Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Isotopic Labeling with Sodium Borodeuteride in the Introductory Organic Chemistry Laboratory

Kjonaas, Richard A.; Fitch, Richard W.; Noll, Robert J.

doi:10.1021/acs.jchemed.6b00949

Cited by 8 publications

(16 citation statements)

References 12 publications

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“…One study limited the number of organic chemistry techniques and repeated them throughout the introductory lab course to enhance retention of course concepts . Integrating organic chemistry lab courses with other courses can help students understand applications and introduces students to cross-disciplinary collaborations. − …”

Section: Introductionmentioning

confidence: 99%

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Hall

Phadke

et al. 2019

J. Chem. Educ.

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Introductory-level laboratory courses provide students with hands-on experience using the discipline's tools and theories. These courses often rely on recipebased experiments due to the constraints of large enrollments, short lab periods, and the desire to minimize complexity. In addition, covering a breadth of topics can lead to a fragmented curriculum with little carryover in learning from week to week. Herein, we describe an overhaul of an introductory organic chemistry laboratory curriculum, informed by the strategies of meaningful learning and a desire to make the course experience mimic a research lab. This new course, primarily taught to first-year undergraduate students at the University of Michigan, is framed with three interconnected modules. We present herein the first module, which focuses on thinlayer chromatography (TLC). In the first week, students learn how to perform TLC using a variety of compounds and solvent mixtures, gaining an understanding of how intermolecular interactions affect their retention. In the second week, they practice using TLC to distinguish reagents and reaction byproducts and in the third week apply TLC to monitor reaction progress and test their hypothesis. We assessed student learning through a writing assignment at the end of the three-week module. We also assessed how the overall course affects student comprehension of TLC concepts and confidence. Our findings suggest that this learn, practice, apply approach toward teaching introductory organic chemistry laboratory concepts leads to learning gains and increased confidence.

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Section: Introductionmentioning

confidence: 99%

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Hall

Phadke

et al. 2019

J. Chem. Educ.

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“…This experiment is performed in our first physical chemistry course, covering thermodynamics and kinetics and taken by juniors and seniors. This experiment and the companion experiment performed in sophomore organic chemistry 2 were designed to facilitate collaboration between students taking different chemistry courses in our department. In the three years of performing the experiment, 65 physical chemistry students and 300 organic chemistry students have participated.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In a cross-course collaboration at our institution, 1 organic chemistry students synthesize the labeled compound used in this experiment, using borohydride or borodeuteride as reducing agent, as described in the companion paper. 2 Household bleach (basic aqueous NaOCl solution) is used as the oxidizer. Bleach is less toxic and more environmentally benign than traditionally used chromic acid.…”

Section: ■ Introductionmentioning

confidence: 99%

Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Primary Kinetic Isotope Effect in the Hypochlorite Oxidation of 1-Phenylethanol in the Physical Chemistry Laboratory

et al. 2017

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A kinetic isotope effect (KIE) experiment is described for the physical chemistry laboratory. Students conduct a hypochlorite (household bleach) oxidation of an equimolar mixture of 1-phenylethanol and 1-deuterio-1-phenylethanol to acetophenone. The reaction occurs in a biphasic reaction mixture and follows first-order kinetics with respect to either isotopomer of 1-phenylethanol. Reaction progress is measured by gas chromatography–mass spectrometry (GC–MS). Alternatively, the experiment could be conducted with each isotopomer serially and followed by GC alone. The reaction rate constant for the disappearance of 1-phenylethanol, k H, ranges from 3 × 10–4 to 2 × 10–3 s–1, while kD, for 1-deuterio-1-phenylethanol, ranges from 9 × 10–5 to 5 × 10–4 s–1. The observed KIE, the ratio k H/k D, is remarkably robust, ranging between 2.3 and 3.6, with a mean of 2.9 and standard deviation of 0.4 over three years of student data. The robustness of the observed KIE stems from using competing reactions. The experiment can be completed in about 3 h; GC–MS data is conveniently acquired overnight using an autosampler. The experiment, as presented here, can stand alone, but is well-suited to cross-course collaboration between the organic and physical chemistry laboratories. The preceding companion paper describes the synthesis of 1-phenylethanol and 1-deuterio-1-phenylethanol using borohydride or borodeuteride reduction of acetophenone as an experiment for the organic laboratory.

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“…Previous experiments reported in this Journal include the intentional conversion of C–H bonds to C–D bonds for the purposes of unambiguously assigning NMR signals to particular resonances. , Also, for many molecules it may be possible to assign NMR signals using well-established two-dimensional NMR techniques . There is a trade-off, of course, in the pedagogic value of each approach: deuteration can be expensive and time-consuming, and the introduction of two-dimensional NMR techniques requires the development of expertise that may or may not be reinforced later in the course or major.…”

Section: Introductionmentioning

confidence: 99%

Distinguishing Vinylic and Aromatic ¹H NMR Signals Using Selectively Deuterated Chalcones

2021

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1H NMR spectroscopy is a molecular characterization technique that is ubiquitously used in research and teaching laboratories alike. Strategic deuteration of molecules is a commonly employed technique in the deconvolution of 1H NMR signals. Here this approach is applied in a second-year chemistry course in which students synthesize 4-methoxychalcone using the Claisen–Schmidt variant of the foundational aldol reaction. The 1H NMR spectrum is complicated by a crowded aromatic and alkene region due in part to extensive conjugation through the two phenyl groups surrounding an α,β-unsaturated ketone. This report demonstrates that students gain competence and confidence in making 1H NMR assignments when presented with a curated set of selectively deuterated chalcones rather than the corresponding spectrum of the fully protiated chalcone. While deuteration does not resolve all of the challenges associated with interpreting this spectrum, it is an invaluable tool to complement chemical shifts (including the predictive nature of resonance structures), integration, and spin–spin splitting. A proposed lecture is presented that is timed to correlate with the performance of the chalcone synthesis lab. Assessment data collected before and after the lecture and then again on the final exam point to the effectiveness of this approach.

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Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Isotopic Labeling with Sodium Borodeuteride in the Introductory Organic Chemistry Laboratory

Cited by 8 publications

References 12 publications

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Primary Kinetic Isotope Effect in the Hypochlorite Oxidation of 1-Phenylethanol in the Physical Chemistry Laboratory

Distinguishing Vinylic and Aromatic ¹H NMR Signals Using Selectively Deuterated Chalcones

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Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Isotopic Labeling with Sodium Borodeuteride in the Introductory Organic Chemistry Laboratory

Cited by 8 publications

References 12 publications

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Adapting Meaningful Learning Strategies for an Introductory Laboratory Course: Using Thin-Layer Chromatography to Monitor Reaction Progress

Cross-Course Collaboration in the Undergraduate Chemistry Curriculum: Primary Kinetic Isotope Effect in the Hypochlorite Oxidation of 1-Phenylethanol in the Physical Chemistry Laboratory

Distinguishing Vinylic and Aromatic 1H NMR Signals Using Selectively Deuterated Chalcones

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Distinguishing Vinylic and Aromatic ¹H NMR Signals Using Selectively Deuterated Chalcones