Hello,

carefully follow the steps below:
Automatically Delete Music

1. Open up iTunes by double clicking on the "iTunes" icon.
2. 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.
3. 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.
4. 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.
5. 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.

1. Connect your iPod to your computer.
2. Open up iTunes.
3. 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."
4. 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.
5. Click on a category or playlist, which will bring up all the songs in the list in the main section of the screen.
6. 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