The electrophilic addition of hydrogen chloride () to 3,3-dimethyl-1-butene primarily yields which o — Hydrocarbons Chemistry Question

💡 Solution & Explanation

Protonation of 3,3-dimethyl-1-butene yields a secondary ($2^{\circ}$) carbocation at carbon-2: $CH_3-C(CH_3)_2-CH^+-CH_3$. Because it is adjacent to a quaternary carbon, a 1,2-methyl shift occurs to form a much more stable tertiary ($3^{\circ}$) carbocation: $CH_3-C^+(CH_3)-CH(CH_3)-CH_3$. The chloride ion then attacks this tertiary center, yielding 2-chloro-2,3-dimethylbutane.