Originally Posted by FlashZ33
Click on your device on the left side of your iTunes screen and then when you see the screen with the amount of memory you have left click on the "Movies" options (its one of the top tabs) and then check the "Sync Movies" options and then hit "Apply."
After you've done all that sync your Ipod again and it should work. Mine did the same thing as yours (it wouldn't sync when I plugged it in) so I just did what I described above and hit "sync" again and it worked fine.
Hope this helps. It takes about 4 hours to convert the file so its compatible with your iPod though.