[li tt le Ce LL 09]

Need to make 2-propoxy-1-propanol using propene as only C source.

This is what I did...

Propene -----> (1.BH3, THF 2. H2O2,OH-) = 1-propanol

Propene -----> (Peroxybenzoic Acid) = 1,2-epoxypropane

1-propanol + 1,2-epoxypropane = 2-propoxy-1-propanol ?

I'm not sure about my last step. Will that work? Will the alcohol from 1-propanol attack the central carbon atom, opening the epoxide?

Thanks


(Also, i need to make 1-propoxy-2-propanol using propene again yet the above doesn't work as I need the hyrdoxy group on carbon-2 this time not one...)

[azmanam]

what conditions do you want to use to open the epoxide.  It can work if you pick the right conditions.

What if I told you that you could use that same epoxide to make the 2nd product too?  any thoughts?

You can use this ppt for hints

http://faculty.smu.edu/ebiehl/Wade14.ppt

[li tt le Ce LL 09]

If i do it under acidic conditions, (H+ and 1-propanol) wouldn't that lead to the formation of -OH on carbon 1? Which is what I need for product #1?

So does that mean in order to synthesize product #2... I do the SAME thing yet under basic conditions (EtOH and 1-propanol) ?

[azmanam]

wouldn't that lead to the formation of -OH on carbon 1?

yes, well done.

I do the SAME thing yet under basic conditions

I'm with you so far,

EtOH and 1-propanol

can't use EtOH... You're only allowed propene as a carbon source.  but in general yes, basic conditions are what you'll need for product 2.