iPod sync?

I have movies on my computer loaded from DVD's and they won't sync to my iPod. When I choose Advanced> Create iPod or iPhone version, itunes freezes and becomes unresponsive and after several minutes of the rainbow spin I have to force close itunes. When I tried to sync them again an error message said that the video format is not supported by my ipod. Is there a way to fix that or in the settings when I used handbrake?