My iPod won't sync any songs or videos that are in the iTunes Library.

I have an iPod classic [80 GB] and it does not, recently since I updated the iTunes to the newest version, for whatever reason iTunes will not be able to sync music or any of the music videos I have giving me a error message [Like rite now it told me: Attempting to copy the disk "RADKE777" -which is the name of my device- Failed. An error has occured (-69)] then iTunes will freeze completely and I cannot do anything with it.
What does that mean? It was just working recently.. the only thing that I have done differently, like I said, was update iTunes.. I'm not really sure as to what to do. If ANYONE can help me I'd appreciate it! >.<

It could be an indication or a damaged or dying hard drive.  I would recommend doing a disk diagnostic on the iPod's HD using the instructions given by turingtest2 in this older thread.  He also covers what the resulting numbers indicate.
https://discussions.apple.com/thread/3784647?start=0&tstart=0
If necessary, post the resultings numbers and we can verify what the next steps to take.
B-rock

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