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Question

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

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Solution

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.
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