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Hmmmm try this link below they are some tools to help you do this, fix.
http://www.copytrans.net/gettingstarteddoctor.php How to fix the iPod There are multiple ways to fix the corrupted iPod, though it’s not 100% gauranteed it will work coz chances of HDD corruption do exist. - Restore method Try putting it in disk mode by holding the Menu + Center buttons until the Apple logo appears, then when it Logo appears, switch to holding Center + Play/Pause buttons until it says “Ok to Disconnect”. Then try formatting or restoring it and see if it fixes it at all. To get out of disk mode, reset your iPod by holding Menu + Center buttons until the Apple logo appears again. If this fails, proceed with the next. - Disk management: plug in iPod > Right click My computer > Manage > under “storage”, click on “disk management” right-click on the iPod it shows. “Change drive letter and paths…” then change the drive letter to something different. Then unplug the iPod and plug it back in again. It should work. - Driver Re-install -Plug your ipod into your computer, My Computer > manage > Device Manager and click on Universal Serial Bus Controller. Then click the plus sign and find the one with your device (it should say something like “USB Mass Storage Device.”. Right-click on that device and select “Uninstall.” Let the screen refresh. Replug your device from the computer, wait about 5 seconds then plug it back in. - Formatting and Restoring Another way is to format the iPod HDD (and then restore) to remove minor disk errors that might have come over usage of iPod. To proceed with this, you need a utility called HP USB. You can either google it or download it here. Format the drive as FAT 32 and then you should be able to restore it with no problem. - Try CopyTrans Doctor Its a good software for iPod recovery and fixes. Guide available here. If All of the above methods fail, probability of having bad clusters is high. How to confirm iPod Hard disk has gone bad? If you succeed in doing the quick format with the utility tool, and can now right click on Apple ipod in “my computer” and get the menu, proceed with this. Select the iPod in “my computer” right click >Properties > Tools > check disk. MAke sure you have the checkbox ” Attempt for the recovery of bad sectors” selected. Now your disk is checked for consistency. It will be checked in 2 phases. If it fails in any one of those with un-repairable message or freezes infinitely, then there is no solution, you would have to rush to apple to get the support. Else try the above steps again with the latest iTunes, it should work.
Try holding down the menu and center button at the same time for about 5 sec until the Apple logo appears on the screen (use two fingers). This may reset the iPod. If not try plugging into the computer and see if it is recognized. This model is a bit more fragile - and more difficult to repair.
Have you tried restoring the iPod yet?
Use the Five Rs to restore the iPod. You will lose the data that is currently on it if you restore but you can always re-sync the data to the iPod.
-=/ Daft Tech /=-
try getting new head phones if the new head phones dont work then it is the jack and u need to get it replaced. If it is the new 2nd gen ipod (has speakers on the bottom) u aren't going to want to check the plug it is dangerous to the ipod to take off the rear or front plate because u can damage the screen or wires and u will have even more things to fix.