Ipod 4th Gen Nano wont sync with Itunes

Win 7
Ipod 4th Gen Nano
Just downloaded newest Itunes
I have a few hundred tunes on my IPod. I recently puchased a song In Itunes store. I attached Ipod to laptop ..clicked on Itunes..saw the song in my library byt it wont sync it to the Ipod. Any ideas? Thanks

Take a look at this link, http://www.apple.com/support/ipod/five_rs/nano4gen/

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