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You'd better cleanup your iTunes library firstly. Just click "View > Show Duplicate Items" and then you would just check off the duplicates that you wanted to remove. After removed all the duplicates in your iTunes, sync it to your iPod, then all duplicates in your iPod will be removed automatically.
Source: http://how-to-delete-duplicates-in-itunes.newgenresoft.com/ How to Delete Duplicates in iTunes 12 11 10 9 automatically
connect to PC to detect the device, then click to show all the files, check on files for deleting and delete.scan the device with a good anti virus to comfirm that the device memory is clean. Hope this works well good day
When you connect the ipodnano to the computer, you can do one of two things: you can go to the ipod's main home page in itunes and go to the bottom where it will have four options listed. 1 of them should say manually manage files. Click on the check box next to it and it should ask you if you are sure and click yes. Then go into your music folder of your ipod and delete the songs you don't want on there. To add music, all you have to do is click and drag what you want onto the oped. The second way you could do it is to go into your library before connecting your nano to your computer and un-checking all of the boxes next to the music you do not want on your nano and then connect it to a computer and let it sync. The first way is easiest and less time consuming as you only have to do it once. Hope this helps!
Below is a URL that you can copy and paste into your browser bar. It will take you directly to the iPod manual that will teach you every thing you need to know about syncing and deleting content on the iPod. :)