IPOD won't eject from Mac even after turning off computer

I finally dsconnected it after trying 5 or 6 times, turning off computer etc. The last time I clicked eject i saw it synchronizing, then it said connected. When I click eject, nothng happens. Not sure what to do.

OS 10,6.8 IPOD. Nano recently puchased. Don't know which version it is.

Thanks