3-step process to make propyl ethanoate from propene I was asked to make propyl ethanoate from propene in three steps. I have access to the reactions below.


Nucleophilic substitution (Both SN1 and SN2)
Electrophilic addition
Hydrogenation
Dehydration
Hydration
Condensation
Free radical substitution
Oxidation of alcohols


I'm assuming that you can add whatever reactants you want, since propyl ethanoate has five carbons and you can't just chop a carbon off of a propene with the above reactions. I know that the final step has to be condensation, since that's how you make esters. So essentially, I need a two-step process to make a primary alcohol that becomes the propyl in propyl ethanoate.

If you use hydrogenation on propene first, you get propane. Once you have that, it takes two steps to make a primary alcohol: one in free radical substitution (to get 1-bromopropane) and one in nucleophilic substitution (to get propan-1-ol).

If you use hydration first, you get a secondary alcohol in one step. However, you can't make propyl ethanoate with propan-2-ol.

If you use electrophilic addition first, you get a secondary haloalkane (2-bromopropane). That can also only get you a secondary alcohol.

Does anyone know how to do this? I'm convinced that it's impossible to do.
My proposal is hydroboration followed by Fischer esterification. It's 2 or 3 steps depending on how many you count hydroboration to be.



Alternatively if you are intent on going through a haloalkane pathway, you could try anti-Markovnikov addition of $\ce{HBr}$ by reacting it in the presence of $\ce{H2O2}$ to prepare 1-bromopropane. Then you could do nucleophilic substitution of $\ce{OH-}$ followed by Fischer esterification. This method would have a lower yield though due to the competing E2 reaction.