[sinjid9]

How do you make 2-Propoxy-3-Cholorobutane. Or more specifically how do you make the parent chain in that reaction (the alcohol) from an alkene?

[Vidya]

you can try an addition reaction on 2-Butene.now you need to select the reagent which can give lead to addition of  propoxy and Cl on the double bond

[sinjid9]

So I used 2-Butene and went to hydrohalogenation with HCI but I lose the double bond, unless you don't need it for hydration. Also, Can I start from 2-Butyne? and undergo hydrohalogenation adding the Cl and H where I want?

[Vidya]

Do not do hydrohalogenation.It will not give you desired product.Use Cl2  and CH3CH2CH2OH First Cl2 is added by electrophilic addition and after that CH3CH2CH2OH

[CrimpJiggler]

From 2-butene you could convert the alkene into an epoxide with a peracid then convert the epoxy into a halohydrin and finally, convert the hydroxyl group of the halohydrin into an ether. I don't really understand the question, where you specifically given 2-butene as the starting reagent? If so, the epoxy route is perfect.

[orgopete]

From 2-butene you could convert the alkene into an epoxide with a peracid then convert the epoxy into a halohydrin and finally, convert the hydroxyl group of the halohydrin into an ether. I don't really understand the question, where you specifically given 2-butene as the starting reagent? If so, the epoxy route is perfect.

Au contraire, the problem is how do you alkylate the chlorohydrin? Won't the alkoxide of a chlorohydrin form an epoxide again? I suggest following Uma's route.