When i sync music on ipod deleted song stay on songs list

When I sync music with iTunes on my ipod deleted songs stay on song list and cannt be deleted.

What happens when you try to sync?
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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