Organic Chemistry Course Research Articles

Retrosynthetic Rummy: A Synthetic Organic Chemistry Card Game

A deck of cards and a card game have been developed in an effort to make practicing organic chemistry and synthesis more fun for students. The game is played as a variation of rummy, in which players collect sets of similar cards and runs of cards in a synthetic sequence. This card game reviews knowledge of functional groups and reaction types and requires an ability to place many organic transformations in an appropriate order to synthesize target molecules. The game was used as a method to review second-year organic reactions for third- and fourth-year students at the beginning of a course in advanced organic chemistry. Students enjoyed the game and even gathered to play it outside of class. Additionally, the deck of cards was constructed so it can function to give a variety of classic card games a chemistry theme.

Creative Report Writing in Undergraduate Organic Chemistry Laboratory Inspires Nonmajors

Laboratory-based courses require students to compose reports based on the performed experiments to assess their overall understanding of the presented material; unfortunately, the sterile and formulated nature of the laboratory report disinterests most students. As a result, the outcome is a lower-quality product that does not reveal full understanding of the material. We have found that by allowing students to be more creative while preparing the introduction of their research reports, a greater enthusiasm for the organic chemistry course is stimulated because students are able to relate to the seemingly irrelevant reactants and mechanisms; this is often reflected in their laboratory reports, which are highly creative while maintaining crucial scientific integrity in the remainder of the report discussing experimental protocol, mechanisms, and all corresponding data.

Operationally Simple Synthesis of N,N-Diethyl-3-methylbenzamide (DEET) Using COMU as a Coupling Reagent

A novel procedure is described where students use COMU [(1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate], as a nonhazardous partner, in the one-pot coupling of a carboxylic acid and amine producing N,N-diethyl-3-methylbenzamide (DEET). Fundamental principles of carbonyl reactivity are understood, with potential for expansion to new methods of amide bond formation. The reaction can be monitored visually by virtue of the color change associated with the conversion, and all byproducts are conveniently water-soluble. This modern, microscale reaction is appropriate for a second-semester introductory undergraduate organic chemistry course: it can be performed during a 3 h laboratory period and is operationally straightforward. Curricular flexibility allows for this protocol to serve as a meaningful discussion of mechanistic organic chemistry and spectroscopy.

Students’ Understandings of Acid Strength: How Meaningful Is Reliability When Measuring Alternative Conceptions?

Most organic chemistry reactions occur by a mechanism that includes acid–base chemistry, so it is important that students develop and learn to use correct conceptions of acids and acid strength. Recent studies have described undergraduate organic chemistry students’ cognitive resources related to the Brønsted–Lowry acid model and the Lewis acid model, providing both qualitative and quantitative analyses of these understandings. To drive changes in pedagogy and curriculum, however, faculty need to be able to quickly assess students’ conceptions of acids and acid strength. We recently reported on the development and assessment of a nine-item, multiple-tier, multiple-choice concept inventory about acid strength, named ACID I. Coefficient α for ACID I was calculated to be below 0.70. In this manuscript, we demonstrate that despite this low coefficient α, the data generated by ACID I are indeed reliable. Thus, the purpose of this paper is to (i) report two significant alternative conceptions about acid strength that persist in organic chemistry students’ minds after nearly two semesters, and (ii) discuss the meaning of reliability for concept inventories, including a description of additional measures for the reliability of data collected using ACID I. Two types of test conditions were employed within second-semester organic chemistry courses in two different regions of the United States: a course at a medium-sized, midwestern liberal arts university and a large, southeastern research university.

Dipeptide Structural Analysis Using Two-Dimensional NMR for the Undergraduate Advanced Laboratory

A laboratory experiment was developed to introduce students in either an organic chemistry or biochemistry lab course to two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy using simple biomolecules. The goal of this experiment is for students to understand and interpret the information provided by a 2D NMR spectrum. Students are provided three unknown samples: a dipeptide and each of the two amino acids that make up the dipeptide. A Fourier transform-NMR (60 MHz) instrument is used to record standard proton (1H) NMR spectra for each of the unknown samples. By interpreting the 1H NMR spectra for the two single amino acid unknown samples, students identify the amino acids in the dipeptide. For the dipeptide molecule, students record the 1H and correlation spectroscopy (COSY or 1H–1H) NMR spectra. The students use the COSY spectrum information to assign all of the proton peaks in the more complicated 1D 1H spectrum of the dipeptide. A comparative analysis of the NMR spectra for dipeptides with the same amino acid constituents reveals that the order in which the amino acids are connected in the dipeptide influences the chemical shift of at least the α-protons.

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.

Using Commercially Available Techniques To Make Organic Chemistry Representations Tactile and More Accessible to Students with Blindness or Low Vision

Organic chemistry courses can present major obstacles to access for students with blindness or low vision (BLV). In recent years, efforts have been made to represent organic chemistry concepts in tactile forms for blind students. These methodologies are described in this manuscript. Further work being done at Illinois State University is also described that allows a student with BLV to independently make properly Braille labeled structures from the organic chemistry online database via ChemDraw.

