Cannot delete music from my new iPod nano

I have just bought an iPod nano 4GB and when I first got it I copied over almost a full 4GB of music to it. I have now ripped a lot of my cds in itunes and have about 20GB of music so I cannot copy the entire library, therefore I would like to copy everything over manually. I have set this option in the iPod preferences but it doesnt seem to do much. I cannot delete any of the music from the iPod. In iTunes, I go to my iPod and select a tune and press delete, then it prompts me about deleting it from the list. I press Yes and it says "do not disconnect" but then when I go to the iPod, the tune is still there. I even tried deleting all of the tunes at once but nothing.
Does anybody have any suggestions?
Thanks
Allan

I have managed to solve the problem. It appears that the file structure on the iPod had been corrupted so I used the iPod utility to erase the disk and install factory settings again. All seems to work fine now...
Allan

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