IPod nano 3rd generation showing up in ITunes but will not synch

I created new playlists in iTunes about 2 months ago and they synched to my Nano with no problems.  I created a new playlist yesterday, plugged in the Nano via a USB and I can't get iTunes to synch with Nano.  So the current playlists on it do not show up in iTunes and vice versa.  I do have the latest version of iTunes installed

If your country's iTunes Store allows you to redownload purchased tracks, I'd delete your current copies of the dodgy tracks and try redownloading fresh copies. For instructions, see the following document:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
Otherwise, I'd report the problem to the iTunes Store.
Log in to the Store. Click on "Account" in your Quick Links. When you're in your Account information screen, go down to Purchase History and click "See all".
Find the items that are not playing properly. If you can't see "Report a Problem" next to the items, click the "Report a problem" button. Now click the "Report a Problem" links next to the items.

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