Question

Starting with isopropyl acetylene, how you would prepare the 2-methyl-2-pentanol?

Answer 1

Isopropyl acetylene reacts with soda amide followed by methyl bromide to form 4-methylpent-2-yne. Hydrogenation in the presence of an excess of Lindalar's catalyst gives 2-methylpentane. Addition of bromine followed by dehydrobromination with ethanolic KOH gives 2-methylpent-2-ene. This is followed by oxymercuration demercuration to form 2-methyl-2-pentanol.