Organic Nomenclature Research Articles

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.

Alcohol or Ethanol? Teaching Organic Chemistry Nomenclature in an Informal Environment

The basics of organic chemistry nomenclature were introduced in a laboratory organized in a nonformal environment such as a science festival. The laboratory, divided into three distinct but interconnected activities, was aimed not only at secondary school students but also at lay people. The intent was to explain the importance of associating a name to a molecular structure and conversely and that this is relevant not only for scientists but also in everyday life in order to better understand the properties of commonly used molecules. The overall goal was to stimulate interest in chemical topics with the aid of fun and engaging activities.

Chem’Sc@pe: an Organic Chemistry Learning Digital Escape Game

This article reports the development of Chem’Sc@pe, an escape game activity for first- and second-year undergraduate students, covering various topics from an introductory organic chemistry course. The objective was to encourage them to review notions learned in class in a fun and collaborative environment. The set comprises a game board representing 6 rooms of a chemistry laboratory, 30 thematic cards with puzzles to solve (multiple-choice questions, exercise, calculation, and model handling), various tools such as molecular models, and an android-based application. Students in teams of three to four had 60 min to solve enigmas related to functional groups, organic nomenclature, hybridization, stereochemistry, as well as lab-based activities. Each correct answer provides players with a 4-digit code, which gives access through the application to further levels and eventually to the conclusion of the game. History cards offering a short biography of famous chemists were also included in the game to promote scientific culture. Chem’Sc@pe was tested in 2021 with 70 first year chemistry students at the University of Montpellier (France). Assessment of the gamification activity by the students returned excellent reviews, showing that they enjoyed playing the game, found it easy to play, and described it as a useful learning experience.

Effect of Computer-Aided Instruction on Chemistry Students’ Achievement in Organic Chemical Nomenclature in Enugu Education Zone of Enugu State, Nigeria

This study investigated the effect of Computer-Aided Instruction on chemistry students’ achievement in organic chemical nomenclature in Enugu Education zone of Enugu State, Nigeria. One research question and one hypothesis guided the study. The design of the study adopted was quasi experimental, pretest-post test, non equivalent control design. The sample for the study comprised of 308 chemistry students (122 male and 186 female) purposively sampled from a population of 2,734 SS1chemistry students in Enugu Education zone of Enugu state. The instrument used for data collection was Teacher Made Organic Nomenclature Achievement Test (TMONAT) with 20 items multiple choice test. The instrument was constructed by the researchers and validated by two experts, one from the department of science education and one from the department of mathematics computer education (measurement and evaluation unit, Enugu State University of Science and Technology, (ESUT). TMONAT achieved a reliability of 0.87 calculated using kuder Richardson 20 (KR-20). Treatment lasted for six weeks. Mean and standard deviation were used to answer research questions while hypothesis was tested at 0.05 significance using Analysis of Covariance (ANCOVA). Males and Females were taught using computer-aided instruction (CAI). The findings of the study revealed that male and female chemistry students taught organic chemical nomenclature (OCN) with Computer-Aided Instruction (CAI) were almost at par in their achievement in OCN. Gender has no significance influence on students’ achievement in OCN with CAI. Based on the findings, it was recommended among others that Curriculum planners should include CAI as a model of instruction that promotes gender-equity.

Chemistry Teacher Trainees’ use of Molecular Models in Learning Spiro and Bicyclic Compounds

The study diagnosed chemistry teacher trainees’ difficulties in naming and writing structures of spiro and bicyclic compounds. The case study design was conducted in a constructivist environment to enhance chemistry teacher trainees’ ability to construct, represent, and interpret the structural formulae of spiro and bicyclic compounds. Purposive sampling technique was employed to select 126 1st-year chemistry teacher trainees from University of Education, Winneba for the study. The results revealed that chemistry teacher trainees had difficulties in naming and writing structural formulae of spiro and bicyclic compounds. However, through the effective use of molecular model kits in teaching naming and writing structures of spiro and bicyclic compounds, these chemistry teacher trainees became conscious of IUPAC rules for naming and writing spiro and other cyclic compounds. A t-test conducted indicated that a statistical significance difference existed between students’ performance before the implementation of the intervention and after the intervention. It is recommended that chemistry teachers should adopt the use of molecular model kits in teaching concepts of organic nomenclature.