Inverted Teaching: Applying a New Pedagogy to a University Organic Chemistry Class

Inverted teaching, not to be confused with hybrid learning, is a relatively new pedagogy in which lecture is shifted outside of class and traditional homework is done in class. Though some inverted teaching (IT) designs have been published in different fields, peer-reviewed reports in university chemistry remain quite rare. To that end, herein is disclosed a sophomore organic chemistry course design in which two groups of students were each taught by one of two methods: Group 1 through traditional lecture (TL) and Group 2 through IT. Design rationale and objectives are discussed. Academic performances are compared, along with anonymous student feedback contrasting the two techniques (TL vs IT). Student attendance and viewership, instructor prep time, and total lecture time are also presented for both styles.

A Three-Step Synthesis of Benzoyl Peroxide

Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using procedures that can be performed in four, 4 h laboratory periods. This process includes a Grignard reaction to turn bromobenzene into benzoic acid, nucleophilic acyl substitution to transform the resulting carboxylic acid into an acid chloride, and the addition of H2O2/NaOH to the acid chloride to yield benzoyl peroxide. Most organic chemistry students are familiar with these traditional reaction mechanisms because they are covered in introductory organic chemistry courses. The starting materials for each reaction are commercially available, and the products can be readily characterized using NMR spectroscopy, IR spectroscopy, and melting point.

Using Web-Based Video as an Assessment Tool for Student Performance in Organic Chemistry

This article shows the potential for using video responses to specific questions as part of the assessment process in an organic chemistry class. These exercises have been used with a postbaccalaureate cohort of 40 students, learning in an online environment, over a period of four years. A second cohort of 25 second-year students taking the organic chemistry course onsite has been using these exercises over a period of three years. The questions in this exercise require the students to use a molecular model kit. The problems presented to the students involve standard concepts in organic chemistry relating to geometric issues with molecules or organic reactions. This method of assessment allows the instructor to see a student’s higher-order thinking on a particular topic to a greater degree than is generally afforded with clicker questions. Students are acclimated to this new environment for assessment through practice exercises that are evaluated and critiqued, but not counted towards a grade. A transitio...

Learning Task Inventories (LTIs). Exploration of Optimal Conditions to Help Students Develop, Improve and Sustain Good Study and Learning Practices

To support students in an introductory organic chemistry course, scaffolding in the form of weekly Learning Task Inventories (LTIs) were introduced. LTIs are chapter-by-chapter lists of detailed learning tasks students are expected to master during the course. This paper describes efforts to effectively implement LTIs, the effect of differing implementations of LTIs on students’ final exam grades and students’ reactions to the use of LTIs.

The development of a Visual‐Perceptual Chemistry Specific (VPCS) assessment tool

AbstractThe development of the Visual‐Perceptual Chemistry Specific (VPCS) assessment tool is based on items that align to eight visual‐perceptual skills considered as needed by chemistry students. This tool includes a comprehensive range of visual operations and presents items within a chemistry context without requiring content knowledge to solve correctly. The VPCS was administrated to a total of 2,713 chemistry students taking general, organic, inorganic, and physical chemistry courses at a large, southeastern university over a period of three academic years. The preliminary validation process involved primarily factor analysis and Item Response Theory. A three‐factor solution was considered appropriate with the most reasonable interpretation labeling Factor 1 as a general visual‐spatial skill, Factor 2 involving multiple viewpoints (frames of reference), and Factor 3 related to memory ability. Our analysis supports an interpretation relevant to chemistry instruction that departs from previous findings where the factors obtained were viewed in terms of static or kinetic qualities (mechanical) and/or two‐dimensional versus three‐dimensional aspects. Several interpretations for the three‐factor solution are discussed as well as implications for teaching and future research. © 2014 Wiley Periodicals, Inc. J Res Sci Teach 51: 963–981, 2014

Use of iSpartan in Teaching Organic Spectroscopy

Spectroscopy is often one of the most difficult subjects in an organic chemistry course for students to master. One difficulty comes from relating peaks in a spectrum with structural features. For example, when teaching infrared spectroscopy, it is often difficult to connect the theory between bending and stretching vibrations to the actual peaks. iSpartan for the iOS platform allows this to be done easily without the high cost of the full Spartan software.

