I am trying to sync my 160gb, but get an error message "the ipod cannot be synced. a duplicate file name was specified. it only syncs a small % of music. any clues?

i am trying to sync my 160gb, but get an error message "the ipod cannot be synced. a duplicate file name was specified. it only syncs a small % of music. any clues?

Hmm. 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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Try looking for and/or deleting incomplete downloads from the the iTunes Media folder. Then try downloading again, so its not resuming or overwriting a previous download.
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Hello WGT52,
It sounds like this error message is preventing you from syncing your content to the iPod. I would recommend the troubleshooting steps in the following article:
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Thank you for using Apple Support Communities.
Take care,
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http://support.apple.com/kb/ts3430
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