How to copy and paste music on iTunes?

I'm trying to music on my dads iphone 4gs (ios 5.0.1) but it won't let me copy the music from my PC's itunes library and paste it into my dad's phone library, any ideas why?

P.S. I have an iPhone3gs (ios 5.1.1) and I'm able to copy and paste the exact same music file onto my phone, that's why this is confusing me.

You can't do this unless you dad's phone is synced to your library.

What you should do is copy the music onto a flash drive, bring it over to your dad's computer and put it into his iTunes library. Then he can sync his phone and get the music.

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