Organic Chemistry Class Research Articles

Highly Regio- and Stereoselective Dehydration of Allylic Alcohols to Conjugated Dienes via 1,4-syn-Elimination with H2 Evolution.

Dehydration of alcohols is one of the most fundamental transformations in the organic chemistry class and one of the most widely used methods for producing alkenes in synthetic research. Numerous methods and reagents have been developed to control the regio- and stereoselectivity as well as the dehydration efficiency of normal alcohols. Despite these achievements, regio- and stereoselective and predictable dehydration of allylic alcohol has seldom been reported, except for limited substrates with a native preferred elimination position, as a result of the challenges that many potential dienes could be formed via 1,2- or 1,4-syn- or anti-elimination. Here, we report a tBuOK/potassium 2,2-difluoroacetate-mediated 1,4-syn-dehydration of allylic alcohol for the synthesis of regio- and stereodefined conjugated dienes via an in situ generated directing group strategy. This reaction exhibits a broad substrate scope and good functional group compatibility for primary-tertiary alcohols. The simple and scalable (up to 0.6 mol) procedure with readily available and inexpensive reagents makes it a practical method for conjugated diene synthesis. Mechanistic studies reveal that an acetate with tert-butoxide and allyloxide acetal moiety is formed as an intermediate, in which the acetate and the acetal act as the directing group for the base-promoted elimination. An unusual H2 evolution is also involved in the reaction.

An Undergraduate Laboratory Module Integrating Organic Chemistry and Polymer Science.

Polymer science is receiving wider acceptance in the organic chemistry community; thus, it is imperative to include it in the undergraduate organic chemistry curriculum. Despite the ever-increasing popularity of the topic of polymer chemistry in undergraduate curricula, a comprehensive laboratory experiment module describing a polypeptide synthesis by ring-opening polymerization of N-carboxyanhydride (NCA ROP) and a homopolymer synthesis by activators-regenerated by electron-transfer for atom transfer radical polymerization (ARGET ATRP) has yet to be proposed. Herein, we report a semester-long, ten week undergraduate laboratory module focusing on the synthesis and analytical characterization of polyalanine and polystyrene for an advanced organic chemistry class. Students received hands-on-experiences in synthesizing polymers followed by their characterization via proton nuclear magnetic resonance (1H NMR) spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), gel permeation chromatography (GPC), thermogravimetry (TGA), differential scanning calorimetry (DSC), and transmission electron microscopy (TEM), which are not well-presented in the typical organic chemistry curricula. These engaging hands-on lessons in the newly designed laboratory module not only increase students' interests in an interdisciplinary environment of organic chemistry and polymer science but also cultivate their research interests and communication skills and promote critical thinking.

0215 Targeting the Knowledge-Behavior Gap in Sleep: The Impact of Augmenting Sleep Education with Implementation Intentions

Abstract Introduction Sleep education programs are increasingly utilized in high schools and universities to address late bedtimes and poor sleep quality in students. While these programs successfully improve sleep knowledge, they often do not change sleep behaviors (e.g., bedtimes), especially during academically demanding/stressful periods. A potential method for bridging the knowledge-behavior gap in sleep is to augment sleep education with implementation intention formation (Education+II), an established goal-fulfillment strategy. We tested this intervention in a highly demanding context: students enrolled in organic chemistry classes. Methods Undergraduate students (N=101) completed baseline questionnaires and actigraphy monitoring before completing a standardized sleep education program (Sleep 101). Afterward, participants were randomly assigned to an Education-Only condition or an Education+II condition. In the Education+II condition, using standardized if-then verbalization and visualization techniques, participants formed specific plans to go to bed earlier for the next five school nights. Participants were sent text reminders to implement their specific plans; nightly texts were also sent to Education-Only participants, but they were asked to reply with an interesting fact about sleep they learned during the education program. Participants completed questionnaires at the end of the intervention period as well as during 1-month and 7-month follow-up periods. Results There were significant time-dependent improvements in total sleep time, global sleep quality, mood, and perceived stress across groups, suggesting benefits of receiving sleep education. Participants in the Education+II condition demonstrated earlier bedtimes than those in the Education-Only condition during the intervention phase (both actigraphy and self-report) and at least one month later. Forming an implementation intention did not improve organic chemistry grades on a group-level, but grades in non-chemistry courses were higher in Education+II participants who maintained earlier bedtimes (a correlational pattern specific to this condition). Conclusion Augmenting sleep education with implementation intentions successfully advanced bedtimes during a rigorous organic chemistry course. Implementation intentions are a no-cost technique that is easy to build into sleep education programs. Doing so will encourage individuals to turn their general intentions to get better sleep into actualizable steps that facilitate behavioral change. Support (if any) National Science Foundation CAREER grant (1943323).

