Hi giggle chops,
Welcome to the Support Communities!
The article below explains why you may get this specific error message. Follow the instructions below to disable any third-party plug-ins by opening iTunes in Safe Mode:
iTunes: Troubleshooting issues with third-party iTunes plug-ins
http://support.apple.com/kb/ts3430
Add-ons, such as plug-ins and scripts, not manufactured by Apple (third-party) add features to iTunes or modify its appearance and behavior. Using these can interfere with how you use iTunes. For example, if you upgrade to a newer version of iTunes, your add-ons may not be compatible.
You see this alert while syncing: "... cannot be synced. A duplicate file name was specified."I
I hope this information helps ....
- Judy