iTunes doesn't update all songs to iPod

[linzykins]

For some reason, when i connect my iPod to the computer, iTunes does an update and it doesn't export all the songs from my library to the iPod. When i watch it updating, some of the songs do not have circles in the leftmost column (showing the update as they are being transferred to the ipod). all of the song boxes are checked in my library. i have tried ejecting and manually updating it to no avail. what am i doing wrong?
this should be easier to figure out...

thank you in advance for your help!