I can't sync apps onto my ipod touch? Help??

I use a Mac.
So here's what will happen: I'll log into my account on Itunes, and then I'll connect my ipod touch (2nd generation) to it. I'll then click on Ipod (on the left hand window) and I'll select apps. I've purchased a couple of them, but whenever I click apply to sync, it won't.  I don't need to authorize it or anything, it just won't sync to my itouch. Help?

Are the apps compatible with ipod touch?
Are they compatible with the software version on your ipod touch?

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