[Jdiorio]

I am working through a work sheet right now and I cannot figure out this problem...

they want me to explain why propofol is insoluble in water and why fospropofol is much more soluble in water than propofol is..

i understand it has everything to do with the difference in connectivity, but i am having a hard time explaining it. Any help would greatly be appreciated. Thanks

[nj_bartel]

What different functionality is there in fospropofol?  Is it neutral/acidic/basic/polar/nonpolar/etc?

[Jdiorio]

the main different is that propofol has an OH group, and in the fospropofol molecule instead of an OH, you have an oxygen bonded to CH2-O-PO3. There are free sodium ions with positive charges attracted to the Oxygens with negative charges...

however, phenol (Ph-OH).. which is part of propofol is soluble in water.. why wouldn't propofol be soluble then as well?

[nj_bartel]

phenol isn't exceedingly soluble in water.  Ions, however, generally are.

[Jdiorio]

so is fospropofol more soluble due to the charges on the sodium and oxygen atoms? They don't exist in propofol and would explain the difference in solubility..

[nj_bartel]

Yes, but I'm not sure you're seeing the big picture.  Could you explain why you think those charges contribute to the solubility?