Bought 5 new songs on itunes. ipod syncs but songs do not show up on any playlist

Bought 5 new songs on itunes . ipod syncs but the new songs don't show up on the play list that is on the ipod . the do appear on itunes library. what am i doing wrong ?

Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
If so have you done anything like update iTunes on the computer since it last successfully synced?
Do the songs play in iTunes?          
Does any media now sync to the iPod?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod       
Try syncing using the manual method                
Managing content manually on iPhone, iPad, and iPod
Do you have any Restrictions (Settings>General>Restrictions) set that would prevent syncing those songs? (iTunes purchases only)

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