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Sep 25, 2012 6:55 AM in response to Sprucerby lllaass,See:
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
iTunes: Frequently asked questions about viewing and syncing videos
You may need a computer app like the free HandBrake to convert the format to one compatible with the iPod.
Sometimes it take three or four time trying recovery mode to get it to work.