Hello jtwatts64,
It appears that you're not able to sync audiobooks between your Mac and your iPod. We noticed that your iPod nano is an older model. However, the steps that we'd like to provide you may be of some assistance:
"The 5 Rs: Reset, Retry, Restart, Reinstall, Restore
Remember these five 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 specific problems.
- Reset iPod nano. See General suggestions, below.
- Retry with a different USB port if you cannot see iPod nano in iTunes.
- Restart your computer, and make sure you have the latest software updates installed.
- Reinstall iTunes software from the latest version on the web.
- Restore iPod nano. See Update and restore iPod software on page 59."
More details here: iPod nano User Guide (7th Gen)
We hope this helps.
Take care.