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UNDERGRADUATE EDUCATION Reactions ShareShare onFacebookTwitterWechatLinked InRedditEmail C&EN, 2023, 101 (7), p 3February 27, 2023Cite this:C&EN 101, 7, 3Letters to the editorOrganic chemistryAs a footnote to Mark M. Green’s letter on how to make organic chemistry “be part of understanding the wider world, to be worth knowing” (Jan. 2, 2023, page 3), I wish to illustrate my approach to “a great story to be told.”For over 50 years I have incorporated five special topics in my sophomore organic chemistry courses starting on day 1. “Chemical Evolution” looks at the simple chemicals and chemical reactions occurring in our universe, Stanley Miller’s exotic prebiotic syntheses of amino acids and peptides, and the simple organic compounds recently found on comets and meteorites. “Insect Pheromones” is introduced during the discussion of alkanes and alkenes, with examples like muscalure, the long-chain alkene of the housefly sex pheromone (a Wittig reaction synthesis), and illustrated by the syntheses of the queen bee pheromone and the Japanese beetle sex pheromone. Halogen addition reactions of alkenes that occur in the ocean via bromonium ions are examples of the natural halogenated alkanes produced by seaweeds (the smell of the ocean), including 1,2-bromochloroalkanes formed when oceanic chloride attacks a bromonium ion generated by bromoperoxidase. “Pesticides and Herbicides” includes the natural insecticides rotenone, caffeine, pyrethrins, and cocaine. Pyrethrins are naturally occurring cyclopropanes, and physostigmine, the “drug of divine justice,” is a natural carbamate. The preparation of DDT and DDD, which includes the cancer drug mitotane, involves electrophilic aromatic substitution and carbonium ion chemistry and illustrates ortho and para ring selectivity. Vietnam defoliants, presented alongside pesticides and herbicides, involve the syntheses of 2,4-D and 2,4,5-T, which illustrate nucleophilic aromatic substitution, benzyne generation, and dioxin formation. “Chemical Carcinogenesis” comprises the metabolism and chemistry of polycyclic aromatic hydrocarbons, benzene versus toluene, aromatic amines, azo dyes, nitrosamines, and natural carcinogens (such as aflatoxin). Protein and nucleic acid chemistry includes “Chemical Warfare,” featuring tear gas, chlorine, phosgene, mustard gas, and organophosphates (such as nerve gas) and the inhibition of acetylcholinesterase. The reaction of pepper spray exemplifies the Michael reaction with nucleic acids, as do the environmental pollutants acrylamide and acrolein.Each special topic occupies 1–3 lectures of the 30–32 course lectures. The special topics and accompanying slides are intermeshed with these conventional organic chemistry topics: alkene and alkyne electrophilic addition, nucleophilic substitution (SN1, SN2), aromatic electrophilic and nucleophilic addition, aryne formation, reductive amination, carbonyl addition and condensation, conjugate addition (Michael reaction), haloform reaction, and Diels- Alder cycloaddition.It will take some work, but it’s worth the effort.Gordon W. GribbleLebanon, New HampshireMuch has already been said about the fiasco surrounding the firing of professor Maitland Jones Jr. by New York University as the result of a student petition claiming that his organic chemistry class was too difficult. Without wishing to comment on this case myself, I am reminded of a related aspect of teaching organic chemistry that I suspect others may also have experienced.Organic chemistry seems to hold a special place in the hearts and minds of most practicing physicians. Some have been left with very positive feelings about this subject, while others have very negative feelings. Both groups of doctors keenly remember how important it was for them to receive good grades in organic chemistry to be admitted to medical school.Today, when I tell my doctor that I’ve taught organic chemistry, this always draws an immediate response. Some light up with a smile and tell me how much they’ve enjoyed this class, while others frown and offer words to the contrary. When the latter happens, this does give me pause for thought. Is this the right doctor for me? On one occasion, only moments before I was anesthetized for a colonoscopy, my gastroenterologist asked me what class I was teaching at my university. When I told her it was organic chemistry, her face lit up with a smile. Oh, what a relief that was.Steven L. RegenBethlehem, Pennsylvania CorrectionsFeb. 13, 2023, page 8: In the news story about Croda’s acquisition of Solus BioTech, the caption incorrectly labels parts of the ceramide NP structure. The sphingosine group is red and the fatty acid is blue, not the other way around.Feb. 13, 2023, page 13: The news story about Alondra Nelson misidentifies the organization she is returning to. It is the Institute for Advanced Study, not the Institute for Advanced Studies. And the institute is in Princeton, New Jersey, not part of Princeton University.

