Can't update ipod with songs bought from itunes store

I buy songs from itunes store and can't get them on the ipod. they are on the itunes library just fine - just can't get them over to the ipod. Get the message "some of the tunes in the library were not copied because your ipod software is too old.... - but I have the up to date software on the ipod - I get the message - "your ipod software is up to date" - - too frustrating - I buy songs but can't get them on the ipod - - any suggestions??

Please help!!
For some reason yesterday, whilst browsing on iTunes, a computer error message came up and closed the site automatically..
After that, the computer 'froze' on me, so I had no other option than to run System Restore, which, after 2 hours, got my system up and running again, although I had JUST remembered at that point, that ALL files etc would be completely deleted.
I opened up iTunes and looked at my Library, and to my horror, I also hadn't originally thought about backing them up, as I knew they were all 'safely' on my iPod.
I have just tried this morning to 'try' to upload tracks from the iPod onto iTunes. I tried this, BUT, it has completely deleted the tracks off there as well - all 985 of them!!
Does anybody know WHETHER I will be able to recover all these tracks, short of contacting iTunes themselves?
I feel so awkward about it!! Any sensible advice would be appreciated!!

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Can't update ipod with songs bought from itunes store

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