1stly, i wanted to say is, u better removed to fact 'bout u know what' which i quote n deleted em. n bout rearranging track arrangement

as u can either change it with right click>properties>summary>advance n change the tracks according to the sshot, or u can open ur itunes>right click>get info n change the one circled accordingly.
coz when u sync ur iPod, it will only put wats in ur current iTunes library, hence wat's in ur bro's itunes list will be there including what he dun have. Apple n his way of DRM/prevent from song sharing (aka piracy/peering or watever u call it) so, the only way is copy his song to ur thumb drive (or u can use ur iPod as external hdd n copy the file into it) n paste it at ur comp n update ur iTunes playlist.