Just got a nano. Wanted to take all my music from my computer that I had even before I had Itunes not all were bought from itunes.  I loaded them into itunes and all of them won't transfer to nano only the ones that I brought from itunes. why not all?

I just purchased a Nano.  I have a ton of music that I on my computer from before I had a nano and had a mp3 player.  I never had a problem transferring that music before.  So I didn't purchase them from Itunes.  Now that I have a Nano I want to put all those songs on my nano.  I also have a iphone that I did buy some songs so those will transfer on my nano.  All of my music shows up in itunes but won't transfer to my nano. grrrr.  Any thoughts? 

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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