Audio Plays in iTunes on Computer, not on iPod

To all,
I used WireTap Pro to move some old language lessons from audio cassette tape to iTunes on my Mac--worked great. No problem, they are stored as Music and are MPEG-1, Layer 3 files.
Synched them to my iPod. They synched alright but everytime I try to play them on the iPod, they crash my iPod?! No other iPod music problems. The crash occurs at the very beginning as it looks like the iPod is trying to figure out what it is opening. Never gets out any sound before crash.
Any ideas on why, or work arounds?
Thanks.
MBPro 2.16 Mac OS X (10.4.8)

you might want to check the file type of the exported file, you may have changed the export settings?
I think only mp3 and aac audio files will play on the ipod (could be wrong)
for example iTunes will play full resolution AIFF files (standard format on retail cd's) but I'm pretty sure the ipod will not play them (again could be wrong on this?)

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