Apps in library not available for syncing

I've searched and searched but can't seem to figure out this problem.
There are some apps in my iTunes library that I had purchased on my iPad and I want to put them on my son's iPod touch. But when I plug in his device those apps don't appear on the sync list for his device. No matter what I do I can't seem to get those apps on the list, which means I can't get them on his iPod. How do I solve this problem?

I see all my smart albums in iTunes when I sync the iPad. But sometimes iTunes is confused about the current library. I have several iPhoto and Aperture Libryries, and I noticed that iTunes sometimes still tries to sync the previously opened library, not the most recently opened one. To be able to tell which library iTunes is showing, I name one of the projects exactly like the library. So I can tell easily, if iTunes is syncing an older copy of the library.
For example a small test library named "iPhoto Library" containing one smart album:
Regards
Léonie

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Message was edited by: BrianH

Library not available to sync with ipod

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We recently bought our son a used 4th generation nano. It seems to be in perfect working order and the software is current.
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<Email Edited By Host>

Hi vivekanandanganesan,
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Can't connect to the iTunes Store
http://support.apple.com/kb/ts1368
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Apps in library not available for syncing

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