[cseil]

My book asks to prepare the isopropyl propyl ether using as organic reagent only propan-2-ol.
I tried with that, do you think that's correct? Could you give me a hint for making it with different steps (if there are)?

[AromaticAcrobatic]

So this would work, however it would not be the route I would take. It seems like it would take awhile, seeing how we would have to wait for the Ots to leave and then something to deprotonate propanol.
I would suggest adding a better leaving group to propene (anti-markov), and then adding a strong enough base to deprotonate alcohols. Think Williamson ether synthesis.

 

[unsu]

To me the steps looks correct.
But again, this exercise is created only for learning purposes as nobody would do that in the lab. Propene is a gas and you can't normally work with it.

[AlphaScent]

Its a good exercise I believe.  Good thought but Aromatic is right...

What is a way to make a better leaving group for Williamson ether synthesis?

Its a totally radical method!!

[cseil]

I could do the free radical addition. The alkene becomes a 1-haloalkane. Then I deprotonate the alcohol and make it react with my haloalkane, I obtain the product.
That's right, I really forgot that reaction