My music wont transfer to my phone from itunes. why?

music problems

To confirm, al songs are already in your iTunes library of current computer, and they all play using iTunes (on the computer)? 
And you are saying all the songs you purchased from the iTunes Store can be synced to the nano without any problems?  But NONE of the other songs (that are NOT from the iTunes Store) can be synced to the nano, or SOME of them?

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