Under standard solvolysis conditions, the uniquely structured neo-pentyl bromide (1-bromo-2,2-dimeth — Haloalkanes and Haloarenes Chemistry Question

💡 Solution & Explanation

A) True. Ionization strictly generates the primary neopentyl cation [$(CH_3)_3C-CH_2^+$], which is fiercely unstable. B) True. To relieve this intense instability, an adjacent methyl group rapidly shifts (1,2-methanide shift) to generate the highly stable tertiary tert-pentyl cation [$(CH_3)_2C^+-CH_2CH_3$]. C) True. Nucleophilic attack by water or ethanol on this rearranged $3^\circ$ cation exclusively yields 2-methyl-2-butanol or 2-ethoxy-2-methylbutane. D) False. The reaction rate is actually incredibly slow because the initial formation of a primary carbocation requires an exceptionally high activation energy; the bulky group offers no hyperconjugative stabilization to the adjacent $C^+$.