If the iPhone has had a jailbreak run on it that would explain why it can't sync. You may also need to do a hard reset on the iPhone. With the iPhone off, connect the dock cable to the bottom of the iPhone.
Make sure the USB end is NOT connected to anything. Next hold down on the "Home" button. While holding down on the "Home" button, connect the USB cable to your Mac or PC, and keep holding down the "Home" button tell you see the "Connect to iTunes" screen on the iPhone.
This should initiate a reset, and should let you reset the iPhone via iTunes. If the iPhone does not power up when you hook the USB docking cable to your computer, then you will need to hit the power button on the top of the iPhone. Just make sure to keep holding down on the "Home" button.
NOTE: This technique will more than likely WIPE OUT ANY DATA you have or had on the iPhone. You have been warned!
As the manufacturer of the iPhone they are going to be very willing to work with you to diagnose your issue right away...in my opinion, you will be better off here instead of trying to tinker around. You should be able to sync individual applications (itunes) and even play lists from the syc drop down menu and then option tabs. Good luck to you!
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