If I edit an audio file that is already on my ipod in the itune library will it change the file on the ipod or will the file on the ipod overwrite the file in itunes?

I have some audio files that could be edited to remove portions I don't need.  They were lectures that has some portions which I like to remove.  If I edit the file in the itunes library will it be able to sense that with even the same name the file has changed and update my ipod, ipad an so forth?  Or will the files on the devices be moved back and overwrite the newer version?  Or perhaps will  I need to do all of this by hand?  Thanks

- Only iTunes purchases will copy from iPod to computer.
- If you sync manually and do not specify those modified songs to sync they will not sync to the iPod nor will the original version be deleted from the iPod
- If you sync automatically and include those songs or select the modified songs to sync manually, the songs in the iPod should be replaced with the modified songs. However sometimes that does not happen

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