Question

Because of the great tendency of the neopentyl cation to rearrange, neopentyl chloride can not be prepared from the alcohol. How might neopentyl chloride be prepared?

Answer 1

Because of the great tendency of the neopentyl cation to rearrange, neopentyl chloride can not be prepared from the alcohol. But in case of free radical pathway, since free radicals usually do not rearrange, the best method to prepare neopentyl chloride is by photo-chemical free-radical chlorination of neopentane as shown.