IPod refuses to sync

Question

I accidently deleted all of my music off my iPod. So, I tried to get all of my songs back onto it. It connects fine, and starts syncing. Then, when it gets to a song (a different one everytime I try to sync), my iPod starts to physically make a grinding noise for about a minute. Finally, a box pops up that says "The iPod (my name) cannot be synced. The required file cannot be found." And then it says the sync is finished. When I look at my iPod, only four of the songs appear.
I do not know if this problem has to do with the iPod itself or iTunes. If anyone has any suggestions as to how to fix this frustrating problem, I would greatly appreciate it! Thankyou!

Answer 1

You could try transferring the music from your iPod back to the computer first of all. There are various ways of doing this, these are for a Windows computer (since you don't tell us what you have).
If you are using iTunes version 7 or later, then you can transfer purchased iTunes store music from the iPod to an authorized computer by using the "file/transfer purchases from iPod" menu. Note that the maximum of 5 authorized computers applies here.
For all other non purchased music (your own CDs etc) try this method which works on some Windows PCs.
Enable your iPod for disk use.
See: iPod Disk Use.
Open iTunes and select edit/preferences/advanced/general. Put a check mark in the box marked "copy files to iTunes music folder when adding to library" and also "keep iTunes music folder organized", then click 'ok'.
Connect the iPod whilst holding down the shift/ctrl keys to prevent any auto sync, and if you see the dialogue window asking if you want to sync to this itunes library, click 'no'.
Then go to file/add folder, open 'my computer', select your iPod and click 'ok'.
The music files should transfer to your iTunes.
If this doesn't work (and it may not because officially it's not supposed to), check out the instructions/suggestions here.
Music from iPod to computer (using option 2). This a manual method using "hidden folders" and although it works, it can be messy.
Much easier ways are to use one of the many 3rd party programs that copy music from the iPod to the computer.
One of the most recommended is Yamipod. This is a free program that transfers music and playlists etc from iPod back to the computer. However, it does not transfer playcounts/ratings etc.
Another free program is Pod Player.
Once the music is back from the iPod and in your new iTunes library, you can sync the iPod as normal.
If you see any message about replacing the library on your iPod with your new iTunes, click 'yes'.
Do not do that until the music is safely in iTunes.