Songs won't update... Really urgent :

I'm using iTunes to put songs on my iPod.
Well, today, I put some songs on my iPod, and everything seems to be OK, and iTunes recognized that the songs are on the iPod, but when I'm trying to find the songs in the iPod, I can't... They're not there, and iTunes still recognizes that the songs are in the iPod.
Please, I need help fast - My brother is going to USA in about five days and I need to put all of his songs in the iPod, and now I'm stuck

I'm having the same problems (I think)... I was updating my iPod with songs, podcasts, and an audiobook. The top bar shows x of x all the way through to the end of the list. Then, I get an "iTunes is dead" message, do I want to send an error report... This happens EVERY TIME I try to update my iPod, since I downloaded both updates (iTunes & iPod) yesterday. I've tried rebooting my computer, and reinstalling iTunes, but that hasn't fixed it. Any ideas, please?

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