Can't copy any more songs to my ipod from itunes - says its full but i have deleted heaps off my ipod to make room!

I can not seem to add any more songs to my ipod. Normally i just click and drag songs i have highlighted in my itunes folders up to the Administrators' ipod and it puts a copy there in my ipod. however i keep getting a message saying there is not enough room  . . . and so can't add another song. I have deleted heaps of songs off my ipod to ensure sufficient room for these new songs i want to load but i keep failing - why would that be? Is the space not freeing up when i delete exiting music off my ipod for some reason - or any other reason?

Try rebooting your iPod with it still connected to iTunes.  To do this, press and hold both the Select (Center) and Menu buttons together long enough for the Apple logo to appear. 
How exactly are you deleting this tracks from the iPod?
B-rock

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    yesterday when i added some songs onto my ipod in
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    wat the... why did u copy what i said
    yesterday when i added some songs onto my ipod in itunes, it said the songs were there. i ejected my ipod and my songs werent there, i tried again and again and it still didnt work! it said C:\something itunes was unreadable or corrupted... i cant add any songs to my ipod, yet itunes says its there and i tried pressing update too

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