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Helpful answers
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Jan 4, 2013 9:33 AM in response to H.Kiddby lllaass,See:
iTunes: May be unable to transfer videos to iPhone, iPad, or iPod
iTunes: Frequently asked questions about viewing and syncing videos
iTunes: Sync purchased HD videos to iPod or iOS device
I suspect the items are HD version. Only the 4G and 5G can play/sync HD. If the suggestion in the above articles do not work you may to redownload an SD version (if available) by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store