Chemistry professors decry firing of colleague at NYU

The firing of New York University (NYU) chemistry professor Maitland Jones Jr. after students complained about one of his organic chemistry classes has prompted concern and dismay among others in the academic chemistry community. As revealed in an Oct. 3 article in the New York Times , Jones was dismissed at the beginning of the fall semester after the university received a petition from 82 of his 350 students last spring complaining about low grades and the difficulty of an organic chemistry course taken by many nonmajors. “I’m very disturbed by it being a decision made by the dean’s office, not by the Chemistry Department,” says David Schuster, an emeritus chemistry professor at NYU. Schuster says he has been in touch with several of his former colleagues and current Chemistry Department members at NYU, all of whom object to the university’s action. The news “was startling on many levels,” says

Exploration of Students’ Social Presence in Web-Based Discussion for Conceptual Learning of Organic Chemistry

The current work reports the results of students’ social presence in web-based discussions for their conceptual learning of organic chemistry. The results in this study were collected from the examined students-students, students-instructor, and students-learning materials interactions via the designed web-based discussion. We created an online forum known as “Universal Chemistry Network” to enhance communication among students and teachers in organic chemistry classes. The population comprises four hundred thirty-two (432) 11th-grade students studying chemistry in these combinations. However, a sample of 138 chemistry students was purposively selected from 36 secondary schools located in Kicukiro District in Rwanda. A questionnaire composed of multiple-choice and open-ended questions and a chemistry achievement test were used to collect data. The obtained data were analyzed by using descriptive statistics, inferential statistics, and interpretive analysis. The results revealed that the use of web-based discussion is a potentially effective teaching method for enhancing student–student and student–teacher interactions in organic chemistry classes. Students appreciated this teaching and learning method as it helped them to search for additional information related to the subject taught and exchange ideas, knowledge, and experiences. The web-based discussion was also found to provide the students with the potential confidence and motivation to express easily their opinions. The repeated measures ANOVA showed that web-based discussion increases students’ academic performance in organic chemistry (p < 0.001, $$\eta =0.406)$$ . However, there is no statistically significant difference in the mean score between males and females (p > 0.05, $$\eta =$$ 0.27). The challenges faced by students during web-based discussions while learning organic chemistry were also examined.

Exploring Electrosynthesis: Bulk Electrolysis and Cyclic Voltammetry Analysis of the Shono Oxidation.

As electrochemistry continues to gain broader acceptance and use within the organic chemistry community, it is important that advanced undergraduate students are exposed to fundamental and practical knowledge of electrochemical applications for chemical synthesis. Herein, we describe the development of an undergraduate laboratory experience that introduces synthetic and analytical electrochemistry concepts to an advanced organic chemistry class. Experiments focus on the electrooxidative α-functionalization of carbamates, more generally known as the Shono oxidation, and include cyclic voltammetry analysis of two cyclic carbamates and a constant current bulk electrolysis reaction. The exercise offers students an authentic experience in organic electrochemistry, lays a practical and theoretical foundation for future engagement with concepts in electrochemistry and redox chemistry, and strengthens fundamental organic chemistry skills.

Not That DDT: A Databank of Dynamics Trajectories for Organic Reactions

The Databank of Dynamics Trajectories (DDT, notthatddt.org) was established to assist students in visualizing the dynamical behaviors occurring during chemical reactions and conformational changes, with a focus on processes taught in introductory organic chemistry classes. Animations of reacting molecules created using ab initio molecular dynamics simulations constitute the key feature of the DDT website.

