Why is the delete on my Ipod greyed out when I try to delete files on the ipod

When I try to delete files from my IPod the 'Delete' button is greyed out.  I swear I have mamge files but I do have Start iTunes when plugged ii.  What settings should I have in order to be able to delete files on my IPod?   Thanks

With the iPod connected to the syncing computer, go to the Music pane for the iPod in iTunes and unckeck the songs you want deleted from your iPod and then sync. The following givesyou some information about syncing.
iOS: Syncing with iTunes

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