Question

Neopentyl alcohol, (ch3)3cch2oh, cannot be dehydrated to an alkene without rearrangement. what is the chief product of dehydration?

Answer 1

Dehydration is removal of water.

In alcohols dehydration is α-β elimination or 1,2 elimination, it means the hydroxyl group will be removed from α-carbon while the hydrogen will be removed from near by carbon.

In case of neopentyl alcohol there is no β hydrogen present on the β carbon [as shown in figure].

The only possible way for it to undergo dehydration is by rearrangement.

The process or mechanism can be understood as:

so the chief product is 2-methylbut-2-ene