Ipod Classic Stops Playing at 1:50

I have an older ipod classic 60 gb. Recently I was trying to add some new music to it and iTunes crashed while syncing which corrupted the data on the ipod and I had to restore it to factory settings. Since restoring it about 3/4 of my 6000 song library stop playing on the ipod at 1:50. I have tried restoring the ipod again since then and readding the music but nothing has changed. All of the music plays fine through iTunes on my computer. Has anyone experienced this or have any ways for me to try to fix the problem? I would appreciate any help.