Syncing Music from

I am having trouble syncing all of my music to my new iPhone 3G. Since the harddrive on my MacBook is small (60 GB), I keep some of my favorite music there and some of it is kept on an external HD. All of my music shows in my iTunes library and as long as the ext. HD is connected all of that music will play normally through iTunes. The problem is that some of the songs that I want on my iPhone are on the Mac HD and some are on the ext HD. Even when that HD is connected, the computer will only sync that music which is contained on the local Mac HD (and not even all of that). I have tried taking all of the music off of the iPhone and resyncing but only the same tracks were resynced. Does anyone know the reason for this? I use my Mac for work and school and do lots of video editing on it despite the small HD so putting more music on the local drive is not an option. Does anyone know how to work around this? Thanks!

What happens when you try using itunes?

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