I see. I am assuming that is because of the DRM they used to attach to all songs purchased in itunes. In 2009 they adopted doing that so if the songs you dropped onto your sdcard were bought before the DRM removal, that is why it doesn't work. If you bought the songs after 2009, I don't know what went wrong.
Sent from my DROIDX
Unfortunately I went thru generations after generations of iPod to the current iTouch and yes these songs were passed on along the way. Ever since I got into Droid, didn't need/want iTouch. But something to remember now u mentioned it. Thanks