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Probing the Reactivity of Cyclic "N,O"-Acetals versus Cyclic "O,O"-Acetals with NaBH[subscript 4] and CH[subscript 3]MgI
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Ciaccio, James A.; Saba, Shahrokh; Bruno, Samantha M.; Bruppacher, John H.; McKnight, Alexa G. – Journal of Chemical Education, 2018
An operationally straightforward, project-like laboratory experiment has been developed in which students directly compare the reactivity of two heterocycles, a cyclic "O,O"-acetal (standard C-O protecting group) and a cyclic "N,O"-acetal (oxazolidine), toward sodium borohydride and methylmagnesium iodide. Students synthesize a…
Descriptors: Organic Chemistry, Undergraduate Students, Spectroscopy, Hands on Science
Using NMR Spectroscopy and Chemical Synthesis to Establish Diastereoselectivity of NaBH[subscript 4] and Meerwein-Ponndorf-Verley (MPV) Reduction of (±)-Benzoin Isopropyl Ether: A Collaborative Discovery-Based Laboratory Experiment
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Saba, Shahrokh; Ciaccio, James A.; McMann, Lauren; Tariverdieva, Tamilla – Journal of Chemical Education, 2020
A discovery-based undergraduate organic chemistry lab experiment has been developed in which students establish the diastereoselectivity of hydride reduction of the a-chiral ketone (±)-benzoin isopropyl ether to erythro and threo diastereomeric alcohols by two different reducing agents. Students achieve this goal by working collaboratively and…
Descriptors: Spectroscopy, Science Laboratories, Laboratory Experiments, Undergraduate Students
Using NMR Spectroscopy to Probe the Chemo- and Diastereoselectivity in the NaBH[subscript 4] Reduction of Benzoin Acetate and Benzoin Benzoate
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Saba, Shahrokh; Cagino, Kristen; Bennett, Caitlin – Journal of Chemical Education, 2015
A pedagogically useful discovery-based undergraduate organic chemistry lab experiment probing the chemo- and diastereoselectivity in the NaBH[subscript 4] reduction of two chiral ketoesters (benzoin acetate and benzoin benzoate) has been developed. This experiment complements a previously described and highly popular discovery-based experiment…
Descriptors: Spectroscopy, Science Instruction, Organic Chemistry, College Science
Reaction of Orthoesters with Amine Hydrochlorides: An Introductory Organic Lab Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery
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Saba, Shahrokh; Ciaccio, James A. – Journal of Chemical Education, 2016
While orthoesters are often used by chemists as alkylating, acylating, and formylating agents, they are rarely encountered in introductory organic chemistry curricula. We describe a second-semester organic chemistry laboratory experiment in which students acetylate unknown amine hydrochloride salts with trimethyl orthoacetate (TMOA) in the absence…
Descriptors: Organic Chemistry, Introductory Courses, Laboratory Experiments, Scientific Concepts
Using NMR to Probe the Regio- and Stereochemistry of the Hydration of 1-Hexene
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Saba, Shahrokh; Clarke, Donald D.; Iwanoski, Christa; Lobasso, Thomas – Journal of Chemical Education, 2010
This undergraduate organic laboratory experiment complements previously described and popular experiments on hydration of 1-hexene where students experimentally establish the Markovnikov regioselectivity of alkene hydration. In this experiment, students explore not only the regiochemistry but also the stereochemistry of 1-hexene hydration and…
Descriptors: Chemistry, Laboratory Experiments, College Science, Undergraduate Study
Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the [superscript 1]H and [superscript 13]C NMR Spectra of N,O-Acetals
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Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. – Journal of Chemical Education, 2007
The stereochemical investigation is conducted to give students the combined experience of chemical synthesis of amines and N-heterocycles and structural stereochemical analysis using NMR spectroscopy. Students are introduced to the concept of topicity-stereochemical relationships between ligands within a molecule by synthesizing N,O-acetals.
Descriptors: Chemistry, Spectroscopy, Science Instruction, Science Experiments