PLEASE HELP, itunes and ipod trouble!

i have upgraded to the new itunes. uploaded new music into itunes, made space to put these songs on my ipod old 15GB model. when i plugged in the ipod into my imac it made the changes i made to deselecting songs but will not upload the new songs i have put into itunes...i tried restoring my ipod and it says that there is an unknown error...what do i do?!?!?! ahhhhh please help
thanks
-tm

i would like to also add that i tried making changes to teh setting of my pod like syncing all songs in the music tab in ipod settingsand its says that the ipod cannot be found!?!?! pleaaaaaaaaaaseeeeee helpppp
-tm

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