Why can't i sync apps from itunes to my iphone 3g?

i can't sync apps on my iphone . when i select the apps on the itunes and click apply the apps will disappear from the preview

3G or 3GS?
What version of iOS?
If it is a 3G, the most current version it can be running is 4.2.1 and many apps require 4.3 or higher.

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