New music does not show up on ipod !

HELP! I have had my nano for a year or so and now when I buy new music it shows up on my pc and appears to transfer to my ipod. But when I disconnect the ipod the music is not there!
PLEASE HELP!!!!!

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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