Problems syncing my ipod nano to iTunes

I have a ipod nano and pc-Windows Vista. Tried to sync my ipod to iTunes for some recent songs, but when I go to file and then to where it states "sync ipod" it is not in bold letters to where I can click it to sync. My ipod was hooked up to the computer and it use to automatically sync, but not this time, I have had no previous problems in the past. Suggestions as to what might be wrong or what I might be over looking?

Why not? What happens when you try?  Any error messages?  If so, what is the exact wording of these error messages?
B-rock

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