I have purchased an audio book which appears downloaded in my purchases but will not sync with my nano

i have recently purchased an audio book which has been downloaded and charged to my account .the book appears under "book" heading,in i tunes but won't sync to my nano.I have tried restoring the nano,re installing i tunes on my pc.any suggestions?

The "missing file" error happens if the file is no longer where iTunes expects to find it. Possible causes are that you or some third party tool has moved, renamed or deleted the file, or that the drive it lives on has had a change of drive letter. It is also possible that iTunes has changed from expecting the files to be in the pre-iTunes 9 layout to post-iTunes 9 layout, or vice-versa, and so is looking in slightly the wrong place.
Select a track with an exclamation mark, use Ctrl-I to get info, then cancel when asked to try to locate the track. Look on the summary tab for the location that iTunes thinks the file should be. Now take a look around your hard drive(s). Hopefully you can locate the track in question. If a section of your library has simply been moved, or a drive letter has changed, it should be possible to reverse the actions.
If another application like Windows Media Player has moved/renamed the files then the chances are that subtle differences in naming strategies will make it hard to restore the media to the precise path that iTunes is expecting. In such cases, as long as the missing files can be found somewhere, you should be able to use my FindTracks script to reconnect them to iTunes. See this post for an explanation of how it works.
tt2

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Hi
I have exactly the same problem.
My computer seems to match the Leopard 10.5 system requirements as follows:
Hardware Overview:
Machine Name:        iMac G5
Machine Model:        PowerMac8,2
CPU Type:                  PowerPC G5 (3.0)
Number Of CPUs:        1
CPU Speed:                  1.8 GHz
L2 Cache (per CPU):    512 KB
Memory:                       512 MB
Bus Speed:                  600 MHz
Boot ROM Version:    5.2.5f1
Serial Number:
What do I do next to upgrade the system from OS X 10.4.11?
Thanks
Theresa

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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.
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Wayland wrote:
The CS.com service account has long been closed. I cannot get it to respond to my years ago password for that account. So I ask them to send me a new password and of course it goes to my years ago email number.
Don't have it send email.
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I have purchased an audio book which appears downloaded in my purchases but will not sync with my nano

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