The electrophilic addition of hydrogen chloride () to 3,3-dimethyl-1-butene primarily yields which of the following compounds as the major product due to intermediate rearrangement?

Question

The electrophilic addition of hydrogen chloride ($HCl$) to 3,3-dimethyl-1-butene primarily yields which of the following compounds as the major product due to intermediate rearrangement?

Prashant Kotian · Accepted Answer

Correct answer: C. Protonation of 3,3-dimethyl-1-butene yields a secondary () carbocation at carbon-2: . Because it is adjacent to a quaternary carbon, a 1,2-methyl shift occurs to form a much more stable tertiary () carbocation: . The chloride ion then attacks this tertiary center, yielding 2-chloro-2,3-dimethylbutane.

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