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This may have something to do with how the ipod is reading the names of the songs. Hook your ipod up to iTunes and when the summary screen comes up uncheck the "automatically sync music" This will put it in Manage Music Manually mode. click the music folder and inspect the song titles. if a son has something in the name such a a number before the name title change the song name to remove the numeral. see if it comes back in order. as for losing songs, the ipod will remove songs when you sync if it doesn;t find it in your playlist. this may be whats going on.
Slide the hold/lock switch on and off and then hold down the "Menu" button and the center button for about 5 seconds. If this doesnt restart your iPod, try the same procedure, but instead, hold down the "Menu" button and the "Play/Pause" button for 5 seconds. This should reset your iPod.
1. Before manually placing the iPod into Disk Mode you should verify that it has a charge, if not you need to either charge iPod before continuing or connect it to power. You can either connect it to a high-powered USB port, or plug the iPod Power Adapter into an electrical outlet and connect iPod to the power adapter.
2. Toggle the Hold switch on and off. (Set it to Hold, then turn it off again.)
3. Press and hold the Menu and Select buttons for at least 6 seconds until the Apple logo appears.
4. When the Apple logo appears, release the Menu and Select buttons and immediately press and hold the Select and the Play/Pause buttons until the Disk Mode screen appears.
5. Disconnect iPod from the power adapter and connect it to your computer; the screen on the iPod will change and say "Do not disconnect"
If you are having difficulty putting an iPod model with a Click Wheel into Disk Mode, set the iPod on a flat surface. Make sure that the finger pressing the Select button is not touching the Click Wheel. Also make sure that you are pressing the Play/Pause button toward the outside of the Click Wheel and not near the center.