Audiobook will not copy from iTunes to iPod!

I've been using my iPod for some time now, and this is a new problem for me. I have copied an audiobook (mp3) from the cd to iTunes. All the chapters show up there, but when I try to drag them to my iPod, only chapters 1 through 5 show up - the others don't copy. Any ideas? This has always worked before - I don't know what has changed!

Are you basing the few that don't get sent to your ipod on the file count? Could there be duplicates? I've noticed that there are some of my movies that don't get sent over but I usually get a warning that they aren't in a compatable format.
There is an option in either file or edit (can't remember exactly where, I'm at work) but you can filter to show all the duplicates. I've noticed that when I drag files over to be copied to my ipod and there are duplicates, it only does one.
After you find the culprits, another thing would be to export the file to your desktop. Delete it from iTunes then reimport it making sure of the file format.
just a thought

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