Which of the following reagents is preferred to synthesize neopentryl halide from neopentyl alcohol ?

Options

A. conc.`HX`
B. `SOCl_(2)`
C. `PBr_(3)`
D. Both (2) and (3)

Answer

D

Explanation

Neopentyl alcohol , though `1^(@)` , is extremely hindered and reacts very slowly by `S_(N)2` displacement from the rear.Formation of neopentyl cation (a `1^(@)` cation) via `S_(N)1` , is also unlikely.

Instead a methyl group migrating from the adjacent `C` atom acts an intramolecular nucleophile , helping to displace `H_(2)O`. The result is a `3^(@)C^(+)` from which the product is formed.
However , rearrangement does not occur when we use `SOCl_(2)` or `PBr_(3)`.