I'm trying to add music to a friends ipod, once I try synching it says an unknown error occurred. Any idea how to fix this?

My friend wants me to add music to his ipod since he's not very techy. I created a playlist and dragged it to his ipod but at the end a message appears saying it was unable to sync for an unknown reason. Any idea what is wrong or why this is happening?

Error 3194, Error 17, or "This device isn't eligible for the requested build" - Apple Support
If iTunes can’t communicate with the update server, you may see one of these messages.
Error 17
Error 1639
Errors 3000-3020
Error 3194
Errors 3100-3999
This device isn't eligible for the requested build

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