SN1, E1, and E2 Reactions of tert-Amyl Compounds: Improved Analysis Using Computational Chemistry and ASAP-HSQC NMR Spectroscopy

A set of inexpensive and pedagogically rich experiments focusing on SN1, E1, and E2 reactions have been updated to include modern computational and spectroscopic analyses. The SN1 experiment involves treatment of tert-amyl alcohol with hydrochloric acid to generate the corresponding alkyl chloride,...

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Bibliographic Details
Published in:Journal of chemical education 2020-08, Vol.97 (8), p.2280-2285
Main Authors: Esselman, Brian J, Hofstetter, Heike, Ellison, Aubrey J, Fry, Charles G, Hill, Nicholas J
Format: Article
Language:English
Subjects:
Chemical reactions
Chemistry
Computational chemistry
Experiments
Hydrochloric acid
Methylbutenes
NMR
NMR spectroscopy
Nuclear magnetic resonance
Reaction mechanisms
Spectroscopy
Sulfuric acid
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Summary:A set of inexpensive and pedagogically rich experiments focusing on SN1, E1, and E2 reactions have been updated to include modern computational and spectroscopic analyses. The SN1 experiment involves treatment of tert-amyl alcohol with hydrochloric acid to generate the corresponding alkyl chloride, which is used as the starting material for the subsequent E2 reaction. The E1 experiment involves reaction of tert-amyl alcohol with sulfuric acid. Both elimination reactions generate a pair of isomeric methylbutenes, with the ratio being dependent on the reaction mechanism. The combination of computational chemistry and a recently developed fast heteronuclear single-quantum correlation spectroscopy method (ASAP-HSQC), in tandem with 1H and 13C NMR and GC–MS analysis, allows the E1 and E2 product mixtures to be fully analyzed by students.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.0c00071