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Well, its just like transferring files to flash drive. You should keep it organized before transferring files. Make a folder labeled "Music."

As for transferring files from iTunes directly to your new folder I'm not sure. I saw a video that showed a guy do this but I don't know whether he downloaded an app or not. I personally just find the actual mp3 file/album and drop it in the newly created Music folder. I don't buy music off iTunes and I know some of the music files from the iTunes store are protected.

Sorry I couldn't be more help.
 
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I have copied music files from a Macbook to my phone several times. It is best if you copy to a music folder. I recently added a music folder to my sd card called "Christmas Music" thinking I could separate the music to play but it didn't work. When I started the music player it combined both music folders into one playlist. So it doesn't matter what you name the music folder, it searches for music and adds it to the playlist. You can name your music folder anything you like or make several folders.

I mounted the sd card to the Macbook and just copied the files to the folder on the phone. It's pretty simple. I also was able to copy several cd's to the phone. Play around with it a little and you'll figure it out. I'm a pc guy but the wife's Macbook was sitting on the counter so I thought I would try it. I'm not a computer genius by any means but after fiddling with it for a few minutes I was able to copy the music files and cd's to my phone.
 
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