Certain songs stop before end on Ipod but not on Itunes

I have over 6000 songs on my ipod and almost all of them work fine. Recently though, I have developed a problem with some but not all of the songs I put on my Ipod. Firstly, most of these newer songs are from youtube to mp3 converters so it could somehow be in relation to that but the quality is fine and all of the songs play perfectly fine on Itunes. On my Ipod however, seemingly random songs have issues. About 3/4 of the way through the song (doesn't seem to be any set amount) the music will stop, and usually it will pause a couple seconds before moving to the next song. While I do get the majority of most of the songs, this is really annoying and even embarrassing when listening with other people. The one thing I have noticed is all of the songs that seem to have issues are listed when I open Itunes under the "determining gapless playback" action. Other than that really quick list it is near impossible to find which songs don't play. I am desperate for help in this as I really don't see any logical reason for these songs to work perfectly fine in Itunes but fail on the Ipod even though the times and everything else are right.