Ipod classic issues syncing

When I connect the iPod I receive an error:
Attempting to copy to the disk "name of iPod" failed. The disk could not be read from or written to.
and in another window:
iTunes could not copy "name of song" to the iPod because the file could not be read or written.
I have a MacBook Pro running OS X 10.9.1 and my iPod is a click wheel 40 GB
I have done the following:
1. I have the most current iTunes software installed
2. Restored the iPod - to erase all content
3. Tried connecting and syncing iPod after a reboot of MacBook Pro
4. Tried different combinations of opening iTunes and connecting iPod (ex. connect before opening iTunes, connecting then letting the system open iTunes, etc)
5. Tried a different USB port when connecting iPod
6. Changed the manual sync properties in iTunes to limit down the number or songs being synced to 4 and I did have success with a couple songs transferring but the same error comes up "could not copy song" after the couple of songs
7. Checked integrity of each of the songs that are listed in the error - these have been different depending on the connection, reboot, etc. and all of them played just fine in iTunes
8. The iPod continually displays the "do not disconnect" message and most often there is no content syncing
9. The iPod does show up in iTunes and I can see the Summary and other tabs
Any help is greatly appreciated.
Thanks,
Eric

My Classic 160GB starting doing the eject thing today the worst part was iTunes wasn't able to do anything because it kept ejecting,I have managed to stop the ejecting temporarily,by switching the iPod over to Disk Mode then connecting it,iTunes detected it fine and I'm in the middle of a very Large Sync (still in Disk Mode)Syncing 5200 320kbs songs)so I am not sure what will happen once the sync is complete,but at least now I can connect and restore if necessary.incidentally iTunes gave me an error stating that Syncing is not possible because a needed folder could not be found.I exited the error msg and that's when the incessant ejecting started.hopefully this will help apple or anyone else fix the issue.
I Finished the Sync,ejected the Ipod and switched it back to normal mode and plugged it back in.iTunes found it and everything seems to be working fine again for me.
Message was edited by: emprcyrul

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