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Synthesis and NMR-Spectral Analysis of Achiral "O,O"- and "N,N"-Acetals: Anisochronous pro-"R" and pro-"S" Ligands in NMR Spectra
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Saba, Shahrokh; Corozo-Morales, Ariel – Journal of Chemical Education, 2019
A pedagogically useful undergraduate organic-chemistry-laboratory experiment has been developed that involves the synthesis of two structurally simple, achiral "O,O"- and "N,N"-acetal substrates with no stereocenters. The experiment introduces students to a "new" and more effective variant of classical acetal…
Descriptors: Undergraduate Students, Undergraduate Study, Organic Chemistry, Laboratory Experiments
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