IUPAC Blue Book

Abstract When the so-called IUPAC Blue Book “Nomenclature of Organic Chemistry (IUPAC Recommendations and Preferred IUPAC Names 2013)” was last published in 2014, it greatly expanded the coverage of the previous edition (1979) and included for the first time recommendations for a preferred IUPAC name (PIN) for those needing a consistent name. Still and for use in general nomenclature, alternative unambiguous names were included. A html version of the whole book including all corrections, changes, and modifications is now available.

Teaching organic nomenclature for pharmacy students: Adapting a course to online mode during COVID-19

Introduction: Due to the confinement of the COVID-19 pandemic, educational centres have remained closed, transferring the teaching process to online mode, thus adapting infrastructure, methodologies, and the university community. Objectives: This work aims to evaluate the effectiveness of strategies in learning organic nomenclature and seek student opinions about committing fraud in organic chemistry course assessments in the online mode in the pharmaceutical career. Methods: The methodologies used allowed the students to understand and apply the organic nomenclature rules, using online collaborative guides and crosswords worked in synchronous classes, previous reading, and the collaborative asynchronous creation of informative files for the recognition of heterocyclic compounds and formative assessment. All assessments were applied in three-people groups in the synchronous classes. Finally, an anonymous survey was administered to know the student perception of the possibility of fraud during the course. Results: A substantial improvement (from 47.7% to 80.5%) was observed in the application of IUPAC rules for organic compounds. Of the students who responded to the anonymous survey, 81% reported that the methodology used decreased the opportunity to commit fraud during assessments.

MET-Organic: A Multilevel Card Game to Promote the Learning of Organic Chemistry Nomenclature

MET-Organic: A Multilevel Card Game to Promote the Learning of Organic Chemistry Nomenclature

Application of Gaming as Strategy for Teaching Organic Nomenclature in a Brazilian Public School

Specific topics in chemistry, such as organic nomenclature, are often considered key subjects for understanding organic chemistry in high school. Several research types have already demonstrated that most high school students and even university students have great difficulty in this topic. In general, the problems come from the approach used to present these contents, sometimes superficial or without the use of interactive methodologies. This work aims to help the teaching & learning chemistry process by a game's applying, which consisted of building organic molecules using jelly beans and toothpicks, the previously published "Fastest Fingers." In the present work, we analyzed the positive impact that gaming can bring for the learning process and knowledge assimilation of this article's topic. This method mainly shows its importance when applied in a state that faces many issues in its education system, like Alagoas-Brazil. It was possible to notice that students' interaction and perception of the game, and molecules representation occurred more efficiently, thus favoring the learning and the interaction improvement between teachers and students.

Go Fischer: An Introductory Organic Chemistry Card Game

The use of games in chemistry education is well-established and is known to have numerous benefits to participants. This contribution describes the student-led development of an introductory organic chemistry card game based on the classic party game Go Fish. The game has been designed to help students practice applying the rules of organic nomenclature, to recognize key functional groups, and to familiarize themselves with simple examples of reactivity of molecules containing these functional groups. The game was used as an organic chemistry revision activity at the end of a freshman introductory general chemistry module (that included a significant amount of introductory organic chemistry). Evaluation of the activity shows that students enjoyed playing the game, found it easy to play, and that they found it a useful learning experience.

Brief guide to the nomenclature of organic chemistry (IUPAC Technical Report)

Abstract This IUPAC Technical Report is one of a series that seeks to distil the essentials of IUPAC nomenclature recommendations. The present report provides a succinct summary of material presented in the publication Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013. The content of this report will be republished and disseminated as a four-sided lift-out document (see supplementary information) which will be available for inclusion in textbooks and similar publications.

