IPod with touch wheel 10GB problem with downloaded audiobooks

Hi,
I might have better luck getting my question answered in this forum. I downloaded some audiobooks from iTunes onto my iMac with no problem. The problem arose when I updated my 10GB iPod with touch wheel (yes, a Jurassic age model from an era when NO ONE knew what an iPod was). Of the five audiobooks I downloaded and subsequently transferred to my iPod, I could only get my iPod to open and play two of them. The other audiobook files would simply be skipped over as if they weren't even there.
I've reset my iPod twice to try and fix this problem.
Does anybody have any other ideas?
Thanks,
Arnel

I have the same model iPod and downloaded and audiobook from iTunes for the first time a couple nights ago and have a similar problem. The book is in three parts. They all play fine on my iBook but my iPod skips the first two parts and will only play the third.
When I select part one on my iPod the screen displays the correct length of the segment, then skips to part two and shows the correct length, then finally skips to part three and plays it just fine.
If I only load part one and part two, the iPod goes through the same process but reverts back to the main menu screen without playing anything.
I had an idea a short while ago I am going to try when I get home. I did a get info on one of the audiobook files and it says it is the same file format as songs from the iTunes store. However, the extension is different. Protected song files are 'name.m4a' (I think, maybe .m4b) and the audiobook files are 'name.m4p.' I think those are the extensions, for some reason I'm having a brain **** right now. Anyway, I'm going to try changing the audiobook extension to match song file extensions and see if that works.
My thought is that the different extension for the audiobooks is how iTunes knows to put the files in the 'Audiobooks' list in iTunes instead of 'Music' or 'Podcasts' etc.
I'll post again after I give it a try.

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