Music not syncing

Good Day,
Today I woke up my Ipod to find that only some of my recent purchases where on the ipod. However, none of the rest of my music (other purchases, music cds, etc) are NOT on my iPod. I tried manualy transfering them from my computer (which only added 5 songs more....) any suggestions as to why this might have happened? and how can I fix this?
thank you for your time.
Edit
I get this message from  iTunes if I try to manually sync:
iTunes cannot add any songs to the iPod “Ricard Bolio’s iPod” because no songs in the playlist “Purchased” can be copied to this iPod.
I also get this
iTunes cannot add any songs to the iPod “Ricard Bolio’s iPod” because no songs in your iTunes library can be copied to this iPod.

I'm having a similar problem, except in my case nothing syncs. Help would be appreciated.

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