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Published November 1, 1955 | public
Journal Article

Rearrangements in Carbonium-ion Type Reactions of C^(14)-Labeled Pentamethylethanol (2,3,3-Trimethyl-2-butanol-1-C^(14))

Abstract

Treatment of 2,3,3-trimethyl-2-butanol-1-C^(14) with concentrated hydrochloric acid and zinc chloride (Lucas reagent) yielded 2-chloro-2,3,3-trimethylbutane with the C^(14) distributed essentially equally among the five methyl groups. Under the conditions used, the aliphatic chloride equilibrated completely with Lucas reagent containing radioactive chloride ion. The rearrangement and chloride exchange may be accounted for by the following equilibria involving solvated carbonium ions.

Additional Information

© 1955 American Chemical Society. Received May 9, 1955. Supported in part by the joint program of research of the Office of Naval Research and the U. S. Atomic Energy Commission. Presented at the Symposium on Reaction Mechanisms at the 75th Anniversary of the American Chemical Society, September 13, 1951.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023