Why is the ipod nano not recognized on my computer in order to sync songs from m music library?

I need help. I was able to put songs on the ipod nano from songs that i bought from itunes... but how can i put songs on the nano from my music library already on my computer. I have tried dragging the songs to the folder.  I have tried copying songs to the itunes cloud but the nano does not show the songs. How do i put songs on the nano that are from my cds? When I try to sync the songs, the nano is not recognized.

When I try to sync the songs, the nano is not recognized.
Is it saying "An iPod has been detected but could not be identified properly"? Or is something a bit different going on?

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