A revolutionary chemistry curriculum based on fundamental principles of chemical structure and reactivity that integrate organic and inorganic chemistry with biochemistry (530.3)

Traditional first year chemistry curricula have remained essentially unchanged for decades although recent movement to an atoms or organic chemistry “first” approach or to introductory biochemistry courses that replace a semester of organic chemistry course have emerged. Outside agencies (American Chemical Society, ASBMB, and the American Association of Medical Colleges) have recently developed guidelines that encourage science departments to develop innovative approaches to content selection and delivery, where competencies and skills replace specified courses. We have embraced these calls and introduced a potentially revolutionary approach to the teaching of chemistry. The unifying principle of our first four courses are based on the structure/reactivity of molecules which “don’t know their classification as organic, inorganic and biochemical structures”. A brief overview of our entire curriculum (content and pedagogy) as well as a more detailed description of our first year courses, Introduction to Chemical Structure and Properties and Introduction to Nucleophiles and Electrophiles (which integrates organic and inorganic with biochemistry) will be presented.Grant Funding Source: Suporting by NSF

An Almost Paperless Organic Chemistry Course with the Use of iPads

The advancement of tablet computer technology has progressed rapidly in the past three years to the point where organic chemistry can be almost completely paperless. Students in one section of organic chemistry were provided iPads equipped with the application Notability to use in lecture to take notes and to use in the laboratory as a laboratory notebook. All laboratory assignments were completed, submitted, graded, and returned to the students electronically. Student feedback about using iPads in class was very positive, with 9-out-of-12 students preferring to use an iPad to take notes rather than the traditional paper and pencil method.

Use of Screen Capture To Produce Media for Organic Chemistry

Although many students learn best in different ways, the widest range of students can be reached when multiple modes of input are employed, especially if the student is simultaneously completing a set of handwritten notes. Computers, meanwhile, have led to countless changes in society, and education has not been exempt from these changes. Students rarely, if ever, are without some sort of electronic device. Be it a smart phone, laptop computer, or tablet, the modern student is nearly perpetually “connected” to the Web. Screen capture has been used to produce high-quality videos for students in organic chemistry classes as an attempt to (i) exploit the students’ perpetually connected state for educational purposes by making not just course materials but also course meetings available online after class; (ii) provide course materials such as assignment keys and demonstrations that go beyond the boundaries of paper-based materials in a way that employs multiple modes of input; and (iii) accommodate legitimate student absences more rigorously. To date, such materials have been implemented in the mainstream organic chemistry course and its corresponding lab, as well as the basic nonmajor, one-semester, organic chemistry class. A description of this implementation is offered here.

Analysis of a Natural Yellow Dye: An Experiment for Analytical Organic Chemistry

This experiment exposes second-year undergraduate students taking a course in analytical organic chemistry to high-performance liquid chromatography (HPLC) and quantitative analysis using the internal standard method. This is accomplished using the real-world application of natural dyes for textiles. The extracted flavonoids of the plant weld are responsible for the yellow color of the dyed wool. Dried and ground weld is extracted for dyeing wool and quantifying the plant’s three main flavonoids. The students also mimic the work of chemists investigating historical textiles by carrying out a small-scale extraction of the dyed wool. Twenty-one students carried out the experiment, and their samples were analyzed using either a traditional 5 μm-particle size HPLC column or a modern 1.8 μm-particle size ultrahigh-pressure liquid chromatography (UHPLC) column mounted in a conventional HPLC system.

A Student-Centered First-Semester Introductory Organic Laboratory Curriculum Facilitated by Microwave-Assisted Synthesis (MAOS)

An instructional laboratory curriculum for a first-semester introductory organic chemistry course has been developed using microwave-assisted organic synthesis (MAOS). Taking advantage of short reaction times, materials were developed to facilitate collaborative experimental design, analysis, and debriefing of results during the normal laboratory period. Assessment results indicate that the new curriculum leads to more positive attitudes toward science, as well as enhanced retention of key concepts.

Free Radical Addition Polymerization Kinetics without Steady-State Approximations: A Numerical Analysis for the Polymer, Physical, or Advanced Organic Chemistry Course

A numerical analysis of the free radical addition polymerization system is described that provides those teaching polymer, physical, or advanced organic chemistry courses the opportunity to introduce students to numerical methods in the context of a simple but mathematically stiff chemical kinetic system. Numerical analysis can lead students to an appreciation of the power of numerical methods applied to chemical systems while providing a better understanding of the steady-state approximation and giving a more complete picture and deeper understanding of reaction dynamics. The description and Mathcad and MATLAB tutorials provided in the Supporting Information offer a variety of levels of student engagement ranging from classroom presentations of numerical and steady-state comparisons to projects requiring students to set up, run, and interpret numerical analyses for a free radical addition polymerization system.

A New Higher Education Curriculum in Organic Chemistry: What Questions Should Be Asked?

Organic chemistry is often considered to be a difficult subject to teach and to learn, particularly as students prefer to resort to memorization alone rather than reasoning using models from chemical reactivity. Existing studies have led us to suggest principles for redefining the curriculum, ranging from its overall structure to the tasks given to the students. We suggest reorganizing the content around the organic chemist's questions and even in the first year implementing teaching based on modeling, organic synthesis, and using a database (the reaction library) in class. Finally, we present a full curriculum reconciling these principles with the current content of an organic chemistry course.