My 30gb Ipod Classic wont sync all the songs in my library

My ipod wont sync all the songs from my library, my library is only about 6gb so that cant be the problem. I tried to sync a playlist of the songs that werent syncing and still didnt show up on my ipod. How can i fix this?

What configurations/options do you have ticked/enabled from under the iPod's Summary and Music tabs in iTunes?
Is the iPod set up to Sync entire library?
B-rock

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