I Pod help

so i put some new songs on my itunes and whenever i plug my i pod into the computer it just says do not disconnect but never updates the new songs. I tried leaving it overnight but it doesent do anything.....any help??
 
after you make your new play list and let it charge etc. you click a little butten that is next to your ---- ipod that ejects it. You may have to set it to manual though if you dont see this thing.
 
change the settings to MANUAL instead of automatic update. so then u just click the songs in ur library and drag them to ur iPod
 
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