Why isnt my ipod playing all my itunes payed songs??

my ipod has all the songs i payed for in my songs list, but it doesnt have them all in my purchased list. i try to play the songs in the purchased but some just jump around and end up not playing the song at all. when i go to my songs list and try to play them from there they dont play at all. there are about 5 out of 169 songs i can exshaly play. so i bought these songs and i cant listen to them?! someone plz help

Have y looked here:
iOS: Device not recognized in iTunes for Windows
If you  have iTunes 11 turn on the Sidebar.  Go to iTunes>View and click on Show Sidebar. You can also do a Crtl+S to show the sidebar

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