Algorithmic Analysis of Cahn-Ingold-Prelog Rules of Stereochemistry: Proposals for Revised Rules and a Guide for Machine Implementation.

The most recent version of the Cahn-Ingold-Prelog rules for the determination of stereodescriptors as described in Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (the "Blue Book"; Favre and Powell. Royal Society of Chemistry, 2014; http://dx.doi.org/10.1039/9781849733069 ) were analyzed by an international team of cheminformatics software developers. Algorithms for machine implementation were designed, tested, and cross-validated. Deficiencies in Sequence Rules 1b and 2 were found, and proposed language for their modification is presented. A concise definition of an additional rule ("Rule 6", below) is proposed, which succinctly covers several cases only tangentially mentioned in the 2013 recommendations. Each rule is discussed from the perspective of machine implementation. The four resultant implementations are supported by a 300-compound validation suite in both 2D and 3D structure data file (SDF) format as well as SMILES ( https://cipvalidationsuite.github.io/ValidationSuite ). The validation suites include all significant examples in Chapter 9 of the Blue Book, as well as several additional structures that highlight more complex aspects of the rules not addressed or not clearly analyzed in that work. These additional structures support a case for the need for modifications to the Sequence Rules.

The United Nations of chemistry

Chemists have been trying to work across international borders for more than 150 years. In 1860, the first international chemistry meeting was organized by German organic chemist F. August Kekule. Other international gatherings followed and led to the Geneva Congress on Organic Nomenclature in 1892, the first attempt to standardize the naming of molecules. As the field of chemistry continued to grow, so did the need for international consensus and standardization in nomenclature, terminology, metrology, and measurement standards. To meet that demand, in 1919 chemists formed the International Union of Pure & Applied Chemistry (IUPAC). Nearly a century later, IUPAC continues to be a worldwide resource for chemistry. Although IUPAC’s work in areas such as nomenclature remains critical—especially to ensure computers across the globe can analyze ever-larger data sets—its efforts have expanded to address matters such as an ethical code for chemists, safety training, standard file formats for spectra, various

Effectiveness of E-Content Package on Teaching IUPAC Nomenclature of Organic Chemistry at Undergraduate Level

Effectiveness of E-Content Package on Teaching IUPAC Nomenclature of Organic Chemistry at Undergraduate Level

Three‐Dimensional Chemical Structure Search Using the Conformational Code for Organic Molecules (CCOM) Program

Searching the 3D structural fragments of organic molecules is challenging because of structural differences between X-ray and theoretically calculated geometries and the conformational flexibility of substituents. The codification program called Conformational Code for Organic Molecules (CCOM) can be used to unambiguously convert 3D conformational data for various molecules to 1D data. Two deviations from Rule E-5.6 of the International Union of Pure and Applied Chemistry (IUPAC) Rules for Nomenclature of Organic Chemistry were introduced to the CCOM program for 3D fragment searching. First, the search for the highest priority atom was limited to a distance of two bonds from the center bond for dihedral angle determination. Second, for indistinguishable atoms in experimentally observed solution structures, the smallest number of atom index in the molecular model was chosen as the priority atom for dihedral angle determination. A search of the 3D conformational fragmentmb_3a6c4c of mevastatin () in combination with the SMiles ARbitrary Target Specification (SMARTS) description suggested that a change in the conformation of this fragment may be the driving force for dissociation of mevastatin from its target protein. Chirality 28:370-375, 2016. © 2016 Wiley Periodicals, Inc.

