Howdy mshair87,
I see you are a new user here in Apple Support Communities - welcome! I hope we find you contributing often in the future.
If you are having an issue with your iPod nano being unable to sync or play audiobooks, I would suggest you follow the troubleshooting steps in this manual - https://manuals.info.apple.com/MANUALS/1000/MA1624/en_US/iPod_nano_2015_user_gui de.pdf
Specifically on page 56 -
Most problems with iPod nano can be solved quickly by following the advice in this chapter.
Tips and Troubleshooting
The 5 Rs: Reset, Retry, Restart, Reinstall, Restore
Remember these ve basic suggestions if you have a problem with iPod nano. Try these steps one at a time until your issue is resolved. If one of the following doesn’t help, read on for solutions to speci c problems.
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Reset iPod nano. See General suggestions, below.
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Retry with a different USB port if you cannot see iPod nano in iTunes.
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Restart your computer, and make sure you have the latest software updates installed.
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Reinstall iTunes software from the latest version on the web.
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Restore iPod nano. See Update and restore iPod software on page 59.
Thanks for using Apple Support Communities.
Best to you .