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

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.