Music Will not transfer to my iPod

I have just reset my iPod thinking that tht was the problem becuase for months now I have not been able to transfer any music from my home computer to my iPod, but it works fine on my computer at work.
Everytime I try to transfer music I get a message come up saying 'Attemping to copy to the disk "CLAIRE'S IP" failed. The disk could not be read from or written to.
If anyone can help me please advise.. Could it be that my musci has not transfer to the main iTunes libary correctly as that is possible my next move to delete all music and put it back on some how? any advice welcomed.
Thanks

What happens when you try?
Has it worked before?
How are your syncing? Automatically or manually?

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