Question

Starting with isopropyl acetylene, how you would prepare the 4-methyl-2-pentanol?

Answer 1

Isopropyl acetylene reacts with soda amide followed by methyl bromide to form 4-methylpent-2-yne. Hydrogenation in presence of 1 mole of Lindlar's catalyst gives (E)-4-methylpent-2-ene. This is followed by oxymercuration demercuration to form 4-methyl-2-pentanol.