Audiobooks download to iTunes, but won't sync to iPod Nano?
I purchased a book and downloaded to my iTunes menu. The book appears in the library, and in audiobooks but will not sync to my iPod device.
I have restored, reset original settings, started over, and still no sync. I can see the book in the library and in playlist/audiob
Sorry but it seems the first Gen iPods are not compatible as they don't run OS4
Requires iPhone and iPod touch with iOS 4 or later. iBooks is not compatible with original iPhone or iPod touch (1st generation).
Refer THIS link for the details from Apple
Under the What are the requirements to use iBooks? iPod nano is not listed so I assume it is not compatible.