# What is/are the product when 2,2-dimethylhex-5-en-3-ol reacts with Lucas reagent?

What would be the product(s) if 2,2-dimethylhex-5-en-3-ol reacts with Lucas reagent?

Would a Methyl shift happen? I've heard that in Groove's process, only primary and secondary alkyl chlorides are formed.

A shift of the methyl group is likely, because this would yield a more stable tertiary carbocation. In concentrated hydrochloric acid, the double bond can also be protonated, producing a secondary carbocation which is captured by $\ce{Cl-}$. If both happens, the product would be 2,4-dichloro-4,5-dimethylhexane.