I just bought an audio book from iStore, it is in my iTunes under "audiobooks" but will not sync with my iPod Classic, any ideas?

I have downloaded several audiobooks from audible and they have synced fine with my iPod but this book from the Apple Store will not sync from my iTunes to my iPod.
I am also having an issue with iTunes U; I have subscribed to the two classes I am taking this term and downloaded the videos to iTunes but when I sync my iPod classic I keep getting this error message: "Some of the videos in your iTunes Library were not copied to the iPod because they cannot be played on this iPod." I'm not sure what is going on because I have used this feature on my iPod classic before and it worked fine.

Those videos are probably not in an iPod-friendly format. It’s picky about that. You can try converting them, if possible.
As for the audiobooks, are you sure they haven’t synced? You’ve enabled it to sync books and checked the “Audiobooks” section of your iPod?

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