It wont sync!

OK, i keep trying to plug in my ipod and i want to press the "sync ipod" option under file but it will not let me click it. It isn't highlighted. Some please help, this is driving me insane. Does anyone know what this is, or how to fix it?
Danielle

Is the iPod signed into the account that purchased the music?
Is the compouter suthorized ofor the account that pourchased the music
Was the iPod synced to another iTunes library?

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