Determination of Linalool in Essential Oils by SPME-GC-MS: Using the Internal Standard Method

A novel undergraduate analytical chemistry experiment involving the identification and quantification of linalool in essential oils was developed. The experiment uses the internal standard method with headspace solid phase microextraction (SPME) and gas chromatography–mass spectrometry (GC-MS). This method is applicable to any linalool-containing essential oil sample but could be expanded to quantify other components. Initial experiments demonstrated the effectiveness of the internal standard method, with the regression analysis of the internal standard calibration curve having excellent linearity (R2 ≥ 0.98) compared to external standard calibration (R2 < 0.50). Several essential oils were tested, and the quantified concentrations were typically within 20% of the expected concentrations from manufacturer data or literature results. With >30% linalool, lavender oil was found to contain the highest concentration of linalool compared to all oils tested. This experiment introduces method development, SPME, GC-MS, and the internal standard method to sophomore and junior level chemistry students. This lab was used in analytical and organic chemistry classes but could be used with any students interested in quantitative instrumental analysis methods. In a survey of three separate groups of students who performed the lab, most students responded that the experiment provided them a better understanding of SPME, GC-MS, and the internal standard calibration method.

The current situation of developing problem-solving ability and creativity through the use of active teaching methods in Organic Chemistry classes in high schools

Problem-solving ability and creativity are one of the key competencies needed to improve for high school students, according to Vietnam’s new education curriculum. This article examines current situation of the implementation of active teaching methods in order to improve that competency for Organic Chemistry students at 13 Vietnamese high schools. Interviews, investigations and statistics are applied in data process. The findings suggest that the level of using active teaching methods to foster the competency in Organic Chemistry classes is currently still low; also, the teachers’ awareness of this issue is not exhaustive. This fact raises the concern of follow-up studies on measures to enhance students’ problem-solving ability and creativity in an effective way.

The Effect of Supplemental Instruction on Educational Accomplishments and Behaviors of Organic Chemistry Scholars

Supplemental Instruction (SI) is proved to be an effective application in universities and colleges around the world. SI is considered to decrease attenuation and enhance educating and accomplishment rate amongst pupils who took part in the study. We have applied SI on Organic Chemistry I lessons to support pupils’ engagement with acquiring the subject and information of Organic Chemistry, that is thought to be a tough and attenuating course. The goal of this study is to scrutinize the effect of SI addition in a big lecturing type Organic Chemistry class and meanwhile supporting scholars’ education and accomplishment in the mentioned class. The aim of the present study is to inspect if SI affects the scholars’ educational accomplishments, behaviors and educational capabilities. The tentative scheme is grounded on an experimental-like method that contains a survey of open-ended and Likert-scaled questions which was given to SI scholars and their scores have been compared with the scores of scholars who were not in SI plan. Results show that adding SI to Organic Chemistry lessons will have positive effects on scholars’ behavior towards the subject and involvement in the class, assist the scholars to grasp the subject and information better, enhance scholars’ abilities to solve the problems, and can be helpful in enhancing scholars’ accomplishment, success and education. SI scholars responded with an average of 81% on overall passing, where non-SI scholars had an average of 50%. SI scheme has delivered a special and personalized educational experience for scholars which ended in an improved conceptual perception.

Explore, Exploit, and Prune in the Classroom: Strategic Resource Management Behaviors Predict Performance

Self-regulated learners strategically manage physical, technological, online, and social resources for learning—by selecting resources that could be useful, reflecting on how useful these resources have been, and adjusting resource use accordingly. We propose a model that conceptualizes resource management as learners’ intentional, self-reflective decisions to explore new resources, exploit (continue to use) previously useful resources, and prune (stop using) previously ineffective resources. We modeled 4,766 students’ reported exploration, exploitation, and pruning between three class exams among four cohorts of an organic chemistry class (i.e., more than 100,000 discrete data points of resource use). Each of these behavioral mechanisms of resource management predicted students’ academic achievement: The more students reported exploring, exploiting, and pruning between their exams, the higher they performed on their subsequent exams, controlling for prior performance. These findings enrich self-regulated learning theories by concretizing the behavioral mechanisms of resource management by which learners take control of their learning.

Teaching an Introductory Organic Chemistry Class for High School Students

A dual-enrollment course was designed in which the elementary concepts of organic chemistry were introduced to high school students. Students were assessed at the end of the term using an American Chemical Society (ACS) standardized exam. The same exam was given to corresponding traditional on-campus sections of the same class taught by the same professor. Intriguingly, when dual-enrollment students’ performance was compared with the performance of the traditional on-campus students studying the same content, no statistical difference was detected. Moreover, the dual-enrollment students have scored at a level significantly higher than the nationwide averages advertised by the Examinations Committee of the ACS.

