Ipod list all the songs of an album purchased on itunes but will skip some

all the songs to a newly purchased album by the while stripes are listed on my ipod (incuding artwork), but everytime i want to listen to this great album it skips the first five songs plays two skips two more plays 2 skips a couple more plays 1 skips 1 and then plays the last song.
help

See if these help.
iPod does not play content purchased from the iTMS.
Troubleshooting songs and audiobooks that won't play on the iPod.
Might be a problem with the download from iTunes. If so, contact them about the issue.
http://www.apple.com/support/itunes/store/download/#form

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    Try these Discussions...
    https://discussions.apple.com/message/10990796#10990796
    https://discussions.apple.com/message/21989767#21989767

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    Francois

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