Neopentyl bromide, solvolysis

Like the previous example, this is a solvolysis reaction. Initial protonation of the alcohol followed by water leaving generates a primary carbocation. The bromide can then add to this carbocation generating neopentyl bromide. Since, for this carbocation, 1,2-hydride shifts cannot occur, a 1,2-alkyl shift generates a more stable tertiary carbocation. This new carbocation is not subject to possible 1,2-hydride shifts because any such transformation would generate either a less stable... 

Neopentyl (2,2-dimethylpropyl) systems are resistant to nucleophilic substitution reactions. They are primary and do not form carbocation intermediates moreover the r-butyl substituent hinders back-side displacement. The rate of reaction of neopentyl bromide with iodide ion is 470 times less than that of n-butyl bromide. Under solvolysis conditions the neopentyl system usually reacts with rearrangement to the... 

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