Songs not playing on Ipod

Having transfered songs from Itunes to Ipod, some songs appear on the ipod list, but when click to play, it skips certain songs.
In one example, it skips 6 songs on an album and starts playing only on track 7.
On itunes, the songs play perfectly well, just not on the ipod
Any thoughts?

Yes. iToons 8 does not work with Windows. I do not understand why Apple still offers it for download except to sabotage Windows users' iPuds.

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