Chlorination of 2,3-dimethylbutane: A quantitative organic chemistry experiment

Markgraf, J. Hodge

doi:10.1021/ed046p610

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Cited by 2 publications

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Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

et al. 2018

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An advanced undergraduate organic chemistry laboratory experiment involving a rhodium-catalyzed intermolecular hydrocarbon C–H oxidation reaction is described. In the initial phase of this lab, students conduct a C–H amination reaction of ethylbenzene and isolate a benzylic amine product. In the second part of the lab, competition experiments are performed to compare the relative rates of C–H insertion with electronically disparate para-substituted ethylbenzene derivatives. Reaction progress is monitored by thin-layer chromatography and the outcome quantitatively assessed using 1H NMR spectroscopy. Data from competition experiments form the basis for a discussion of reaction mechanism including analysis of putative transition structures and relative potential energy barriers for C–H oxidation. Experiments have been designed such that instructors can tailor the level of detail and discussion from introductory to advanced.

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Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

et al. 2018

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Application of¹H and 1D TOCSY NMR Spectroscopy to the Free Radical Chlorination of Alkanes Experiment

Soulsby

2016

ACS Symposium Series

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Chlorination of 2,3-dimethylbutane: A quantitative organic chemistry experiment

Abstract: This paper describes the quantitative study of a free radical chlorination in which the student determines the relative reactivity of selected hydrogens.

Cited by 2 publications

References 15 publications

Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

Application of¹H and 1D TOCSY NMR Spectroscopy to the Free Radical Chlorination of Alkanes Experiment

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Chlorination of 2,3-dimethylbutane: A quantitative organic chemistry experiment

Abstract: This paper describes the quantitative study of a free radical chlorination in which the student determines the relative reactivity of selected hydrogens.

Cited by 2 publications

References 15 publications

Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

Rhodium-Catalyzed C–H Amination: A Case Study of Selectivity in C–H Functionalization Reactions

Application of1H and 1D TOCSY NMR Spectroscopy to the Free Radical Chlorination of Alkanes Experiment

Contact Info

Product

Resources

About

Application of¹H and 1D TOCSY NMR Spectroscopy to the Free Radical Chlorination of Alkanes Experiment