Can not sync files due to itunes not being able to find orginal file

I have purchased these songs and video from apple on previous computer and have not had trouble until recently I believe it occured when i went to ver. 9. I have a touch and nano and these files that are on touch will not go to nano. I am afraid i will lose these if something happens to touch. It says it wil not sync with the touch also on 100 songs.

Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
Do the songs play in iTunes?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod        
Do you have any Restrictions (Settings>General>Restrictions) set that would prevent syncing those songs?

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