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
- 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.