Sync does not work correctly

I replaced an iPod Nano with a new iPod classic. When I sync it from my MacBook Pro's iTunes, many songs and playlists are not synced to the iPod. I never had a problem with the old Nano. All songs are checked (selected). Sometimes syncing changes the contents of a playlist even though all songs are selected in itunes.

Connect phone to PC, open PC Suite , select syncronise - settings - create new settings (accept the warning that old sync settings will be deleted) , run through the sync wizard, select what you want to syncronise, then sync and see what happens.

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