Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown Substance

Shine, Timothy D.; Glagovich, Neil M.

doi:10.1021/ed082p1382

Cited by 21 publications

(8 citation statements)

References 10 publications

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“…Compared to traditional single-outcome procedures, the aforementioned variances allow more unique learning experiences to occur in the classroom and create a more synergistic relationship with the associated lecture presentation. ,,, An example of an MOE recently developed and implemented into the undergraduate organic instructional laboratory explores the oxidation of alcohols. This new MOE addresses the challenges previously mentioned and also specifically reinforces the utility of NMR spectroscopy by providing access to benchtop 1 H NMR technology to undergraduate students, thereby encouraging engagement and ownership of the experiment. ,,− Commonly used NMR instruments have high operation costs, requiring the use of cryogens and specially trained staff members. Since the advent of benchtop 1 H NMR technology, spectra of neat samples spiked with tetramethylsilane (TMS) are collected in a matter of seconds and processed within a few minutes using NMR processing software such as MestreNova or TopSpin.…”

Section: Multioutcome Experimentsmentioning

confidence: 90%

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

2019

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Single-outcome experiments are used in the undergraduate instructional laboratory, particularly for large lectures associated with multiple sections of instructional laboratories, due in large part to efficiencies associated with chemical purchases, experiment preparations, and assessments. Despite the practical advantages, single-outcome experiments are not effective in encouraging students to critically analyze and interpret their acquired individual results. Instead, students are satisfied if their results are the same as or similar to all of their classmates’ results, limiting the opportunity for engagement with the laboratory content. In contrast, multioutcome experiments (MOEs) require students to explore the same chemical reaction or transformation but obtain individual results. Individualization of results is accomplished by using a set of starting materials or reagents, one of which is assigned to each student. Students do not know the identity of the assigned component but may be given possible options for its identity. Students elucidate the identity of their individualized products, using modern analytical techniques such as gas chromatography, Fourier-transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy, and deduce the unknown component of their experiment. An example MOE for the oxidation of alcohols is described herein. A traditional single-outcome experiment that utilized a common household oxidizing agent (hypochlorite bleach), rather than a heavy metal-containing alternative, was modified. For the MOE modification, one unknown secondary alcohol (2-pentanol, 3-pentanol, or 3-methyl-2-butanol) was oxidized using bleach. Each student pair was assigned one of three possible unknown alcohols, all of which were constitutional isomers of secondary alcohols. Students knew the identities of the three possible alcohols. Analysis of their oxidation products was accomplished using FTIR and benchtop 1H NMR spectroscopies. Students interpreted their spectra and deduced the identity of the unknown alcohol they were assigned. This experiment provides a tangible framework to understand the applicability of the oxidation reaction and the utility of FTIR and 1H NMR spectroscopies.

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Section: Multioutcome Experimentsmentioning

confidence: 90%

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

2019

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“…In the second semester, they complete a two-step synthesis and an independent research project. The first-semester goals are met through two unknown identification laboratories , and two discovery-based projects , that require students to think critically, make hypotheses, test their hypotheses, interpret experimental data, and write formal lab reports. In the larger courses at UD, the first semester is dedicated to purification techniques and the art of running reactions, from setup to purified product.…”

Section: Transition Of Organic Laboratoriesmentioning

confidence: 99%

Maintaining an Active Organic Class during the COVID-Induced Online Transition at Two Undergraduate Institutions

Baker

Dannatt

2020

J. Chem. Educ.

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This communication contains the experience of two early-career organic professors at primarily undergraduate institutions during the rapid transition to an online learning environment during the COVID-19 pandemic. The techniques and methods for transitioning both the organic lecture and lab of two class sizes (∼50 and ∼10) are juxtaposed, and conclusions are drawn that provide insight into improvements for both online and on-site learning.

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“…There are many more examples of published organic-chemistry undergraduate experiments originally developed for high-field instruments that can now be easily conducted on benchtop systems. − However, in terms of physical and inorganic chemistry, there is only a handful of published NMR experiments, − and to our knowledge, only a few of those papers can be classed as physical-chemistry experiments. This includes the use of a 45 MHz benchtop NMR spectrometer to determine the octanol–water partition coefficient .…”

Section: Introductionmentioning

confidence: 99%

Molecular Properties of Caffeine Explored by NMR: A Benchtop NMR Experiment for Undergraduate Physical-Chemistry Laboratories

Kent

Bell

2019

J. Chem. Educ.

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NMR is a fundamental part of any undergraduate chemistry degree, and training students how to measure and interpret NMR spectra is essential for postgraduate research or chemistry-based careers. Traditionally, the undergraduate laboratory experience with NMR is restricted to sample submission for NMR analysis, which is typically conducted by a technician. However, instant access to NMR instrumentation is now possible because of the development of benchtop NMR spectrometers. These can be placed on the lab bench alongside other spectroscopic equipment. The simplicity of operation and variety of experiments available allows the development of new undergraduate experiments across organic-, inorganic-, and physical-chemistry laboratories. Here we describe a new experiment for undergraduate physical-chemistry laboratories that incorporates relaxation measurements to understand the behavior of caffeine in a variety of conditions. The experiment uses the T 1 and T 2 experiments available on most benchtop spectrometers, which can be processed using a variety of software packages. The experiment, performed in the third year of a 4 or 5 year Bachelor’s or Master’s degree, follows a five-lecture unit on NMR spectroscopy as part of a third undergraduate chemistry course. It can be conducted in pairs or groups of three in three 3 h laboratory sessions, but it can be tailored to reduce the required time. The experiment allows students to become proficient users of a new piece of equipment, incorporate taught theory, and handle data in different platforms and software packages. Allowing students hands-on access to NMR instrumentation gives them a complementary experience to their NMR lectures and offers a unique way to inspire a new generation of chemists.

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Organic Spectroscopy Laboratory: Utilizing IR and NMR in the Identification of an Unknown Substance

Cited by 21 publications

References 10 publications

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

Developing and Implementing Multioutcome Experiments in Undergraduate Teaching Laboratories To Promote Student Ownership of the Experience: An Example Multioutcome Experiment for the Oxidation of Alcohols

Maintaining an Active Organic Class during the COVID-Induced Online Transition at Two Undergraduate Institutions

Molecular Properties of Caffeine Explored by NMR: A Benchtop NMR Experiment for Undergraduate Physical-Chemistry Laboratories

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