First-Semester Organic Chemistry during COVID-19: Prioritizing Group Work, Flexibility, and Student Engagement

Our first-semester organic chemistry class focused on structured group work to enable active learning in class. When Smith College switched to online learning after spring break, the class was adapted to fit into an online learning model while retaining active learning. Using feedback from students, we implemented two tracks, one focused on independent work and one focused on group work. Using Zoom’s breakout rooms, we were able to simulate the full-class and small-group experiences of our in-person class with the help of student learning assistants to facilitate group learning. Slack was introduced for class questions and communications. Student feedback was positive overall and indicated that their perceptions about group work improved over the semester. In the case of in-person classes in the fall, this method might be preferable to a class in which social distancing hampers student-to-student discussion.

What Is the Value of Synchronous Engagement in Small Remote Organic Chemistry Classes? Analysis of Multiple-Choice Polling Data from the COVID-Impacted Spring Semester of 2020

The author’s organic chemistry course at Thomas Jefferson University incorporated student engagement activities through Nearpod, a web-based classroom response system. After transitioning to remote instruction due to the COVID-19 outbreak in the spring of 2020, students were given the option to complete multiple-choice poll questions either synchronously with a videoconference lecture or asynchronously while watching the recorded lecture video. This provided a unique opportunity to investigate whether completing the polls synchronously (as opposed to asynchronously) is advantageous. Correlations between the rate of synchronous participation, the rate of correctness in answering polls, and exam scores were analyzed across the two class sections. The majority of students chose to participate synchronously. The cohort that participated synchronously the majority of the time had higher exam scores, but these differences were not statistically significant for most exams. Although these results suggest that synchronous engagement is correlated with slightly improved learning outcomes, further studies are needed to examine the generality and causality of this phenomenon. Ultimately, offering both synchronous and asynchronous delivery may be the optimal approach to student engagement in the small-enrollment remote classroom.

Local and Timely Class Project Promotes Student Engagement in a Nonmajors’ Course: Organic Chemistry at the North Carolina State Fair

As a means to encourage student engagement and satisfaction in a large introductory organic chemistry class, students were tasked with the creation of instructional posters relating an organic comp...

Career Ladder: Abril Estrada

1998 Choosing chemistry Abril Estrada was born in El Paso, Texas, and raised just over the border in Juárez, Mexico. She always had a general interest in science, though she wasn’t drawn to any particular discipline. But she saw what was happening to Juárez, which in the 1990s rapidly became an industrialized city. Estrada witnessed how globalization, manufacturing, and a huge influx of people affected the environment of her hometown. When it came time for her to head off to the University of Texas at El Paso, Estrada thought she would be studying environmental science. However, after taking her first organic chemistry class, she knew she had found her niche. “Maybe I could help fix a lot of those issues through science and through chemistry,” she says. While at UTEP, she worked in a lab doing combinatorial solid-based organic synthesis, which set her off on the path toward her PhD.

Reorganization of the Organic Chemistry Curriculum to Improve Student Outcomes

The material of a standard second-year undergraduate organic chemistry class has been reorganized and reframed to emphasize the mechanistic connections between reactions and to clarify the language...

CASE (Computer-Assisted Structure Elucidation) Study for an Undergraduate Organic Chemistry Class

Structure determination via NMR spectroscopy is a fundamental topic taught in many advanced level chemistry courses. Despite its importance as an analytical instrument, many students find the princ...

Teaching green chemistry earlier

An injection of cash helped the University of California, Berkeley, reform its general chemistry lab instruction. Back in 2012, the College of Chemistry got a gift of money from the Dow Chemical Company Foundation. Most of the funds were used to completely renovate the teaching labs, adding new equipment and modern instrumentation. But, says Anne M. Baranger, UC Berkeley’s director of undergraduate chemistry, $1 million was earmarked for developing a new teaching curriculum to match the labs. And the focus was on sustainability. The result, which has been up and running since fall 2016, is a general chemistry lab curriculum that focuses on green chemistry. Rather than waiting to introduce green chemistry later—for example, in more advanced organic chemistry classes—the revamped lab introduces the concepts of green chemistry earlier, integrating them into the experiments and tests that make up the laboratory for general chemistry for nonchemistry majors (Chem 1AL). At