Songs wont copy onto ipod

i have a 2nd generation 4 GB ipod nano, i recently added more songs to the playlist and am now upto 616 songs, but not all the new songs will copy onto my ipod. for example there are 3 songs by The Clash on the playlist but only one ever transfers to my ipod, i have restarted my ipod and this didnt help... what is wrong?

Is there anything different about those that do and do not sync? Such as when you optained them, the formate if they are age rated
Did they sync before?

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Hi all,
Bought my first ever tune from Itunes yesterday and
have been trying to get it onto my ipod ever since.
Have read some of the previous advice and tried all
r's, updated ipod, itunes and windows software,
tried to drop and drag in manually manage music mode
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WAV
AA (audible.com spoken word, formats 2, 3, and 4)
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Message was edited by: StarDeb55

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Songs wont copy onto ipod

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