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Full-Text Articles in Physical Sciences and Mathematics
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Erik A. Sgariglia, Regina Schopp, Kostas Gavardinas
Ram S. Mohan
Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram S. Mohan, Steven R. Shadwick
Ram S. Mohan
We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.