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Generally speaking, you'll clean up your iPod with iTunes to erase unwanted songs and add new songs. You have two ways to delete music from iPod with iTunes, and they can be helpful when you want to get rid of the unwanted songs. iTunes provides automatic and manual methods to help you manage the songs in your device. When you are using the automatic way to manage iPod music, every time you connect iPod to computer with USB cable, your iPod will sync with iTunes Music library. If you have your iTunes Music library organized, you can delete unwanted music from iPod with this easy method. If you want to manually edit your iPod music, you can check Prevent iPods, iPhones and iPads from syncing automatically in iTunes by clicking Edit > Preferences > Devices. Then you can manually sync the songs and playlists to your iPod with iTunes. How to Delete Music from iPod
There are two ways to delete music from your iPod. The first is to delete songs in your iTunes library and have iTunes sync your library to your iPod automatically when you plug your iPod into the computer. The second is to manually delete music by resetting the options to a manual setting and deleting music directly from your iPod without affecting the songs in your iTunes library. Follow these steps to delete music from your iPod. Open up iTunes by double clicking on the "iTunes" icon. Go to "Library" on the far left side of the screen. Click "Music" from this list, which will bring up all your music on the main part of the screen. Choose a song you would like to delete from the list and right click on it. Click "Delete" from the drop-down menu that appears to delete your song. Go to the bottom of the left column on the screen to "Playlists." Click on one of your playlists to bring up the list of songs in the list. From there you can delete a song on the list. Connect your iPod to your computer. The iTunes program will automatically sync your iPod to whatever you have changed in your iTunes library as long as it is set to the default settings. Manually Delete Music Connect your iPod to your computer. Open up iTunes. Choose the third option in the "Options" menu called "Manually manage music" by checking the box next to it. It will ask you if you are sure you want to manually manage music on your iPod. Click "OK." Go to "Devices" on the far left column on your screen. You will see your iPod's name directly underneath that with an arrow pointing to the right. Click on the arrow, which will cause it to rotate until it is pointing downward and a drop-down menu will appear with all your songs listed. Click on a category or playlist, which will bring up all the songs in the list in the main section of the screen. Choose on a song listed that you would like to delete and right click on it, then click "Delete" from the drop-down menu that appears to delete your song.
The first way is uncheck the songs you want to delete on iTunes and then sync iTunes with ipod again, then the songs you want to delete will lose from iPod.
The second way is use leawo iTransfer to delete songs from iPod, the way is connect iPod to leawo iTransfer, then right click on the music you want to delete from iPod on leawo iTransfer to choose "Delete", then the music will be deleted soon. However, this tool can only work on Windows computer.
Go to itunes and click on a song that you want to delete and press the delete button on your keyboard and it will ask you if you are sure you want to delete this song from all playlists and off the ipod and click yes and it will delete. Unfortunately, it will not let you delete it from the ipod menu without connecting it to a computer.
What youve probably done is unselected the playlists that was previously on your ipod so you could sync the new playlists. By doing this the ipod would automatically delete the old songs off your ipod and then sync the new ones. I'm guessing youve managed to upload new songs onto your ipod?
It could also be your using a different computer and by syncing the ipod to a new computer it would automatically delete previous playlists.
I suggest using a programme called sharepod where you dont need to use itunes and is much more simpler. The link is below.