Ipod won't play tracks but itunes will

I have bought some singles from itunes (mp4) and since I have ripped the album from CD. The problem is that the tracks (mp3) that I have bought from itunes will not play and the album freezes when it gets to this track. If I play the original single (mp4) this will play.
If I try and play the mp3 ripped track on itunes it plays perfectly.
Any ideas?

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