5th Generation Ipod Nano Audiobook Playback

Hey all.

I've had to fall back on my old 5th Gen Ipod nano after my touch got washed and I've stumbled upon an issue with several of my audiobooks.

When I put an audiobook on the nano, it will play but when it comes to the end of the first chapter, it stops playing. The files on my computer are not corrupted. I can get them to play in itunes. When I manually select any chapter past the first one, it will act like it's playing the book, but there will be no sound nor will it actually play. I don't have this issue with all my audiobooks. Some of them will work, but others will not. I have looked around for answers in the community but I haven't been able to find them. Has anyone else had this issue? Is there a solution?