ipad – unsuccessful syncing – Ask Different

i have a movie file on my mac, and when i sync my iPad it fails to copy across, with the message that the file cannot be found. I have the feeling that TV Programs, Movies, Podcasts and Home Movies need to be stored in particular locations for them to sync properly, and maybe this file is not where my iPad is looking for it??! Is there a correct location to keep files like this, or might it be a different problem?
(i’m syncing from a finder window not from iTunes)