A Mailman Analogy: Retaining Student Learning Gains in Alkane Nomenclature

Visual analogies play an important role in the teaching and learning of many diverse topics in chemistry. Organic nomenclature is an essential skill needed for student success in organic chemistry; however, it is a topic most students have difficulty in mastering. Without a strong foundation of nomenclature, students will struggle to follow more advanced organic chemistry topics. The project described uses the analogy of a mailman, who is new to an area and trying to remember the destinations of his postal route, to teach alkane nomenclature. Once students master the topic of alkane nomenclature, they are ready to take on the task of naming other organic molecules. Application of the Teaching-With-Analogies (TWA) model defines a stepwise approach to generate an effective analogy and hence was used in the development of the mailman analogy. An easily understandable picture of a mailman, a route system, and housing along the route provides an analogy capable of developing students’ understanding of alkane nomenclature in organic chemistry. The assessment of student learning gains was performed in two different settings (Analogy versus Nonanalogy Groups) and it reveals that students who learn nomenclature with the analogy retain their learning gains through the course, whereas students who learn nomenclature without the analogy lose some of their gains as the semester continues.

Evaluating students' learning gains and experiences from using nomenclature101.com

Skill in organic chemistry nomenclature is fundamental for communicating more complex concepts. Interpreting and using functional group names is particularly important. With nomenclature101.com, students can create tailored interactive quizzes according to their learning needs; the tool is free and available in English and French. The present study investigated students' nomenclature learning in three different learning environments to determine (1) what learning gains participants make when using nomenclature101.com independently, when guided, or taught nomenclature through a traditional classroom tutorial and (2) students' perceptions of the usefulness, ease of use, and overall learning experience in each of the settings. We invited students from first and second semester organic chemistry courses at a large, research-intensive Canadian university to participate in a nomenclature workshop. When participants arrived, they were randomly sorted into one of three treatment groups: classroom tutorial, independent use of nomenclature101, or guided use of nomenclature101. Before the session, participants completed a pre-test; at the end, they completed a post-test and a questionnaire related to affective aspects of their experience. We analyzed participants' scores and questionnaire responses, and qualitatively analyzed their test answers, including errors. Learning gains were significant with large effect sizes for all three groups although there were no significant differences in learning gains between groups. The largest gains were observed in the ability to correctly identify and draw functional groups. Exploratory factor analysis showed that the post-workshop questionnaire about nomenclature101.com reliably measured participants’ perceptions about two latent factors: usefulness and ease of use. Based on questionnaire results, most participants liked the learning tool and found it useful and easy to use. Participants in all groups reported enjoying their learning experience. Few participants postdicted their quiz grades accurately, suggesting that metacognitive skillfulness was lacking among workshop participants. The large learning gains observed after using nomenclature101.com or learning in a classroom setting for just one hour shows the potential that instruction has to help students learn functional group identification skills, which ideally will mitigate barriers to communication and understanding. These results offer flexibility to educators as they make instructional choices such as teaching nomenclature in a course period or tutorial setting or asking students to learn nomenclature independently with nomenclature101.com. Students have the flexibility to work outside of class in the manner of their choosing.

Systematic Flexibility and the History of the IUPAC Nomenclature of Organic Chemistry

For chemists and chemistry students around the world, “IUPAC” is synonymous with “nomenclature” – especially the nomenclature of organic chemistry. Generations of chemists have learned – sometimes grudgingly – to read and write systematic names for organic compounds using guidelines codified by the International Union of Pure and Applied Chemistry. [1,2,3] The prefixes, suffixes, numbers, and parentheses of IUPAC names put molecules in order: individually, by expressing the network of atoms and bonds that constitutes the structure of an organic compound, and collectively, by situating each compound among the tens of millions of known organic chemical substances. IUPAC names carry this order out of chemical journals and into such sites as patent records, customs lists, and environmental regulatory databases.

In Memoriam: Peter A.S. Smith

Peter Smith (1920-2014), from the Chemistry Department of the University of Michigan, was a member of the Commission on Nomenclature of Organic Chemistry (III.1) from 1979-1991. He was an Associate Member 1979-83, a Titular Member 1983-91, and chair 1987-91. As chair of the Class Names project, he was an author of "Glossary of class names of organic compounds and reactive intermediates based on structure. Recommendations 1995",

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.