggest that this unconventional interpretation of C-C and C-X bonds is more generally applicable than previously anticipated, it may well affect our understanding of organic chemistry in general.

A Poster Session in Organic Chemistry That Markedly Enhanced Student Learning

Chemistry courses worldwide have experienced dwindling student numbers and decreasing success rates in recent years. This has led to many proposals on ways to get students actively involved in their courses. At the University of the Witwatersrand, South Africa, our ChemII course has suffered a similar fate and the introduction of cooperative small group tutorials to get students actively involved in the learning process has met with limited success. Further innovations were introduced into the Organic II module, but students' perception of the module remained negative and their commitment to it has dwindled over the years. In the first semester of 1998 the ChemII class at Wits performed particularly poorly and only 23% of the students passed. In an attempt to improve this situation in the second semester, a poster presentation session was introduced into the Organic II module. The choice of topic for the poster was found to be crucial to the success of the innovation, which resulted in students' increased enthusiasm for, commitment to, and understanding of organic chemistry. Relative to the previous year, the class average for the Organic II module increased by 10% and the pass rate by 30% while the class average and pass rates in the other three ChemII modules (inorganic, analytical and physical) dropped by comparable amounts. This improvement in performance in the Organic II module is credited to the poster presentations shifting most students from a "futile learning cycle" into a "productive" one.

Generation of molecular graphs based on flexible utilization of the available structural information

Classical theory of chemical structure has remained the basis for a comprehensive understanding of organic chemistry. Graph theory provides an extremely useful mathematical language for the description of both chemical structure and its properties. In many practical computer applications such as structure elucidation, synthesis planning and molecular design the generation of sets of candidate-structures (molecular graphs) is required. It is essential, that the generation process is constrained by the input structural information derived from any spectral, physical, chemical, etc., data. On the other hand, in most of the cases this information is incomplete, overlapping and ambiguous, which calls for approaches reflecting these features. Several problems, such as the isomorphism problem, and the combinatorial explosion complicate additionally the generation process. They should find their solutions under these constraints. Hence, the application of any general method for graph generation does not produce satisfactory results. All this calls for the development of specific graphgeneration schemes flexibly constrained by the input structural information. Some procedures treating special classes colored graphs (describing the real chemical structure), and employing sets of subgraphs (molecular fragments), etc., are introduced within the generation scheme. Furthermore, the generation method must reflect the fuzzy character of the information usually available to the chemist and to provide a straightforward pathway to the correct solution in the process of automated reasoning. In the present paper a wide variety of problems emerging from the generation of molecular graphs in the case of computer-aided structure elucidation are addressed and their possible solutions discussed.

The Teaching of Organic Chemistry

In spite of the great advances made during the last thirty years or so in the understanding of organic chemistry, the teaching of the subject, at least at an elementary level, has remained more or less unchanged. It is not uncommon for teachers to adopt exactly the same approach to the subject as was used when they themselves were students and the somewhat dreary repetition of ‘preparations, properties and uses’ is still the most widely used teaching method. Many of the textbooks used have been current for three or more decades and are devoid of modern ideas; even the more recent ones are predominantly old‐fashioned in approach. Good textbooks are, of course, available and they are used to some extent, but unfortunately the old favourites still dominate the field.