Apps purchased on itunes not syncing with iphone

I recently purchased some apps from the App Store using iTunes but when I synced it with my iPhone it didn't work. This is the first time it's happened. All the other times I purchased apps through my macbook, they synced perfectly once I connected my iPhone, except for the ones I downloaded last night. I tried downloading them straight from the App Store in my iPhone, and when asked "You already purchased this, would you like to download it again for free?" I clicked Ok, but still nothing happened. Now I have five apps missing which I paid for and haven't even used.
Any suggestions as to what else I should try?

Similar problem. Apps downloaded to iTunes do not sync to my iPhone (Edge/2.0) despite clicking "Sync" in iTunes. The icons do not appear on the iPhone. My account shows the apps ordered in the receipt, but they only remain on my Mac.
Workaround: I had to download the apps directly (wirelessly) to the iPhone. I did not restart the iPhone.
Expected behaviour: the apps should appear on the iPhone after syncing with iTunes.

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The minimum requirements for your Mac for an iPhone is Leopard 10.5.8.
iPhone minimum requirements:
Mac computer with USB 2.0 port
Mac OS X v10.5.8 or later
iTunes 10.1 or later (free download fromwww.itunes.com/download)
iTunes Store account
Internet access
You will have to upgrade to Leopard if your Mac meets v10.5 minimum requirements in order to sync, restore, or backup an iPhone.
Requirements for Mac OS X v10.5
iPhone 3GS Tech Specs: http://store.apple.com/us/browse/home/shop_iphone/family/iphone?mco=MTAyNTQzMjI

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Hello irish3kr,
You may need to download and install the Podcasts app.
About the Podcasts app for iOS
http://support.apple.com/kb/HT5295
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not just not sync it does not recognize the windows itunes recognizes not only the most work when he wants ¬ ¬

Apps purchased on itunes not syncing with iphone

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